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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Guest favorite

Cottage in La Romana, Dominican Republic

5.0 out of 5 average rating, 141 reviews

Chic Cottage Nature Casa de Campo

Walking distance to Altos de Chavon. Shower alfresco under the stars by lush ferns. Indoor-outdoor living flows out from an open-concept living area to a pool and golf course beyond. An organic palette of white and earthy hues, with bamboo and rattan accents, mirrors the grassy views. Within the amenities you have a fully equipped kitchen, a terrace with your own pool, and an indoor and outdoor shower if you feel like showering under the stars. Cedar wood walking closet with your own safe. Daily housekeeping service included. You have access to all that Casa de Campo has to offer. The resort charges a $25 pp daily fee in order to receive your own resort-pass to access the beach, golf courses, restaurants etc. We can help you arrange that. Car rental or golf cart can be arranged at your convenience. We have been living and vacationing in Casa de Campo for almost 30 years. This beautiful area is surrounded by golf courses and overlooking a lake. On this 1.5 acre property we built our house and created a separate area for our cottage. You will have all the privacy you want. We want you to enjoy your stay. The cottage is set on an upscale resort, surrounded by gardens and a lake. You will have access to all the facilities within the resort which include a beach club, marina, equestrian center, championship golfs, restaurants, bars, and shopping. Casa de Campo charges $25 pp daily to each guest staying within the resort. This will be paid when you register at the entrance of Casa de Campo. You can also take an enchanting stroll to the Altos de Chavón village, it is walking distance from the house. https://www.airbnb.com/become-a-host/28779017/title Concierge service at your disposition to coordinate anything from a private yoga class, to a in house chef. Martina is a certified health coach, if you want to take extra care of yourself during your stay she will help you create a plan tailored to your needs. Anything can be coordinated, from getting your day started with a healthy breakfast, to a detox post partying, in combination with yoga or massages. All while learning new ways to be healthy and feel amazing ... Your vacation can be turned into a retreat if you wish.

Jun 10 – 17

R7,299 ZAR per night

Guest favorite

Home in San Cayetano de Venecia, Costa Rica

4.96 out of 5 average rating, 134 reviews

Quinta La Ceiba Modern Home with Pool in DairyFarm

A contemporary roomy vacation home situated in a dairy farm. Embrace serenity, unwind in a tranquil haven surrounded by cows grazing in lush green fields. It's a birdwatcher's paradise too. This is an ideal escape to disconnect and reconnect with nature. Dine and lounge outdoors make the most of the property's features. Our in-house travel concierge will be glad to arrange tours and activities for you at no additional cost. Consider our private chef service for an even more memorable experience.

Oct 23 – 30

R3,726 ZAR per night

Guest favorite

Villa in La Fortuna, Costa Rica

4.96 out of 5 average rating, 340 reviews

House of Views w/ King Bed + Volcano View

This exclusive and stylish property features gorgeous views of the volcano that can be enjoyed from anywhere in the house. Take a moment to breathe fresh air from the terrace and connect with the nature surrounding you, all this while you savor a warm cup of Costa Rica’s best coffee. After a day of exploring and hiking to the famous waterfall come back to unwind at the jetted pool and reload for another day of fun. Discover La Fortuna like a local while enjoying of privacy, comfort and luxury

Nov 29 – Dec 6

R14,894 ZAR per night

Guest favorite

Condo in Miami, Florida, US

4.9 out of 5 average rating, 151 reviews

ICON 2B/2B Skyline Free Pool, Spa, HotTub

INSTA READY, This unit provides over 1,350SqFt of breathtaking ocean and city views with Two Bedrooms and Two Bathrooms. Located within the luxurious Icon building. The Icon is a 5 star condominium. It is located inside the heart of Downtown Miami/ Brickell. It includes the same amenities as the W Hotel, such as free access to spa, pool, hot tub, and 4 restaurants, including Cipriani. The apartment comes with three flat screen TVs, HighSpeed WiFi, and toiletries. As well as four separate beds.

Sep 24 – Oct 1

R8,002 ZAR per night

Guest favorite

Apartment in Fitts Village, Barbados

4.93 out of 5 average rating, 107 reviews

La Porta Della Casa - Sunset Platinum West Coast

La Porta Della Casa is a modern, contemporary accommodation located on the platinum coast of Barbados, within walking distance to the nearest beach and close to great restaurants such as The Tides, The Cliff, Cin Cin By The Sea, Nishi and Fusion, to name a few. 7 minutes' drive from the famous Limegrove Mall in Holetown with duty-free shopping and supermarkets . On Sunday night, 2nd street comes alive with their street party. 7 minutes' drive from the city of Bridgetown with more duty-free.

