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Islamorada cottage on deep water canal Tavernier, Florida

Islamorada cottage on deep water canal

Located in Tavernier, Florida, United States. Islamorada cottage on deep water canal Our cottage is set in a quiet neighborhood on a deep, clear, wide canal. Situated bayside at mile marker 89, there is a 61 foot concrete dock and room for up to a 30' boat. backwater fishing is a short boat ride and there is easy ocean access through both Tavernier Creek and Snake Creek. A boat ramp is available at nearby Founders Park. There are 2 bedrooms each with ensuite bathrooms. The living room is large and airy with sliders opening to the back screened porch. The fenced private back garden has a lighted gazebo, water toys, bbq grill, bait freezer, swim ladder and platform.

🛏 2 beds · 👥 6 guests
$126 /night
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Oceanfront, Dockage, Luxury, Paddleboards, Gaming - Paradise Palms Islamorada Islamorada, Florida

Oceanfront, Dockage, Luxury, Paddleboards, Gaming - Paradise Palms Islamorada

Located in Islamorada, Florida, United States. Oceanfront, Dockage, Luxury, Paddleboards, Gaming - Paradise Palms Islamorada Welcome to Paradise Palms - Your Ultimate Oceanfront Getaway in Islamorada, Florida with Boat Dockage. YOUR VACATION STARTS NOW!Indulge in luxury at Paradise Palms, your new construction oceanfront gated home with waterfront dockage. With unmatched ocean views, this three-story retreat boasts a perfect fusion of modern design and tropical charm. Enjoy three spacious bedrooms and over 2000 square feet of air-conditioned spacious living areas along with two expansive oceanfront patios. Entertainment provided for all! This place offers an unforgettable high-end escape to the heart of the Florida Keys. Reserve today!Key property features include the following:• Panoramic Ocean Views: Bask in breathtaking sunrises and sunsets as the expansive windows frame panoramic ocean views. The inviting turquoise waters of the Atlantic are on display from the kitchen, living room, both patios and Primary Suites.• Spacious Liv

🛏 3 beds · 👥 8 guests
$551 /night
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SAVE in Apr/May! True OceanFRONT - Wide Ocean Views-Huge Decks-Yaks/SUPs-Dock Islamorada, Florida

SAVE in Apr/May! True OceanFRONT - Wide Ocean Views-Huge Decks-Yaks/SUPs-Dock

Located in Islamorada, Florida, United States. SAVE in Apr/May! True OceanFRONT - Wide Ocean Views-Huge Decks-Yaks/SUPs-Dock THERE ARE SOME HOMES WITH OCEAN PEEKS OR PARTIAL VIEWS THRU THE TREES, BUT FOR PANORAMIC UNOBSTRUCTED OCEAN VIEWS - FROM INSIDE AND OUT - THERE IS ONLY ANGLERS REEF 140! See our many REVIEWS, which tell it all! Our home is known as "Aqua Vistas" and for good reason: THE OCEAN VIEWS DON'T GET ANY BETTER THAN FROM THIS HOME - inside from every room and outside from the two covered wraparound decks that offer OVER 700 SQFT of outdoor living area! Although the Anglers Reef community is oceanfront, we are one of only 5 truly OceanFRONT HOMES in the community, and the only rental with unobstructed ocean views. See the community layout in the photo gallery for our QUIET corner location away from highway traffic noise, pool noise, and the late night music from Hog Heaven on the other side of the community.AND WE CAN PROVIDE A BOAT SLIP FOR YOUR STAY IF DESIRED.ANGLER'S REEF is a boutique gated community of 52 ho

🛏 3 beds · 👥 8 guests
$430 /night
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Sunset Peninsula—a multi-family, original,  Florida Keys waterfront retreat! Tavernier, Florida

Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat!

Located in Tavernier, Florida, United States. Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat! Welcome to the Sunset Peninsula! This gated, multi-family compound is perfect for those traveling in larger groups with family and/or friends who want to share great memories while maintaining their privacy. This unique and private tropical oasis welcomes all guests with lush vegetation uniquely indigenous to our fragile ecosystem. The paved driveway adds appeal and functionality, making parking for all an easy convenience. Beyond the gate, you will notice a private half ramp where small boats, jet skis, or kayaks could be launched. Often referred to as the "cruise-ship shaped" house, this solidly built, all concrete home, offers a 3 bedroom/2 bath main house (2/1 up, 1/1 master quarters down), and a separate, recently renovated 2/2 ground level/ranch style apartment. For chefs who wish to indulge their guests, the property is equipped with 2 full kitchens and a small galley. The roof top deck imparts a great

🛏 5 beds · 👥 12 guests
$343 /night
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Penthouse view - Futura Yacht Club #604 Tavernier, Florida

