Vacation 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.

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Top guest favorite

A private pool deck features a refreshing blue pool surrounded by lush greenery. New patio furniture includes two chaise lounges and a table for four, complemented by a gas grill. Views of the ocean create a peaceful outdoor atmosphere under a clear blue sky.

Villa in Christiansted

5 out of 5 average rating, 121 reviews

Mojito Hill - private hilltop pool oasis!

Beautiful 1-bedroom ocean view villa with private pool. Relax on the private pool deck with brand new patio furniture featuring chaise lounges, table seating for 4, and a gas grill. Sweet dreams await you in the four-poster king sized master suite, complete with french doors that open to the pool deck and allow for the ocean breezes to keep you cool. The shower is a fully stocked oversized marble shower with room for two. A fully equipped kitchen with granite countertops and modern appliances, including a Keurig latte machine, will make you feel right at home. Mojito Hill includes many conveniences such as a smart TV, wifi, air conditioning, washer/dryer, and much more. Extra guests are no problem, as the couch features a pull-out bed. Villa Madeleine is a gated community on St. Croix’s relaxing East End, where you will enjoy the privacy, amazing views, tennis court, and close proximity to the Reef Golf Course, Duggan’s Reef restaurant, Divi Casino and Resort, Grapetree beach to the south and Reef Beach to the north. All these amenities are within walking distance, but do require traversing a steep hill, so driving is typically preferred. We have an on-island manager, and Tom & Hillery are available at any time via email/text/phone if needed. If you don't see the dates you are looking for, please message us, we also have a Splash of Lime in the same complex that has a spectacular northern facing view.

Top guest favorite

An entrance is framed by open louvered doors, leading to a stylish living space bathed in evening light. A cozy seating area faces large windows that showcase a scenic view of the sunset over the sea, with greenery and decorative elements enhancing the ambiance.

Villa in Treasure Beach

5 out of 5 average rating, 84 reviews

Treasure Beach Sanguine Villa Fall Special rate

Sanguine's spacious fully staffed beachfront Villa with an infinity pool is located in Treasure Beach on Jamaica's South Coast. Home to the renowned Calabash Literary festival. 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 to go home with, you sit back and relax while we do the grocery shopping and look after you.

Top guest favorite

An infinity pool is featured with views of surrounding mountains and lush greenery. Sunlight reflects off the water's surface, creating a serene atmosphere. Chaise lounges are positioned nearby, offering a comfortable space to relax and enjoy the picturesque landscape.

Tiny home in Caonillas Arriba

5 out of 5 average rating, 94 reviews

Sun and Moon 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, Puerto Rico, just 50 minutes from Ponce's Airport.

Top guest favorite

A serene balcony setting is depicted, featuring a small dining table with two chairs. The table is set with plates and a pitcher, overlooking a scenic view of palm trees and a tranquil sea. The horizon stretches out toward distant islands under a clear blue sky.

Apartment in Cabezas

4.96 out of 5 average rating, 163 reviews

Luxury Ocean Front Studio

Luxurious beachfront apartment to spend a beautiful day. It is located next to the Hotel El Conquistador with an incredible view. With a view to the sea, you can see Palomino Island, Icaco Cay, Island Culebra and Vieques. This apartment is unique, romantic and elegant to have a good time. It has different attractions nearby such as the Yunque, Seven Seas Beach,Snorkel and beach tours, Ferry to Culebra and Vieques. Different areas for night activities such as the Bio Bay in the Croabas.

Top guest favorite

A serene outdoor area features a sparkling pool surrounded by lush greenery and tropical plants. A shaded seating area is provided by a large umbrella, along with a cozy hanging chair in the background. The peaceful ambiance is enhanced by bright blue skies.

Guest suite in Luquillo

5 out of 5 average rating, 190 reviews

Casa Encanto - Experience El Yunque Rainforest.

This Guest Suite, on the lower level of our exclusive luxury villa, Casa Encanto, is the perfect tropical getaway. Nestled in the peaceful and lush foothills of the El Yunque Rain Forest, Located in Luquillo with many nearby attractions. You’ll have easy access to downtown Luquillo, El Yunque National Rainforest, Luquillo Beach, Caribali Adventure Park, Las Paylas, charter boat trips, snorkeling, zip lines and much more. The Guest Suite is fully solar with Tesla Batteries and backup water

Top guest favorite

A modern sanctuary is showcased amidst lush tropical foliage, featuring an inviting plunge pool. The structure's open design highlights floor-to-ceiling glass walls, allowing natural light to fill the interior. A vibrant sunset sky adds warmth to the scene, enhancing the tranquil surroundings.

