
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.

Casa Lola PR
In Casa Lola, nature is the protagonist of a hidden spot surrounded by mountains in Isabela. Unique views and a perfect place to disconnect and reconnect with your couple…. Come and enjoy our beautiful cabin on top of the mountain, completely private and experience the best nature environment. Fully equipped kitchen, indoor and outdoor showers, loft room with amazing sunrise and sunset views, infinity pool, sun chairs and relaxing hammock. A place that invites you to come again…..just enjoy.
LocationValueLong stay
4.99 out of 5 average rating, 298 reviews
“CASA ROARK” is a one-of-a-kind oceanfront chalet.
“CASA ROARK” IS A ONE-OF-A-KIND OCEANFRONT CHALET WITH VIEWS THAT CAN EASILY BE AMONG THE MOST BEAUTIFUL WORLDWIDE. IT IS ONLY A FEW STEPS FROM THE BEACH. THE RECENTLY REMODELED CHALET HAS 4 BEDROOMS, ALL WITH A/C AND 65"TVS; THE 1st MASTER ROOM HAS A KING-SIZE BED AND A TWIN SOFA BED, THE 2nd MASTER BEDROOM HAS A QUEEN SIZE BED, THE 3rd HAS 2 BUNK BEDS AND THE 4th ROOM HAS TWO TWIN SIZE BEDS. YOU HAVE A BEAUTIFUL HEATED POOL OVERLOOKING THE OCEAN. POOL USE IS ONLY FOR OUR GUESTS.
FamilyLocationCleanliness
4.95 out of 5 average rating, 308 reviews
Exclusive Studio w/ Balcony & King Bed - Cap Cana
Daydreaming about escaping to the beach during your next vacation? Look no further! Our beachfront studio in front of Marina Cap Cana is a beautiful spot to get serious about relaxation. Check out the highlights of our space below: ➢ 1 Spacious Bedroom/1 Bathroom with Shower/Bathtub ➢ Private Beach Access ➢ Beach/Ocean View with balcony ➢ Fully Equipped Kitchenette ➢ Swimming Pool ➢ Free Wifi ➢ 24/7 Security ➢ Portable Crib provided upon request ➢ Bath and beach towels provided
FamilyValueParking
4.96 out of 5 average rating, 126 reviews
Casa O Cochera Luxury Boutique House
Welcome to Casa O Cochera! Immerse yourself in luxury at this new 4-story haven in San Diego's enchanting Walled City. Designed by the renowned architect Vladimir Caballero, our house accommodates 8 guests with utmost comfort. Enjoy complimentary delicious breakfast, airport transfer and attentive housekeepers. Elevate your stay with optional catering, entertainment, and exciting tours. Your unforgettable getaway awaits! Book now and create beautiful memories at Casa O Cochera.
ValueFamilyNearby
4.93 out of 5 average rating, 127 reviews
Villa DelEvan 4A / 1-bedrm Beach front villa
Centrally located on the Grace Bay Beach, a perfect place for luxury, rest & tasting the best island cuisine. Close to everything you need for a great vacation: Walking dist. from 4 restaurants - Mango Reef, Shark Bite, Baci & Simone’s. 10 min drive to the famous island Fish Fry, 15 min drive to the Airport, 5 min drive to the supermarket. Gated property, private parking, 24hr security. Boating/fishing/sightseeing/wind surfing & more. Water sports pick-up on property.
FamilyValueLong stay
4.99 out of 5 average rating, 144 reviews
Sanguine Villa Treasure Beach 1-2-3 bed option
Sanguine's spacious fully staffed beachfront Villa with an infinity pool is located in Treasure Beach on Jamaica's South Coast. Treasure Beach is where one comes to get away from the hustle and bustle of everyday life and happily ensconce themselves in our laid-back community. Latoya will be here to ensure that you have a holiday of memorable meals, you sit back and relax while we do the grocery shopping and look after you. Message me re airport and transport options
ValueLocationSleep quality
5.0 out of 5 average rating, 106 reviews
Luxury villa & Infinity Pool
Immerse yourself in tranquility and natural beauty with this spectacular house in the middle of the forest, designed to offer you a unique experience of luxury and relaxation. This property combines modern elegance with the charm of nature. Wake up to the sounds of the forest and enjoy the peace that only this natural setting can provide. The house offers total privacy, but is located in the heart of Monteverde, a short drive away from local restaurants and shops.
