58,368 properties available

Located in Islamorada, Florida, United States. Islamorada HappyTarpon House:Private Heated Pool - Private Boat Dock- Family Fun Happy Tarpon - the best of the Florida Keys and the best of Islamorada! Enjoy privacy in our beautifully renovated home in the heart of Islamorada. It is furnished for easy tropical living inside and out. Swim in the heated pool after a day on the water. Boating, fishing, lobstering, sailboarding, skindiving or canoeing. We have it all. Your boat is right next to the house in our deep-water boat dock. Enjoy a cold drink while you watch the sun set across the Florida Bay. The boat dock holds up to a 28' foot boat in the deep water protected canal. Happy Tarpon is a great place to be between fishing trips or water sports. There is direct access to the Back country and world-class flats fishing or a short run to the Ocean for world-class deep sea fishing. The center-piece of our home is a heated private Pool directly outside of the living room and kitchen. There is a sunning deck/wading area built

Located in Islamorada, Florida, United States. BAYSIDE PARADISE ~ Heart of Islamorada ~ Private Boat Dockage Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle to every place in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and a half bathrooms, to comfortably accommodate up to 6 adults plus children. The bright living area fully opens up to a private patio, where you'll love to gather by the heated plunge pool with a view of the sunset over the bay. Truly in the heart of Islamorada, yet secluded within a protected cove among the mangroves. Less than a mile away from many of the best restaurants, bars and shops in town, including Lorelei, Morada Bay, Chef Michael's, Kaiyo Grill, Green Turtle Inn, Islamorada Beer Company, Florida Keys Brewery, Miss Monroe Boutique and Backcountry Cowboy. The Trading Post grocery store is located within 200 feet and open 365

Located in Islamorada, Florida, United States. Just a Few Friends - Ocean View and Bring your Boat! Experience all the Florida Keys has to offer in this stunning 2 bed/ 2 ½ bath condominium with an Ocean View, located in Bay Harbour, Islamorada Florida. This quiet gated community allows one to truly escape. Have the trip of a lifetime with Just a couple of friends & BRING YOUR BOAT too (up to 30')! Amenities include; Large heated/cool pool, jetted hot tub, fitness center, clubhouse, tennis courts, grills, covered parking + guest parking, and a private boat slip (Insurance required & trailers must be parked off-premises- we can make recommendations for that storage) with power & water giving easy access to both the Bay & Oceanside. The attention to detail in this unit is unmatched. Chic coastal decor, modern appliances, & ocean/pool views allow those staying to truly immerse themselves in the luxurious island life. Enjoy mornings on your private balcony watching the sunrise. Unwind in the evenings watching movies on your massive

Located in Islamorada, Florida, United States. 1 BR Condo Oceanfront Resort and Marina Experience the inviting comfort of our 1-bedroom, 2-bathroom suite, designed as a serene sanctuary for guests. Relax in the bedroom with two queen beds, an ensuite bathroom, and a private balcony. The living area exudes warmth, featuring a snug queen sofa bed, a functional kitchenette, and an additional balcony. While our property enjoys a prime oceanfront location, not all units guarantee direct ocean views.At Caloosa Cove Resort, enjoy breathtaking vistas, a heated swimming pool, a serene beachfront, a convenient General Store, boat slips, and exciting boat charters. With a variety of activities nearby, it's the perfect destination to unwind and fully immerse yourself in the captivating ambiance of Islamorada. Our onsite marina offers boat slip rentals and charters for adventurous guests. Additionally, a private beach and large, heated pool provide relaxation options.

Located in Islamorada, Florida, United States. Elegant Bay Harbor Condo with 50 Foot Boat Slip, Heated Pool, Hot Tub, and Gym Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new flat screen HD TVs in living room, master and queen guest! Gourmet kitchen has granite countertops, stainless steel appliances and a great selection of cookware and utensils. Open floor plan with wet bar and formal dining room. Enjoy your morning coffee or afternoon cocktail with the gentle ocean breeze on the wonderful screened in water front balcony. This unit is the model for all of Bay Harbour and is professionally decorated and furnished.The condo includes all linens and is equipped with a full washer and dryer. Also included is the use of a 50-foot boat slip in a protected harbor with four-foot control depth. The large screened in balcony looks

Located in Islamorada, Florida, United States. Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing getaway, look no further. Relax with the family in this cozy Island retreat. Completely remodeled! Come enjoy the community heated pool and a morning bike run. Enjoy the Florida Keys with your own private backyard and private parking.

