72,107 properties available

Located in Islamorada, Florida, United States. SPECTACULAR SUNSETS AND FRESH OCEAN BREEZE AWAIT YOU IN ISLAMORADA, FLORIDA! Just under 1.5 hours from Miami International Airport, you will find the beautiful gated community of Executive Bay Club. This townhouse has 3 bedrooms, 2 full baths, and a private patio with bbq. The unit has been beautifully renovated, decorated, and has all the comforts for a relaxing vacation. Amenities include a private beach, dock, pool, clubhouse, tennis courts, as well as 24 hour security. It is surrounded by amazing restaurants, shops, and spas. This vacation oasis is right next door to Founder's Park /Yacht Harbor and Marina. Whether you want a relaxing getaway or a vacation full of outdoor adventure, Islamorada Florida has the best of both worlds. Come stay with us and see for yourself!

Located in Islamorada, Florida, United States. Latitude Adjustment FLKeys Latitude Adjustment, Islamorada, FloridaThis home is our families' paradise in the Florida Keys and we want to share it with you. When our family is not using it, it is ready for you to make your own memories. This home offers much more than your average resort stay -- and is a perfect home base for all of your water activities:snorkeling, boating, and fishing.

Located in Islamorada, Florida, United States. Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker Located in prestigious Venetian Shores Islamorada's premier waterfront community! This home was completely remodeled.... everything is tasteful, high quality, spotless and NEW!! HI SPEED WIFI and NetFlix is INCLUDED! Luxury heated pool / spa! Surrounded by a spectacular Dominican coral paver deck that does not get hot and has superior non skid properties! 20K Insane resort quality landscape lighting package installed in 2021. The home sits on a huge 70 x 100 foot lot (almost a 1/4 acre) on a crystal clear deep water canal just off world famous Snake Creek which takes you to the Atlantic and beautiful Florida Bay in just minutes. A one of a kind professionally designed lush tropical keys landscape creates an ambiance that you will enjoy and never leave as it gives you the feeling of having your own private resort all to yourself. Custom made and extremely comfortable Adirondack chairs and chaise lounges,

Located in Tavernier, Florida, United States. Islamorada Keys Waterfront .Pool Luxury Home Waterfront Islamorada 4 bedroom 3 bathroom home on the absolute best Waterfront Deep Water Canal w direct ocean access. Bring your boat or rent one locally and spend your keys vacation in paradise. Spacious Dock area .This home has a Pool, pool table, King size beds, Wifi, Gated yard, Flat-screen Tvs, BBQ, screened porch , washer and dryer. Located near the best restaurants and shops. Free access to Founders park and beach , Plenty of parking.Note:5% monroe County tax will be collected seperatelyBus Tax ID #138028Tourism Tax Acct Active(Boat Lift Use available at extra fee)Small pet considered. please inquire with details.

Located in Tavernier, Florida, United States. Canal home in Islamorada. Views from 2nd fl pool, partial 65' of dock. Location, location, location! A tropical palmy dream and playground for ocean lovers.Minutes on boat from the best sand bars, fishing and diving spots in Islamorada. The property is a beautiful and charming water front house, which has been newly renovated with a light, open and airy tropical Florida Keys feel. The newly landscaped and tropical back yard that precedes its 65' of dock (partial for docking) will immediately transport you to your own personal Margaritaville. Situated by the entrance on a wide canal right off Tavernier Creek, this home’s location offers you very easy and quick access to the ocean and bay. The property is homey, but also unique. It’s structure is made up completely out of concrete and its linear architecture design delightfully compliments an outdoor pool on the 2nd floor, offering you great water views from the pool deck, interior of the home, and inside the pool.Upstairs has two bedro

Located in Islamorada, Florida, United States. Keys Paradise with Private Beach and Pool NOTE:--PLEASE SEND AN INQUIRY TO BE SURE YOUR DATES ARE AVAILABLE. --DOCKAGE AVAILABLE AT FOUNDERS PARK MARINA RIGHT NEXT DOOR FOR A FEE. NO DOCKAGE AND NO TRAILERS ALLOWED ON PROPERTY. (Condo rules, not ours!!)Luxury resort amenities with all the comforts of home! Gorgeous, spacious condo with modern updates just steps from the crystalline waters of the Florida Bay. Updated kitchen appliances, granite counter tops and fully equipped with all the extras you might imagine make the kitchen a gourmet cook's delight. Breakfast bar and large wooden table accommodate up to 10 comfortably in the adjoined dining area. The open floor plan makes it a great space to sit with your family and friends while others are preparing food in the kitchen in one of three couches and three comfy chairs. You'll find one full bath downstairs and another upstairs, both completely remodeled this year with tile and luxury finish.Enjoy sitting under the stars or making yo