LocationValueComfort
4.97 out of 5 average rating, 113 reviews
Villa Mano de Tigre, A Volcano in your Garden!
The Holiday Villa with the closest and most SPECTACULAR view of Arenal Volcano Beautiful natural landscapes, a cool and private area, away from mass tourism. Safe gated property. 10 minutes to downtown La Fortuna. Fully equipped. Private hot tub. Campfire area. Optic fiber high speed Wi-Fi Located 1.5 kilometers from the main road atop a private hill where you will be surrounded by flora and fauna. Base rate for 2 people. Vehicle is recommended.
ValueFamilyAccuracy
4.98 out of 5 average rating, 216 reviews
Sea Loft, Breathtaking View – Private Pool
* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with lounge chairs, garden furniture, outdoor table and BBQ * Office area * 100 Mbps Wi-Fi * TV with thousands of channels from around the world * 250 m walk to Fort Louis de Marigot Marina * 5 min walk to Marigot city center with its restaurants, boutiques and other shops * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station
ValueFamilyWalkability
5.0 out of 5 average rating, 202 reviews
Villa Yazmin - Ocean Front Villa
Follow us @villa_yazmin_curacao Experience refined luxury with stunning ocean views. A beautiful piano for serene moments, a magnesium pool gentle on body and skin, and elegant bedrooms each with a private bathroom. A fully equipped kitchen with cappuccino machine and Quooker. Car rental, early check in and late check out available upon request. Please contact Mary in advance for personalized arrangements. Warm greetings, Villa Yazmin Mary
LocationValueSleep quality
4.91 out of 5 average rating, 133 reviews
Treetop cabin - hot tub, pool & private rainforest
An unique and modern treetop cabin hidden in 10 acres of private primary rainforest, in a peaceful small town of rural Costa Rica, with La Fortuna, Bajos del Toro and Sarapiquí all within reach. Soak in your own private heated hot tub on the balcony while the forest does the talking, waterfall sounds included. Full kitchen, rain shower looking at the treetops, river, trails and two pools with natural spring water. Local owned ✌️🇨🇷
FamilyLocationIndoor spaces
5.0 out of 5 average rating, 113 reviews
La Ceiba, Villa w/Infinity Pool on a Dairy Farm
Escape to La Ceiba, a private retreat on our family dairy farm surrounded by lush pastures, cows and mountain views. Relax by the infinity pool, enjoy beautiful sunrises and sunsets, and gather in the spacious open-air living and dining areas. With 3 bedrooms, 4 queen beds and space for up to 8 guests, it’s ideally located between Bajos del Toro and La Fortuna. Private chef service available.
ValueLocationWifi
4.97 out of 5 average rating, 224 reviewsPopular amenities for Caribbean rentals with a pool
House rentals with a pool

Waterfall House
FamilyValueCheck-in
4.97 out of 5 average rating, 202 reviews
Hacienda del Mar
ValueLocationSleep quality
4.89 out of 5 average rating, 210 reviews
Ki Loft in Las 9 Gotas (The 9 Drops)
FamilyValueWalkability
4.96 out of 5 average rating, 128 reviews
Tranquil Times villa
ValueLocationCheckout
4.94 out of 5 average rating, 311 reviews
Loma Del Sol House
LocationFamilyIndoor spaces
4.95 out of 5 average rating, 155 reviews
Villa Mata de Mango, private pool, Las Terrenas
FamilyLocationBeach
4.9 out of 5 average rating, 115 reviews
VeoMar - Casita Axel 4 bdr villa w/ endless views
FamilyLocationAccuracy
4.93 out of 5 average rating, 161 reviews
Villa Estrella PR (near Airport & Beach)
FamilyValueComfort
4.98 out of 5 average rating, 238 reviewsApartment rentals with a pool

Oceanfront 1BR Lux Apt Pool Beach Gym Pickleball
ValueLocationSleep quality
4.94 out of 5 average rating, 158 reviews