Located in Islamorada, Florida, United States. DELUXE ISLAMORADA PENTHOUSE CONDO WITH 50' BOAT SLIP AND 25,000# LIFT This stunning top floor end unit in Bay Harbour with ocean and harbor views also includes a 50' boat slip with Boat Lift! The interior design is spectacular. Coffered ceilings in the living area, top of the line Miele and Thermador appliances, custom kitchen cabinetry, intricate tilework in the baths exceptional views from all common areas and primary bedroom. The Bay Harbour complex amenities include a pool, spa, gym, tennis courts and a clubhouse for friendly gatherings. Covered parking and a ground level storage unit are also included.

Located in Islamorada, Florida, United States. Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Family Compound. This Beautifully renovated Compound / Property Comes With A recently completed Magnificent Landscape Oasis , That Begins With Coral Stones And Fire Bowl Entrance To A Large Golf Putting Green For Everyone In The Family To Enjoy ⛳️, Plenty Of Shaded Areas With Palm Trees 🌴 , A Fire Pit and Hammock area With Confortable Sittings that’s just perfect For Family Gatherings and fishing stories , (including the one that got away) and/or just total relaxation . and Much More . Truly The Perfect Vacation Home For Any Size Family. .Has 3 distinct Sleeping Quarters ,one in the Upper Floor Home ( This Spacious And Accommodating 2nd Floor Suite have its Own Entrance ,King Size Bed , Small Fridge/ Microwave Oven , Nespreso Coffee Maker , Sitting Vanity With Mirror , A 65 In TV And A Large Confortable Scenic And Relaxing Wrap - Around Balcony ). On Ground Floor and With Access from the Swimming Pool Area ,you’ll find Entra

Located in Islamorada, Florida, United States. Canal-front home with private dock, wraparound deck, & central AC - snowbirds OK Plaza Del SolOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to the Keys for a serene stay at this family-friendly home, sitting waterfront right on a canal and boasting its own dock. Wake up with a sunrise coffee on the wraparound deck each morning, then slip into the provided kayak for a quiet paddle. Or, spend the day deep-sea fishing - a private boat ramp and watercraft floating ramp are just a short drive away. Beach bums will love having access to a one-half-mile-long private, white-sand beach, but if you’d rather stay dry, all the shops, restaurants, beach bars, and amenities of Islamorada are just a short drive away. The world-famous Seven Mile Bridge is around 28 miles further down the Overseas Highway. At home, you’ll find a bright, open living space on the main level, featuring coastal decor, high ceil

Located in Islamorada, Florida, United States. Beautiful Maison #307 Maison Matecumbe #307 - Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centrally located right in the heart of Islamorada within walking and biking distance to many restaurants, cafes, shopping, marinas and Islamorada's Art District. The unit has been totally renovated, brand new kitchen, beautiful bathrooms, decor and bedding. The unit offers an open lower level living room with kitchen and guest bedroom and full bath. Beautiful views of the Atlantic from the screened balcony. The upper level has a king master en suite and third bedroom with two queen beds. Newly renovated swimming pool and hot tub to spend your days lounging along with Maison's beach, outdoor kitchen, tiki hut and spa. VACATION RENTAL LICENSE: 24-0074If 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

Located in Islamorada, Florida, United States. Best Location in Islamorada!! Beach access - Boat trailer parking! Gorgeous and highly appointed luxury Island villa with beach access. You are right in the middle of it all with this perfect location. Walk or bike to some of the best restaurants and shopping Islamorada has to offer.

Located in Islamorada, Florida, United States. Jamaican Palm House 3 Bedrooms, 2 Bath, Poolside Poolside,3 Queen Beds,1 Pull OutWelcome to the Jamaican Palm. Our most recently renovated home is a sight to behold. Every detail and fixture was handpicked and custom crafted from the finest materials and builders.Inspired by the Caribbean lifestyle and design from Ocean Gardens Showroom. The Jamaican Palm is an expansive 3 bedroom, two-bathroom single home with a large great room, chefs kitchen and outdoor wrap-around veranda. Chisel stone flooring, granite countertops, Keys Stone Coral wall and custom cabinets are just a few of the high quality features the home holds. The chefs commercial kitchen features a Wolf stove, Subzero refrigeration and a separate built-in wine cooler.Nautical decor includes one of a kind Marine Antiques and ship lighting throughout the home. Like all our other homes, The Jamaican Palm also comes with a washer-dryer, Weber BBQ gas grill, wireless Internet and cable TV.This home includes a full washer-dryer, W

