
Holiday rentals with a pool in Antilles
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Antilles
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.

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!

My Kinda Party - Luxury Rental in Walking Distance
Welcome to My Kinda Party. My Kinda Party is gorgeous, breathtaking four-bedroom, three full bathroom luxury Villa with amazing amenities. This brand-new construction was just finished end of 2022. My Kinda Party is situated in the highly desirable SW Cape. Centrally located with Gulf Access, walking distance to restaurants and shopping, near Cape Harbor with all of its restaurants and shops. The area is a favorite for walking, biking and relaxing. As soon as you open the double glass door

RATED #1 Airbnb in W. Palm Beach! Heated Pool! 🏳️🌈
The cottage is within walking distance to The Square, the intracoastal, and many local restaurants. Clematis St. is close by and is full of fun restaurants and cafes. You can ride a bike to the beach and enjoy our wonderful Historic District and Howard Park. 10 minutes from new Outlet mall. We will be happy to assist you with area information to help plan a wonderful vacation. We have another cottage on property for large families or groups.. https://www.airbnb.com/rooms/13128914?s=51

Hacienda Sol y Luna Mountain Retreat
Enjoy the lovely setting of this romantic spot in nature and discover the serenity in our cozy farmhouse. This private villa wraps you in a lovely and peaceful environment with majestic mountains all around. The house is fully equipped for your convenience. It is ideal for couples in need of a nice getaway or just reconnect with yourself and nature. It is on a gorgeous tropical private 3 acre estate with private pool. Located in Villalba, Puerto Rico, just 50 minutes from Ponce's Airport.

Airstream With Pool, Amazing Ocean & Nature Views
This beautifully appointed Eco friendly 30' Feet Flying Cloud RV is the only luxury Airstream glamping experience in the Caribbean. Located in peaceful nature on the North Coast of Aruba, featuring a private, deep saltwater pool and amazing cacti and ocean views. Exceptional service with attention to detail prioritizing sustainability. Connecting guests to unique local experiences and products, creating a truly one of a kind vacation. Looking for the coolest stay in Aruba? This is it!

Oceanfront Sunset Patio w/ BBQ + Pool, Gym & Spa
Welcome to Sunset Point #29 — a brand-new 1-bedroom, 1.5-bath oceanfront condo in Grand Cayman’s quiet North West Point. This 1,016 sq ft ground-floor retreat features floor-to-ceiling windows, a private patio with Weber grill, and the island’s best sunset views. Relax by the oversized pool and spa, work out in the fully equipped gym, or stroll 2 minutes to Macabuca for world-class diving, cocktails, and Cayman sunsets. Perfect for couples or small families seeking style and serenity.

Caribbean Paradise I
This is a studio on a cliff with a spectacular view facing mangroves, Middlesex and Poza El Teodoro beaches and the Atlantic Ocean. Each studio has Smart TV internet, private bathroom, kitchenette microwave, electric coffee maker, small refrigerator, queen size bed, side table, futon (convertible to twin size bed), AC and a balcony with ocean view. The common areas for the studios are a pool, gazebo, sitting area by the pool and they all have ocean view. Pets are not allowed.

Chalet De Los Vientos
Chalet de Los Vientos is a beautiful and cozy tiny house located in 25 acres , in the mountains of Caguas , PR at 2000ft above sea level with a spectacular view, heated pool and the privacy you deserve! This Chalet is a couples retreat and the perfect getaway for you and your loved one to disconnect from the daily routine. If you love coffee as much as we do, there is a dedicated coffee bar for you to make your espresso drink. We also have a 19Kw Caterpillar backup generator 💡

Paradise Escape-Charming Oceanfront Guest Suite
A tranquil oceanfront escape for couples and solo adventurers... Wake-up in bed to a lovely view of a luscious green landscape that melds with the emerald green and blue ocean, sip a hot cup of coffee on the porch, enjoy a sunset cocktail by the ocean front pool, break a sweat in a friendly game of tennis, or take a blanket out to the lawn under the palm trees for breathtaking star gazing. PLEASE NOTE: WE ARE NOT LOCATED ON BATS CAVE BEACH. AIRBNB HAS THIS WRONG!

Caribia Cottage-Elegant Villa w/Private Pool
Caribia Cottage is located in a private Estate with access only through an electronic gate. The spectacular panoramic view of the St. Thomas Harbor is unforgettable and one which many a famous star toasted to when the property was formerly owned by a celebrated Broadway Producer. Walk just two steps from the Cottage into the spacious swimming pool. Enjoy gazing at the busiest Harbor in the Caribbean, as the mega yachts, seaplanes and cruise ships come and go.

Escape Puerto Rico | Luxury Dome + Pool + Views
Escape to a romantic and luxurious glamping dome surrounded by the lush mountains of Cayey, Puerto Rico🌿. Enjoy total privacy with a private heated pool, panoramic views, and elegant design — the perfect retreat for couples or solo travelers seeking peace, comfort, and connection with nature. Wake up to mountain sunrises, relax under the stars, and experience a serene escape just an hour from San Juan — were nature and luxury meet in perfect harmony.
Popular amenities for Antilles rentals with a pool
House rentals with a pool

Private Villa Tropical Escape Close to GB Beach

Ask about the Long Stay Discount!

Mountain Retreat • Private Pool • Nature + Peace

The Breakaway: Heated Pool with Outdoor Kitchen in

Casa Cascada

Casa Dalila - Luxury Home with Private Pool

Cabaña Serena: Saltwater Pool-King Bed-In Puntas

La Casita: Private Heated Pool W/ Ocean Views
Condo rentals with a pool

SUNNY ISLES GORGEOUS 15A OCEAN FRONT (+hotel fees)

Luxury Beach & City View Condo 5 min walk to beach

Exclusive Studio w/ Balcony & King Bed - Cap Cana

ON CANAL! Pool+Walk to BEACH! Boat Watch! 2b/2b

Modern luxury condo: Steps from Atlantis & Beach

The Quarry, Beachfront sub penthouse 150m to clubs

Ritz-Carlton Beach Penthouse by Guaranteed Rental

Oceanfront 1BR Lux Apt Pool Beach Gym Pickleball
Home rentals with a private pool

1BR Oasis with Breathtaking Ocean View Pool

Gorgeous Colonial House near Cafes and Bars

Walk Along the Beach From Casa Serene

Casa Pantheon Luxury Colonial House

Condado Beach Vistas by Cesar 2501
Luxury Island Villa with Private Pool & Garden BBQ

Beachfront Casa Maeva 4 bedrooms-

Idyllic Beachfront Penthouse w/Private Plunge Pool
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