Penthouse view - Futura Yacht Club #604

Located in Tavernier, Florida, United States. Penthouse view - Futura Yacht Club #604 Condo #604, 3 Bedrooms, 2.0 Baths, (Sleeps 6)Enjoy penthouse views of the fabulous blue waters of the Atlantic and Florida Bay-- all from the comfort of your own three bedroom, two bath condo. This condo can sleep 6 comfortably and features a kitchen with every convenience you might require. The master bedroom has a king size bed, bath with clothes hanging rack. The second bedroom has a queen size bed, closet and attached bath with shower. The converted third bedroom, off of kitchen, has a full bed.Heated swimming pool with Tiki Bar, lighted tennis courts as well as plenty of beautifully landscaped property for walking are all available within this safe gated complex. Relax seaside at the sandy beach and view the fabulous sunsets every evening from our penthouse balcony.For you boaters, Futura Yacht Club offers the best deep water dockage and on site boat ramp in the area. Rental does not include boat slip. However, pending availability, other sl

🛏 3 beds · 👥 5 guests
$114 /night
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Relax in this beautiful townhome overlooking the sparkling Atlantic Ocean Islamorada, Florida

Relax in this beautiful townhome overlooking the sparkling Atlantic Ocean

Located in Islamorada, Florida, United States. Relax in this beautiful townhome overlooking the sparkling Atlantic Ocean Windy Cove #1 - Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features three bedrooms and two bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak up the sun on the beach under a palm tree, or wake up early to catch a sunrise from your own balcony overlooking the water. If booking more than a year in advance current prices may not reflect annual cost of living increase. Many of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. Vacation Rental License# 24-0384 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.Please note: before proceeding with your booking, kindly review the following infor

🛏 3 beds · 👥 6 guests
$266 /night
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Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool! Islamorada, Florida

Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!

Located in Islamorada, Florida, United States. Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool! Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon arrival.- Following property rules, the minimum age required for check-in is 21 years old;We're

🛏 1 bed · 👥 4 guests
$220 /night
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Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal Islamorada, Florida

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Located in Islamorada, Florida, United States. Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal Vacation Rental License No VR-001 WEEKLY RENTALLocated on the peaceful upper Keys, in Islamorada, this home is situated in the quiet residential neighborhood of Venetian Shores MM 86. Immediate access to ocean and Bay side off of Snake Creek. Islamorada is is just 75 miles from Miami and 86 miles from Key West. The average temperature is 80 degrees and 78 degrees for the water. Islamorada sits between the clear waters of the Florida Bay and the Gulf of Mexico, it is bestowed with a Coral Reef three to five miles offshore that is filled with spectacular life. Two story homeThis 3 bedroom, 3 bath, private home is equipped with many extras including this heated (at 80-82 degrees) swimming pool that is partially shaded so you can enjoy floating with a cool drink leisurely. WIFI ready. This vacation gem boasts large rooms furnished in rattan and decorated with a tropical flair. You can see this view from the livi

🛏 3 beds · 👥 8 guests
$470 /night
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Ocean View Condo is a Fisherman's Paradise in Islamorada Islamorada, Florida

Ocean View Condo is a Fisherman's Paradise in Islamorada

Located in Islamorada, Florida, United States. Ocean View Condo is a Fisherman's Paradise in Islamorada This spacious two bedroom, two bath condominium overlooking the ocean is located on a quiet 12 acre private gated community. Includes a 30 foot boat slip in a protected marina with direct access to the ocean. Eat in kitchen with breakfast bar open to living area that looks out over the water. Expansive patio for open air dining or lounging. Main bedroom has an ocean view, opens to screened patio, a king sized bed, private bath with soaking tub and walk in shower. The split floor plan design provides a private additional bedroom with a spacious bathroom. Ideal for remote workers, retirees wishing to spend winter in a warm, sunny locale or families looking for an adventurous escape. Large heated community pool and hot tub. Lighted tennis courts. Onsite boat ramp. Club house features a large community room and full gym. Outdoor covered dining area with picnic tables, a gas grill, and ice machine.

🛏 2 beds · 👥 6 guests
$179 /night
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Florida Keys Tour! Private Beach Access with Marina! Pets Allowed, FREE Parking Islamorada, Florida

Florida Keys Tour! Private Beach Access with Marina! Pets Allowed, FREE Parking

Located in Islamorada, Florida, United States. Florida Keys Tour! Private Beach Access with Marina! Pets Allowed, FREE Parking Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon arrival.- Following property rules, the minimum age required for check-in is 21 years old;We're

🛏 1 bed · 👥 4 guests
$216 /night
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Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals! Islamorada, Florida

Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!

