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Vacation rentals with a pool in Leeward

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Leeward

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
An outdoor area features a private pool surrounded by lush indigenous foliage. Comfortable lounge chairs are positioned nearby, with colorful towels neatly arranged. The scene overlooks a serene landscape, enhancing the inviting atmosphere for relaxation and enjoyment.
Cottage in Long Bay Hills
4.95 out of 5 average rating, 114 reviews

Flame Tree Cottage|Ocean view&pool.Walk to beach

Built in 2013. 1 bedroom 2 bathroom cottage with PRIVATE POOL. Sunrise & ocean view from the front deck and only 1/4 mile to the beach. Perfect for 2, but can sleep up to 6. Full kitchen, 2 bathrooms + outdoor shower. No bathtub. Propane Grill. AC in master bedroom. WIFI throughout & local cell provided. This quaint clutter-free 1200 square foot home is surrounded by indigenous foliage, cactus', succulents and native stonework. A rental car is recommended to explore all the island has to offer!

Top guest favorite
Villa in The Bight Settlement
4.97 out of 5 average rating, 133 reviews

Ideal private getaway villa | 250 yds to the beach

The perfect getaway villa, just 250 yards from Grace Bay beach, Gracehaven Getaway is tucked away from passing traffic in a little garden oasis of its own. It is an ideal venue to celebrate anniversaries, birthdays, or honeymoons, or just for a couple seeking a romantic, private setting. Enjoy your own private pool hidden away from main roads and just a 2-minute walk to the Grace Bay beach and Coral Gardens Reef. Easily walk to local restaurants or visit the nearby supermarket for groceries.

Guest favorite
An outdoor pool area is illuminated by natural sunlight, featuring lounge chairs with blue cushions arranged around the pool. Palm trees provide shade, while ocean views extend in the background, showcasing the vibrant blue water and greenery of the hillside.
Condo in Turtle Cove
4.95 out of 5 average rating, 200 reviews

🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝

🏖 NEWLY RENOVATED, SPACIOUS one bedroom condo with an ocean view at La Vista Azul Condo Resort. Located hillside in the exciting area of Turtle Cove, Providenciales, the unit is close to several excellent restaurants, cafes, bars, a casino, and a marina. Most notably, the studio is a 10 minute walks to Smith's Reef in the Princess Alexandra Park National beach. Smith’s Reef is located near Turtle Cove on the north coast of Providenciales, and about 3.5 miles (5.6 km) from Grace Bay 🏝

Guest favorite
A contemporary living area features a sleek white sectional sofa with plush cushions, positioned around a minimalist coffee table. Decorative pillows and a small vase with flowers add subtle color. Soft natural light brightens the space, enhancing the modern design.
Apartment in Leeward Settlement
5 out of 5 average rating, 102 reviews

Luxury Spacious 1 Bed Condo close to the Beach

Just renovated: The perfect condo, and only 3 minutes from the famous Grace Bay Beach! Located in the exclusive Leeward area, a gated, secure residential area where all the major luxury villas are. The beach is a short stroll away & the main Grace Bay shopping / resort area is 5 minutes by car. The condo boasts a large pool, stunning modern finish and appliances. This 925 sqft luxury 1 bedroom, freshly renovated (Jan 2023), provides all necessary amenities for your home away from home.

Superhost
Condo in Grace Bay
4.82 out of 5 average rating, 136 reviews

Gated Condo in Grace Bay/ Short Walk to Everything

This studio in Grace Bay offers comfort and convenience. It's a few minutes walk to the beach, grocery stores, restaurants, activities, and a medical center. The Caicos Key condo is new and includes a 55-inch smart TV with Fire Stick, fast Wi-Fi, a dishwasher, and a washer/dryer combo. For your security, the property has a smart lock and is gated. Guests can also use the swimming pool and BBQ area. We aim to make your stay comfortable and can provide anything you need on demand.

Superhost
A tranquil outdoor space features a bright blue pool surrounded by palm trees. Comfortable lounge chairs are positioned beside the pool, and a shaded bar area with a pink umbrella adds to the relaxing atmosphere. Lush greenery and colorful flowers enhance the tropical setting.
Cottage in Grace Bay
4.82 out of 5 average rating, 145 reviews

Tropical Guest House

This stylish studio sits within a lush tropical garden behind a semi-detached villa. Enjoy cold AC, a well-equipped space, and your own private grill. Grace Bay Beach is just a 15-minute walk—or less than a minute by car—making it easy to enjoy one of the world’s most beautiful shorelines. Coco Bistro, a renowned island restaurant, and Coco Van are close by, with shops and a grocery store also within easy reach. A fantastic location, great value, and close to everything! 🏠🌴

Guest favorite
A covered balcony offers outdoor seating with two armchairs and a coffee table. Lush greenery surrounds the area, and a pool can be seen in the background. The tiled floor complements the natural elements of the space.
Condo in Providenciales
4.89 out of 5 average rating, 152 reviews

*Balcony View* Modern Studio C202

Welcome to our little piece of paradise in Providenciales, Turks and Caicos. We hope that you will enjoy our modern style condo as much as we do. Our condominium is situated at Queen Angel Resort, walking distance to the #1 beach in the world, Turtle Cove Marina, and Smith’s Reef the best snorkelling spot on the island. Turtle Cove is a tourist hot spot with many restaurants, excursions and attractions available. The condo has recently been fully renovated and remodelled.