Located in Tavernier, Florida, United States. Oceanfront home ON Tavernier Creek This home is a fisherman's dream come true. New dock right on Tavernier Creek. You will be in open ocean in minutes!! Sandy beach and tiki hut. Main house is a 2/2 and the guest cottage is a 1/1 with a separate entrance. Perfect for family and friends get togethers. Walking distance to shops and restaurants. BONUS with your rental agreement you have free access to Founder's Park at mile marker 87, where you can enjoy the beach and snorkeling, etc. They often have free concerts and other free events too. The park has trails for running, walking and biking and a marina plus much more!**There is an extra fee of $1000/month to use the boat lift.***Pet fee of $350 is for 1 or 2 dogs weighing 50lbs or less combined. If you have more than 2 dogs or big dogs, there is an extra fee depending on quantity, size and breed.

Located in Islamorada, Florida, United States. Islamorada 3/2 condo. Dockage, swimming pool, sunsets Your own tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada. Futura Yacht Club is a 70 unit community with a 53 slip marina and accommodations available for that tranquil tropical getaway you've always imagined. Futura Yacht Club is a gated community. This is a 4th floor condo with 3 bedrooms, 2 baths and a fantastic view of the Florida Bay. This condo is one of our nicest units with beautiful decor, a full kitchen with granite counter tops, barstool seating, living room, dining table for 6, and a balcony overlooking with stunning water views. Elevator building and community laundry located on each floor. Protected dockage is available for boats up to 36 feet with easy ocean access through Snake Creek or Tavernier Creek. Dockage is $200 week / $250 during holiday weeks

Located in Tavernier, Florida, United States. Canal Front Beautifully Renovated Home w/ Great Deck, Private Boat Ramp + WI-FI This comfortable house, located in the quiet neighborhood of Plantation Key Colony, Offers three inviting bedrooms and 2 full baths. The Master suite has a queen bed, full bath and a view. Downstairs guestroom has 2 full beds & bathroom across the hall. Upstairs guest room has one queen size bed and a toddler day bed with seating area and 55" Samsung Smart TV. The newly renovated kitchen opens up to the dinning & living room with a large fully reclining sofa and huge 70" LG Smart TV. High speed WI-FI Internet is also available to all guests.The oversized living terrace has two sitting areas overlooking the canal with comfortable sofas and chairs perfect for a family gathering or a nice afternoon nap. Outside the sliding doors you have a cover open porch with a large dinning table, two fans to cool off and a Charcoal BBQ. The tropical landscape patio has lounge chairs, tables and a fire place. A 50' foot do

Located in Islamorada, Florida, United States. Anglers Reef- Family Friendly Community at a Fraction of the Cost. This Property is fully insured for rentals and licensed by the Village of Islamorada, license #24-0318.Welcome to 134 Anglers, a luxurious escape for your vacation needs. Perfect for families, couples, or a friends getaway. Located in Anglers Reef, a gated community with heated swimming pool and two private beaches. Our availability calendar is always up to date and current.Our beautiful house has 2 Bedrooms, 2.5 Bathrooms, A/C, Quartz counter tops, modern stainless steel appliances, SMART Tv's. Open porches and balconies, rich hard wood floors, dining room seating for 6, coastal décor. A truly unique place to stay in the keys, with a boutique – style feel.Anglers Reef is one of the Florida Keys most luxurious developments with 52 villas and 30 boat slips. Set in meticulously landscaped gardens, overlooking a private heated 75 ft. swimming pool, private beach and the magnificent Atlantic Ocean. Anglers Reef is the pe

Located in Islamorada, Florida, United States. Islamorada Bayfront Townhouse in Executive Bay Club Bayfront beautiful double townhouse with stunning bay views. Watch the sunsets from your balcony or from the beach right outside. This one a kind unit offers 4 bedrooms, 3 bathrooms and over 2800 square feet of living and entertaining space. Located inside of Executive Bay Club. Amenities include a sandy beach, large swimming pool, clubhouse, tennis/basketball/ pickleball courts, gated entrance with 24 hour security and much more! Located right next door to the Florida Key's largest and nicest park, Founder's Park. Also within Founder’s Park is the Yacht Harbor and Marina.

