58,368 properties available

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

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

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

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

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

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.

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

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

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

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

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

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

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

Located in Islamorada, Florida, United States. Venetian 4/4 Waterfront Canal Home W/Pool, 70' Dock w/access to ocean and bay This beautiful deep saltwater canal front 3 bedroom 3 bathroom pool home with an additional one bedroom one bath "in-laws" quarters is located inside of one of the finest neighborhoods in all of the Florida Keys - Venetian Shores. Inside, the home is fully equipped for entertaining, cooking, or just kicking back and relaxing. Outside the home offers a 70' concrete dock for your boat, a beautiful freshwater heated swimming pool, davits, fish cleaning table, 2 outdoor showers, gas grill, hammock, covered parking, and a 3rd floor deck for your enjoyment. The canal is clean and clear and great for swimming as well as providing easy access by boat to both the Florida Bay and the Atlantic Ocean via Snake Creek Channel. The floor plan is spread out over 3 floors and will sleep up to 11 people comfortably. The top 2 floors offer 3 bedrooms and 3 bathrooms (sleeps 9) and are connected via interior staircase. The bot

Located in Islamorada, Florida, United States. Wonderful 2 Bedroom Condo with Ocean Views Seagull's #406 - OFF-SEASON SPECIAL~ $2,500/month (plus taxes and fees) if you stay with us from now until November 15 This newly renovated and remodeled two-bedroom condo is only about an hour and fifteen-minute drive from Miami International Airport and about 90 minutes from Ft. Lauderdale in the Village of Islamorada, the 'Fishing Capital of the World.' This unit is comfortably and stylishly furnished, it has (2) queen beds and a sleeper sofa and offers sea breezes and ocean views. Seagulls Condo offers a beautiful, heated pool overlooking the ocean, tennis court and charcoal grills. This unit is centrally and conveniently located near restaurants, shopping, fishing, diving, grocery store, liquor store, dollar store, movie theater, sports bar, Post Office and more. ** This complex has shared coined laundry on each floor. If booking more than a year in advance current prices may not reflect annual cost of living increase. Many of our guests

Located in Islamorada, Florida, United States. Oceanside Oasis in Private Gated Marina Community Ocean Harbour (a gated community) contemporary 2 bedroom 2 bath condo with breathtaking views of the Atlantic Ocean and Marina . This spacious well-appointed recently renovated condo features an impact glass slider Lanai, direct access to the pool, resort amenities, and a convenient assigned parking.

Located in Islamorada, Florida, United States. Executive Bay Club Condo (2 bds + loft & 3 full baths) Come stay and watch the sunsets at our beautifully updated Keys townhouse at Executive Bay Club located in Islamorada on the bay. It has 2 bedroom with a loft, 3 full bathrooms and washer/dryer in the unit. It is a private, gated community with a clubhouse, heated swimming pool, a private beach area, a fishing dock and 2 tennis courts. Founders Park right next door to the complex (100 yards from entrance) with marina slips rental available. You'll be one of the first to stay at our recently updated town home with new floors, TVs (Amazon Fire), bedroom & patio furniture, Weber grill, fresh paint, light fixtures and decorations.

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

Located in Islamorada, Florida, United States. Best Place to Stay in Florida! 3 Pet-Friendly Units, Free Breakfast, 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.- 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 i

Located in Rotonda West, Florida, United States. Rotunda West Canal View House 7 miles from Gulf Beaches Rotunda West Private Vacation Home - 7 Miles To Gulf BeachesOur 3-bedroom, 2 Bathroom private vacation home offers a fantastic property perfect for your relaxing South Florida Gulf Coast Vacation * Rotunda West Vacation Home * 3 Bedrooms / 2 Bathrooms + Florida Room* Canal View* 7 miles to Englewood Beach* Fully Equipped Kitchen* Dining for up to 6 at the dining table* Parking for two cars in the drivewayBEDROOMS (Single-story home)- Bedroom 1: Master King Bedroom (Private attached Bathroom)- Bedroom 2: One Queen Bedroom - Bedroom 3: One Queen BedroomGarage:No parking in the garage. Owner's vehicles are parked in the garage.BBQ:- There is a BBQ at this property for complimentary guest use. - While there is a propane tank included with the BBQ, we do not provide refills. - Guests are welcome to swap the tank at any local store. - BBQ must be cleaned upon guest departure or an additional $56 fee will be charged. No Pets AllowedRotun

