Holiday 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.
Holiday 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
Home in DO, Dominican Republic
4.92 out of 5 average rating, 309 reviewsBeautifull Guest House with panoramic views
Home in Sarasota, Florida, US
4.94 out of 5 average rating, 154 reviewsModern, Bright Downtown SRQ A-Frame West of Trail
Home in Playa Tivives, Costa Rica
4.97 out of 5 average rating, 187 reviewsLovely beachfront family house with private pool
Home in Cartagena, Colombia
4.95 out of 5 average rating, 173 reviewsCartagena walled casa Mónaco
Home in Naples, Florida, US
4.97 out of 5 average rating, 210 reviewsIsland lifestyle family vacation home (Salt Pool)
Home in Rincon, Puerto Rico
4.91 out of 5 average rating, 207 reviewsCasa Ensenada- Rincon Puerto Rico
Home in Lake Worth, Florida, US
4.97 out of 5 average rating, 159 reviewsTropical Beach Villa with Heated Salt Water Pool
Home in Adjuntas, Puerto Rico
4.97 out of 5 average rating, 185 reviewsSecluded Coffee Farm House w/Chimney & Heated Pool
Apartment rentals with a pool
Apartment in Playa Hermosa, Costa Rica
4.86 out of 5 average rating, 500 reviewsAmazing Oceanview Condo with Private Pool
Apartment in Miami, Florida, US
4.81 out of 5 average rating, 105 reviewsNew Listing - Gorgeous Fontainebleau Sorrento 1BR
Apartment in Miami, Florida, US
4.8 out of 5 average rating, 155 reviewsWaterfront Spacious Luxury 1 Bedroom IconBrickell
Apartment in Bal Harbour, Florida, US
4.9 out of 5 average rating, 248 reviews3MM Oceanfront Residence Finest Bal Harbour Resort
Apartment in Carolina, Puerto Rico
4.99 out of 5 average rating, 138 reviewsBeach Front Condo with Endless Ocean Views
Apartment in Carolina, Puerto Rico
4.92 out of 5 average rating, 189 reviewsBreathtaking Views, Beachfront, Remodeled!
Apartment in Punta Cana, Dominican Republic
4.99 out of 5 average rating, 105 reviewsG38 Peaceful studio Oceanfront Punta Palmera
Apartment in Punta Cana, Dominican Republic
4.96 out of 5 average rating, 113 reviewsSea view corner aptm with private pool / terrace
Home rentals with a private pool
Cottage in La Romana, Dominican Republic
5.0 out of 5 average rating, 143 reviewsChic Cottage Nature Casa de Campo
Bungalow in Punta Cana, Dominican Republic
4.86 out of 5 average rating, 195 reviewsLush and Tropical Bungalow
Villa in Santo Domingo, Dominican Republic
4.93 out of 5 average rating, 284 reviewsCasa Pantheon Luxury Colonial House
Townhouse in Cartagena, Colombia
4.87 out of 5 average rating, 179 reviewsLuxurious Townhouse With Private Pool in The Old City
Villa in Cartagena, Colombia
4.86 out of 5 average rating, 135 reviewsVilla Old City, Butler & Breakfast Included
Loft in Rincon, Puerto Rico
4.98 out of 5 average rating, 253 reviewsWalk to Sandy Beach from a Hilltop Villa with a Pool
Guest house in West Palm Beach, Florida, US
4.99 out of 5 average rating, 155 reviewsTropical Cabana with Pool in West Palm Beach
Home in West Palm Beach, Florida, US
4.95 out of 5 average rating, 147 reviewsSoak up the Beachy Vibe at a Vibrant Poolside Paradise
Destinations to explore
- Rentals with pools Cuba
- Serviced apartment rentals Caribbean
- Motorhome rentals Caribbean
- Pet-friendly rentals Caribbean
- House rentals Caribbean
- Cabin rentals Caribbean
- Earth house rentals Caribbean
- Boutique hotel rentals Caribbean
- Rentals with a patio Caribbean
- Rentals with a sauna Caribbean
- Rentals with a firepit Caribbean
- Ski-in/ski-out rentals Caribbean
- Bed and breakfasts Caribbean
- Rentals with beach access Caribbean
- Flat rentals Caribbean
- Luxury rentals Caribbean
- Rentals with breakfast Caribbean
- Guest house rentals Caribbean
- Rentals with a kayak Caribbean
- Boat rentals Caribbean
- Family-friendly rentals Caribbean
- Townhouse rentals Caribbean
- Villa rentals Caribbean
- Houseboat rentals Caribbean
- Private suite rentals Caribbean
- Smoking-friendly rentals Caribbean
- Holiday home rentals Caribbean
- Fitness-friendly rentals Caribbean
- Hotel rentals Caribbean
- Treehouse rentals Caribbean
- Nature eco lodge rentals Caribbean
- Aparthotel rentals Caribbean
- Cottage rentals Caribbean
- Castle rentals Caribbean
- Dome rentals Caribbean
- Rentals with an EV charger Caribbean
- Tent rentals Caribbean
- Family-friendly rentals Caribbean
- Rentals with a washing machine and dryer Caribbean
- Monthly Rentals Caribbean
- Rentals with a fireplace Caribbean
- Waterfront rentals Caribbean
- Campsite rentals Caribbean
- Tiny house rentals Caribbean
- Apartment rentals Caribbean
- Beachfront rentals Caribbean
- Chalet rentals Caribbean
- Resort rentals Caribbean
- Rentals with an accessible-height bed Caribbean
- Rentals with outdoor seating Caribbean
- Hostel rentals Caribbean
- Farm stay rentals Caribbean
- Loft rentals Caribbean
- Container rentals Caribbean
- Beach house rentals Caribbean
- Rentals with an accessible-height toilet Caribbean
- Wheelchair-accessible rentals Caribbean
- Island rentals Caribbean
- Rentals with a balcony Caribbean
- Rentals with a cinema Caribbean
- Rentals with lake access Caribbean
- Bungalow rentals Caribbean
- Rentals with a hot tub Caribbean
- 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