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
4.76 out of 5 average rating, 41 reviewsHome in Oakland park with pool
Home
4.93 out of 5 average rating, 205 reviewsBeautiful House w private Pool
Home
4.96 out of 5 average rating, 56 reviews2223 Doud Street, Sarasota, FL
Home
4.9 out of 5 average rating, 29 reviewsPool/3BR 11 min SJU airprt/beach
Home
4.87 out of 5 average rating, 186 reviewsNature Getaway Resort with private pool
Home
4.97 out of 5 average rating, 31 reviewsHidden Gem in Miami with Heated Pool
Home
4.83 out of 5 average rating, 126 reviewsLIVING in PARADISE 🌴 ⛱️ 😎
Home
4.92 out of 5 average rating, 49 reviewsKING SUITE | BlG PRlVATE Backyard w. Pool | 2 LVRM
Apartment rentals with a pool
Apartment
4.93 out of 5 average rating, 106 reviewsModern BEACH Condo in Peaceful Hutchinson Island
Apartment
4.91 out of 5 average rating, 140 reviewsSpacious 2 Bedroom Luxury Condo.
Apartment
4.8 out of 5 average rating, 61 reviewsSerenity Ocean 2 Luxury condo —Parking Included
Apartment
4.87 out of 5 average rating, 71 reviews3 BDR Condo w/pool, walk to beach & restaurants
Apartment
4.92 out of 5 average rating, 243 reviewsON CANAL! Pool+Walk to BEACH! Boat Watch! 2b/2b
Apartment
4.97 out of 5 average rating, 59 reviewsPeaceful retreat, pool, hot tub, near Siesta Key!
Apartment
4.81 out of 5 average rating, 21 reviewsSerene and Secure 2 Bedroom Condo with Pool and AC
Apartment
4.78 out of 5 average rating, 114 reviewsLuxury Condo with Rooftop Pool & Private Balcony
Home rentals with a private pool
Home
4.94 out of 5 average rating, 383 reviewsGorgeous Colonial House near Cafes and Bars
Home
4.95 out of 5 average rating, 153 reviewsSoak up the Beachy Vibe at a Vibrant Poolside Paradise
Villa
4.93 out of 5 average rating, 313 reviewsCasa Pantheon Luxury Colonial House
Villa
4.87 out of 5 average rating, 144 reviewsOld City Villa - Breakfast & Housekeeping Included
Bungalow
4.8 out of 5 average rating, 300 reviewsSink into the Pool of a Wonderful Bungalow
Townhouse
4.86 out of 5 average rating, 197 reviewsLuxurious Townhouse With Private Pool in The Old City
Villa
4.95 out of 5 average rating, 22 reviewsTropical Retreat - Private Pool, Steps to Beach
Apartment
4.9 out of 5 average rating, 242 reviewsCondado Beach Vistas by Cesar 2501
Destinations to explore
- Rentals with pools Cuba
- Serviced apartment rentals Caribbean
- Rentals with a fireplace Caribbean
- Bungalow rentals Caribbean
- Motorhome rentals Caribbean
- Tiny house rentals Caribbean
- Rentals with beach access Caribbean
- Resort rentals Caribbean
- Rentals with a firepit Caribbean
- Pet-friendly rentals Caribbean
- Monthly Rentals Caribbean
- Guest house rentals Caribbean
- Rentals with lake access Caribbean
- Rentals with an accessible-height bed Caribbean
- Boat rentals Caribbean
- Family-friendly rentals Caribbean
- Townhouse rentals Caribbean
- Villa rentals Caribbean
- Nature eco lodge rentals Caribbean
- Cottage rentals Caribbean
- Rentals with a cinema Caribbean
- Rentals with an accessible-height toilet Caribbean
- Houseboat rentals Caribbean
- Earth house rentals Caribbean
- Bed and breakfasts Caribbean
- Treehouse rentals Caribbean
- Fitness-friendly rentals Caribbean
- Hotel rentals Caribbean
- Luxury rentals Caribbean
- Rentals with a balcony Caribbean
- Campsite rentals Caribbean
- Holiday home rentals Caribbean
- Container rentals Caribbean
- Flat rentals Caribbean
- Rentals with a hot tub Caribbean
- Rentals with an EV charger Caribbean
- Waterfront rentals Caribbean
- Beach house rentals Caribbean
- Aparthotel rentals Caribbean
- Smoking-friendly rentals Caribbean
- Private suite rentals Caribbean
- Rentals with a kayak Caribbean
- Ski-in/ski-out rentals Caribbean
- Tent rentals Caribbean
- Island rentals Caribbean
- Chalet rentals Caribbean
- Farm stay rentals Caribbean
- Loft rentals Caribbean
- Rentals with breakfast Caribbean
- Dome rentals Caribbean
- Hostel rentals Caribbean
- Cabin rentals Caribbean
- Beachfront rentals Caribbean
- Rentals with outdoor seating Caribbean
- Apartment rentals Caribbean
- Boutique hotel rentals Caribbean
- Family-friendly rentals Caribbean
- Rentals with a washing machine and dryer Caribbean
- Rentals with a patio Caribbean
- Rentals with a sauna Caribbean
- House 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