Located in Islamorada, Florida, United States. Bayside Retreat - Adorable 3 Bedroom Bayfront Duplex with Dockage Bayside Retreat - Completely renovated bayfront duplex home. This bayfront home consists of three bedrooms and three baths in Lower Matecumbe. With charming island decor and the open concept living room, kitchen and dining area, the home is light and airy. The screened balcony directly off the kitchen enables you to enjoy outdoor dining with beautiful bay views. The master en-suite with a king bed and bay views, and the guest room with two twin beds are located on the main level. The loft queen en-suite on the second level with sliding doors leading out to an open balcony offers open Gulf views to the west and ocean views on the east. This home offers both ocean views and bay views from the kitchen and living room. Dockage for smaller boats and skiffs up to 24' with easy bay access and ocean access through Channel 5 Bridge. Enjoy paddle boarding and kayaking right from the bayfront beach area. There are 2 paddle boards f

Located in Islamorada, Florida, United States. Tarpon Bend ocean view with boat lifts 3/2 Waterfront Home in Lower Matecumbe Key in Islamorada, Florida. Featuring a 70' ft private dock with 2 boatlifts (1- 10,000 lbs capacity, 1- 20,000 lb capacity)- both available for rental separately. Home is minutes away from most attractions. This beautiful home accommodates up to eight people and is completely decorated.Master Bedroom has a King-size bed with a flat panel LCD Television. Southern facing window lets in plenty of natural light. Bedroom features a master bath and a walk in closet with ample room for storage.Bathroom #2 has a queen sized bed and a private televisionBathroom #3 has two full size bunk beds and a private television. One full sized bathroom in addition to master bath is conveniently located by bedrooms.The living room has an entertainment center with a flat panel LCD Television. Lovely Kitchen /dining area featuring a table for 8. Upstairs balcony extends width of property and contains a BBQ and seating area. Do

Located in Islamorada, Florida, United States. Perfect Home for a get away! Private homeowners beach, enjoy Islamorada. Perfect home for a get away! Home is located in Islamorada. 3 bedroom 3 bath gorgeous private homeowners beach and private dock, close to the best restaurants, and sight seeing. Peaceful, quiet and relaxing! Just what is needed to take your mind off of business and a great place to spend the winter months in turquoise, warm waters. Fish, read a book, swim, head to Key West, shop, eat, drink, enjoy the Florida Keys.

Located in Islamorada, Florida, United States. Sunset Splendor: 2 Units Near Theater of the Sea! Parking, Pool, BBQ Facilities Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and bustle. Step outside your door and be greeted by the breathtaking beauty of our private beach. Feel the soft sand between your toes as you stroll along the shoreline or soak up the sun on a beach lounger. For those seeking adventure, indulge in various water sports activities nearby, such as kayaking or paddle boarding, Our newly renovated resort boasts an array of amenities to enhance your experience. Take a dip in our sparkling outdoor pool, surrounded by lush tropical gardens. Our friendly staff is always ready to provide recommendations and assist you in planning memorable excursions. Experience the epitome of coastal elegance and create timeless memories at our exclusive retreat. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from ty

Located in Islamorada, Florida, United States. Oceanside townhome 2/2 with boat ramp and dockage This beautiful newly renovated townhouse is the prefect vacation home for you and your family. The third floor has a master bedroom with king bed and bathroom with a balcony that has ocean views. The second floor has a bedroom with queen bed and bathroom right off of the living room and fully equipped and updated kitchen with a huge island. There is a sleeper sofa in the living room. The balcony on the second floor provides you with a view of the pool, tennis courts, pickle ball, shuffle board, tiki hut with picnic area, charcoal grill, and dock. You have a view of the dock where you can keep your boat up to 25' as stated in boat registration. The dock has fresh water, electric, 2 filet stations. There is a community boat ramp which you have access to at anytime as long as you have provided insurance and registration to the dock master. On the first floor there is a garage where you can store your fishing rods, a freezer to store your

Located in Islamorada, Florida, United States. Oceanfront Condo @ Maison Matecumbe - 3 bedrooms overlooking pool, Ocean & beach Welcome to your dream vacation home in Islamorada, the jewel of the Florida Keys! This 3-bedroom condo boasts a prime location, with breathtaking views of the crystal-clear pool, Atlantic Ocean, and glistening white sand beach.As soon as you step inside, you'll be enchanted by the bright and airy living space. The living area and balcony features plenty of entertaining areas inside and out… Perfect for relaxing after a long day of fishing and swimming. Add optional dockage to any rental. Contact for rates.The master suite features a king-size bed and a private balcony with stunning views of the pool and beach. The other two bedrooms offer a full-size bed and two twin beds, respectively, making it the perfect accommodation for families or groups of friends.Step outside onto your private balcony and soak up the sun while enjoying the panoramic views of the pool, hot tub, and beach. Sip on a refreshing drink