Jan 4 – 11

R6,176 ZAR per night

Guest favorite

Villa in Guayacanes, Dominican Republic

4.9 out of 5 average rating, 123 reviews

Guayacanes Village- Front beach house

Lujosa casa frente al mar ubicada en el municipio de Guayacanes, equipada con todo lo necesario para una estadia placentera. La casa se encuentra a 15 minutos del aeropuerto y 45 minutos de la ciudad de Santo Domingo. Esta es una propiedad para disfrutar con la familia y amigos cercanos. No permitimos fiestas, bodas y eventos de muchas personas. Tampoco permitimos la entrada de personas extrañas como strippers y prostitutas. El turismo sexual no esta permitido en nuestra propiedad.

Apr 6 – 13

R11,850 ZAR per night

Guest favorite

Villa in Montego Bay, Jamaica

4.93 out of 5 average rating, 148 reviews

VIBES COVE enjoy your stay while getting pampered

FREE Arrival meal , the first day you arrive to vibes cove you’ll receive a complementary arrival meal by our personal chef on the property. Vibes coves villa is super Spacious and private enjoy your vacation by getting pampered. This property comes with a personal chef , Butler, and housekeeper. Enjoy V.I.P services your entire stay. Property staff stays in their helpers quarters ( not apart of the property ) only those listed on the Airbnb is allowed at the property.

Oct 24 – 31

R12,629 ZAR per night

Superhost

Shipping container in Aguada, Puerto Rico

4.88 out of 5 average rating, 216 reviews

Visum Luxury Container House

Experience the beauty of the west side of Puerto Rico has to offer. A shipping container house full of glam and luxury that will enhance an unforgettable stay. A two bedroom and two bathroom house full of amenities such as infinity pool, a fully equipped kitchen, 100% powered house with renewable energy and outstanding views from every corner of the house. From the first sip of coffee until the moment to go to bed you will experience “Visum” at it’s best.

Oct 24 – 31

R5,909 ZAR per night

Guest favorite

Farm stay in Bonao, Dominican Republic

5.0 out of 5 average rating, 231 reviews

Hacienda del Río, Bonao - Casa doña Celia Eco Farm

Ideal for a group of friends and/or family, capacity for 6 people, with everything you need to spend a quiet and family holiday. Safe place, staffed for 24/7 assistance. Convenient location; close to the capital and Santiago. Ideal for nature lovers, hikers, cyclists, and all those looking for greenery, and peace. We include programs of activities with the animals of our farm. Routes available for trails, enduro and cycling. A real paradise!

Dec 20 – 27

R3,648 ZAR per night

Guest favorite

Dome in Orocovis, Puerto Rico

4.93 out of 5 average rating, 160 reviews

The LM1 Domescape

Acompáñanos a un lugar mágico e inolvidable en los interiores de nuestra isla, Orocovis PR. Disfruta del encantador entorno de este Domo y todo de lo que ha de ofrecer. A solo minutos de lugares turísticos como lo es Toro Verde, Toro Negro y ciertos rios en donde puedes dar un chapuzon! Además estamos a solo minutos de ciertos restaurantes donde puedes tener un brunch, almuerzo, cena o simplemente pasar a darse un trago o picadera.

Mar 13 – 20

R5,166 ZAR per night

Guest favorite

Cottage in Monteverde, Costa Rica

4.97 out of 5 average rating, 156 reviews

Villa 3 - Heated private pool and amazing sunsets

Relax and enjoy the best sunsets at Villa 3, this new house is fully equiped for your perfect getaway. Fully furnished with everything you need for your holidays. Connect with nature and enjoy the amazing views that surround the house. You will hear birds chanting every day during the sunrise and sunset. We are located on privileged spot that has an amazing view of the gulf of Nicoya.

Jul 2 – 9

R8,292 ZAR per night

Guest favorite

Villa in Santa Teresa beach, Costa Rica

4.96 out of 5 average rating, 106 reviews

Villa Melody

Welcome to Villa Melody ! A beautiful and spacious luxury villa with a stunning ocean and jungle view. Located in an incredible area in the center of Santa Teresa. It is provided with full equipment for your comfort and it’s located just walking distance to the white sand beach, supermarkets, some restaurants and coffee shops.

May 11 – 18

R11,658 ZAR per night