Located in Islamorada, Florida, United States. Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals! Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon arrival.- Following property rules, the minimum age required for check-in is 21 years old;We're de

🛏 1 bed · 👥 4 guests
$187 /night
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Deep Blue Vacation Oceanfront Estate, Millionaire's Row, Private Saltwater Pool Islamorada, Florida

Deep Blue Vacation Oceanfront Estate, Millionaire's Row, Private Saltwater Pool

Located in Islamorada, Florida, United States. Deep Blue Vacation Oceanfront Estate, Millionaire's Row, Private Saltwater Pool Deep Blue Vacation Rental - Beautiful Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, Winding Staircase, Expansive Ocean Views, Over 4000 Sq. Ft. of Living Space. Saltwater Pool, Sandy Back Yard, Gated Entrance Lined With Palm Trees. House has its own private observation pier that extends 200 feet into the ocean providing easy ocean access for fishing, swimming and snorkeling. Enjoy the Ocean Views and Breeze. Once upstairs, everyone will enjoy breeze off the ocean while you barbecue, look out over the palm trees and expansive ocean view. Home has 5 bedrooms, include two twins, four kings, and a convertible that sleeps two children. Large kitchen to accommodate all the family and entertaining.Located in the heart of Islamorada, near world class fishing, boating, snorkeling, and sun bathing7 Night Min. / Saturday to Saturday Only # 120

🛏 5 beds · 👥 12 guests
$815 /night
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Great Townhome with Basin & Bay Views Islamorada, Florida

Great Townhome with Basin & Bay Views

Located in Islamorada, Florida, United States. Great Townhome with Basin & Bay Views Futura Townhome #731 - Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a two bedroom two and a half bath unit. There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the property. Make yourself at home in our home away from home. Boat dockage available please inquire within. The Futura Yacht Club HOA charges- onsite-$150 per trailer and $50 per boat fee. These fees will not show up on your rental agreement, as the fees are collected upon check in at Futura Yacht Club. VACATION RENTAL LICENSE: VR 24-0413 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.If booking more than a year in advance current prices may not reflect the annual cost of living increase. Many of our guests' re-book the same property on

🛏 2 beds · 👥 4 guests
$225 /night
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Paradise in Plantation Key/Deep Water Canal House/Boat Dock/MM 89 Plantation Key, Florida

Paradise in Plantation Key/Deep Water Canal House/Boat Dock/MM 89

Located in Plantation Key, Florida, United States. Paradise in Plantation Key/Deep Water Canal House/Boat Dock/MM 89 Paradise in Plantation Key. If you are looking to relax and learn about “Keys Time” you are looking in the right area! Sometimes I come down and relax on the water and others I am paddleboarding, kayaking, fishing, scuba diving etc. It is the epitome of true mental relief. My home is conveniently located at Mile Marker 89. It is the upstairs unit only. The downstairs is not available for rental. The units are separate with there own private entrances. If you are planning to bring your boat great! They are welcome, I have plenty of parking at the residence. This is a 28 day rental. This is a pet free rental - we do not allow pets on the property. There is room for your boat and recreational watercraft with 45 feet of dock space available in this deep water canal however, you will need to load it at a local ramp. The closest ramp and pool is at Founders Park (MM 87). Founders Park offers activity or relaxa

🛏 2 beds · 👥 4 guests
$132 /night
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Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage Islamorada, Florida

Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage

Located in Islamorada, Florida, United States. Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards and more. The main living area is located on the upper level of this oceanfront cottage and has open ocean views throughout. The open concept kitchen, living and dining room are great for entertaining. The main level has two bedrooms and two baths. The lower level is a separate living area with 2 sets of bunk beds, a living room, kitchenette and bathroom. It can be added when renting the upstairs for an additional $600 weekly. The Leatherback Cottage can be rented separately or in combination with any of the four other homes.VACATION RENTAL LICENSE: 24-0386If booking more than a year in advance current prices may not reflect th

🛏 2 beds · 👥 6 guests
$478 /night
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Vacation At its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool Islamorada, Florida

Vacation At its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool

Located in Islamorada, Florida, United States. Vacation At its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- These are TWO separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms. - The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and

🛏 2 beds · 👥 8 guests
$387 /night
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TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED Islamorada, Florida

TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED

Located in Islamorada, Florida, United States. TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED New In Ground Heated pool , Just remodeled with new furniture, flat screen tvs throughout ( including the patio) and a dock with direct ocean view / access. Minutes away from some of the best fishing, diving or sightseeing in the Florida Keys. Walk or boat to Tavernier Marina ( 3 Dive shops, Boat Rental, Charter fishing and sightseeing boats, Jet Ski Rentals, Bait and Tackle Store, Fuel, parts and service on sight). Grill, Smoker, and less than a mile away from Tavernier Towne which has Winn Dixie, Movies, Restaurants, Post Office and liquor store. Please confirm reservation with owner within 72 hours of booking.

