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Holiday 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 favourite
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.

Guest favourite
Apartment in Tulum
4.97 out of 5 average rating, 117 reviews

Mayan-Inspired Luxe Villa & Concierge| Top Rated

Experience the epitome of Tulum-style elegance at our Bohemian Chic Residence with style, comfort, and convenience. TEMPLIA is a unique, luxurious 2BR/2BA home with a private pool, outdoor hot tub, and award-winning Mayan-inspired design with fully equipped kitchen, concierge service, fast WiFi, and any additional service needed. Discover a harmonious blend of luxury and comfort perfect for travelers who value design, privacy, and quality.. Unforgettable moments await in refined Tulum living!

Top Guest favourite
Villa in Playa Bejuco
4.98 out of 5 average rating, 130 reviews

Modern Villa+Private Pool+Ocean View+Gated+Beaches

This modern and secluded jungle paradise is surrounded by 40 acres of lush tropical forest with magnificent mangrove and ocean views, less than one kilometer away from one of the most stunning beaches in Costa Rica! The villa has a private pool, BBQ, and a fully equipped 2-bedroom guest house. The property is located 2 hours from San Jose's Juan Santa Maria International Airport (SJO), close to 3 National Parks: Manuel Antonio, Carrara, and Cangreja, with several restaurants and a market nearby.

Top Guest favourite
Cabin in Isabela
4.98 out of 5 average rating, 186 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.

Top Guest favourite
Tiny home in Fajardo
4.99 out of 5 average rating, 267 reviews

Magical! Ocean view Cabana w/ Pool Spa on mountain

This memorable place is anything but ordinary. You will get to enjoy this amazing and super private space surrounded by nature and unbelievable views of the ocean and the city. Fully equipped with everything you will need during your stay to include kitchen, full bath with rain shower, A/C, living space with 55" TV, dinning and sleeping areas, terrace with killer views, and of course the pool spa with infinity view! And many more. All of this while enjoying of a complementary bottle of Wine!

Top Guest favourite
Home in Quepos
4.99 out of 5 average rating, 202 reviews

Costa Rica jungle home: remodeled/waterfall path!

Serene, beautiful 2 BR/3BA open concept home with infinity pool bordering Manuel Antonio National Park. Last home on a quiet street in the community of Colina Monito. Frequented by wildlife as the house borders the National Park- it’s as though you’re staying in the park! Minutes away from shopping and local restaurants, yet private. Concierge service and maid service included along with many amenities. Short drive to the beach. Also NEW modern bathrooms and NEW path to the waterfall!

Guest favourite
Villa in Mal Pais
4.97 out of 5 average rating, 136 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 favourite
Home in Palm Beach
5 out of 5 average rating, 230 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.

Top Guest favourite
Cabin in Aguadilla
5 out of 5 average rating, 129 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 favourite
Villa in La Fortuna
4.98 out of 5 average rating, 304 reviews

Villa Heliconia, A Volcano in your Garden.!

The vacation villa with the closest and most SPECTACULAR view of the Arenal Volcano 10 minutes to downtown La Fortuna Fully equipped Private hot tub Grill and fire pit area Optic fiber high speed 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! All guests can enjoy the 1-day pass to the nearby resort's hot springs Base rate for 2 people. Vehicle recommended

Top Guest favourite
Apartment in Cruz Bay
5 out of 5 average rating, 151 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.

Top Guest favourite
Home in Savegre
4.96 out of 5 average rating, 134 reviews

Private 2BR Villa | Pool + Manuel Antonio Views

Private 2BR/2BA home with a stunning infinity pool and unobstructed ocean + jungle views over Manuel Antonio. Enjoy indoor-outdoor living, AC, fast Wi-Fi, 55” Smart TV, and a full kitchen. Perfect for families or couples. Minutes to waterfalls, surf towns, and beaches. We’re happy to help you arrange private chefs, massages, stocked groceries, tours, and transportation—relax while we handle the details.

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