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, 119 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

Cabin in Isabela

4.98 out of 5 average rating, 180 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.

Guest favorite

Cottage in Coral Bay

4.99 out of 5 average rating, 127 reviews

Sweet Spice: A Nifty Little Cottage. With A Pool!

This very small 1 BR cottage lives BIG with a screened porch, SOLAR POWER, valley views, ac, dishwasher, outdoor fitness, and plunge pool. With a clean modern vibe, Sweet Spice is more laidback getaway than luxury villa. It’s an ideal HQ for 2 active STJ adventurers - but with a few extra amenities! Located off the beaten path on the quiet side of STJ, it feels secluded but is only a 5 minute drive to the shops of Coral Bay. Note: road is rough and requires a 4WD and there are LOTS of stairs.

Top guest favorite

Villa in Quepos

4.98 out of 5 average rating, 214 reviews

Tulemar Resort - Salty Breeze - Premium 2 Bedroom

Tulemar Resort-Villa Salty Breeze-Premium 2 Bedroom Villa. Very Private Ocean View Balcony. -Major Monkey Corridor -Balcony Hanging Couch with Amazing Views -Balcony Jacuzzi -Superfast Wifi -Arcade game with 3000+ games -Never ending hot water 2 person open air showers in each bedroom -Huge Bedroom Smart TV's -Furnture made from recycled river logs(no trees killed) -Access to Tulemar beach, van, and pools -Room Service anywhere in Tulemar including beach -Daily Cleaning -Full Time Concierge

Top guest favorite

Dome in Cayey

4.99 out of 5 average rating, 534 reviews

Escape to Puerto Rico

¡Vive una experiencia única y mágica de glamping en las hermosas montañas de Puerto Rico! Xcape Dome PR es el lugar perfecto para darte un “xcape” de la rutina y reconectar con la naturaleza. Ubicado en el pueblo de Cayey, PR, a solo 10 minutos de las vías principales. Sumérgete en esta aventura romántica diseñada para parejas, aventureros o viajeros y disfruta de las imponentes montañas, paisajes, flora y fauna, así como, de los detalles únicos que hacen de Xcape Dome PR un lugar especial.

Top guest favorite

Condo in Montego Bay

4.95 out of 5 average rating, 141 reviews

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

Guest favorite

Tiny home in Naguabo

4.99 out of 5 average rating, 147 reviews

Casa Suiza (Mountainous Area)

Casa Suiza es un lugar para escapadas románticas, sólo para parejas. Estamos ubicados en lo alto de la montaña, es muy privado y alejado de la ciudad, a una hora de distancia de San Juan y el Aeropuerto Internacional de Puerto Rico. Tenga en cuenta que dirigirse a nuestra propiedad es por calles con curvas y algunas pendientes empinadas, pero completamente transitables. Recomendamos rentar un vehículo SUV o un 4x4 para su tranquilidad, si no está acostumbrado a transitar en la Montaña.

Top guest favorite

Home in Palm Beach

5 out of 5 average rating, 227 reviews

Aruba Private Resort. Its All Yours and Only Yours

Welcome to Casa Carmela. Relax in the resort sized pool and outdoor oasis. Melt the day away under the exotic palapas or toast your buns in the sun. Whatever your pleasure, Casa Carmella aims to please. She’s a short walk to Palm Beach one of the top rated beaches in the world. Restaurants, casinos and nightlife are walkable as well. She comes with a comfy king size bed, gas grill, fully equipped kitchen, beach chairs & beach towels and cooler. This is all yours and only yours.

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 Provincia de Puntarenas

4.87 out of 5 average rating, 126 reviews

Ocean view villa, big infinity pool

Escape to a tropical paradise at Sol to Soul. Nestled in a small gated community on a lush hillside overlooking the South Pacific this recently updated villa has a unique panoramic view of the jungle and ocean. Dubbed “Million Dollar View” it is a 2 bedroom, 2.5 bathroom private villa, steps from Dominicalito Beach and Poza Azul waterfall with a fabulous big infinity pool. There are lots of great activities to do nearby, but save some time to enjoy a sunset. Pura Vida!

Top guest favorite

Loft in Tulum

4.98 out of 5 average rating, 117 reviews

Casa Copal Luxury Design Penthouse with Pool

Luxury Design Penthouse located in Tulum what comes with unique features as double hight ceiling living, large Rooftop Pool, a luxury high end speaker system from Bang & Olufsen, beautiful bed textiles and large spaces with unique decoration located in the most trendy Area of Tulum. Beside concierge services the property offers 2 high speed fiber optic internet networks for the best service in Tulum. This serene, elegant and quiet place is a Design Heaven!

Top guest favorite

Cottage in Vieques

4.99 out of 5 average rating, 230 reviews

Casa Corona - Amazing Views, Pool, Close to Beach

Experience this newly renovated home with constant ocean breezes and breathtaking views of the Corona Reef, Culebra and the "Big Island." This cozy cottage offers 'casual luxury' with premium furnishings and cool, comfortable linens and fabrics. Enjoy the ocean-facing plunge pool and outdoor shower. Located just past the former W Resort on a private fenced/gated lot that's minutes from everything (airport, ferry, restaurants, beaches and shopping).