
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.
ValueLocationComfort
4.99 out of 5 average rating, 298 reviews
Oceanfront 1BR Lux Apt Pool Beach Gym Pickleball
Discover the ultimate tropical retreat at the Soleil Residences, where luxury meets serenity. This elegant oceanfront one-bedroom condominium features a stunning balcony with 180-degree views of the Bay, inviting you to bask in the beauty of Jamaica's coastline. Highlights - Lge Waterfront Pool & Pool Deck * Private Beach Access * Gym * Tennis/Pickleball* Kids Play Area * Gated Community * Fast Fibre WiFi* Chef on request * Spa Services * Concierge Services * Full Time Driver Upon Request
ValueLocationOutdoor spaces
4.94 out of 5 average rating, 158 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.
FamilyLocationBeach
4.95 out of 5 average rating, 308 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.
FamilyValueComfort
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
ValueLocationCheck-in
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.
ValueFamilyLong stay
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.
ValueFamilyGetting around
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
LocationFamilyAccess
5.0 out of 5 average rating, 202 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 ✌️🇨🇷
LocationFamilyBathroom
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.
ValueFamilyLong stay
4.97 out of 5 average rating, 224 reviews
Magnolia Suite, therapeutic salt Jacuzzi, Monteverde
Bio Habitat Monteverde invites you to live a unique experience surrounded by primary forest. From the balcony, watch animals and enjoy the starry sky in the Net. Relax in our glass jacuzzi with salt water, while watching unforgettable sunsets over the Nicoya peninsula. An exclusive corner where nature, comfort and well-being come together to give you a true paradise in Monteverde.
LocationFamilyBathroom
4.99 out of 5 average rating, 233 reviews
Monte Sereno · Private Heated Pool Retreat
Escape to a private and romantic getaway with a heated pool, stunning mountain views and total privacy. Just minutes from rivers, waterfalls and local dining, this modern retreat is designed for couples looking to relax and disconnect. Enjoy peace of mind with a backup generator, water cistern and solar heater for a comfortable and uninterrupted stay.
ValueLocationSleep quality
4.97 out of 5 average rating, 101 reviewsPopular amenities for Caribbean rentals with a pool
House rentals with a pool

Waterfall House
FamilyLocationLaundry
4.97 out of 5 average rating, 203 reviews
Tranquil Times villa
FamilyLocationIndoor spaces
4.94 out of 5 average rating, 311 reviews
Hacienda del Mar
ValueLocationAmenities
4.89 out of 5 average rating, 210 reviews
Loma Del Sol House
FamilyLocationPets
4.95 out of 5 average rating, 155 reviews
Oceanfront relaxation with energy support
LocationFamilyQuiet
4.91 out of 5 average rating, 309 reviews
Ki Loft in Las 9 Gotas (The 9 Drops)
LocationValueWifi
4.96 out of 5 average rating, 128 reviews
Villa Mata de Mango, private pool, Las Terrenas
FamilyValueAccuracy
4.9 out of 5 average rating, 116 reviews
VeoMar - Casita Axel 4 bdr villa w/ endless views
FamilyValueCheck-in
4.93 out of 5 average rating, 161 reviewsApartment rentals with a pool

Luxury Beachfront Apartment In Playa Bonita
LocationValueCondition
4.93 out of 5 average rating, 117 reviews
Beachfront, super luxurious & pool
FamilyLocationDecor
4.97 out of 5 average rating, 120 reviews
Exclusive Studio w/ Balcony & King Bed - Cap Cana
FamilyValueWalkability
4.96 out of 5 average rating, 126 reviews
Caribbean Comfort I
LocationValueAmenities
4.94 out of 5 average rating, 252 reviews
Sail Away II-WOW Beachfront to Paradise Remodeled
LocationValueHospitality
4.95 out of 5 average rating, 145 reviews
"Cosón Penthouse" Daily Service Included
ValueFamilyGetting around
4.98 out of 5 average rating, 171 reviews
A beautiful apartment 600 meters from the beach
FamilyValueTV
4.96 out of 5 average rating, 181 reviews
Beautiful oceanfront condo in peaceful North Side
ValueLocationSleep quality
4.99 out of 5 average rating, 117 reviewsHome rentals with a private pool

Casa Pantheon Luxury Colonial House
FamilyLocationTV
4.94 out of 5 average rating, 386 reviews
Idyllic Beachfront Penthouse w/Private Plunge Pool
FamilyValueShared spaces
4.99 out of 5 average rating, 136 reviews
Gorgeous Colonial House near Cafes and Bars
LocationFamilyQuiet
4.94 out of 5 average rating, 464 reviewsWalk to Sandy Beach from a Hilltop Villa with a Pool
FamilyValueAir conditioning
4.98 out of 5 average rating, 342 reviews
Lush Waterfront Home On Bay St. Lucie
ValueLocationComfort
5.0 out of 5 average rating, 103 reviews
Condado Beach Vistas… Elevate Your Stay!
FamilyLocationCleanliness
4.9 out of 5 average rating, 303 reviews
Walled City Villa | Free Housekeeping and Staff
LocationFamilyQuiet
4.88 out of 5 average rating, 163 reviews
Sink into the Pool of a Wonderful Bungalow
FamilyLocationDecor
4.77 out of 5 average rating, 400 reviewsDestinations to explore
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