Located in Islamorada, Florida, United States. 132 Anglers Reef Islamorada- POOL, DOCK, BIKES INCL VR License #24-4011132 Anglers Way is an Adorable Key West style home in Anglers Reef. Small gated community located at MM 85 in Islamorada. Beautiful oceanfront pool, two beaches and a very convenient marina just stops from your front porch. Call me for more information 305-240-0592. Two bedrooms and two and a half baths with all the comforts of home. The master bedroom is a king size bed and the guest bedroom has two twin size beds with twin trundles underneath. There is a very nice living room with a sleeper sofa and dining room set up downstairs and all the things you would need to create a gourmet meal in the kitchen.Dock included in pricing. 31'max length and 9' bridge height.Please note, as of Aug 1, 2024. you will no longer be able to store a trailer outside the gate on the grass any longer. Trailers fitting under the carport are able to be stored there. Otherwise, we can recommend local storage lots you can contact.

Located in Islamorada, Florida, United States. Venetian Shores Home -DOCK remodeled 3/3 POOL/Hot Tub! Deep water Dockage 126 Palermo DriveCheck out this new to the Vacation Rental Market home in Venetian Shores on canal with 70' dock, pool, tiki hut and hot tub.Call Jennifer for more information 305-240-0592.Completely remodeled in 2021, this concrete home has very spacious bedrooms (each with a KING bed), beautifully appointed with all new furniture, new gourmet kitchens and new bathrooms.70’ of Deep Water dockage included in rate. Bring your big boat(s)! Large, deep canals with Drawbridge out to ocean via Snake Creek! Parking for one trailer on lot.Two Bedrooms and Two full Bathrooms upstairs with large kitchen and open living floor plan. There is also a full sized washer and dryer and large closets. Wonderful screened porch for your morning coffee where you will be sure to see some great wildlife (tarpon rolling, birds and an occasional dolphin or turtle)!Downstairs (separate) you will find a Large ONE King Bedroom and Full

Located in Islamorada, Florida, United States. Better Choice for your Vacation! 2 Pet-Friendly Units, Free Breakfast, 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 is r

Located in Islamorada, Florida, United States. Prime Location! Beachfront Property with Outdoor Pool, Pets are Welcome! Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residentia

Located in Islamorada, Florida, United States. Brand New Unique Deep Water Gulf Front Estate. Beach, Pool, Hot tub and docks This is a brand new house. Just completed August 2014 This unique Gulf Front property is located among Gumbo Limbo, Mahogany, Royal Ponciana and palm trees sprinkled with other tropical foliage set directly on the Florida Bay/Gulf of Mexico. Hammocks and swings hang from the trees offering places to take frequent naps. The fabulous beach area and 60 ft. dock is an outdoor paradise. The dock is a boaters dream. It is fully protected from weather with deep water access. The property location is within direct view of Everglades National Park where back country fishing is world famous. Or possibly you would want to go deep sea fishing or scuba diving in the Atlantic Ocean just 15 minutes away through Snake Creek or Tavenier Creek. This estate is a three level home right on the water. The complete back of the house is windows allowing beautiful vistas and sunsets 24 /7. Appointed beautifully. High end

Located in Islamorada, Florida, United States. Fabulous " Sea Breeze 41 ", 3 / 2 Condo located Oceanside in Islamorada Experience high-end coastal luxury while staying at “Sea Breeze 41” in the highly sought-after Coral Harbour Club Condominium (CHC) . Your spacious 3 Bedroom / 2 Bathroom island getaway exudes luxury tropical vibes and is professionally decorated in Tropical Modern style. A 33' Boat Slip for your next fishing or sandbar adventure. Call 786-763-3121 for additional info. ---------------------------------------------------- “Sea Breeze 41” features an open floor plan in the main living, dining and kitchen areas creating a warm and inviting setting. The custom gourmet kitchen offers stainless steel appliances, Corian countertop and an abundance of cabinets for all your cooking needs. The dining table is situated in the center of the room for easy entertaining. Additionally, the full motion 65” Smart TV unit allows you to enjoy it from almost any angle in the main area. For wine enthusiast

