
House holiday rentals in Windley Key
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Top-rated house rentals in Windley Key
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Windley Key
House rentals with a pool

Overlooking Ocean/Marina Free Kayaks Pickleball

Paradise found!Key Colony Beach,Cabana Club.

Tiny Home on Waterfront | Bay Views | Deck | Pool

Florida Keys Cottage with Pool - Hawks Cay Resort

Chiquita Waterfront Canal Home

Waterfront House with 37 ft Dock & Cabana Club

Bohemian Beach Bungalow

Sunshine & Serenity on Waterfront, Tiki/50ft dock!
Weekly house rentals

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

Florida Keys Oceanside Utopia

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

Newely Renovated 3/2-private pool/dock/cabana club

Beach House, Private Pool & Dock, Gulf Sunset view

“La casa azul” step 3’ to a private pool

Golf Coast Oasis
Private house rentals

Updated Key Colony Tiki Hut-37.5 Dock-Cabana Club

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

Sombrero beach vacation oasis, great location

Keys to Ohana. Ocean views. Private Pool, Hot Tub

4BR 3B, Heated Pool & Spa, 60' Dock

Endless Summer

Waterfront Key Largo Home - Tropical Paradise

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