
Waterfront vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windley Key waterfront rentals
Waterfront apartment rentals

Sublime Oceanfront Condo at Ocean Pointe

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

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Hidden Gem Islamorada | 1st Floor

Panoramic Ocean Views, Ocean Pointe Condo

Little Venice in Marathon (in the Beautiful Keys)
Waterfront house rentals

Islamorada Cay Home Elegant home- holiday home

Waterfront Home 37.5-ft dock, Cabana Club Included

Waterfront Haven House with Boat Basin & Ramp!

Bay Sunsets Free Kayaks/Paddleboard Jacuzzi

Waterfront House with 37 ft Dock & Cabana Club

Marathon one-level home on the Marina - with slip!

Anglers Terrace, Condé Nast Traveler's Best Airbnb

Coco Plum Waterfront Hideaway Home in Marathon
Waterfront condo rentals

Reel Large END Unit in Ocean Point Suites

500 Burton Drive Tavernier, Key Largo

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

Enjoy sunsets & sunrise in your home away home.

Ocean Views at Ocean Pointe

Modern and Coastal Ocean Pointe 2307

🏝 Oceanfront Paradise Awaits You

Tropical Getaway
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Coral Castle
- Cannon Beach
- Calusa Beach & Loggerhead Beach
- Cocoa Plum Beach
- Theater of the Sea
- Conch Key
- Deering Estate
- Far Beach
- Everglades Alligator Farm
- Monkey Jungle
- Sea Oats Beach
- Long Key State Park
- Horseshoe Beach
- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Bahia Honda State Park
- Keys' Meads
- Sandspur Beach
- Schnebly Redland's Winery & Brewery