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
4.96 out of 5 average rating, 107 reviewsCasa Anya @ Hilltop (private infinity plunge pool)
Home
4.99 out of 5 average rating, 172 reviewsAirstream With Amazing Pool, Ocean & Nature Views
Home
4.96 out of 5 average rating, 163 reviewsCasa Cascada
Home
4.92 out of 5 average rating, 186 reviewsArenal Kabata luxury infinity and jacuzzi spa
Home
5 out of 5 average rating, 191 reviewsAruba Private Resort. Its All Yours and Only Yours
Home
4.96 out of 5 average rating, 159 reviewsQuinta La Ceiba Modern Home with Pool in DairyFarm
Home
4.97 out of 5 average rating, 108 reviewsCayo Loco Beachfront Villa Deserted PinkSand for 2
Home
4.94 out of 5 average rating, 243 reviewsTranquil Times Villa
Apartment rentals with a pool
Apartment
5 out of 5 average rating, 173 reviews"H2Oh What a Beach!" condo: Walk-out Beach Access!
Apartment
4.95 out of 5 average rating, 151 reviewsModern apt ,EagleBeach,Sea view,Oasis condominium
Apartment
4.93 out of 5 average rating, 138 reviewsHeavenly Luxury Ocean View Beach Front Penthouse
Apartment
4.94 out of 5 average rating, 113 reviews1br Lux Oceanfront 180 View Pool Beach Tennis Gym
Apartment
4.92 out of 5 average rating, 386 reviewsJus' Beachy Luxury Apt in a B/front Gated Cmnty.
Apartment
4.93 out of 5 average rating, 107 reviewsComfort of the Caribbean
Apartment
4.98 out of 5 average rating, 146 reviewsSandyDreams BeachFront 1BD/2BR
Apartment
4.85 out of 5 average rating, 162 reviewsGreenLeafOasis #1 | Turquoise Ocean Views
Home rentals with a private pool
Home
4.94 out of 5 average rating, 379 reviewsGorgeous Colonial House near Cafes and Bars
Home
4.95 out of 5 average rating, 152 reviewsSoak up the Beachy Vibe at a Vibrant Poolside Paradise
Villa
4.93 out of 5 average rating, 312 reviewsCasa Pantheon Luxury Colonial House
Villa
4.87 out of 5 average rating, 141 reviewsOld City Villa - Breakfast & Housekeeping Included
Bungalow
4.79 out of 5 average rating, 296 reviewsSink into the Pool of a Wonderful Bungalow
Townhouse
4.87 out of 5 average rating, 194 reviewsLuxurious Townhouse With Private Pool in The Old City
Apartment
4.9 out of 5 average rating, 238 reviewsCondado Beach Vistas by Cesar 2501
Guest house
4.96 out of 5 average rating, 166 reviewsTropical Cabana with Pool in West Palm Beach
Destinations to explore
- Rentals with pools Cuba
- Nature eco lodge rentals Caribbean
- Cabin rentals Caribbean
- Family-friendly rentals Caribbean
- Rentals with a washing machine and dryer Caribbean
- Campsite rentals Caribbean
- Bed and breakfasts Caribbean
- Private suite rentals Caribbean
- Houseboat rentals Caribbean
- Bungalow rentals Caribbean
- Smoking-friendly rentals Caribbean
- Ski-in/ski-out rentals Caribbean
- House rentals Caribbean
- Boutique hotel rentals Caribbean
- Rentals with beach access Caribbean
- Rentals with a patio Caribbean
- Rentals with a sauna Caribbean
- Flat rentals Caribbean
- Rentals with a firepit Caribbean
- Pet-friendly rentals Caribbean
- Rentals with an EV charger Caribbean
- Boat rentals Caribbean
- Family-friendly rentals Caribbean
- Townhouse rentals Caribbean
- Villa rentals Caribbean
- Rentals with an accessible-height bed Caribbean
- Motorhome rentals Caribbean
- Fitness-friendly rentals Caribbean
- Hotel rentals Caribbean
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- Aparthotel rentals Caribbean
- Serviced apartment rentals Caribbean
- Holiday home rentals Caribbean
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- Island rentals Caribbean
- Rentals with a kayak Caribbean
- Rentals with a hot tub Caribbean
- Rentals with a cinema Caribbean
- Rentals with breakfast Caribbean
- Treehouse rentals Caribbean
- Beach house rentals Caribbean
- Hostel rentals Caribbean
- Farm stay rentals Caribbean
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- Chalet rentals Caribbean
- Rentals with lake access Caribbean
- Rentals with a fireplace Caribbean
- Beachfront rentals Caribbean
- Apartment rentals Caribbean
- Tent rentals Caribbean
- Rentals with an accessible-height toilet Caribbean
- Rentals with a balcony Caribbean
- Container rentals Caribbean
- Earth house rentals Caribbean
- Resort rentals Caribbean
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- Tiny house rentals Caribbean
- Monthly Rentals Caribbean
- Yurt Rentals United States
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- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
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- Farm Houses United States
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- Holiday Chalets United Kingdom
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- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
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- Beach Houses United Kingdom
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