Villa in Mal Pais

4.97 out of 5 average rating, 138 reviews

House of the Earth and the Sea - stunning luxury

Escape to La Casa Tierra y el Mar: A romantic luxurious mountain top sanctuary where architecture meets wilderness in Costa Rica's Nicoya Peninsula. Breathtaking ocean views, plunge pool, and wildlife at your doorstep. Gourmet kitchen, indoor outdoor living. Moments from pristine beaches, this architectural marvel offers the perfect blend of privacy, comfort, and adventure. Your secure and completely private tropical dream retreat awaits—where extraordinary design meets untamed nature.

Top guest favorite

A sweeping view captures the vibrant turquoise waters of the coastline, framed by lush green hills. Islands dot the horizon under a clear blue sky, while the wooden railing in the foreground provides a picturesque viewing point of the landscape.

Guesthouse in BL

4.98 out of 5 average rating, 176 reviews

les Ramiers

Spend your holidays at Villa les Ramiers, where the sun is with you from sunrise and throughout the day. The accommodation is independent, not overlooked, with its small kitchen and terrace overlooking the pool, a top-deck to enjoy the sunrise, a large bedroom overlooking the covered patio with lounge area with sea view. Located on the well-ventilated heights with stunning views of Petite Anse. Private parking is located next to the Villa. Welcome!

Superhost

Home in Saint Martin

5 out of 5 average rating, 4 reviews

Villa Josefa panoramic sea view

✨ Exceptional villa overlooking Friar’s Bay, with breathtaking panoramic views of the sea, Anguilla and the Lowlands. 🏡 3 master suites with king beds and private bathrooms, fully equipped kitchen (private chef optional), spacious lounge and sea-view terrace for up to 10 guests. 🌅 Secure residence, absolute tranquility, just minutes from Grand Case and the island’s best beaches. 💎 Comfort, style, and unforgettable Caribbean sunsets await you!

Top guest favorite

A striking A-frame house is illuminated at night, showcasing its wooden exterior and large glass front doors. Lush greenery and neatly arranged stones adorn the pathway leading up to the entrance, while subtle lighting enhances the surrounding landscape.

Cabin in Aguadilla

5 out of 5 average rating, 130 reviews

Blackandwoodcabin Cabin/chalet in Aguadilla

****Actividades privadas tienen un costo adicional y deberá ser coordinada y aprobada por la Gerencia. Tenemos piscina de agua salada, jacuzzi todo calentador. Un cuarto con tina 🛀. Un cuarto con sofá cama y televisor. Cocina completa, microondas, una lavadora y secadora. Además tenemos una vinera. Planta eléctrica de 20k y cisterna con bomba de agua. Sistema de riegos para los jardines de ensueño. Iluminación nocturna en armonía.

Top guest favorite

Aerial view of a modern villa designed with a spacious upper terrace that overlooks an infinity pool. The terrace is furnished with a dining table and chairs. Lush greenery surrounds the property, with a paved parking area visible in the foreground.

Villa in Sint Michiel

5 out of 5 average rating, 64 reviews

Beautiful new luxurious villa in Caribbean style

Beautiful new luxurious villa in Caribbean style with private pool just 2 minutes walking distance from the beach. From the semi-covered terrace, you can enjoy the panoramic views overlooking the sea and golf course. The villa is located on the well secured and beautifully maintained Blue Bay Golf and Beach Resort. Entrance to Blue Bay Beach is included with every stay, along with the use of a sunlounger on the beach area.

Guest favorite

An air-conditioned villa is surrounded by lush greenery, featuring large glass windows that invite natural light. A private pool sits in front of the building, and outdoor seating is arranged on the terrace, providing serene garden views.

Home in Jarabacoa

5 out of 5 average rating, 11 reviews

Oslo – Norwegian Style House

Boasting a private entrance, this air-conditioned villa comes with 1 living room, 1 separate bedroom and 1 bathroom with a shower. In the kitchen, guests will find a refrigerator, kitchenware, a microwave and a tea and coffee maker. Featuring a terrace with garden views, this villa also features a minibar and a flat-screen TV. 1 Queen Size Bed Queen Sofa Bed Fully Equipped Kitchen Hot Water Private Climatized Pool

Top guest favorite

An outdoor seating area is showcased, featuring two cushioned armchairs and a wooden coffee table. The space offers views of lush greenery and a pool below, framed by a wrought iron railing. Bright skies and distant hills enhance the tranquil ambiance.

Apartment in Cruz Bay

5 out of 5 average rating, 152 reviews

Sieben Apartment * Pool* next to Hiking trails

Spacious Luxury 2 Bedroom, 2 bathroom apartment with fully equipped kitchen and washer/dryer. Both rooms have memory foam mattresses from Loom & Leaf. The master bedroom has 1 King bed with private bathroom, and the second bedroom can be set up as 2 Twin beds or 1 King bed. 10 min drive from Cruzbay, Restaurants and grocery Stores. Shared brand Pool (4ft deep) with two other apartments. Shared BBQ by the Pool.