Top guest favorite
A serene beachfront scene showcases two yellow lounge chairs positioned under white umbrellas. The calm turquoise waters are framed by a clear blue sky, with fluffy white clouds dotting the horizon. Native greenery and sandy pathways lead to the water's edge.
Villa in Providenciales
4.95 out of 5 average rating, 132 reviews

Villa DelEvan 4D / 1-bedroom villa

Centrally located on the Grace Bay Beach, a perfect place for luxury, rest & tasting the best island cuisine. Close to everything you need for a great vacation: Walking dist. from 4 restaurants - Mango Reef, Shark Bite, Baci & Simone’s. 10 min drive to the famous island Fish Fry, 15 min drive to the Airport, 5 min drive to the supermarket. Gated property, private parking, 24hr security. Boating/fishing/sightseeing/wind surfing & more. Water sports pick-up on property.

Guest favorite
The exterior of a modern two-story villa is showcased, featuring large windows and multiple outdoor lounge areas. A private pool is centrally located, surrounded by sun loungers. Soft lighting illuminates the villa's facade, enhancing its contemporary design against a sunset backdrop.
Villa in Long Bay Hills
4.86 out of 5 average rating, 132 reviews

Modern Villa with Private Pool Near Long Bay Beach

- Immerse yourself in tranquil luxury at a gated two-story villa just minutes from Long Bay Beach. - Enjoy bright, spacious interiors, a modern kitchen, and a private, secure setting throughout. - Relax by the private pool, fire up the BBQ, and unwind in peaceful outdoor lounge areas. - Stay connected with fast WiFi and explore Grace Bay’s beaches, shops, and dining nearby. - Reserve your stay for a refined tropical retreat designed for comfort and relaxation.

Guest favorite
Home in Providenciales
4.96 out of 5 average rating, 363 reviews

Modern Villa with Pool Minutes to Grace Bay Beach

Villa Cocuyo offers complete privacy, comfort, and consistent 5⭐️ hospitality. Couples love the safe and secure , peaceful setting, private solar heated pool, modern interior, and garden oasis. Enjoy fast WIFI, premium amenities, and a spotless space designed for true relaxation. Our 5-star reviews reflect our dedication to exceptional hosting, attention to detail, and a worry-free, private island getaway close to everything including beach

Top guest favorite
The expansive resort pool area features multiple sections, including a large main pool with a central gazebo. Vibrant palm trees surround the space, enhancing the tropical atmosphere, while sun loungers and umbrellas are positioned nearby for guest relaxation.
Condo in Providenciales
4.92 out of 5 average rating, 258 reviews

★★★★★ Modern Condo | Amazing Pool | On Site Spa

• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access • Hot tub • Highest Rated Spa on Island onsite • Fully equipped kitchen • Private front patio • Garage parking for 1 car • Onsite washer + dryer • Fitness center access • Queen sofa bed with extra linens in living room • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

Guest favorite
A private villa features a sparkling pool surrounded by lush palm trees and a spacious patio. Comfortable lounge chairs are positioned near the water, while the interior of the villa can be seen through expansive glass doors, seamlessly integrating indoor and outdoor living.
Villa in Caicos Islands
4.95 out of 5 average rating, 125 reviews

Cheers 🥂 Villa 🌴

Beautiful private Villa in a superb location. Just 2 minutes by car, or 10 minute walk to Grace Bay Beach & Shopping! Cheers Villa is filled with love ❤️ where you can relax in peace during your holiday. We have all the essentials to enjoy the climate of Turks & Caicos. You can relax by the private pool after a day at the beach! 2 bedrooms (King & Queen) 2.5 bathroom. Each room has its own AC as well as the downstairs living space.

Popular amenities for Leeward rentals with a pool

Quick stats about vacation rentals with a pool in Leeward

  • Total vacation rentals

    Explore 270 vacation rentals in Leeward

  • Nightly prices starting at

    Leeward vacation rentals start at G$29,214 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,420 verified reviews to help you choose

  • Family-friendly vacation rentals

    210 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    270 of Leeward vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Leeward rentals

  • 4.8 Average rating

    Leeward stays are highly rated by guests—averaging 4.8 out of 5!