🛏 3 beds · 👥 8 guests
$267 /night
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Reel Paradise at Sea Gulls Tavernier, Florida

Reel Paradise at Sea Gulls

Located in Tavernier, Florida, United States. Reel Paradise at Sea Gulls Summary:Stunning ocean views and beautiful island sunrises!The Space:Welcome to Reel Paradise! This beautiful condo is located in the Sea Gulls community of Tavernier. The post card views will have you coming back year after year. Wake up and enjoy the beautiful sunrise from your private balcony. Take the kayaks out and paddle out to the nearby islands and take in everything the keys has to offer. Come back from a day on the water and relax by the pool or on the beach. You will also have access to the community gym. This unit has two bedrooms and two bathrooms. Kitchen is equipped with all essentials for cooking at home. There are televisions in both bedrooms as well as the living room. Both bedrooms have patio access with views of the ocean. There is also a view of the nearby High School football field, to catch some Friday night football during the season. The location in Tavernier puts this community close to both Islamorada, Key Largo, the best restaurant

🛏 2 beds · 👥 4 guests
$118 /night
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3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed! Islamorada, Florida

3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed!

Located in Islamorada, Florida, United States. 3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed! Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- These are THREE separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms. - The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is

🛏 3 beds · 👥 12 guests
$676 /night
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Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast Islamorada, Florida

Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast

Located in Islamorada, Florida, United States. Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon arrival.- Following property rules, the minimum age required for check-in is 21 years old;We're de

🛏 1 bed · 👥 4 guests
$264 /night
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Oceanfront Estate with 4 Cozy Cottages Islamorada, Florida

Oceanfront Estate with 4 Cozy Cottages

Located in Islamorada, Florida, United States. Oceanfront Estate with 4 Cozy Cottages Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave of four charming cottages nestled in beautiful landscaping with a total of seven bedrooms and seven bathrooms. When entering through the gate you will feel a sense a tranquility that makes you realize your vacation has started. Each cottage has it's own personality with an array of unique, yet tasteful decor. The property offers a boat basin, tiki hut, oceanfront pool, outdoor showers, paddle boards, kayaks and bikes. All of this combined to make the perfect family retreat. Your own little oasis you'll never have to leave. VR#24-0385, 24-0386, 24-0416, 24-0134If booking more than a year in advance current prices may not reflect annual cost of living increase. Many of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. Please note: before proceeding with your booking, kindl

🛏 7 beds · 👥 16 guests
$1,528 /night
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Comfort & Convenience, 3 Classy Units, Free Breakfast, Free Parking, Pool Islamorada, Florida

Comfort & Convenience, 3 Classy Units, Free Breakfast, Free Parking, Pool

Located in Islamorada, Florida, United States. Comfort & Convenience, 3 Classy Units, Free Breakfast, Free Parking, Pool Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- These are THREE separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms. - The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is r

🛏 3 beds · 👥 12 guests
$602 /night
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Get ready to dive into your Islamorada Retreat Tavernier, Florida

Get ready to dive into your Islamorada Retreat

Located in Tavernier, Florida, United States. Get ready to dive into your Islamorada Retreat 134 Tequesta Street - Get ready to dive into your Islamorada Winter Retreat! Move in ready today!This beautiful three-bedroom three bath pool home is located at mile marker 89 on a deep-water canal. Bring your boat (20' or less only please) and fish Islamorada in the winter while your family and friends dig their way out of the snow. When you walk through the front door you will find yourself in a beautifully renovated home and in your family TV room. (Located on the ground level). The first floor includes two bedrooms, with a shared bath, chef’s kitchen, large dining room, and another full bath off the pool/porch/outdoor entertaining area.Upstairs is the master bedroom suite. It's beautifully decorated and includes a large bedroom, bathroom, and private porch with a hot tub! The outside is where you will spend most of your days and nights. Large couches surround the pool. There's an awesome tiki with a summer kitchen including a BBQ grill

🛏 3 beds · 👥 6 guests
$274 /night
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Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed! Islamorada, Florida

Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!

Located in Islamorada, Florida, United States. Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed! Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- These are FOUR separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms. - The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT an

🛏 4 beds · 👥 16 guests
$905 /night
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Islamorada cottage on deep water canal

Tavernier, Florida

Islamorada cottage on deep water canal

🛏 2 bed · 👥 6 guests

Located in Tavernier, Florida, United States. Islamorada cottage on deep water canal Our cottage is set in a quiet neighborhood on a deep, clear, wide canal. Situated bayside at mile marker 89, there is a 61 foot concrete dock and room for up to a 30' boat. backwater fishing is a short boat ride and there is easy ocean access through both Tavernier Creek and Snake Creek. A boat ramp is available at nearby Founders Park. There are 2 bedrooms each with ensuite bathrooms. The living room is large and airy with sliders opening to the back screened porch. The fenced private back garden has a lighted gazebo, water toys, bbq grill, bait freezer, swim ladder and platform.

