
Holiday rentals with a pool in Florida Keys
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Florida Keys
Guests agree: These homes with a pool 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 Florida Keys rentals with a pool
House rentals with a pool

Waterfront Escape -VACA-23-408

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

Cancellation Deal: 08/02 thru 08/09

Grouper Getaway @ Ocean Isles Fishing Village

Waterfront 2-bedroom Home w/Pool and Spa

Oceanfront with Pool near Sombrero Beach

Waterfront Home 37.5-ft dock, Cabana Club Included

Beach House, Private Pool & Dock, Gulf Sunset view
Condo rentals with a pool

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Your Happy Place - Oceanfront

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

2B/2B w Water View ⢠FREE Parking ⢠Pool ⢠Lux Spa

Beachside Unit 33-Private Tropical Beach Plus Pool

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba

Best View Ocean Pointe Pool Beach King Bed, Gated
Home rentals with a private pool

Casa Lucia 5br Home W/ Pool Near Hard Rock Casino

Sandcastle of Marco Island Waterfront Private Pool

Incredible Beach Getaway Condo W Resort Amenities

Magnificent Gulf View Condo

Lighthouse 1124

New! Gulf-View Condo with Resort-Style Amenities

Private 2br Side Ocean View at Hyde Beach Resort
Destinations to explore
- Miami Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Key West Holiday rentals
- Havana Holiday rentals
- Central Florida Holiday rentals
- Tampa Bay Holiday rentals
- Kissimmee Holiday rentals
- St Petersburg Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Rentals with outdoor seating Florida Keys
- Rentals with an accessible height toilet Florida Keys
- Ski-in/ski-out rentals Florida Keys
- Condo rentals Florida Keys
- Guesthouse rentals Florida Keys
- Mansion rentals Florida Keys
- Rentals with an accessible height bed Florida Keys
- Resort rentals Florida Keys
- Kid-friendly rentals Florida Keys
- Fitness-friendly rentals Florida Keys
- Campsite rentals Florida Keys
- Boutique hotel rentals Florida Keys
- Rentals with a patio Florida Keys
- RV rentals Florida Keys
- Townhouse rentals Florida Keys
- Family-friendly rentals Florida Keys
- Private suite rentals Florida Keys
- Waterfront rentals Florida Keys
- Houseboat rentals Florida Keys
- Cottage rentals Florida Keys
- Tiny house rentals Florida Keys
- Rentals with a home theatre Florida Keys
- Beach condo rentals Florida Keys
- Rentals with a kayak Florida Keys
- Rentals with lake access Florida Keys
- Bungalow rentals Florida Keys
- Rentals with a hot tub Florida Keys
- House rentals Florida Keys
- Rentals with a fire pit Florida Keys
- Rentals with a fireplace Florida Keys
- Apartment rentals Florida Keys
- Rentals with breakfast Florida Keys
- Serviced apartment rentals Florida Keys
- Rentals with a sauna Florida Keys
- Bed and breakfasts Florida Keys
- Smoking-friendly rentals Florida Keys
- Villa rentals Florida Keys
- Rentals with an EV charger Florida Keys
- Beach house rentals Florida Keys
- Pet-friendly rentals Florida Keys
- Rentals with beach access Florida Keys
- Luxury rentals Florida Keys
- Rentals with a washing machine and dryer Florida Keys
- Hotel rentals Florida Keys
- Beachfront rentals Florida Keys
- Rentals with pools Florida
- Rentals with pools United States
- 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
- Bayfront Park
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Trump National Doral Miami
- Crandon Beach
- Phillip and Patricia Frost Museum of Science
- Key Biscayne Beach
- Coral Castle
- Biscayne National Park
- Hobie Island Beach Park North
- Cannon Beach
- Biltmore Golf Course Miami
- Conch Key
- Fairchild Tropical Botanic Garden
- Venetian Pool
- Miami Seaquarium
- Theater of the Sea
- Matheson Hammock Park
- Everglades Alligator Farm
- EAA Air Museum
- Cocoa Plum Beach
- Darwin Beach
- Things to do Florida Keys
- Art and culture Florida Keys
- Sports activities Florida Keys
- Tours Florida Keys
- Sightseeing Florida Keys
- Things to do Florida
- Art and culture Florida
- Wellness Florida
- Sightseeing Florida
- Tours Florida
- Nature and outdoors Florida
- Entertainment Florida
- Food and drink Florida
- Sports activities Florida
- Things to do United States
- Food and drink United States
- Sightseeing United States
- Sports activities United States
- Entertainment United States
- Tours United States
- Art and culture United States
- Wellness United States
- Nature and outdoors United States