
Vacation rentals with a pool in Caribbean Sea
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Caribbean Sea
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.
4.99 out of 5 average rating, 298 reviews
Oasis on the beach| Private Pool | AC
Tucked away in the safe, idyllic tropical rainforest of Costa Rica’s South Pacific Coast, where lush green jungle meets the bright blue Pacific. One of the most biologically diverse regions on Earth, it’s home to Zancudo: a sleepy, off-the-beaten-path fishing village happily untouched by mass tourism. Zancudo delivers all the creature comforts, sodas, grocery shops, bars, local eateries, tours, and plenty to do - making it perfect for adventurers, digital nomads, couples, and families alike.
4.98 out of 5 average rating, 130 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.
4.95 out of 5 average rating, 308 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
5.0 out of 5 average rating, 106 reviews
Villa Arthur 600 · 9 Guests · Permanent staff
Villa Arthur 600 is a luxurious private villa with permanent staff, ideally located near La Veleta, Gypsea Market, and downtown access. Perfect for 9 guests, the villa features a spacious pool, master suites with tubs overlooking the pool, a large living room with a professional kitchen, a dining table for 10, and comfortable sofas. Enjoy a large park and a rooftop with BBQ. With daylight surveillance to ensure safety. Daily breakfast is available at an extra cost.
4.97 out of 5 average rating, 109 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.
4.97 out of 5 average rating, 113 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
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 ✌️🇨🇷
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.
4.97 out of 5 average rating, 224 reviews
Modern gated villa w/ Pool and Beach Club access
Casa Malibu is a tropical retreat in a gated community with a private 46-foot infinity pool, daily cleaning service, and golf cart accessibility. This 5,000-square-foot haven—just steps from Tamarindo Beach—includes complimentary access to Puerta de Sal Beach Club, managed by the acclaimed team behind Pangas Restaurant. Enjoy effortless luxury, privacy, and the best of Costa Rica
4.96 out of 5 average rating, 162 reviews
💎 Caribbean Jewel! 💎 Panoramic views and pool!
At La Joya #5 you will find a beautiful 2 bedroom 2 bathroom, spacious condo with amazing ocean views! We are located on the second floor of an intimate, 7 unit condo building. The staff are the heart of the building and work hard to make your vacation special! Choose La Joya #5 for you next getaway and you will not be disappointed!
4.99 out of 5 average rating, 119 reviews
La Batterie Villa • Boutique Villa • Amazing Views
Tucked away in the prestigious Anse Chastanet / Jade Mountain area of Soufrière, the Villa is a private retreat designed for relaxation, comfort, and unforgettable views. Perched 300 feet above the Caribbean Sea and facing the iconic Pitons, the villa enjoys cooling island breezes and panoramic scenery that never fails to impress.
4.97 out of 5 average rating, 157 reviewsPopular amenities for Caribbean Sea rentals with a pool
House rentals with a pool

Casa Cascada
4.97 out of 5 average rating, 202 reviews
Stunning Oceanfront house with private pool
4.83 out of 5 average rating, 167 reviews
Oceanfront 4BR w/ Private Pool + Beach Access
4.86 out of 5 average rating, 162 reviews
Tranquil Times villa
4.94 out of 5 average rating, 311 reviews
Three Bedroom Beachfront Villa on Playa Redonda
4.93 out of 5 average rating, 127 reviews
Villa Estrella PR (near Airport & Beach)
4.98 out of 5 average rating, 238 reviews
Loma Del Sol House
4.95 out of 5 average rating, 155 reviews
VeoMar - Casita Axel 4 bdr villa w/ endless views
4.93 out of 5 average rating, 161 reviewsCondo rentals with a pool

The Quarry, Beachfront sub penthouse 150m to clubs
4.93 out of 5 average rating, 487 reviews
Luxury apartment Near Casco Antiguo 1501
4.95 out of 5 average rating, 107 reviews
"Cosón Penthouse" Daily Service Included
4.98 out of 5 average rating, 171 reviews
Caribbean Comfort I
4.94 out of 5 average rating, 252 reviews
Oceanfront 1BR Lux Apt Pool Beach Gym Pickleball
4.94 out of 5 average rating, 158 reviews
Charming beach apartment with private Pool
4.91 out of 5 average rating, 240 reviews
Beachfront Apt. Ocean-Facing Bed & City Views+Pool
4.89 out of 5 average rating, 444 reviews
Luxury 3 bedroom 2 Story Loft Near Perlas Beach!
4.77 out of 5 average rating, 167 reviewsHome rentals with a private pool

Beachfront Casa Maeva 4 bedrooms-
4.96 out of 5 average rating, 129 reviews
Villa Bikini pool garden jacuzzi priv Security24/7
4.86 out of 5 average rating, 237 reviews
Gorgeous Colonial House near Cafes and Bars
4.94 out of 5 average rating, 464 reviews
Casa Pantheon Luxury Colonial House
4.94 out of 5 average rating, 386 reviews
Idyllic Beachfront Penthouse w/Private Plunge Pool
4.99 out of 5 average rating, 136 reviews
Wonderful Jungle Villa (private pool)
4.84 out of 5 average rating, 237 reviews
Villa LaGú | Luxury 5BR Jungle Villa · Pool & Chef
4.98 out of 5 average rating, 207 reviewsWalk to Sandy Beach from a Hilltop Villa with a Pool
4.98 out of 5 average rating, 342 reviewsDestinations to explore
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