Holiday houses in Matecumbe Keys

4.95 out of 5 average rating, 106 reviews

A comfortable living area is highlighted by a light-colored sofa with textured cushions, accompanied by a woven coffee table. Natural light enters through multiple windows, revealing touches of coastal decor and a glimpse of a bedroom in the adjacent space.

Cottage in Islamorada

Islamorada bungalow 2 bed & pool

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

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4.92 out of 5 average rating, 401 reviews

The eco-friendly two-story River Queen vessel is anchored in a calm harbor, showcasing a modern design. The structure features large windows and a rooftop terrace, with a wind turbine on the left. The surrounding landscape includes lush greenery, complementing the serene water view.

Boat in Tavernier

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

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5.0 out of 5 average rating, 21 reviews

OceanView 2/2.5 w Beach Pool & Marina Islamorada

Everything you need for your Islamorada vacation is here including 2 gorgeous private beaches, kayaks, paddle boards, heated resort style pool, porch seating with ocean view, and 2 balconies. Located in the middle row of Anglers Reef, this home accommodates up to 6. Boat slip can be reserved for additional fee, if available. REELaxation is our only vacation rental and with an extensive background in customer service, extraordinary guest service and helping to make lifetime memories are our goal.

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4.93 out of 5 average rating, 154 reviews

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

Home in Key Colony Beach

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

FamilyValueAccess

4.97 out of 5 average rating, 35 reviews

A serene waterfront view captures the modern multi-story building surrounded by lush greenery. The calm water reflects the clear blue sky, while a private wooden dock extends into the water, providing an inviting entrance to the property.

Townhouse in Islamorada

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

🌊Welcome to The Seascape🌊 Experience waterfront living at its finest at The Seascape, a modern, newly constructed retreat nestled directly on the ocean where every morning begins in color, and every evening ends in calm. Here, the ocean isn’t just a view. It’s a presence. Come make memories at Islamorada's famous sandbar, legendary fishery, or gather on sunlit shores to relax and revel in life’s simplest joys with stunning views, direct water access, and a stylish escape from the everyday.

LocationFamilyPool

5.0 out of 5 average rating, 9 reviews

Life On A Rock Luxury Home in Downtown Islamorada

This Tommy Bahama Inspired Home Located at Mile Marker 81. Restaurants, Bars, Shops, and Beach all Walkable in this location. Located in the Heart of Downtown Islamorada. If you need specific dates please reach out to us. The Home features all Tommy Bahama Furniture, New Tempur-Pedic Breeze Mattresses. If you need specific dates please reach out to us. Room for Boat / Trailer Storage Perfect Biking Location Full Kitchen Washer / Dryer 65 Inch TV in Living Room Wifi Natural Light House

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4.79 out of 5 average rating, 68 reviews

A floating home is anchored in clear waters, surrounded by lush greenery. The structure is highlighted by solar panels on the roof and a spacious white deck, featuring railings that outline the edges. Bright blue skies and distant mangroves create a serene backdrop.

Houseboat in Islamorada

Perfect escape to the ocean

Enjoy the sounds of nature when you stay in this unique place. What awaits you is fun filled days living and exploring out on the fabulous florida keys waters in your own private floating paradise that is completely solar powered and all the amenities run 24/7! This fabulous floating home was build in 2025 and very nice, update and comfortable, it is 100% solar powered and eco friendly All the amenities run off batteries and solar power so you'll be able to enjoy cold ac, fridge, tv , 24/7

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The living area features a comfortable light blue sofa and a glass-top coffee table, complemented by tropical-themed decor. A ceiling fan circulates air above, while a kitchen bar with high chairs is visible in the background. Natural light enters through multiple windows, enhancing the welcoming atmosphere.

4.97 out of 5 average rating, 220 reviews

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

ValueFamilyLaundry

5.0 out of 5 average rating, 15 reviews

Off The Charts-Waterfront Tiki Bar & Private Dock

Welcome to a one-of-a-kind Florida Keys escape! This unique home, originally used as the Islamorada Courthouse, has been thoughtfully transformed into a stunning waterfront getaway while keeping its historic charm. Located in the heart of Islamorada, this property offers access to what the Keys are known for: the best fishing, dining, and great sunsets. For the comfort and safety of all guests, our accommodation is designed for guests aged 12 years and older. Pets are not permitted.

LocationFamilyIndoor spaces

4.93 out of 5 average rating, 394 reviews

A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

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Superhost

4.81 out of 5 average rating, 42 reviews

Islamorada Bungalow # 5

Bring the whole family to this great place with lots of room for fun.Escape to our charming 2-bedroom, 1-bathroom bungalow in Islamorada, FL, where luxury and convenience await! Relax on the spacious patio and take a refreshing dip in the pool, perfect for unwinding after a day of exploring nearby attractions. You're just moments away from pristine beaches, world-class fishing. Whether you seek adventure or relaxation. Secure your stay now for an unforgettable experience!

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