$126

/ night

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Oceanfront, Dockage, Luxury, Paddleboards, Gaming - Paradise Palms Islamorada

Islamorada, Florida

Oceanfront, Dockage, Luxury, Paddleboards, Gaming - Paradise Palms Islamorada

🛏 3 bed · 👥 8 guests

Located in Islamorada, Florida, United States. Oceanfront, Dockage, Luxury, Paddleboards, Gaming - Paradise Palms Islamorada Welcome to Paradise Palms - Your Ultimate Oceanfront Getaway in Islamorada, Florida with Boat Dockage. YOUR VACATION STARTS NOW!Indulge in luxury at Paradise Palms, your new construction oceanfront gated home with waterfront dockage. With unmatched ocean views, this three-story retreat boasts a perfect fusion of modern design and tropical charm. Enjoy three spacious bedrooms and over 2000 square feet of air-conditioned spacious living areas along with two expansive oceanfront patios. Entertainment provided for all! This place offers an unforgettable high-end escape to the heart of the Florida Keys. Reserve today!Key property features include the following:• Panoramic Ocean Views: Bask in breathtaking sunrises and sunsets as the expansive windows frame panoramic ocean views. The inviting turquoise waters of the Atlantic are on display from the kitchen, living room, both patios and Primary Suites.• Spacious Liv

$551

/ night

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SAVE in Apr/May! True OceanFRONT - Wide Ocean Views-Huge Decks-Yaks/SUPs-Dock

Islamorada, Florida

SAVE in Apr/May! True OceanFRONT - Wide Ocean Views-Huge Decks-Yaks/SUPs-Dock

🛏 3 bed · 👥 8 guests

Located in Islamorada, Florida, United States. SAVE in Apr/May! True OceanFRONT - Wide Ocean Views-Huge Decks-Yaks/SUPs-Dock THERE ARE SOME HOMES WITH OCEAN PEEKS OR PARTIAL VIEWS THRU THE TREES, BUT FOR PANORAMIC UNOBSTRUCTED OCEAN VIEWS - FROM INSIDE AND OUT - THERE IS ONLY ANGLERS REEF 140! See our many REVIEWS, which tell it all! Our home is known as "Aqua Vistas" and for good reason: THE OCEAN VIEWS DON'T GET ANY BETTER THAN FROM THIS HOME - inside from every room and outside from the two covered wraparound decks that offer OVER 700 SQFT of outdoor living area! Although the Anglers Reef community is oceanfront, we are one of only 5 truly OceanFRONT HOMES in the community, and the only rental with unobstructed ocean views. See the community layout in the photo gallery for our QUIET corner location away from highway traffic noise, pool noise, and the late night music from Hog Heaven on the other side of the community.AND WE CAN PROVIDE A BOAT SLIP FOR YOUR STAY IF DESIRED.ANGLER'S REEF is a boutique gated community of 52 ho

$430

/ night

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Sunset Peninsula—a multi-family, original,  Florida Keys waterfront retreat!

Tavernier, Florida

Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat!

🛏 5 bed · 👥 12 guests

Located in Tavernier, Florida, United States. Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat! Welcome to the Sunset Peninsula! This gated, multi-family compound is perfect for those traveling in larger groups with family and/or friends who want to share great memories while maintaining their privacy. This unique and private tropical oasis welcomes all guests with lush vegetation uniquely indigenous to our fragile ecosystem. The paved driveway adds appeal and functionality, making parking for all an easy convenience. Beyond the gate, you will notice a private half ramp where small boats, jet skis, or kayaks could be launched. Often referred to as the "cruise-ship shaped" house, this solidly built, all concrete home, offers a 3 bedroom/2 bath main house (2/1 up, 1/1 master quarters down), and a separate, recently renovated 2/2 ground level/ranch style apartment. For chefs who wish to indulge their guests, the property is equipped with 2 full kitchens and a small galley. The roof top deck imparts a great

$343

/ night

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Penthouse view - Futura Yacht Club #604

Tavernier, Florida

Penthouse view - Futura Yacht Club #604

🛏 3 bed · 👥 5 guests

Located in Tavernier, Florida, United States. Penthouse view - Futura Yacht Club #604 Condo #604, 3 Bedrooms, 2.0 Baths, (Sleeps 6)Enjoy penthouse views of the fabulous blue waters of the Atlantic and Florida Bay-- all from the comfort of your own three bedroom, two bath condo. This condo can sleep 6 comfortably and features a kitchen with every convenience you might require. The master bedroom has a king size bed, bath with clothes hanging rack. The second bedroom has a queen size bed, closet and attached bath with shower. The converted third bedroom, off of kitchen, has a full bed.Heated swimming pool with Tiki Bar, lighted tennis courts as well as plenty of beautifully landscaped property for walking are all available within this safe gated complex. Relax seaside at the sandy beach and view the fabulous sunsets every evening from our penthouse balcony.For you boaters, Futura Yacht Club offers the best deep water dockage and on site boat ramp in the area. Rental does not include boat slip. However, pending availability, other sl

$114

/ night

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Relax in this beautiful townhome overlooking the sparkling Atlantic Ocean

Islamorada, Florida

Relax in this beautiful townhome overlooking the sparkling Atlantic Ocean

🛏 3 bed · 👥 6 guests

Located in Islamorada, Florida, United States. Relax in this beautiful townhome overlooking the sparkling Atlantic Ocean Windy Cove #1 - Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features three bedrooms and two bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak up the sun on the beach under a palm tree, or wake up early to catch a sunrise from your own balcony overlooking the water. If booking more than a year in advance current prices may not reflect annual cost of living increase. Many of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. Vacation Rental License# 24-0384 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.Please note: before proceeding with your booking, kindly review the following infor

$266

/ night

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Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!

