House vacation rentals in Windley Key
Find and book unique houses on Airbnb
Top-rated house rentals in Windley Key
Guests agree: these houses 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 house rentals
House rentals with a pool
Home in Key Largo
4.88 out of 5 average rating, 164 reviewsOutdoor Paradise - Beach, Boats, Snorkeling & Sun!
Jan 7 – 14
Home in Key Colony Beach
4.81 out of 5 average rating, 132 reviewsWaterview from three sides, Cabana Club, 30' Docks
Dec 16 – 23
Home in Islamorada
4.83 out of 5 average rating, 53 reviewsOceanfront 114 Anglers Reef Islamorada Fla Keys
Feb 1 – 8
Home in Key Largo
5.0 out of 5 average rating, 50 reviewsThe Paradise 2
Nov 8 – 15
Home in Islamorada
4.94 out of 5 average rating, 18 reviews3 Lux Ensuites Walk/Boat Island!
Mar 29 – Apr 5
Home in Marathon
5.0 out of 5 average rating, 16 reviewsHorizon
Aug 31 – Sep 7
Home in Marathon
4.97 out of 5 average rating, 33 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Dec 14 – 21
Home in Islamorada
4.96 out of 5 average rating, 57 reviewsTropical Getaway 3/3 with 100’ boat dock and pool
Oct 2 – 9
Weekly house rentals
Home in Key Largo
4.99 out of 5 average rating, 74 reviewsLittle Cottage on an island
Jul 18 – 25
Home in Key Largo
4.97 out of 5 average rating, 32 reviewsTreetops
Sep 9 – 14
Home in Key Largo
5.0 out of 5 average rating, 14 reviewsPrivate 1 Acre House~Private Beach~Tiki Hut~Dock
Dec 14 – 21
Home in Key Largo
4.97 out of 5 average rating, 60 reviewsLuxury Heated Pool/Jacuzzi, Games & Nice Backyard.
Aug 16 – 23
Home in Marathon
4.97 out of 5 average rating, 35 reviewsThe Gulf Cottage at Marathon Key
Jun 29 – Jul 6
Home in Key Largo
4.93 out of 5 average rating, 15 reviewsKeys Paradise 3/3 Waterfront, Jacuzzi, Kayaks+More
Nov 7 – 14
Home in Key Largo
4.93 out of 5 average rating, 55 reviewsOcean Breeze Home
Oct 15 – 22
Home in Key Colony Beach
5.0 out of 5 average rating, 15 reviewsCoral House: 2/2 Waterfront in KCB w/ King Beds
May 11 – 18
Private house rentals
Home in Marathon
5.0 out of 5 average rating, 24 reviewsCoral Lagoon #23- Private Home with Boat Slip
Nov 5 – 12
Home in Key Colony Beach
4.98 out of 5 average rating, 51 reviewsCaptain’s Quarters Ahoy Mateys! Florida, Keys
Oct 3 – 10
Home in Key Largo
4.95 out of 5 average rating, 57 reviewsLittle Peace of Haven
Jun 6 – 13
Home in Key Largo
4.86 out of 5 average rating, 80 reviewsCary’s Oceanside
Dec 8 – 15
Home in Marathon
5.0 out of 5 average rating, 9 reviewsOceanfront *PARADiSE* Amazing views, pool, dock
Feb 1 – 8
Home in Key Colony Beach
5.0 out of 5 average rating, 65 reviews“La casa azul” step 3’ to a private pool
Nov 2 – 9
Home in Key Largo
4.92 out of 5 average rating, 87 reviewsSunsets In Palms Paradise
Jan 6 – 13
Home in Marathon
5.0 out of 5 average rating, 15 reviewsFlorida Keys Oceanside Utopia
Nov 11 – 18
Destinations to explore
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Key West Vacation rentals
- Fort Lauderdale Vacation rentals
- Boca Raton Vacation rentals
- Naples Vacation rentals
- West Palm Beach Vacation rentals
- Varadero Vacation rentals
- Havana Vacation rentals
- Nassau Vacation rentals
- Sarasota Vacation rentals
- Anna Maria Island Vacation rentals
- Beach house rentals Miami
- Townhouse rentals Miami
- Tiny house rentals Miami
- House rentals Miami
- Guesthouse rentals Miami
- Guesthouse rentals United States
- Townhouse rentals United States
- House rentals United States
- Earth house rentals United States
- Lighthouse rentals United States
- Guesthouse rentals Miami Beach
- Beach house rentals Miami Beach
- House rentals Miami Beach
- Townhouse rentals Miami Beach
- Townhouse rentals Florida
- Beach house rentals Florida
- Lakehouse rentals Florida
- Tiny house rentals Florida
- Guesthouse rentals Florida
- House rentals Florida
- Beach house rentals Fort Lauderdale
- Guesthouse rentals Fort Lauderdale
- Townhouse rentals Fort Lauderdale
- House rentals Fort Lauderdale
- Guesthouse rentals Monroe County
- Tiny house rentals Monroe County
- Townhouse rentals Monroe County
- House rentals Monroe County
- Rentals with pools Windley Key
- Rentals with outdoor seating Windley Key
- Rentals with beach access Windley Key
- Family-friendly rentals Windley Key
- Rentals with a patio Windley Key
- Fitness-friendly rentals Windley Key
- Pet-friendly rentals Windley Key
- Waterfront rentals Windley Key
- Monthly Rentals Windley Key
- Rentals with a washer and dryer Windley Key
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom