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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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Dome in Ponce, Puerto Rico

4.93 out of 5 average rating, 545 reviews

Bubble Puerto Rico

Tenemos otra Villa disponible con las mismas características - https://www.airbnb.com/h/bubblepuertoricoeternal ¡Experimenta por primera vez en PR quedarte en una habitación de burbuja! Bubble PR es una estancia ecológica, mágica, escondida en las montañas de Ponce, PR. A 18 minutos de la Ciudad, podrás sumergirte en una experiencia única, romántica, para parejas o viajeros solos, rodeada de naturaleza, abundante en flora, fauna y situados en la orilla de uno de los ríos mas abundante de Ponce

Sep. 26 – Oct. 3

$429 CAD per night

Guest favourite

Villa in La Fortuna, Costa Rica

4.95 out of 5 average rating, 342 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

Dec. 6 – 13

$878 CAD per night

Guest favourite

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.

Oct. 2 – 9

$629 CAD per night

Guest favourite

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. 6 – 13

$449 CAD per night

Guest favourite

Tiny homes in Jobos, Isabela, Puerto Rico, Puerto Rico

4.94 out of 5 average rating, 284 reviews

Salida Escondida La Barraca Beach/Rest, 6 min car.

Cabaña de Madera en El campo de Isabela, situada a 7minutos en carro de playa Jobos Isabela, paseo tablado, restaurants y 15 minutos del Aeropuerto Rafael Hernandez Aguadilla. Las facilidades tiene generador y cisterna de agua, Ducha de baño agua caliente. Porton, hamacas, mesa picnic, Cocina con neverita playa, estufita, A/C BbQ y utensilio, mesa pinpong, genga, Domino y sillas para dos con sombrilla para relajacion. Wooden cabin in El Campo de Isabela, located 6 minutes by car from Jobos.

Aug. 9 – 16

$177 CAD per night

Guest favourite

Condo in Montego Bay, Jamaica

4.92 out of 5 average rating, 367 reviews

Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.

This new beach theme apartment is located in 22 Freeport – A gated community in Freeport Montego Bay. 22 Freeport is a beach front complex on a Marina that features 24 hour security, a gym, infinity edge pool and playground; whilst the unit on the ground floor opens onto a cozy back yard space that flows into an open green space. Be sure to check out my other units in this community on my profile if your dates are not available or if you would like to book them all for your large group.

Mar. 1 – 8

$318 CAD per night

Guest favourite

Villa in Guayacanes, Dominican Republic

4.9 out of 5 average rating, 124 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.

Nov. 7 – 14

$857 CAD per night

Villa in Soufriere, St. Lucia

4.86 out of 5 average rating, 166 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!

Jul. 8 – 15

$785 CAD per night

Guest favourite

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.

Apr. 13 – 20

$964 CAD per night

Guest favourite

Dome in Orocovis, Puerto Rico

4.93 out of 5 average rating, 161 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

$400 CAD per night

Guest favourite

Cottage in Monteverde, Costa Rica

4.97 out of 5 average rating, 157 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.

Nov. 5 – 12

$690 CAD per night

Treehouse in La Palmera, Costa Rica

4.84 out of 5 average rating, 836 reviews

Rainforest Tree House with Hot Springs

No children under 7 years of age for safety reasons. The Tree House is hand-crafted, one of 3 casitas and 3 treehouses at the Bio Thermales natural resort organically integrated into our 35 acre rainforest. Guests enjoy free access, from 9 am to 10 pm to the 15 natural hot and cool springs pools of various temperatures and rainforest trails.

Sep. 8 – 15

$126 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Houses

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Bungalows

Intimate homes, inviting architecture

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Popular amenities for Caribbean rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

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

Oct. 26 – Nov. 2

$276 CAD per night

Guest favourite

Home in Playa Tivives, Costa Rica

4.97 out of 5 average rating, 186 reviews

Lovely beachfront family house with private pool

Oct. 1 – 8

$326 CAD per night

Guest favourite

Home in Cartagena, Colombia

4.95 out of 5 average rating, 171 reviews

Cartagena walled casa Mónaco

Apr. 13 – 20

$1,306 CAD per night

Guest favourite

Home in Naples, Florida, US

4.98 out of 5 average rating, 206 reviews

Island lifestyle family vacation home (Salt Pool)