Located in Islamorada, Florida, United States. Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe Bay Harbour A-304 – Beautiful three bedroom two and a half bath luxury penthouse condo located at mile marker 74.5 bayside. This condo is nicely decorated, fully appointed, and very spacious for you and your family. The unit has a beautiful, screened lanai off the living room and master bedroom with brand new furnishings to relax and watch the sun rise over Alligator Reef. The complex has a pool, hot tub, gas grills, tennis courts, weight room, dockage, fish cleaning stations, and a community club house. The unit has recently been updated to make your stay even more comfortable and enjoyable. It has Wi-Fi as well as cable. The condo includes all linens and is equipped with a full washer and dryer. The condo overlooks its 50-foot private boat slip in a protected harbor with deep water access. There is immediate bay access and quick ocean access via Channel Two and Channel Five bridges. Fish cleaning stations, s

Located in Islamorada, Florida, United States. Mini Ray's of Sunshine Mini Ray's of Sunshine - Beautiful New Pool Home located in a gated community in the Heart of Islamorada. This home, designed and owned by a prominent Chicago designer, is located in one of Islamorada's premier gated neighborhoods, close to shopping and Islamorada's finest fishing fleets. Throughout the house you will find beautiful floors, whimsical décor, and open living room/kitchen. Any family would feel totally at home. The back yard is beautifully landscaped giving you a very private feel. The amazing pool and back porch area is completely screened in, so no pesky bugs. What are you waiting for. This one is going to go fast! 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. Please note: before proceeding with your booking, kindly review the following information. This property is managed b

Located in Islamorada, Florida, United States. Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna Welcome to your luxurious retreat in Islamorada! Experience the epitome of luxury living at our stunning condo located at Mile Marker 75 on the serene Bayside in Islamorada. This stunning 5BR and 3.5BA property is the perfect getaway for you and your group. Featuring a private hot sauna, a wet sauna, and a rooftop area, you'll have plenty of opportunities to relax and unwind. Located in a beautiful area with access to the beach as well as to nearby attractions and activities.The Space:Immerse yourself in luxury and comfort at our expansive 3,500-square-foot penthouse, perfect for a lavish getaway in Islamorada. Unwind in style with ample space to relax and entertain, complete with a private movie theater for cinematic experiences at your fingertips.Master bedroom:Walking closet.Beds: 1 King bed Private bathroom: Shower, toilet, and two sinks. Smart TV. Second bedroom:Closet.Beds: 2 queen bedsPrivate bathroom: Shower with tub, toilet, a

Located in Islamorada, Florida, United States. Your Ultimate Islamorada Hideaway! Full Kitchen, Swimming Pool, Pets Allowed! Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of the guest rooms and suites in our three-bedroom house is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual elegance of the tropics with our resort amenities. Guests have access to all the amenities they might possibly need right on the premises, including a restaurant, bar, swimming pool, and slips for those visiting with boats. But if you want to venture offsite, we have a shuttle service that can take you around.PLEASE NOTE:- The property requires a damage deposit of USD 100/night/unit 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 upo

Located in Islamorada, Florida, United States. Modern Oceanview Paradise at Islamorada Breathtaking 3bedroom 3bathroom oceanfront vacation home is ready to welcome your family for your next getaway. Enjoy sunrises ad private beach views right from your bedroom. This house was built in 2019, and was only used by the owner. It features all new appliances and has everything you might need for an unforgettable vacation. During your stay, our team will be available for you 24/7 so you can relax and unwind while we make sure your getaway experience is perfect.***notwithstanding anything in the rates page minimal rental is 7 days***

Located in Islamorada, Florida, United States. "Our Happy Place" Paradise in Islamorada with Heated Pool and 90 ft Dock Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the most beautiful crystal clear waters. The house is just minutes from Channel 5 and Channel 2 which give you quick access to the best ocean and backcountry fishing. You are also just minutes away from a beautiful private beach that you can only access by water. Famous Alligator Reef and Tennessee Reef are just 15 minutes away. This is a beautiful boating, fishing, snorkeling, scuba diving or just relaxing paradise.Within walking distance you have Anne’s Beach. Also, within walking distance you have Caloosa Cove Marina and a convenience store which offer fuel, fishing supplies, bait, etc. You also have the famous Safari Lounge which was recently beautifully renovated.The house can accommodate up to 10 people comfortably. Upstairs you have 3 bedrooms and 3 full bathrooms offering a split plan for pr