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 Saint-Barthélemy
4.96 out of 5 average rating, 125 reviewsNorth Star
Home in Palm Beach
5 out of 5 average rating, 175 reviewsAruba Private Resort. Its All Yours and Only Yours
Home in Providenciales
4.96 out of 5 average rating, 299 reviewsVilla Cocuyo Micro Villa with pool
Home in San Cayetano de Venecia
4.96 out of 5 average rating, 143 reviewsQuinta La Ceiba Modern Home with Pool in DairyFarm
Home in Juana Diaz
4.96 out of 5 average rating, 235 reviewsLa Casa Alejandrina: Heated Pool + SeaView + Wi-Fi
Home in Jarabacoa
4.98 out of 5 average rating, 218 reviewsVilla Romantica for couples , jarabacielo
Home in DO
4.92 out of 5 average rating, 313 reviewsBeautifull Guest House with panoramic views
Home in Tower Isle
4.94 out of 5 average rating, 227 reviewsTranquil Times Villa
Condo rentals with a pool
Condo in Punta Cana
4.99 out of 5 average rating, 110 reviewsG38 Peaceful studio Oceanfront Punta Palmera
Condo in Montego Bay
4.94 out of 5 average rating, 101 reviews1br Lux Oceanfront 180 View Pool Beach Tennis Gym
Condo in East End
5 out of 5 average rating, 168 reviews"H2Oh What a Beach!" condo: Walk-out Beach Access!
Condo in East End
4.97 out of 5 average rating, 116 reviewsBeautiful corner unit condo right on the beach!
Condo in Montego Bay
4.92 out of 5 average rating, 374 reviewsJus' Beachy! Luxury Apt in a B/front Gated Cmnty.
Condo in Luquillo
4.88 out of 5 average rating, 255 reviewsBreathtaking Oceanfront and City View “Playa Luna”
Condo in Nassau
5 out of 5 average rating, 116 reviewsBeautiful Ocean Front 2BD/2BTH
Condo in Tower Isle
4.89 out of 5 average rating, 137 reviews2 bedroom Oceanfront condo with a pool
Home rentals with a private pool
Bungalow in Punta Cana
4.86 out of 5 average rating, 195 reviewsLush and Tropical Bungalow
Villa in Santo Domingo
4.93 out of 5 average rating, 293 reviewsCasa Pantheon Luxury Colonial House
Cottage in La Romana
5 out of 5 average rating, 145 reviewsChic Cottage Nature Casa de Campo
Guesthouse in West Palm Beach
4.96 out of 5 average rating, 158 reviewsTropical Cabana with Pool in West Palm Beach
Home in West Palm Beach
4.95 out of 5 average rating, 149 reviewsSoak up the Beachy Vibe at a Vibrant Poolside Paradise
Loft in Rincon
4.98 out of 5 average rating, 256 reviewsWalk to Sandy Beach from a Hilltop Villa with a Pool
Home in Santo Domingo
4.94 out of 5 average rating, 359 reviewsGorgeous Colonial House near Cafes and Bars
Townhouse in Cartagena
4.87 out of 5 average rating, 183 reviewsLuxurious Townhouse With Private Pool in The Old City
Destinations to explore
- Rentals with pools Cuba
- Campsite rentals Caribbean
- Private suite rentals Caribbean
- Ski-in/ski-out rentals Caribbean
- Rentals with a fireplace Caribbean
- Apartment rentals Caribbean
- Nature eco lodge rentals Caribbean
- Kid-friendly rentals Caribbean
- Rentals with a washer and dryer Caribbean
- Rentals with breakfast Caribbean
- Boat rentals Caribbean
- Family-friendly rentals Caribbean
- Townhouse rentals Caribbean
- Villa rentals Caribbean
- Guesthouse rentals Caribbean
- Cabin rentals Caribbean
- Serviced apartment rentals Caribbean
- Earth house rentals Caribbean
- Houseboat rentals Caribbean
- Treehouse rentals Caribbean
- Fitness-friendly rentals Caribbean
- Hotel rentals Caribbean
- RV rentals Caribbean
- Cottage rentals Caribbean
- Aparthotel rentals Caribbean
- Rentals with beach access Caribbean
- Luxury rentals Caribbean
- Resort rentals Caribbean
- Smoking-friendly rentals Caribbean
- Bungalow rentals Caribbean
- Bed and breakfasts Caribbean
- House rentals Caribbean
- Castle rentals Caribbean
- Rentals with an EV charger Caribbean
- Rentals with a fire pit Caribbean
- Tiny house rentals Caribbean
- Pet-friendly rentals Caribbean
- Vacation home rentals Caribbean
- Rentals with a patio Caribbean
- Rentals with a sauna Caribbean
- Rentals with a balcony Caribbean
- Beach house rentals Caribbean
- Boutique hotel rentals Caribbean
- Rentals with a home theater Caribbean
- Condo rentals Caribbean
- Beachfront rentals Caribbean
- Farmstay rentals Caribbean
- Loft rentals Caribbean
- Shipping container rentals Caribbean
- Chalet rentals Caribbean
- Tent rentals Caribbean
- Rentals with outdoor seating Caribbean
- Island rentals Caribbean
- Rentals with an accessible height toilet Caribbean
- Monthly Rentals Caribbean
- Hostel rentals Caribbean
- Rentals with lake access Caribbean
- Waterfront rentals Caribbean
- Rentals with a hot tub Caribbean
- Rentals with a kayak Caribbean
- Rentals with an accessible height bed 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
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom