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
Home in DO, Dominican Republic
4.92 out of 5 average rating, 306 reviewsBeautifull Guest House with panoramic views
Home in Cartagena, Colombia
4.95 out of 5 average rating, 172 reviewsCartagena walled casa Mónaco
Home in Naples, Florida
4.98 out of 5 average rating, 208 reviewsIsland lifestyle family vacation home (Salt Pool)
Home in Rincon, Puerto Rico
4.91 out of 5 average rating, 205 reviewsCasa Ensenada- Rincon Puerto Rico
Home in Lake Worth, Florida
4.97 out of 5 average rating, 158 reviewsTropical Beach Villa with Heated Salt Water Pool
Home in Adjuntas, Puerto Rico
4.97 out of 5 average rating, 183 reviewsSecluded Coffee Farm House w/Chimney & Heated Pool
Home in Isabela, Puerto Rico
4.98 out of 5 average rating, 168 reviewsCosta Bonita Beach House /With Solar System
Home in Stake Bay, Cayman Islands
5.0 out of 5 average rating, 37 reviewsModern Oceanfront, 2Primary Suites, sleeps 6, pool
Condo rentals with a pool
Condo in Playa Hermosa, Costa Rica
4.86 out of 5 average rating, 499 reviewsAmazing Oceanview Condo with Private Pool
Condo in Miami, Florida
4.8 out of 5 average rating, 102 reviewsNew Listing - Gorgeous Fontainebleau Sorrento 1BR
Condo in Miami, Florida
4.8 out of 5 average rating, 154 reviewsWaterfront Spacious Luxury 1 Bedroom IconBrickell
Condo in Bal Harbour, Florida
4.9 out of 5 average rating, 248 reviews$3 Million Oceanfront Residence ★★★★★ Resort
Condo in Carolina, Puerto Rico
4.99 out of 5 average rating, 136 reviewsBeach Front Condo with Endless Ocean Views
Condo in Carolina, Puerto Rico
4.92 out of 5 average rating, 188 reviewsBreathtaking Views, Beachfront, Remodeled!
Condo in Punta Cana, Dominican Republic
4.99 out of 5 average rating, 104 reviewsG38 Peaceful studio Oceanfront Punta Palmera
Condo in Punta Cana, Dominican Republic
4.95 out of 5 average rating, 111 reviewsSea view corner aptm with private pool / terrace
Home rentals with a private pool
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, 281 reviewsCasa Pantheon Luxury Colonial House
Townhouse in Cartagena, Colombia
4.87 out of 5 average rating, 176 reviewsLuxurious Townhouse With Private Pool in The Old City
Home in Santo Domingo, Dominican Republic
4.94 out of 5 average rating, 349 reviewsGorgeous Colonial House near Cafes and Bars
Villa in Cartagena, Colombia
4.86 out of 5 average rating, 135 reviewsOld City Luxury Villa - Staff & Cleaning Included
Loft in Rincon, Puerto Rico
4.98 out of 5 average rating, 252 reviewsWalk to Sandy Beach from a Hilltop Villa with a Pool
Guesthouse in West Palm Beach, Florida
4.99 out of 5 average rating, 154 reviewsTropical Cabana with Pool in West Palm Beach
Home in West Palm Beach, Florida
4.95 out of 5 average rating, 146 reviewsSoak up the Beachy Vibe at a Vibrant Poolside Paradise
Destinations to explore
- Rentals with pools Cuba
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- Aparthotel rentals Caribbean
- Vacation home rentals Caribbean
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- Bungalow rentals Caribbean
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- Fitness-friendly rentals Caribbean
- Hotel rentals Caribbean
- Rentals with a fireplace Caribbean
- Campsite rentals Caribbean
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- Apartment rentals Caribbean
- Pet-friendly rentals Caribbean
- Farmstay rentals Caribbean
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- Rentals with a patio Caribbean
- Rentals with a sauna Caribbean
- Condo rentals Caribbean
- Chalet rentals Caribbean
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- Rentals with a balcony Caribbean
- Rentals with a fire pit Caribbean
- Tiny house rentals Caribbean
- Rentals with outdoor seating Caribbean
- Treehouse rentals Caribbean
- Rentals with an accessible height toilet Caribbean
- Rentals with breakfast Caribbean
- Nature eco lodge rentals Caribbean
- Rentals with an accessible height bed Caribbean
- Beachfront rentals Caribbean
- Rentals with beach access Caribbean
- Cottage rentals Caribbean
- Luxury rentals Caribbean
- Wheelchair accessible rentals Caribbean
- Rentals with a hot tub Caribbean
- Guesthouse rentals Caribbean
- Rentals with a home theater Caribbean
- Serviced apartment rentals Caribbean
- Island rentals Caribbean
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- Townhouse rentals Caribbean
- Villa rentals Caribbean
- Rentals with a kayak Caribbean
- Beach house rentals Caribbean
- Tent rentals Caribbean
- Resort rentals Caribbean
- Monthly Rentals Caribbean
- Waterfront rentals Caribbean
- Shipping container rentals Caribbean
- Rentals with lake access Caribbean
- Yurt Rentals United States
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