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.

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Top guest favorite

Villa in Christiansted

5 out of 5 average rating, 117 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.

Guest favorite

Home in Willemstad

4.95 out of 5 average rating, 160 reviews

Private Oceanfront luxurious city villa with pool

Welcome to a beautiful Paradise in Pietermaai District. This 300yr old estate has been restored to perfection after having suffered severe neglect. The unique design style and decoration has been done with love for architecture. The villa can be found in Pietermaai District also known as the ‘Soho of Curacao’’, where monuments meet modern times. With an oceanfront stunning view + private pool, the villa is ideal to get away from it all whilst still be close to great restaurants and live music.

Guest favorite

Villa in Tulum

4.93 out of 5 average rating, 124 reviews

Villa Petricor, 24/7 security & beach club access

Brand new custom residence! Villa Petricor, a sanctuary where you enjoy modern amenities without sacrificing the beauty, balance and bliss of the Mayan jungle. Are you a digital nomad looking to rekindle creativity lost in the boring tope walls of your office? Maybe you are a group of friends & family looking to experience the best of Tulum? Located in Aldea Zama, 5 mins from the beach and 5 mins from downtown. We commit to everything needed to immerse in your lavish but deserved getaway.

Top guest favorite

Condo in Montego Bay

4.95 out of 5 average rating, 139 reviews

1br Lux Oceanfront 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

Top guest favorite

Loft in Marigot

4.99 out of 5 average rating, 162 reviews

Sea Loft Vue imprenable - piscine privée

* Loft de 200m² * Vue mer exceptionnelle * Piscine privée * A 250 mètres de la petite plage de Galisbay * Terrasse avec chaises longues, salon de jardin, table d'extérieur et BBQ * Espace bureau * Wifi 100 Mbps * TV avec milliers de chaines du monde entier * A 250 m à pied de la marina Fort Louis de Marigot * A 5 min à pied du centre ville de Marigot avec ses restaurants, boutiques et autres commerces * A 5 min de l'embarcadère pour Saint-Barth et Anguilla, et de la station de taxis

Superhost

Villa in Soufriere

4.87 out of 5 average rating, 189 reviews

Villa Piton Caribbean Castle

Certified to host on St Lucia government website at stlucia.org. Super private and provides a secure and isolated retreat far from any crowds! We provide cooking service for breakfast lunch or dinner for an extra fee prepaid through Airbnb prior to your arrival. We incorporate heightened cleaning procedures and trained staff. Built by John DiPol, designer of the world-famous Ladera resort, Villa Piton elaborates on the open-aired concept providing breathtaking views everywhere!

Guest favorite

Home in Akumal

4.89 out of 5 average rating, 142 reviews

Low rate Sargassum Season until end of October

Modern, Artsy, chic and completely renovated four bedroom deluxe house located on Half Moon Bay, place where turtles nest and lay their eggs every year. IMPORTANT NOTE: With the intention of being totally upfront with you: the SARGASSUM has reached our area, being a matter out of our control, we do the best effort to clean up the beach as much as possible. You can see the actual status on the last photos. We hugely appreciate your support and understanding to this matter.

Guest favorite

Home in Montezuma

4.94 out of 5 average rating, 119 reviews

Luxury Cliffside Escape - Casa Cocobolo Villa

Perched 200m above the ocean in Montezuma on a vast 30-hectare private reserve, Casa Cocobolo offers breathtaking ocean views and a tranquil escape in lush, tropical gardens. Our dedicated concierge ensures a personalized, unforgettable stay in this bio-diverse haven. Explore jungle trails with expert-guided hikes, discovering hidden waterfalls and secret pools. Immerse yourself in the beauty of nature while enjoying modern comforts in your secluded oasis of paradise.

Top guest favorite

Chalet in Naranjito

4.97 out of 5 average rating, 243 reviews

Chalet Vista Hermosa

Enjoy the lovely setting of this romantic & magical cozy home . Hidden in the mountains of Naranjito . 45 minutes from the airport, you can immerse yourself in a unique, romantic experience in PR surrounded by nature. The view from the moment you enter our property is magical. Here you can find a hugely inspiring environment for your writing, reading, music, to spend quality time with your partner, to spend time alone. A magical place of art, peace, and inspiring.

Top guest favorite

Home in Playa Zancudo

4.98 out of 5 average rating, 100 reviews

Oceanfront Oasis: beach, private pool, AC & jungle

We are located in the idyllic tropical rainforest of the South Pacific Coast where the lush green jungle meets the blue pacific ocean. A region in Costa Rica that is regarded as one of the most biologically diverse places in the world. Zancudo is a sleepy village off the beaten path, unimpacted by mass tourism and crowds – yet supplying creature comforts with sodas, grocery shops, bars, eateries and plenty of activities for the solo traveler and families alike.

Top guest favorite

Home in Valladolid

4.95 out of 5 average rating, 193 reviews

Villa La Pausa - Valladolid

Es difícil no enamorarse de Valladolid, con sus casi 500 años de antigüedad, La Pausa es una ancestral casa restaurada que busca ser una re-interpretación de la vida en la región, un lugar en donde el lujo esté en el encuentro familiar. El interior es una combinación de estilos e historias, artículos vintage y muebles hechos a medida mezclados con una selección de artículos mexicanos. Un recinto de descanso después de un largo día bajo el soy de Yucatán.

Guest favorite

Home in Ciales

4.96 out of 5 average rating, 172 reviews

Casa privada- piscina, jacuzzi, vista espectacular

Hemos creado un espacio único para que vivas momentos inolvidables. Disfruta de un jacuzzi con agua caliente con una vista espectacular entre otras comodidades . En el exterior podrás disfrutar de una amplia piscina (sin calefacción) mientras te bronceas y te relajas viendo las montañas y aves de Ciales. El cantar del COQUI es el protagonista de la noche así es que prende la fogata y relájate con tu bebida favorita.