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 Fort Lauderdale
4.76 out of 5 average rating, 41 reviewsHome in Oakland park with pool
Home in Salinas
4.93 out of 5 average rating, 205 reviewsBeautiful House w private Pool
Home in Hollywood
4.79 out of 5 average rating, 121 reviewsAmazin spacious 4/2 Pool Home in Hollywood FLL-MIA
Home in Sarasota
4.95 out of 5 average rating, 94 reviewsBeautiful heated pool home, minutes from beaches
Home in San Juan
4.9 out of 5 average rating, 30 reviewsPool/3BR 11 min SJU airprt/beach
Home in Las Lomas #2
4.87 out of 5 average rating, 186 reviewsNature Getaway Resort with private pool
Home in Lehigh Acres
4.83 out of 5 average rating, 126 reviewsLIVING in PARADISE 🌴 ⛱️ 😎
Home in Oranjestad
4.92 out of 5 average rating, 138 reviewsVacation Home! Big Pool Area! Near Beaches&Center!
Apartment rentals with a pool
Apartment in Bradenton
5 out of 5 average rating, 4 reviewsLovely Condo, Heated Pools, AMI, IMG, Top beaches
Apartment in Fort Pierce
4.93 out of 5 average rating, 106 reviewsModern BEACH Condo in Peaceful Hutchinson Island
Apartment in Rockley
4.91 out of 5 average rating, 140 reviewsSpacious 2 Bedroom Luxury Condo.
Apartment in Boynton Beach
4.8 out of 5 average rating, 61 reviewsSerenity Ocean 2 Luxury condo —Parking Included
Apartment in Pompano Beach
4.92 out of 5 average rating, 245 reviewsON CANAL! Pool+Walk to BEACH! Boat Watch! 2b/2b
Apartment in Sarasota
4.97 out of 5 average rating, 59 reviewsPeaceful retreat, pool, hot tub, near Siesta Key!
Apartment in Prospect
4.81 out of 5 average rating, 21 reviewsSerene and Secure 2 Bedroom Condo with Pool and AC
Apartment in Kingston
4.78 out of 5 average rating, 115 reviewsLuxury Condo with Rooftop Pool & Private Balcony
Home rentals with a private pool
Home in Santo Domingo
4.94 out of 5 average rating, 383 reviewsGorgeous Colonial House near Cafes and Bars
Home in West Palm Beach
4.95 out of 5 average rating, 153 reviewsSoak up the Beachy Vibe at a Vibrant Poolside Paradise
Villa in Santo Domingo
4.93 out of 5 average rating, 313 reviewsCasa Pantheon Luxury Colonial House
Villa in Cartagena
4.87 out of 5 average rating, 144 reviewsOld City Villa - Breakfast & Housekeeping Included
Bungalow in Punta Cana
4.8 out of 5 average rating, 301 reviewsSink into the Pool of a Wonderful Bungalow
Townhouse in Cartagena
4.86 out of 5 average rating, 197 reviewsLuxurious Townhouse With Private Pool in The Old City
Apartment in San Juan
4.9 out of 5 average rating, 242 reviewsCondado Beach Vistas by Cesar 2501
Guest house in West Palm Beach
4.96 out of 5 average rating, 168 reviewsTropical Cabana with Pool in West Palm Beach
Destinations to explore
- Rentals with pools Cuba
- Fitness-friendly rentals Caribbean
- Hotel rentals Caribbean
- Earth house rentals Caribbean
- House rentals Caribbean
- Aparthotel rentals Caribbean
- Serviced apartment rentals Caribbean
- Beachfront rentals Caribbean
- Treehouse rentals Caribbean
- Rentals with an EV charger Caribbean
- Campsite rentals Caribbean
- Flat rentals Caribbean
- Waterfront rentals Caribbean
- Private suite rentals Caribbean
- Bed and breakfasts Caribbean
- Boutique hotel rentals Caribbean
- Boat rentals Caribbean
- Family-friendly rentals Caribbean
- Townhouse rentals Caribbean
- Villa rentals Caribbean
- Family-friendly rentals Caribbean
- Rentals with a washing machine and dryer Caribbean
- Guest house rentals Caribbean
- Tent rentals Caribbean
- Chalet rentals Caribbean
- Cottage rentals Caribbean
- Rentals with a cinema Caribbean
- Cabin rentals Caribbean
- Tiny house rentals Caribbean
- Rentals with an accessible-height toilet Caribbean
- Rentals with a firepit Caribbean
- Pet-friendly rentals Caribbean
- Rentals with an accessible-height bed Caribbean
- Nature eco lodge rentals Caribbean
- Luxury rentals Caribbean
- Island rentals Caribbean
- Bungalow rentals Caribbean
- Farm stay rentals Caribbean
- Loft rentals Caribbean
- Apartment rentals Caribbean
- Rentals with lake access Caribbean
- Rentals with beach access Caribbean
- Rentals with a fireplace Caribbean
- Houseboat rentals Caribbean
- Resort rentals Caribbean
- Rentals with a patio Caribbean
- Rentals with a sauna Caribbean
- Rentals with a kayak Caribbean
- Rentals with a balcony Caribbean
- Container rentals Caribbean
- Smoking-friendly rentals Caribbean
- Rentals with breakfast Caribbean
- Ski-in/ski-out rentals Caribbean
- Rentals with outdoor seating Caribbean
- Monthly Rentals Caribbean
- Rentals with a hot tub Caribbean
- Hostel rentals Caribbean
- Beach house rentals Caribbean
- Motorhome rentals Caribbean
- Dome rentals Caribbean
- Holiday home rentals Caribbean
- Rentals with pools Trinidad
- 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