
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

Sandbox

Waterfront Miami Oasis w/ Kayaks | Heated Pool

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

Oceanfront with Pool near Sombrero Beach

Spacious lux home, private pool/spa, 80' dock

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

Amazing Bayfront New House with Dock and Pool!
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

🏝 Oceanfront Paradise Awaits You

Beachside Unit 33-Private Tropical Beach Plus Pool

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba
Home rentals with a 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
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- 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
- Cocoa Plum Beach
- EAA Air Museum
- Darwin Beach
- Things to do Florida Keys
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