
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.

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

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.

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

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.

Villa Mata de Mango, private pool, Las Terrenas
Charming tropical villa in Portillo, Las Terrenas. Nestled in nature, just 8 minutes from the center with semi-private beach access. Features 3 AC bedrooms (including a guest house), 3 bathrooms, an island kitchen, and a spacious living room. Outside, enjoy a spectacular infinity pool with a natural stone hot tub and a dream garden. Located in a 24/7 secure residence with tennis courts, Wi-Fi, Smart TV, parking, and daily cleaning. Your Caribbean paradise awaits!

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

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

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 ✌️🇨🇷

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.

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.

Villa Heliconia, A Volcano in your Garden!
The Holiday Villa with the closest and most SPECTACULAR view of Arenal Volcano 10 minutes from downtown La Fortuna Fully equipped Private jacuzzi. Grill and campfire area high-speed fiber optic Wi-Fi Located 1.5 kilometers from the main road on top of a private hill, where you will be surrounded by flora and fauna. Base rate for 2 people. A vehicle is recommended

Luxury Beachfront Apartment In Playa Bonita
Relax yourself in this beautiful beachfront apartment, located in the most exclusive residence in Las Terrenas, Dominican Republic: Playa Bonita Beach Residences. A luxury complex that lives in harmony with nature. Where with just a few steps you can enjoy the award-winning Playa Bonita, classified by National Geographic among the 10 best beaches in the world.
Popular amenities for Caribbean rentals with a pool
House rentals with a pool

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Apartment rentals with a pool

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Home rentals with a private pool

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Gorgeous Colonial House near Cafes and Bars
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Condado Beach Vistas… Elevate Your Stay!

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Sink into the Pool of a Wonderful Bungalow
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