Oct. 25 – Nov. 1

$378 CAD per night

Guest favourite

Home in Rincon, Puerto Rico

4.91 out of 5 average rating, 205 reviews

Casa Ensenada- Rincon Puerto Rico

Sep. 24 – Oct. 1

$737 CAD per night

Guest favourite

Home in Adjuntas, Puerto Rico

4.97 out of 5 average rating, 183 reviews

Secluded Coffee Farm House w/Chimney & Heated Pool

Nov. 14 – 21

$955 CAD per night

Guest favourite

Home in Lake Worth, Florida, US

4.97 out of 5 average rating, 156 reviews

Tropical Beach Villa with Heated Salt Water Pool

Sep. 1 – 8

$696 CAD per night

Guest favourite

Home in Stake Bay, Cayman Islands

5.0 out of 5 average rating, 36 reviews

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

Apr. 12 – 19

$794 CAD per night

Condo rentals with a pool

Guest favourite

Condo in Playa Hermosa, Costa Rica

4.86 out of 5 average rating, 499 reviews

Amazing Oceanview Condo with Private Pool

Mar. 27 – Apr. 3

$250 CAD per night

Condo in Miami, Florida, US

4.8 out of 5 average rating, 154 reviews

Waterfront Spacious Luxury 1 Bedroom IconBrickell

Oct. 15 – 22

$335 CAD per night

Guest favourite

Condo in Carolina, Puerto Rico

4.99 out of 5 average rating, 135 reviews

Beach Front Condo with Endless Ocean Views

Mar. 27 – Apr. 3

$600 CAD per night

Condo in Bal Harbour, Florida, US

4.9 out of 5 average rating, 247 reviews

$3 Million Oceanfront Residence ★★★★★ Resort

Aug. 19 – 26

$1,372 CAD per night

Condo in Carolina, Puerto Rico

4.92 out of 5 average rating, 187 reviews

Breathtaking Views, Beachfront, Remodeled!

Oct. 21 – 28

$682 CAD per night

Guest favourite

Condo in Punta Cana, Dominican Republic

4.99 out of 5 average rating, 104 reviews

G38 Peaceful studio Oceanfront Punta Palmera

Feb. 21 – 28

$225 CAD per night

Guest favourite

Condo in Punta Cana, Dominican Republic

4.95 out of 5 average rating, 107 reviews

Sea view corner aptm with private pool / terrace

Mar. 9 – 16

$296 CAD per night

Guest favourite

Condo in Sosúa, Dominican Republic

4.96 out of 5 average rating, 110 reviews

Heavenly Luxury Ocean View Beach Front Penthouse

Jul. 18 – 25

$355 CAD per night

Home rentals with a private pool

Guest favourite

Cottage in La Romana, Dominican Republic

5.0 out of 5 average rating, 141 reviews

Chic Cottage Nature Casa de Campo

Jun. 4 – 11

$524 CAD per night

Bungalow in Punta Cana, Dominican Republic

4.86 out of 5 average rating, 194 reviews

Lush and Tropical Bungalow

Jul. 1 – 8

$226 CAD per night

Guest favourite

Home in Santo Domingo, Dominican Republic

4.94 out of 5 average rating, 348 reviews

Gorgeous Colonial House near Cafes and Bars

Oct. 4 – 11

$233 CAD per night

Guest favourite

Townhouse in Cartagena, Colombia

4.87 out of 5 average rating, 176 reviews

Luxurious Townhouse With Private Pool in The Old City

Nov. 21 – 28

$911 CAD per night

Guest favourite

Villa in Cartagena, Colombia

4.86 out of 5 average rating, 135 reviews

Old City Luxury Villa - Staff & Breakfast Included

Dec. 17 – 24

$1,404 CAD per night

Guest favourite

Loft in Rincon, Puerto Rico

4.98 out of 5 average rating, 251 reviews

Walk to Sandy Beach from a Hilltop Villa with a Pool

Oct. 5 – 12

$297 CAD per night

Guest favourite

Guesthouse in West Palm Beach, Florida, US

4.99 out of 5 average rating, 154 reviews

Tropical Cabana with Pool in West Palm Beach

Nov. 22 – 29

$343 CAD per night

Guest favourite

Home in West Palm Beach, Florida, US

4.95 out of 5 average rating, 146 reviews

Soak up the Beachy Vibe at a Vibrant Poolside Paradise

Jun. 24 – Jul. 1

$733 CAD per night

Destinations to explore