Islamorada, Florida

Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!

🛏 1 bed · 👥 4 guests

Located in Islamorada, Florida, United States. Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool! Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon arrival.- Following property rules, the minimum age required for check-in is 21 years old;We're

$220

/ night

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Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Islamorada, Florida

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

🛏 3 bed · 👥 8 guests

Located in Islamorada, Florida, United States. Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal Vacation Rental License No VR-001 WEEKLY RENTALLocated on the peaceful upper Keys, in Islamorada, this home is situated in the quiet residential neighborhood of Venetian Shores MM 86. Immediate access to ocean and Bay side off of Snake Creek. Islamorada is is just 75 miles from Miami and 86 miles from Key West. The average temperature is 80 degrees and 78 degrees for the water. Islamorada sits between the clear waters of the Florida Bay and the Gulf of Mexico, it is bestowed with a Coral Reef three to five miles offshore that is filled with spectacular life. Two story homeThis 3 bedroom, 3 bath, private home is equipped with many extras including this heated (at 80-82 degrees) swimming pool that is partially shaded so you can enjoy floating with a cool drink leisurely. WIFI ready. This vacation gem boasts large rooms furnished in rattan and decorated with a tropical flair. You can see this view from the livi

$470

/ night

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Ocean View Condo is a Fisherman's Paradise in Islamorada

Islamorada, Florida

Ocean View Condo is a Fisherman's Paradise in Islamorada

🛏 2 bed · 👥 6 guests

Located in Islamorada, Florida, United States. Ocean View Condo is a Fisherman's Paradise in Islamorada This spacious two bedroom, two bath condominium overlooking the ocean is located on a quiet 12 acre private gated community. Includes a 30 foot boat slip in a protected marina with direct access to the ocean. Eat in kitchen with breakfast bar open to living area that looks out over the water. Expansive patio for open air dining or lounging. Main bedroom has an ocean view, opens to screened patio, a king sized bed, private bath with soaking tub and walk in shower. The split floor plan design provides a private additional bedroom with a spacious bathroom. Ideal for remote workers, retirees wishing to spend winter in a warm, sunny locale or families looking for an adventurous escape. Large heated community pool and hot tub. Lighted tennis courts. Onsite boat ramp. Club house features a large community room and full gym. Outdoor covered dining area with picnic tables, a gas grill, and ice machine.

$179

/ night

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Florida Keys Tour! Private Beach Access with Marina! Pets Allowed, FREE Parking

Islamorada, Florida

Florida Keys Tour! Private Beach Access with Marina! Pets Allowed, FREE Parking

🛏 1 bed · 👥 4 guests

Located in Islamorada, Florida, United States. Florida Keys Tour! Private Beach Access with Marina! Pets Allowed, FREE Parking Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon arrival.- Following property rules, the minimum age required for check-in is 21 years old;We're

$216

/ night

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Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!

Islamorada, Florida

Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!

🛏 1 bed · 👥 4 guests

Located in Islamorada, Florida, United States. Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals! Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon arrival.- Following property rules, the minimum age required for check-in is 21 years old;We're de

$187

/ night

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Deep Blue Vacation Oceanfront Estate, Millionaire's Row, Private Saltwater Pool

Islamorada, Florida

Deep Blue Vacation Oceanfront Estate, Millionaire's Row, Private Saltwater Pool

🛏 5 bed · 👥 12 guests

Located in Islamorada, Florida, United States. Deep Blue Vacation Oceanfront Estate, Millionaire's Row, Private Saltwater Pool Deep Blue Vacation Rental - Beautiful Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, Winding Staircase, Expansive Ocean Views, Over 4000 Sq. Ft. of Living Space. Saltwater Pool, Sandy Back Yard, Gated Entrance Lined With Palm Trees. House has its own private observation pier that extends 200 feet into the ocean providing easy ocean access for fishing, swimming and snorkeling. Enjoy the Ocean Views and Breeze. Once upstairs, everyone will enjoy breeze off the ocean while you barbecue, look out over the palm trees and expansive ocean view. Home has 5 bedrooms, include two twins, four kings, and a convertible that sleeps two children. Large kitchen to accommodate all the family and entertaining.Located in the heart of Islamorada, near world class fishing, boating, snorkeling, and sun bathing7 Night Min. / Saturday to Saturday Only # 120

$815

/ night

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Great Townhome with Basin & Bay Views