Luxury Beachfront Apartment In Playa Bonita
LocationValueWalkability
4.93 out of 5 average rating, 117 reviews
Beachfront, super luxurious & pool
FamilyLocationKitchen
4.97 out of 5 average rating, 120 reviews
Caribbean Comfort I
ValueLocationAir conditioning
4.94 out of 5 average rating, 252 reviews
"Cosón Penthouse" Daily Service Included
ValueFamilyWifi
4.98 out of 5 average rating, 171 reviews
A beautiful apartment 600 meters from the beach
FamilyLocationQuiet
4.96 out of 5 average rating, 181 reviews
Charming beach apartment with private Pool
LocationFamilyOutdoor spaces
4.91 out of 5 average rating, 240 reviews
"SeaBird" studio, feet in the water on the beach
LocationValueSolo travel
4.96 out of 5 average rating, 154 reviewsHome rentals with a private pool

Idyllic Beachfront Penthouse w/Private Plunge Pool
ValueFamilyQuiet
4.99 out of 5 average rating, 136 reviews
Casa Pantheon Luxury Colonial House
ValueLocationComfort
4.94 out of 5 average rating, 386 reviews
Gorgeous Colonial House near Cafes and Bars
LocationValueOutdoor spaces
4.94 out of 5 average rating, 464 reviewsWalk to Sandy Beach from a Hilltop Villa with a Pool
ValueLocationBathroom
4.98 out of 5 average rating, 342 reviews
Lush Waterfront Home On Bay St. Lucie
FamilyValueQuiet
5.0 out of 5 average rating, 103 reviews
Condado Beach Vistas… Elevate Your Stay!
ValueFamilyDecor
4.9 out of 5 average rating, 303 reviews
Walled City Villa | Free Housekeeping and Staff
FamilyLocationComfort
4.88 out of 5 average rating, 163 reviews
Sink into the Pool of a Wonderful Bungalow
FamilyLocationView
4.77 out of 5 average rating, 400 reviewsDestinations to explore
- Aparthotel rentals Caribbean
- Campsite rentals Caribbean
- Flat rentals Caribbean
- Castle rentals Caribbean
- Dome rentals Caribbean
- Cottage rentals Caribbean
- Barn rentals Caribbean
- Boat rentals Caribbean
- Family-friendly rentals Caribbean
- Townhouse rentals Caribbean
- Villa rentals Caribbean
- Serviced apartment rentals Caribbean
- Holiday home rentals Caribbean
- Luxury rentals Caribbean
- Cabin rentals Caribbean
- Pet-friendly rentals Caribbean
- Guest house rentals Caribbean
- Ski-in/ski-out rentals Caribbean
- Bungalow rentals Caribbean
- Tipi rentals Caribbean
- Hotel rooms Caribbean
- Private suite rentals Caribbean
- House rentals Caribbean
- Treehouse rentals Caribbean
- Motorhome rentals Caribbean
- Boutique hotels Caribbean
- Bed and breakfasts Caribbean
- Rentals with a sauna Caribbean
- Ranch rentals Caribbean
- Nature eco lodge rentals Caribbean
- Earth house rentals Caribbean
- Houseboat rentals Caribbean
- Rentals with beach access Caribbean
- Rentals with breakfast Caribbean
- Island rentals Caribbean
- Apartment rentals Caribbean
- Beach house rentals Caribbean
- Beachfront rentals Caribbean
- Resort rentals Caribbean
- Waterfront rentals Caribbean
- Tiny house rentals Caribbean
- Hostel rentals Caribbean
- Farm stay rentals Caribbean
- Loft rentals Caribbean
- Rentals with a kayak Caribbean
- Container rentals Caribbean
- Tent rentals Caribbean
- Rentals with an accessible-height bed Caribbean
- Chalet rentals Caribbean
- Rentals with a hot tub Caribbean
- Mansion rentals Caribbean
- Rentals with lake access Caribbean
- Rentals with an accessible-height toilet Caribbean
- Things to do Caribbean
- Outdoors Caribbean
- Cultural tours Caribbean
- Shopping and fashion Caribbean
- Landmarks Caribbean
- Wildlife Caribbean
- Performances Caribbean
- Wellness Caribbean
- Food tours Caribbean
- Water sports Caribbean
- Art workshops Caribbean
- Workouts Caribbean
- Galleries Caribbean
- Tastings Caribbean
- Flying Caribbean
- Cooking Caribbean
- Dining Caribbean
- Architecture Caribbean
- Museums Caribbean





