Holiday rentals in Plantation Key

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Top-rated holiday rentals in Plantation Key

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Top guest favourite
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
4.92 out of 5 average rating, 396 reviews

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.

Guest favourite
A serene pool area is framed by lush palm leaves, highlighting a sparkling pool with a bubbling spa. Sun loungers are arranged around the pool, complemented by a large blue umbrella providing shade.
Cottage in Islamorada
4.96 out of 5 average rating, 139 reviews

Charming 2BR cottage in prime keys location w/pool

Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

Guest favourite
Home in Islamorada
5 out of 5 average rating, 7 reviews

FL Keys Ocean Front Escape

Welcome to FL Keys Ocean Front Escape in beautiful Islamorada! This 2-bedroom, 3-bathroom retreat offers stunning ocean views and all the comforts of home. Enjoy essentials like WiFi, air conditioning, a fully equipped kitchen, and a washer. Relax in paradise with the perfect blend of modern amenities and tropical charm. Experience 360' views of the finest Islamorada sunrise from the private roof top deck! Whether you're fishing, snorkeling, or just unwinding, your dream getaway starts here!

Guest favourite
Houseboat in Islamorada Tavernier
4.9 out of 5 average rating, 265 reviews

Florida Keys Houseboat, unique waterfront stay-

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers the perfect blend of comfort, adventure and true waterfront living. Wake up to breathtaking sunrises, sip your morning coffee as the marine life glide by, and fall asleep to the gentle sway of the water. Whether you’re celebrating something special or simply craving a one-of-a-kind getaway, this houseboat is the ideal home base for both keys adventures and peaceful retreats 💫

Top guest favourite
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
4.96 out of 5 average rating, 27 reviews

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.

Top guest favourite
A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.
Tiny home in Key Largo
4.97 out of 5 average rating, 199 reviews

Oasis2 in Key Largo With a million dollar view

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Top guest favourite
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.
Home in Islamorada
4.97 out of 5 average rating, 210 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.

Top guest favourite
Home in Islamorada
5 out of 5 average rating, 13 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.

Guest favourite
Villa in Islamorada
4.92 out of 5 average rating, 24 reviews

Angler’s Reef home • Pool • Kayaks • Paddle boards

Relax with the whole family at this peaceful Angler's Reef boutique complex. Oceanfront community located at Mile Marker 85 has a beautiful community pool overlooking the Atlantic ocean. The community also offer kayaks, which can be launch from the private beach. This home has 2 bedrooms located on the 2nd floor with their private bathroom. The kitchen is fully equipped with stainless appliances, granite counters, 3 TVs & WiFi. The property has parking for 2 vehicles. License 26-5143

Guest favourite
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
4.93 out of 5 average rating, 379 reviews

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.

Superhost
Home in Islamorada
5 out of 5 average rating, 4 reviews

Islamorada Cay Home Elegant Canal home

Stunning Islamorada Home off Tavernier Creek Enjoy your private own pool w/pavers all around. OUTDOOR ICE MACHINE. w/30 amp. Elegant 4 bedroom, 3 bath home feels like a mini resort when you arrive. Small private beach. Game room. Master bedroom en suite 3rd floor. Private gated home. 1 dog under 30lbs w/Fee. If using pool heater in the winter you pay for the propane usage any time. Boating access truly mins to ocean & bay & Fuel & Marina. Guest love the Coastal home.

Guest favourite
A window reveals a lush garden filled with tropical plants and flowers. The words 'Keys Life' are displayed on a wooden sign above the window, enhancing the connection to the surrounding nature.
Cottage in Key Largo
4.9 out of 5 average rating, 402 reviews

Cottage By The Sea

Cottage By The Sea....Your home away from home in the Florida Keys!!! Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. Be sure to meet Frank out 120 pound Sulcata tortoise.Minutes from either Oceanside or Bayside boat ramps. It is walking distance to a famous local's Tiki Bar and Restaurant as well as Jet ski and Kayak rentals

Popular amenities for Plantation Key holiday rentals

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  4. Monroe County
  5. Plantation Key