Islamorada, Florida

Great Townhome with Basin & Bay Views

🛏 2 bed · 👥 4 guests

Located in Islamorada, Florida, United States. Great Townhome with Basin & Bay Views Futura Townhome #731 - Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a two bedroom two and a half bath unit. There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the property. Make yourself at home in our home away from home. Boat dockage available please inquire within. The Futura Yacht Club HOA charges- onsite-$150 per trailer and $50 per boat fee. These fees will not show up on your rental agreement, as the fees are collected upon check in at Futura Yacht Club. VACATION RENTAL LICENSE: VR 24-0413 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.If booking more than a year in advance current prices may not reflect the annual cost of living increase. Many of our guests' re-book the same property on

$225

/ night

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Paradise in Plantation Key/Deep Water Canal House/Boat Dock/MM 89

Plantation Key, Florida

Paradise in Plantation Key/Deep Water Canal House/Boat Dock/MM 89

🛏 2 bed · 👥 4 guests

Located in Plantation Key, Florida, United States. Paradise in Plantation Key/Deep Water Canal House/Boat Dock/MM 89 Paradise in Plantation Key. If you are looking to relax and learn about “Keys Time” you are looking in the right area! Sometimes I come down and relax on the water and others I am paddleboarding, kayaking, fishing, scuba diving etc. It is the epitome of true mental relief. My home is conveniently located at Mile Marker 89. It is the upstairs unit only. The downstairs is not available for rental. The units are separate with there own private entrances. If you are planning to bring your boat great! They are welcome, I have plenty of parking at the residence. This is a 28 day rental. This is a pet free rental - we do not allow pets on the property. There is room for your boat and recreational watercraft with 45 feet of dock space available in this deep water canal however, you will need to load it at a local ramp. The closest ramp and pool is at Founders Park (MM 87). Founders Park offers activity or relaxa

$132

/ night

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Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage

Islamorada, Florida

Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage

🛏 2 bed · 👥 6 guests

Located in Islamorada, Florida, United States. Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards and more. The main living area is located on the upper level of this oceanfront cottage and has open ocean views throughout. The open concept kitchen, living and dining room are great for entertaining. The main level has two bedrooms and two baths. The lower level is a separate living area with 2 sets of bunk beds, a living room, kitchenette and bathroom. It can be added when renting the upstairs for an additional $600 weekly. The Leatherback Cottage can be rented separately or in combination with any of the four other homes.VACATION RENTAL LICENSE: 24-0386If booking more than a year in advance current prices may not reflect th

$478

/ night

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Vacation At its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool

Islamorada, Florida

Vacation At its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool

🛏 2 bed · 👥 8 guests

Located in Islamorada, Florida, United States. Vacation At its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- These are TWO separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms. - The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and

$387

/ night

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TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED

Islamorada, Florida

TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED

🛏 3 bed · 👥 8 guests

Located in Islamorada, Florida, United States. TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED New In Ground Heated pool , Just remodeled with new furniture, flat screen tvs throughout ( including the patio) and a dock with direct ocean view / access. Minutes away from some of the best fishing, diving or sightseeing in the Florida Keys. Walk or boat to Tavernier Marina ( 3 Dive shops, Boat Rental, Charter fishing and sightseeing boats, Jet Ski Rentals, Bait and Tackle Store, Fuel, parts and service on sight). Grill, Smoker, and less than a mile away from Tavernier Towne which has Winn Dixie, Movies, Restaurants, Post Office and liquor store. Please confirm reservation with owner within 72 hours of booking.

$267

/ night

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Reel Paradise at Sea Gulls

Tavernier, Florida

Reel Paradise at Sea Gulls

🛏 2 bed · 👥 4 guests

Located in Tavernier, Florida, United States. Reel Paradise at Sea Gulls Summary:Stunning ocean views and beautiful island sunrises!The Space:Welcome to Reel Paradise! This beautiful condo is located in the Sea Gulls community of Tavernier. The post card views will have you coming back year after year. Wake up and enjoy the beautiful sunrise from your private balcony. Take the kayaks out and paddle out to the nearby islands and take in everything the keys has to offer. Come back from a day on the water and relax by the pool or on the beach. You will also have access to the community gym. This unit has two bedrooms and two bathrooms. Kitchen is equipped with all essentials for cooking at home. There are televisions in both bedrooms as well as the living room. Both bedrooms have patio access with views of the ocean. There is also a view of the nearby High School football field, to catch some Friday night football during the season. The location in Tavernier puts this community close to both Islamorada, Key Largo, the best restaurant

$118

/ night

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3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed!

Islamorada, Florida

3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed!

