
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.

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.

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

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

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

Turtle-By-The-Sea: the Best Deal in KCB!
A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

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.

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!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

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.

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.

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.

Two Authentic Conch Houses Private Beach on FL BAY
Looking for the perfect Florida Keys vacation rental? Nestled between Key Largo and Islamorada, Sunset Beach Hideaway is a unique waterfront retreat directly on the Florida Bay. Set on 1.16 acres of lush tropical landscaping with coral rock block fences, this private getaway blends Old Florida charm with modern comforts. 📍 Conveniently located in Tavernier, Florida, just steps from Circle K and Dairy Queen. 🎥 Watch the video tour: Sunset Beach Hideaway

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!
Popular amenities for Windley Key waterfront rentals
Waterfront apartment accommodation

*NEW* Sea La Vie-Pool & Beach

Beachside Unit 22 - Private Beach on Atlantic

Ocean View 2br/2ba w/pool, bar, gym + dockage 28ft

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths

Hidden Gem Islamorada | 1st Floor

Panoramic Ocean Views, Ocean Pointe Condo

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

Boho FL Keys Condo
Waterfront house rentals

Paradise found!Key Colony Beach,Cabana Club.

Islamorada Cay Home Elegant home- holiday home

Blue House Marine in Key Largo

Conch Cottage at Hawks Cay - Chic Tropical Retreat

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Escape to the Seaside!

NEW! CASA AZUL - Golf Cart, 2 Kings, Pool, Kayaks

Keezy Dream House+Beach, Pool & Kayaks at Anglers
Waterfront condo accommodation

Mariner's Club 522 - Don't worry Beach Happy!

Waterfront Apt Key Largo #4, 10% Off 7+, 5% Off 4+

Enjoy sunsets & sunrise in your home away home.

Ocean Views at Ocean Pointe

Tequila Sunrise

2026 Jan-Feb Islamorada Sandy Sunset Beach+Pool

🏝 Oceanfront Paradise Awaits You

*NEW* Private Beach, pool & fully loaded kitchen
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- Saint Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Rentals with a washing machine and dryer Windley Key
- Rentals with a kayak Windley Key
- Hotel rentals Windley Key
- Family-friendly rentals Windley Key
- Fitness-friendly rentals Windley Key
- Rentals with a patio Windley Key
- Rentals with pools Windley Key
- Rentals with an EV charger Windley Key
- Rentals with outdoor seating Windley Key
- Beachfront rentals Windley Key
- Serviced apartment rentals Windley Key
- Rentals with beach access Windley Key
- Pet-friendly rentals Windley Key
- House rentals Windley Key
- Waterfront rentals Islamorada
- Waterfront rentals Monroe County
- Waterfront rentals Florida
- Waterfront rentals United States
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Coral Castle
- Cocoa Plum Beach
- Cannon Beach
- Calusa Beach & Loggerhead Beach
- Conch Key
- Theater of the Sea
- Far Beach
- Deering Estate
- Everglades Alligator Farm
- Sea Oats Beach
- Monkey Jungle
- Long Key State Park
- Horseshoe Beach
- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Schnebly Redland's Winery & Brewery
- Sandspur Beach
- Bahia Honda State Park
- Keys' Meads