Located in Rotonda West, Florida, United States. The Mumbles, full refund*, heated pool, sleeps 6 Enjoy "The Mumbles" a private villa located in Rotonda West on Florida's Gulf Coast, renowned for its numerous championship golf courses and beautiful soft, white, sandy beaches. A perfect location to satisfy everyone's ideal vacation requirements. We are proud to offer some of the finest and cleanest vacation villas in the area as well as a top of the line service for guests. This 3 bedroom, 2 bathroom light filled open floor split plan home ensures you'll always have privacy! It boasts a West-facing screened lanai with heated pool and spa. The master bedroom is furnished with a Queen-size bed, closet, 32" HD TV and offers private access to the lanai and pool area through sliding glass doors. The en-suite has a double vanity, hairdryer, toilet and a bath tub and seperate shower. The 2nd bedroom has 1 Queen-size bed and 32” HD TV The 3rd bedroom has 2 Twin-size beds and 26" HD TV The large living area has 1 sofa, 1 love seat and 1 cha

Located in Rotonda West, Florida, United States. NEW! Golf Course frontage with HEATED pool, 20min to BEACH! Welcome to paradise! From the moment you walk in the door, you will be able to see what Florida living is all about! The panoramic view of the Rotonda West Palms Golf Course is outside the back sliding doors. With close to 1800 square footage of living space inside the house, you’ll have plenty of room to enjoy and entertain guest if needed. There are 3 bedrooms and 3 bathrooms, and two of the bedrooms have master en-suites! This would be perfect for two couples to enjoy a vacation together, but still have their own privacy. The guest bedroom has two twin beds. Tile is throughout the house, except in one guest bedroom with the twin beds. The kitchen has been updated with granite countertops and white wood cabinetry. The kitchen is fully equipped. There is a breakfast bar top with stools for anyone to enjoy your morning breakfast. Just off the kitchen is a breakfast nook/dining area with enough seating for 6 people with

Located in Rotonda West, Florida, United States. Tranquil Brand New Central Location Lake Front Summary:Experience the contemporary design and modern comfort of this brand-new 3BR 2Bath house, just a few mins from sun-soaked Gulf Coast beaches, tasty restaurants, exciting shops, parks, attractions, and landmarks. To top it all off is the tranquil backyard with the dreamy lake creating a peaceful relaxation haven. ✔ 3 Comfortable BRs✔ Open Design Living✔ Fully Equipped Kitchen ✔ Screened-In Patio✔ Backyard with a Pond✔ High-Speed Wi-Fi✔ Smart TVs✔ Workspace✔ Free ParkingSee more below!The Space:We take great pride in welcoming you to the brand-new home, where abundant natural light enhances the contemporary design. It boasts a spacious interior and a dreamy screened-in patio overlooking the backyard and the charming Lake.The entire home is furnished with state-of-the-art amenities and tasteful decoration. Elegant furniture and details dominate the space and are highlighted by rays of healthy sunlight during the day and cozy lighting

Located in Rotonda West, Florida, United States. Turtle Bay, full refund*, pool heat, dogs ok, pool Enjoy “Turtle Bay” a private villa located in Rotonda West on Florida's Gulf Coast, renowned for its numerous championship golf courses and beautiful soft, white, sandy beaches. A perfect location to satisfy everyone's ideal vacation requirements. We are proud to offer some of the finest and cleanest vacation villas in the area as well as a top of the line service for guests, This 3 bedroom, 2.5 bathroom that sleeps 8 is a light filled open floor split plan home ensures you'll always have privacy! It boasts a Northwest-facing screened lanai with heated pool, games room with pool table and darts. The master bedroom is furnished with a King-size bed, closet, 55” smart HD TV and offers private access to the lanai and pool area through sliding glass doors. The en-suite has a double vanity, hairdryer, toilet and a soaking tub and separate Roman shower. The 2nd bedroom has 1 Queen-size bed and 42” smart HD TV The 3rd bedroom has 2 Full-si