🛏 3 bed · 👥 12 guests

Located in Islamorada, Florida, United States. 3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed! Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- These are THREE separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms. - The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is

$676

/ night

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Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast

Islamorada, Florida

Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast

🛏 1 bed · 👥 4 guests

Located in Islamorada, Florida, United States. Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon arrival.- Following property rules, the minimum age required for check-in is 21 years old;We're de

$264

/ night

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Oceanfront Estate with 4 Cozy Cottages

Islamorada, Florida

Oceanfront Estate with 4 Cozy Cottages

🛏 7 bed · 👥 16 guests

Located in Islamorada, Florida, United States. Oceanfront Estate with 4 Cozy Cottages Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave of four charming cottages nestled in beautiful landscaping with a total of seven bedrooms and seven bathrooms. When entering through the gate you will feel a sense a tranquility that makes you realize your vacation has started. Each cottage has it's own personality with an array of unique, yet tasteful decor. The property offers a boat basin, tiki hut, oceanfront pool, outdoor showers, paddle boards, kayaks and bikes. All of this combined to make the perfect family retreat. Your own little oasis you'll never have to leave. VR#24-0385, 24-0386, 24-0416, 24-0134If booking more than a year in advance current prices may not reflect annual cost of living increase. Many of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. Please note: before proceeding with your booking, kindl

$1,528

/ night

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Comfort & Convenience, 3 Classy Units, Free Breakfast, Free Parking, Pool

Islamorada, Florida

Comfort & Convenience, 3 Classy Units, Free Breakfast, Free Parking, Pool

🛏 3 bed · 👥 12 guests

Located in Islamorada, Florida, United States. Comfort & Convenience, 3 Classy Units, Free Breakfast, Free Parking, Pool Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- These are THREE separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms. - The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is r

$602

/ night

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Get ready to dive into your Islamorada Retreat

Tavernier, Florida

Get ready to dive into your Islamorada Retreat

🛏 3 bed · 👥 6 guests

Located in Tavernier, Florida, United States. Get ready to dive into your Islamorada Retreat 134 Tequesta Street - Get ready to dive into your Islamorada Winter Retreat! Move in ready today!This beautiful three-bedroom three bath pool home is located at mile marker 89 on a deep-water canal. Bring your boat (20' or less only please) and fish Islamorada in the winter while your family and friends dig their way out of the snow. When you walk through the front door you will find yourself in a beautifully renovated home and in your family TV room. (Located on the ground level). The first floor includes two bedrooms, with a shared bath, chef’s kitchen, large dining room, and another full bath off the pool/porch/outdoor entertaining area.Upstairs is the master bedroom suite. It's beautifully decorated and includes a large bedroom, bathroom, and private porch with a hot tub! The outside is where you will spend most of your days and nights. Large couches surround the pool. There's an awesome tiki with a summer kitchen including a BBQ grill

$274

/ night

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Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!

Islamorada, Florida

Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!

🛏 4 bed · 👥 16 guests

Located in Islamorada, Florida, United States. Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed! Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- These are FOUR separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms. - The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT an

$905

/ night

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Islamorada cottage on deep water canal

Tavernier, Florida

$126/night

Oceanfront, Dockage, Luxury, Paddleboards, Gaming - Paradise Palms Islamorada

Islamorada, Florida

$551/night

SAVE in Apr/May! True OceanFRONT - Wide Ocean Views-Huge Decks-Yaks/SUPs-Dock

Islamorada, Florida

$430/night

Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat!

Tavernier, Florida

$343/night

Penthouse view - Futura Yacht Club #604

Tavernier, Florida

$114/night

Relax in this beautiful townhome overlooking the sparkling Atlantic Ocean

Islamorada, Florida

$266/night

Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!

Islamorada, Florida

$220/night

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Islamorada, Florida

$470/night

Ocean View Condo is a Fisherman's Paradise in Islamorada

Islamorada, Florida

$179/night

Florida Keys Tour! Private Beach Access with Marina! Pets Allowed, FREE Parking

Islamorada, Florida

$216/night

Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!

Islamorada, Florida

$187/night

Deep Blue Vacation Oceanfront Estate, Millionaire's Row, Private Saltwater Pool

Islamorada, Florida

$815/night

Great Townhome with Basin & Bay Views

Islamorada, Florida

$225/night

Paradise in Plantation Key/Deep Water Canal House/Boat Dock/MM 89

Plantation Key, Florida

$132/night

Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage

Islamorada, Florida

$478/night

Vacation At its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool

Islamorada, Florida

$387/night

TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED

Islamorada, Florida

$267/night

Reel Paradise at Sea Gulls

Tavernier, Florida

$118/night

3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed!

Islamorada, Florida

$676/night

Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast

Islamorada, Florida

$264/night

Oceanfront Estate with 4 Cozy Cottages

Islamorada, Florida

$1,528/night

Comfort & Convenience, 3 Classy Units, Free Breakfast, Free Parking, Pool

Islamorada, Florida

$602/night

Get ready to dive into your Islamorada Retreat

Tavernier, Florida

$274/night

Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!

Islamorada, Florida

$905/night