
Vacation rentals with a pool in Caribbean Sea
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Top-rated rentals with a pool in Caribbean Sea
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Starfish Cottage, Hummingbirds, Mountain, Sea View
IMPORTANT NOTE: We do not accept children under 13. Wake to hummingbirds at your balcony feeder, with views of the Blue Mountain peak, Nonsuch Falls and the Port Antonio coastline. Starfish has a treehouse feel: private bathroom, kitchenette, AC, and a hammock built for doing nothing at all. Swim laps in our 25m pool, train in the open-air Jungle Gym, and reach Frenchman’s Cove in 5 minutes. A quiet retreat for couples and solo travellers who want to disconnect and let the jungle do the rest.
4.97 out of 5 average rating, 246 reviews
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, 299 reviews
Hacienda Sol y Luna Mountain Retreat
Enjoy the lovely setting of this romantic spot in nature and discover the serenity in our cozy farmhouse. This private villa wraps you in a lovely and peaceful environment with majestic mountains all around. The house is fully equipped for your convenience. It is ideal for couples in need of a nice getaway or just reconnect with yourself and nature. It is on a gorgeous tropical private 3 acre estate with private pool. Located in Villalba PR just 50 min. from Ponce PSE, 1:50 from San Juan SJU.
5.0 out of 5 average rating, 143 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
Villa Lasai - Brand New Luxury Villa
Villa Lasai is a 280m² luxury 3 Bedroom vacation home, built on 2 levels and sleeps up to 6 people. Elegantly constructed with a great mix of tropical architecture, styled with materials such as exposed polished concrete and natural stone as the indoor and outdoor areas blend together. Facing the ocean and jungle, enjoy the view from the 25m² saltwater pool. Villa Lasai is conveniently located less than a 3 minute drive to the world-class surfing beaches and downtown Santa Teresa.
4.94 out of 5 average rating, 128 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
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, 115 reviews
Upper Casita Catalina in Tamarindo w Great Views
From this hilltop location above Tamarindo Bay, you will enjoy a panoramic view that is unbelievable. You’ll see what we mean when you get here! The Casita offers a King bed and a pull-down Queen bed, fully equipped with a private bathroom, kitchen, and a small balcony perfect for watching monkeys in the surrounding trees! You will also have access to the property's shared social space including a breezy covered terrace by the ocean-view pool and rooftop lounge!
4.98 out of 5 average rating, 309 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.
4.98 out of 5 average rating, 217 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
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 reviewsPopular amenities for Caribbean Sea rentals with a pool
House rentals with a pool

Villa Jeremi
4.99 out of 5 average rating, 132 reviews
Private Oceanfront luxurious city villa with pool
4.96 out of 5 average rating, 182 reviews
Casa Cascada
4.97 out of 5 average rating, 203 reviews
Bubble Puerto Rico Panoramic Private Heating Pool
4.93 out of 5 average rating, 150 reviews
Tranquil Times villa
4.94 out of 5 average rating, 311 reviews
Canopy Cove 3Bd 3Bth Pool Gated in Manuel Antonio
4.99 out of 5 average rating, 191 reviews
Aruba Private Resort. Its All Yours and Only Yours
5.0 out of 5 average rating, 271 reviews
Loma Del Sol House
4.95 out of 5 average rating, 155 reviewsCondo rentals with a pool

The Quarry, Beachfront sub penthouse 150m to clubs
4.93 out of 5 average rating, 487 reviews
Cap Cana Peaceful Studio Oceanfront Punta Palmera
5.0 out of 5 average rating, 214 reviews
Luxury apartment Near Casco Antiguo 1501
4.95 out of 5 average rating, 108 reviews
Oceanfront 1BR Lux Apt Pool Beach Gym Pickleball
4.94 out of 5 average rating, 158 reviews
Beachfront Apt. Ocean-Facing Bed & City Views+Pool
4.89 out of 5 average rating, 444 reviews
The Artist
4.89 out of 5 average rating, 711 reviews
Cartagena Sky Loft: Ocean & Old City Views
4.98 out of 5 average rating, 109 reviews
Beachfront, Sea Views, Pool, Sleeps 1-4 Akumal MX
4.96 out of 5 average rating, 181 reviewsHome rentals with a private pool

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