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
4.93 out of 5 average rating, 335 reviewsBeautifull Guest House with panoramic views
Home in Paradera
4.99 out of 5 average rating, 172 reviewsAirstream With Amazing Pool, Ocean & Nature Views
Home in Sosua
4.96 out of 5 average rating, 163 reviewsCasa Cascada
Home in Grace Bay
4.96 out of 5 average rating, 141 reviewsFollow Your Dreams Villa!
Home in San Cayetano de Venecia
4.96 out of 5 average rating, 159 reviewsQuinta La Ceiba Modern Home with Pool in DairyFarm
Home in Governor's Harbour
4.97 out of 5 average rating, 108 reviewsCayo Loco Beachfront Villa Deserted PinkSand for 2
Home in Anse La Raye
4.94 out of 5 average rating, 102 reviewsBrigand Hill: Full staff included
Home in Tower Isle
4.94 out of 5 average rating, 245 reviewsTranquil Times Villa
Apartment rentals with a pool
Apartment in East End
5 out of 5 average rating, 173 reviews"H2Oh What a Beach!" condo: Walk-out Beach Access!
Apartment in Siesta Key
4.96 out of 5 average rating, 296 reviewsWE ARE OPEN—On the Beach; Siesta Key SunBum Studio
Apartment in Oranjestad
4.95 out of 5 average rating, 151 reviewsModern apt ,EagleBeach,Sea view,Oasis condominium
Apartment in Montego Bay
4.92 out of 5 average rating, 387 reviewsJus' Beachy Luxury Apt in a B/front Gated Cmnty.
Apartment in Montego Bay
4.94 out of 5 average rating, 113 reviews1br Lux Oceanfront 180 View Pool Beach Tennis Gym
Apartment in East End Tortola
4.85 out of 5 average rating, 162 reviewsGreenLeafOasis #1 | Turquoise Ocean Views
Apartment in Playa El Cortecito, Bavaro, Provincia La Altagracia
4.98 out of 5 average rating, 146 reviewsSandyDreams BeachFront 1BD/2BR
Apartment in Noord
5 out of 5 average rating, 104 reviewsAruba Oceanfront Top Floor Condo Eagle Beach
Home rentals with a private pool
Home in Santo Domingo
4.94 out of 5 average rating, 379 reviewsGorgeous Colonial House near Cafes and Bars
Home in Port St. Lucie
5 out of 5 average rating, 94 reviewsLush Waterfront Home On Bay St. Lucie
Home in West Palm Beach
4.95 out of 5 average rating, 152 reviewsSoak up the Beachy Vibe at a Vibrant Poolside Paradise
Villa in Santo Domingo
4.93 out of 5 average rating, 312 reviewsCasa Pantheon Luxury Colonial House
Villa in Cartagena
4.87 out of 5 average rating, 141 reviewsOld City Villa - Breakfast & Housekeeping Included
Bungalow in Punta Cana
4.79 out of 5 average rating, 296 reviewsSink into the Pool of a Wonderful Bungalow
Townhouse in Cartagena
4.87 out of 5 average rating, 194 reviewsLuxurious Townhouse With Private Pool in The Old City
Apartment in San Juan
4.9 out of 5 average rating, 238 reviewsCondado Beach Vistas by Cesar 2501
Destinations to explore
- Rentals with pools Cuba
- Treehouse rentals Caribbean
- Aparthotel rentals Caribbean
- Smoking-friendly rentals Caribbean
- Private suite rentals Caribbean
- Earth house rentals Caribbean
- Boat rentals Caribbean
- Family-friendly rentals Caribbean
- Townhouse rentals Caribbean
- Villa rentals Caribbean
- Tent rentals Caribbean
- Rentals with a patio Caribbean
- Rentals with a sauna Caribbean
- Rentals with outdoor seating Caribbean
- Flat rentals Caribbean
- Holiday home rentals Caribbean
- Rentals with a firepit Caribbean
- Houseboat rentals Caribbean
- Bed and breakfasts Caribbean
- Rentals with breakfast Caribbean
- Rentals with an accessible-height bed Caribbean
- Rentals with an EV charger Caribbean
- Rentals with a balcony Caribbean
- Beachfront rentals Caribbean
- Ski-in/ski-out rentals Caribbean
- Fitness-friendly rentals Caribbean
- Hotel rentals Caribbean
- Rentals with a cinema Caribbean
- Waterfront rentals Caribbean
- Rentals with beach access Caribbean
- Luxury rentals Caribbean
- Cabin rentals Caribbean
- Cottage rentals Caribbean
- Campsite rentals Caribbean
- Chalet rentals Caribbean
- Container rentals Caribbean
- Nature eco lodge rentals Caribbean
- Boutique hotel rentals Caribbean
- Motorhome rentals Caribbean
- Island rentals Caribbean
- Farm stay rentals Caribbean
- Loft rentals Caribbean
- Tiny house rentals Caribbean
- Rentals with a hot tub Caribbean
- Beach house rentals Caribbean
- Resort rentals Caribbean
- Rentals with a fireplace Caribbean
- Monthly Rentals Caribbean
- Family-friendly rentals Caribbean
- Rentals with a washing machine and dryer Caribbean
- Pet-friendly rentals Caribbean
- Guest house rentals Caribbean
- Rentals with lake access Caribbean
- Apartment rentals Caribbean
- Hostel rentals Caribbean
- Bungalow rentals Caribbean
- Rentals with a kayak Caribbean
- Serviced apartment rentals Caribbean
- House rentals Caribbean
- Rentals with an accessible-height toilet 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