Located in Tavernier, Florida, United States. Private 150 Ft Oceanfront 2.5 Acre Estate with Saltwater Pool, Spa, Dock Completely renovated and expanded to over 3,700 square feet. San Roc is a private ocean front home with spectacular views of the Atlantic Ocean. Beautiful 5 Bedroom 5 Bath Home that accommodates 10 guests . It is situated on over 2.5 acre secluded wooded grounds in a premier area of Islamorada, Florida known as "Millionaires Row"Enjoy spectacular sunrises, on a private sandy beach with ocean breeze and a private heated saltwater pool with hot tub. Dock for boat and fishing.The main upper level offers 4 bedrooms and 4 full baths.Ground level offers one bedroom with king size bed, with ocean views, separate access from upstairs. The ground level does not have direct access to the upper floor. The chef's kitchen, great room overlooks the beach, pool, palm trees and open ocean waters with breathtaking scenery. 7 Night Min. / Saturday to Saturday Only# 24-2128

Located in Islamorada, Florida, United States. Canal-Front Oasis in the Florida Keys Escape to paradise in this stunning 3-bedroom, 2-bathroom vacation home in the heart of the Florida Keys. Situated on a picturesque canal with its boat lift, this updated retreat offers the perfect blend of relaxation and adventure.Key Features:• Prime Location: Nestled in the beautiful Florida Keys, this vacation rental is just minutes away from world-class fishing, snorkeling, and waterfront dining.• Waterfront Living: Enjoy direct access to the canal, perfect for boating, fishing, and soaking in the breathtaking sunset views.• Boat Lift: Bring your boat and take advantage of the convenient boat lift, ensuring hassle-free access to the sparkling waters of the Keys.• Spacious Interiors: Step inside to discover a modern, open floor plan adorned with stylish furnishings and ample space for your entire group to unwind.• Gourmet Kitchen: Prepare delicious meals in the fully-equipped kitchen featuring stainless steel appliances, granite countertops, wi

Located in Islamorada, Florida, United States. Venetian Shores Pool Home Desirable Venetian Shores neighborhood. Newly renovated home with open concept kitchen, dining and living room. Convenient access either bay or ocean with protected dockage. This canal front home has 2 king en-suites upstairs and a relaxing screen porch off of the living room. There is a downstairs apartment with 2 bedrooms and 1 bathroom and small kitchen area. The pool is situated canal side and perfect after a long day of boating. Enjoy grilling your catch in your outdoor canal side kitchen. There is a 28 day minimum requirement on this home…please do not request or ask for altered time as it will not be accepted.

Located in Islamorada, Florida, United States. Sportfishing in Florida Keys! Elegant Villa w/ Beach Access and Pool! 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

Located in Tavernier, Florida, United States. Bayside Waterfront Home with 40 ft Dock 28-day minimum rentalWelcome to our paradise vacation home, away from home. This Florida Keys house has 3 bedrooms, 2.5 bathrooms, and sleeps up to 10. Includes a 40’ boat dock space (no extra charge), fish cleaning station, an ice machine and has all the comforts of home. It is conveniently located bayside, in Plantation Key Colony, between Key Largo and Islamorada, just outside of Tavernier Creek for easy ocean access. Enjoy fishing, snorkeling, sandbars and water front dining nearby.Comfort and convenience makes this an ideal rental, with plenty of parking for cars and your boat trailer in the front yard. Enter on the first floor to the downstairs living room, with a recliner sofa, large smart TV (55 inch), twin size daybed with trundle,  full-sized murphy bed,  and a half bathroom down the hall. The master bedroom has a King bed and full en-suite bathroom. A separate laundry room and tackle storage room for fishing poles and dive gear leads t

Located in Islamorada, Florida, United States. Pet Friendly 2 Bedroom in Venetian Shores Sleeps 10 The Salty B is located in the popular neighborhood of Venetian Shores! Canal front home on Snake Creek gives you fast access to both Ocean & Bay, fuel, bait, and provisions.Key Features of Salty B:- The House: Upstairs has Two Bedrooms, with a king-size bed in the Master, and a Full/Twin Bunks (2) in the other guest suite, There is one Bathroom upstairs and one downstairs. Downstairs has a queen-sized Murphy bed Enjoy the convenience of a first-floor bathroom, and refrigerator, sink, and Microwave – perfect for those lazy outside days!- The Dock: Have your boats or yacht waiting just outside your door. Large, deep-draft sailboats or yachts are easily accommodated with a waterway 20 feet deep and 100 feet wide. Even tall vessels travel quickly between the Ocean and Florida Bay using the drawbridge just 1000 yards from the dock. With gas, bait, and tackle shops located before the bridge, your convenience is assured. Your 35-foot priva

Located in Islamorada, Florida, United States. Snorkeling in Islamorada! Premium Villa, Bike Rentals & Water Sports Equipment! 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