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Waterfront vacation rentals in Windley Key

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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 favorite
The two-story eco-friendly River Queen vessel is anchored on tranquil waters. Its modern design is complemented by expansive windows, and a spacious rooftop deck is visible. The 10-foot dinghy is secured alongside, providing easy access to the shore.
Boat in Tavernier
4.91 out of 5 average rating, 378 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 favorite
Houseboat in Islamorada Tavernier
4.89 out of 5 average rating, 249 reviews

Florida Keys Dockside Paradise, Luxury Houseboat

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers a unique blend of comfort, adventure, and waterfront living. Wake up to breathtaking sunrises, sip your morning coffee with all the marine life, and fall asleep to the gentle movement of the boat. Whether your celebrating something special or simply want a one of a kind getaway-it's the perfect home base for Keys adventures or peaceful retreats. An amazing experience Free park

Guest favorite
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
4.87 out of 5 average rating, 155 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 favorite
A collage showcases four images: A serene sunrise over water, a cozy bedroom with a flat-screen TV, an open-concept living area with a kitchen and dining space, and a tranquil view of the evening sun reflected on the bay, complete with a kayak along the shoreline.
Home in Key Largo
4.9 out of 5 average rating, 168 reviews

Tiny Home on Waterfront | Bay Views | Deck | Pool

Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

Guest favorite
A serene sunset is visible over the Atlantic Ocean, with warm orange and yellow hues blending into the sky. A sailboat is seen on the horizon, adding a touch of tranquility to the scenic view.
Condo in Tavernier
4.85 out of 5 average rating, 296 reviews

Condo in the Keys, Peaceful ocean view retreat!

Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key West, this condo is close to state parks and coral reefs great for diving, fishing, and snorkeling. Relax on the private beach where kayak and paddle board rentals are available. Then enjoy a stroll on the pier to the gazebo. Splash around in the beautifully renovated heated pool and hot tub with mermaid bar! You can also enjoy food and beverages in the on-site cafe and bar

Guest favorite
A cozy living area features a light-colored sofa with decorative pillows, complemented by a coffee table and a patterned area rug. Expansive glass sliding doors provide natural light and views of palm trees outside, while a small dining table adds functionality to the space.
Apartment in Key Largo
4.89 out of 5 average rating, 302 reviews

Seaside Vista - Ocean Front 2/1 with dockage

The Seaside Vista is a luxurious ocean front retreat located in Key Largo. Only 1 hour from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From great dining, to water sports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled , enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer. MC Permit #: 21302180

Guest favorite
A serene waterfront view is framed by palm trees, with two green chaise lounges positioned for relaxation. The setting sun casts warm hues across the sky, reflecting on the water's surface. A Tiki structure adds charm, creating an inviting outdoor space.
Tiny home in Key Largo
4.96 out of 5 average rating, 166 reviews

Oceanfront Lookout Point w/two Kayaks & Deck

Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

Guest favorite
A private beach area is revealed, featuring rows of blue lounge chairs set on soft, sandy ground. Lush greenery borders the beach, while a wooden pier extends into the calm, turquoise water. A thatched gazebo provides shade, and scattered palm trees complete the coastal scene.
Condo in Tavernier
4.94 out of 5 average rating, 112 reviews

Your Happy Place - Oceanfront

Experience the ultimate coastal getaway at Ocean Point in the Florida Keys. Nestled along the Atlantic Ocean, our 2 bed/2 bath condo offers unrivaled ocean views from the moment you step inside.  Indulge in the array of amenities available at our property including a private beach, pier, marina, snorkeling, family pool and a full service restaurant. Our condo comfortably sleeps 6-7 guests. Equipped with full kitchen and washer/dryer, we provide all the conveniences for a seamless stay. 

Top guest favorite
A private porch overlooks the tranquil harbor, featuring blue chairs beside a white railing. A boat is secured at the dock, with sailboats moored in the distance. Bright sunlight reflects off the water's surface, creating a serene atmosphere.
Vacation home in Key Largo
4.99 out of 5 average rating, 224 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

Top guest favorite
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, 166 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 favorite
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, 357 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 favorite
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, 101 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.

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