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.
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Popular amenities for Caribbean rentals with a pool
House rentals with a pool
Home in San Cayetano de Venecia, Costa Rica
4.96 out of 5 average rating, 134 reviewsQuinta La Ceiba Modern Home with Pool in DairyFarm
26 Oct – 2 Nov
Home in Playa Tivives, Costa Rica
4.97 out of 5 average rating, 186 reviewsLovely beachfront family house with private pool
1–8 Oct
Home in Cartagena, Colombia
4.95 out of 5 average rating, 171 reviewsCartagena walled casa Mónaco
13–20 Apr
Home in Naples, Florida, US
4.98 out of 5 average rating, 206 reviewsIsland lifestyle family vacation home (Salt Pool)
25 Oct – 1 Nov
Home in Rincon, Puerto Rico
4.91 out of 5 average rating, 205 reviewsCasa Ensenada- Rincon Puerto Rico
24 Sep – 1 Oct
Home in Adjuntas, Puerto Rico
4.97 out of 5 average rating, 183 reviewsSecluded Coffee Farm House w/Chimney & Heated Pool
14–21 Nov
Home in Lake Worth, Florida, US
4.97 out of 5 average rating, 156 reviewsTropical Beach Villa with Heated Salt Water Pool
1–8 Sep
Home in Stake Bay, Cayman Islands
5.0 out of 5 average rating, 36 reviewsModern Oceanfront, 2Primary Suites, sleeps 6, pool
12–19 Apr
Apartment rentals with a pool
Apartment in Playa Hermosa, Costa Rica
4.86 out of 5 average rating, 499 reviewsAmazing Oceanview Condo with Private Pool
27 Mar – 3 Apr
Apartment in Miami, Florida, US
4.8 out of 5 average rating, 154 reviewsWaterfront Spacious Luxury 1 Bedroom IconBrickell
15–22 Oct
Apartment in Carolina, Puerto Rico
4.99 out of 5 average rating, 135 reviewsBeach Front Condo with Endless Ocean Views
27 Mar – 3 Apr
Apartment in Bal Harbour, Florida, US
4.9 out of 5 average rating, 247 reviews$3 Million Oceanfront Residence ★★★★★ Resort
19–26 Aug
Apartment in Carolina, Puerto Rico
4.92 out of 5 average rating, 186 reviewsBreathtaking Views, Beachfront, Remodeled!
21–28 Oct
Apartment in Punta Cana, Dominican Republic
4.99 out of 5 average rating, 104 reviewsG38 Peaceful studio Oceanfront Punta Palmera
21–28 Feb
Apartment in Punta Cana, Dominican Republic
4.95 out of 5 average rating, 107 reviewsSea view corner aptm with private pool / terrace
9–16 Mar
Apartment in Sosúa, Dominican Republic
4.96 out of 5 average rating, 110 reviewsHeavenly Luxury Ocean View Beach Front Penthouse
18–25 Jul
Home rentals with a private pool
Cottage in La Romana, Dominican Republic
5.0 out of 5 average rating, 141 reviewsChic Cottage Nature Casa de Campo
4–11 Jun
Bungalow in Punta Cana, Dominican Republic
4.86 out of 5 average rating, 194 reviewsLush and Tropical Bungalow
1–8 Jul
Home in Santo Domingo, Dominican Republic
4.95 out of 5 average rating, 347 reviewsGorgeous Colonial House near Cafes and Bars
4–11 Oct
Townhouse in Cartagena, Colombia
4.87 out of 5 average rating, 176 reviewsLuxurious Townhouse With Private Pool in The Old City
21–28 Nov
Villa in Cartagena, Colombia
4.86 out of 5 average rating, 135 reviewsOld City Luxury Villa - Staff & Breakfast Included
17–24 Dec
Loft in Rincon, Puerto Rico
4.98 out of 5 average rating, 251 reviewsWalk to Sandy Beach from a Hilltop Villa with a Pool
5–12 Oct
Guest house in West Palm Beach, Florida, US
4.99 out of 5 average rating, 154 reviewsTropical Cabana with Pool in West Palm Beach
22–29 Nov
Home in West Palm Beach, Florida, US
4.95 out of 5 average rating, 146 reviewsSoak up the Beachy Vibe at a Vibrant Poolside Paradise
24 Jun – 1 Jul
Destinations to explore
- Rentals with pools Cuba
- Family-friendly rentals Caribbean
- Tiny house rentals Caribbean
- Guest house rentals Caribbean
- Ski-in/ski-out rentals Caribbean
- Cabin rentals Caribbean
- Rentals with a cinema Caribbean
- Bed and breakfasts Caribbean
- Campsite rentals Caribbean
- Beach house rentals Caribbean
- Earth house rentals Caribbean
- Villa rentals Caribbean
- Pet-friendly rentals Caribbean
- Houseboat rentals Caribbean
- Rentals with an accessible-height bed Caribbean
- Rentals with a fireplace Caribbean
- Cottage rentals Caribbean
- Holiday home rentals Caribbean
- Treehouse rentals Caribbean
- Boutique hotel rentals Caribbean
- Rentals with a hot tub Caribbean
- Rentals with a kayak Caribbean
- Rentals with a washing machine and dryer Caribbean
- House rentals Caribbean
- Bungalow rentals Caribbean
- Townhouse rentals Caribbean
- Apartment rentals Caribbean
- Serviced apartment rentals Caribbean
- Rentals with breakfast Caribbean
- Chalet rentals Caribbean
- Tent rentals Caribbean
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- Monthly Rentals Caribbean
- Rentals with beach access Caribbean
- Loft rentals Caribbean
- Motorhome rentals Caribbean
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- Wheelchair-accessible rentals Caribbean
- Luxury rentals Caribbean
- Rentals with a sauna Caribbean
- Nature eco lodge rentals Caribbean
- Rentals with an accessible-height toilet Caribbean
- Fitness-friendly rentals Caribbean
- Container rentals Caribbean
- Island rentals Caribbean
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- Beachfront rentals Caribbean
- Rentals with a patio Caribbean
- Private suite rentals Caribbean
- Farm stay rentals Caribbean
- Rentals with outdoor seating Caribbean
- Hostel rentals Caribbean
- Rentals with lake access Caribbean
- Boat rentals Caribbean
- Resort rentals Caribbean
- Hotel rentals Caribbean
- Flat rentals Caribbean
- Rentals with a balcony Caribbean
- Rentals with a firepit Caribbean
- Smoking-friendly rentals Caribbean
- Rentals with an EV charger 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
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- Holiday Bungalows United Kingdom
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- Condo Rentals United States
- Holiday Apartments Australia
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- 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
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- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
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- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom