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Waterfront holiday rentals in Windley Key

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Windley Key

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Guest favourite
A plate of vibrant dragon fruit sits on an aqua blue chair on a waterfront patio. Two glasses filled with a refreshing beverage are placed nearby, while lush greenery and boats are visible in the background under a clear blue sky.
Holiday home in Key Largo
4.85 out of 5 average rating, 320 reviews

4. Cozy Waterfront Apartment in Key Largo!

Enjoy water front living in Key Largo! Watch the boats go by with fresh catch served daily at the local restaurants. See manatees, nurse sharks and fish swim by the canal all day. Dock your boat at the Pilot House Marina just down the street. Our unit is Modern, Spacious and Spotless with Private Parking, Fast Wifi, Netflix, Cold AC, Plush Pillows and a Cozy bed. We are on a main canal to open ocean. Near Rodriguez Key, Mosquito Bank, Christ of the Abyss and many sunken shipwrecks for exploring.

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
4.91 out of 5 average rating, 385 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 serene waterfront scene captures a vibrant sunset reflecting off calm waters. Multiple boats are docked along the marina, with silhouettes of masts against the colorful sky, creating a peaceful atmosphere ideal for relaxation.
Home in Key Largo
4.98 out of 5 average rating, 223 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Guest favourite
Houseboat in Islamorada Tavernier
4.89 out of 5 average rating, 257 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.
Apartment 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
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, 186 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
Flat in Tavernier
4.95 out of 5 average rating, 224 reviews

Oceanview | Jacuzzi | Private Beach | Marina | BBQ

Oceanview beach condo with tennis courts, pickleball, hot tub, BBQ, marina & private beach. ★ "Exactly as described & very clean. Beautiful views & a nice peaceful escape." ➠ Resort heated pool + Jacuzzi ➠ Balcony w/ ocean + pool views ➠ Private beach access w/ sunloungers ➠ Fully equipped + stocked kitchen ➠ Master suite w/ king + bathroom ➠ 55” smart TVs w/ cable ➠ Car park (2 cars max) ➠ 250 Mbps wifi Quick drive to… ↝ Downtown Tavernier (5 mins) ↝ Theater of the Sea (15 mins)

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, 369 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.

Guest favourite
Apartment in Tavernier
4.91 out of 5 average rating, 113 reviews

Blue Haven Key Largo | Ocean Pointe 1315

Tastefully decorated and newly renovated 2 Bedroom & 2 Bathroom Condo with a wonderful view of Florida Keys Nature. Relax and escape to this beautiful getaway in the heart of Tavernier, ideally located between Key Largo & Islamorada. The property itself has amenities galore: sparkling pool with hot tub and newly re opened POOL BAR, boat ramp and marina, tennis courts which convert into pickle ball courts, beach with pier, free parking and charcoal grills to cook your catch!

Guest favourite
A spacious living area features a large sectional sofa in a soft gray hue, complemented by a glass coffee table. A modern light fixture hangs overhead, while a decorative plant adds a touch of greenery. Large sliding doors provide an outdoor view, enhancing the bright atmosphere.
Townhouse in Key Largo
4.92 out of 5 average rating, 141 reviews

Kawama N2 Relaxing Lagoon View free bikes & kayaks

Relax and enjoy our family friendly 3 bedroom/3 bathroom Villa Lago in Key Largo! Salt water swimming lagoon, Pools, the Ocean, fishing pier, Marina, Tennis, Bikes, fire pit and playground. Enjoy resort like amenities in the comfort of a home. This beautifully decorated villa sleeps 8 and is conveniently located in a very central location in Key Largo. Close to some great restaurants, diving, fishing, boat tours, State Park. Kawama is fun for all ages.

Top guest favourite
Apartment in Tavernier
4.94 out of 5 average rating, 126 reviews

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath

Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

Top guest favourite
A spacious bedroom features a king bed with light bedding and decorative throw pillows. Large windows offer unobstructed ocean views and allow natural light to fill the room. A comfortable seating area is positioned nearby, facing the beach and tiki huts.
Apartment in Key Colony Beach
4.91 out of 5 average rating, 202 reviews

Exquisite Oceanfront Paradise - Key Colony Beach

Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated ground floor with a stunning, clean white interior and just a few steps from our private beach and heated pool. Continental Inn Unit #10 offers one King size bed that sleeps two people. A fully equipped kitchen with essentials (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Reliable WiFi and Smart TV.

Popular amenities for waterfront rentals in Windley Key

Destinations to explore

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