Waterfront holiday rentals in Windley Key

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Top-rated waterfront accommodation in Windley Key

Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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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, 390 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.

Top Guest favourite
A private dock extends over calm waters, lined with white posts and illuminated by a golden sunset. A thatched-roof structure is visible at the end of the dock, surrounded by gentle waves reflecting the muted sky.
Condo in Key Largo
4.99 out of 5 average rating, 121 reviews

Enjoy sunsets & sunrise in your home away home.

Keys largo best kept secret. Enjoy all that Florida keys have to offer. Superb location close to main land and best of all on the water. Enjoy sunset on your private dock. Don't worry about parking you have you very own private spot. Very close to miami if you wish to venture out off the Florida keys. Great beaches and great restaurants. Come and enjoy the best that Florida has to offer. Great location to relax. You can enjoy the pool, tennis and basketball. You can eat in the club on the water.

Guest favourite
A serene sunset view showcases a circle of white Adirondack chairs positioned around a fire pit. The calm waters reflect vibrant hues of orange and purple from the sky, creating a peaceful atmosphere.
Townhouse in Key Largo
4.86 out of 5 average rating, 167 reviews

Sunrise Escape - Ocean Front Villa - Sleeps 10

Enjoy the sunrise while sitting on one of two terraces and sipping your morning coffee in the exclusive part of Kawama Yacht Club overlooking the Marina and Ocean. Enjoy the many choices for the day: Kayaking/paddle boarding just 20 steps from your door, walking to the south beach just 100 yards away, or walking to the beach jetty just across the marina. Or take a swim/snorkel in our swimmable lagoon or one of our two pools. Then bring a glass of wine to watch the breathtaking sunsets from our o

Guest favourite
Houseboat in Islamorada Tavernier
4.9 out of 5 average rating, 260 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 💫

Guest favourite
An open-concept living area features a comfortable sofa and loveseat, designed for relaxation. A stylish dining table accommodates four. A wall-mounted TV and electric fireplace add modern touches, while large sliding glass doors offer natural light and views of the surrounding landscape.
Condo in Tavernier
4.95 out of 5 average rating, 165 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

Top Guest favourite
Condo in Tavernier
4.96 out of 5 average rating, 213 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

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, 192 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.

Guest favourite
A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.
Home in Key Colony Beach
4.94 out of 5 average rating, 135 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Top Guest favourite
The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.
Boat in Islamorada
4.93 out of 5 average rating, 372 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.

Top Guest favourite
The living area features a spacious blue sectional sofa with decorative pillows and throws. A round coffee table sits at its center. Natural light fills the room, illuminating two framed beach-themed artworks on the wall, and the open kitchen and dining area are visible in the background.
Townhouse in Key Largo
4.96 out of 5 average rating, 110 reviews

Kawama K1 Beautiful Lagoon View free bikes & kayak

Escape to paradise at Kawama Yacht Club, a private community featuring 24-hour security and an array of exclusive amenities: Salt water lagoon, 2 heated pools, Kids playground, Tennis courts, Marina boat ramp, boat parking, Jetty & Fire pits. We also provide kayaks and bikes so you can fully immerse yourself in the beauty of the surrounding area. Don't miss out on the ultimate Florida Keys getaway, book your stay at Kawama Yacht Club now.

Top Guest favourite
A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.
Home in Marathon
4.95 out of 5 average rating, 112 reviews

Coco Plum Waterfront Hideaway Home in Marathon

This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.

Top Guest favourite
A two-story duplex is set amidst palm trees, featuring a blue exterior and multiple balconies. A vehicle is parked in the driveway, with a pathway leading towards the entrance, surrounded by landscaped areas that include gravel and greenery.
Home in Key Largo
4.92 out of 5 average rating, 186 reviews

Blue House Marine in Key Largo

The house is a Duplex style house for guest it is very quite and private it has 3 bedrooms and two bathrooms kitchen living room and dining area also a walk around balcony its screen in, it has 2 queen style beds and two twin beds. the home has been remodel you have canal views and open ocean viewsfull bathroom by the pool, barbecue area table and chairs for dining plus out door furniture. P.S There is no longer pool heating

Popular amenities for Windley Key waterfront rentals

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Windley Key
  7. Waterfront rentals