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Waterfront holiday rentals in Windley Key

Find and book unique waterfront accommodation on Airbnb

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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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, 221 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!!!

Top Guest favourite
A bright living area features a light wood floor and various seating options, including a wicker chair and a sofa adorned with colorful cushions. A coffee table is placed at the center, complemented by decorative wall art and a potted plant nearby.
Condo in Tavernier
4.95 out of 5 average rating, 120 reviews

Sugar Cane - Florida Keys tropical retreat

We have just completely renovated this condo at Ocean Pointe Resort and it's Insta-worthy. Every detail has been designed and considered. Sugar Cane is conveniently located near the best of the Florida Keys - close to Islamorada and Key Largo. The property boasts a large outdoor pool with a pool bar, hot tub, oceanfront beach and boardwalk, boat ramp, marina, tennis courts and children's play area. We manage Sugar Cane ourselves and live nearby so we have local knowledge and are very responsive

Guest favourite
Houseboat in Islamorada Tavernier
4.89 out of 5 average rating, 256 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, 164 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!

Guest favourite
Apartment in Tavernier
4.95 out of 5 average rating, 223 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)

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, 368 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
A serene beach area is highlighted by sandy shores and gentle waves. Palm trees sway in the breeze, while lounge chairs are arranged neatly in the foreground. A wooden dock extends into the water, framed by lush greenery in the background.
Home in Key Largo
4.79 out of 5 average rating, 152 reviews

Escape to the Seaside!

Our 2-story ocean front home is a quite and tranquil oasis. Centrally located in south Key Largo, allows for easy travel to the lower Keys. Our home is decorated in a casual coastal style to provide a comfortable and relax setting. Upstairs is 3 bedroom 2 baths and spacious open concept living room, dining room and kitchen. It provides all the comforts of home. Equipped with flat screen TV, complimentary Wi-Fi and premium cable programming. Here, you’ll have everything you need.

Guest favourite
Condo in Key Colony Beach
4.93 out of 5 average rating, 263 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Guest favourite
Condo in Tavernier
4.92 out of 5 average rating, 111 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 wooden pier extends over calm waters, leading toward a thatched-roof gazebo. The scene is illuminated by a vibrant sunset, casting warm hues across the sky and reflecting on the water's surface. Lush greenery frames the sides, enhancing the serene atmosphere.
Condo in Tavernier
4.97 out of 5 average rating, 102 reviews

Ocean views at “Sangria Sunrise” 10% off Charters

Welcome to Sangria Sunrise at Ocean Pointe Suites in the beautiful Tavernier Key Florida. Relax and enjoy all of the options offered such as Jr. Olympic sized pool, beach, marina, kayak rentals, tennis courts, and so much more! We invite you to come stay at this cozy and updated one bedroom and one bathroom top floor condo with the most amazing ocean views. We offer a very comfortable queen sized bed and also a queen sleeper sofa that's equally as comfortable.

Top Guest favourite
Condo in Tavernier
4.94 out of 5 average rating, 124 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!

Guest favourite
A bright living room features a large flat-screen TV mounted on a wooden console. A blue sofa and complementing armchair adorned with vibrant cushions provide comfortable seating. Large glass doors lead to a private balcony, offering views of the ocean and surrounding greenery.
Condo in Tavernier
4.92 out of 5 average rating, 107 reviews

Luxury Top Floor Suite W/ Unobstructed Ocean View

Our spacious, 2 bedroom, well-appointed condo provides the perfect home away from home. Step onto your private balcony and soak in the mesmerizing views of the azure ocean and lush mangrove gardens. Escape to a tropical paradise and experience the ultimate keys retreat! Nestled in Tavernier, this property offers a perfect blend of comfort and breathtaking natural beauty. Indulge in the array of fantastic amenities available to our guests.

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