
Vacation rentals with a pool in Caribbean
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Caribbean
Guests agree: these homes with a pool 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 Caribbean rentals with a pool
House rentals with a pool

•Floasis• Your private FL oasis 5 min to beach!

Casa Cascada

"Seaside Luxury" - Ocean Front, Private Pool, Wifi

Villa Jeremi

Cayo Loco Villa 2 Deserted PinkSand Beach 2 Adults

Etoile du Nord

VeoMar - Casita Axel 4 bdr villa w/ endless views

La Casa Alejandrina: Pool + Sea View + Wi-Fi
Condo rentals with a pool

The Ocean Ridge - Ocho Rios, Stunning Sea Views

VIEWS! Condo by Magen's Beach w/ POOL & generator

ON CANAL! Pool+Walk to BEACH! Boat Watch! 1b/1b

Aruba Oceanfront Top Floor Condo Eagle Beach

Beachfront • King • W/D • By RH • Pool • Marina

Lux 2BR • Water View • Pool • Spa • FREE Parking

Purapura _Jungle House w/ pool, walk to beach

Gorgeous 1 Bdrm 1 Bath - Magical City Views
Home rentals with a private pool

Gorgeous Colonial House near Cafes and Bars

Soak up the Beachy Vibe at a Vibrant Poolside Paradise

Casa Pantheon Luxury Colonial House

Old City Villa - Breakfast & Housekeeping Included
Walled City Luxurious Townhouse With Private Pool

Condado Beach Views by Cesar 2501

Tropical Cabana with Pool in West Palm Beach

Beachfront Condo With Private Pool, Patio & Resort Access
Destinations to explore
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