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Holiday 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 favourite
The spacious bedroom features a king-size bed with striped bedding and a decorative pillow. A wall-mounted Smart TV is positioned across from a wooden desk and chair. Large sliding doors lead to a balcony, allowing natural light to illuminate the room, which has a vibrant blue floor design.
Guest house in Providenciales
5 out of 5 average rating, 101 reviews

“Sail Loft Port”, Duplex with a Pool, Beach Access

Sail Loft Port is the left side of our purpose-built guest duplex. Our Sail Loft duplex features two separate but identical efficiency suites, each one equipped with a King Sized bed, bath and kitchenette. The pool is shared with guests who may be staying in the other side. Wander down to the dock and use our SUPs and kayaks in the canal where you are guaranteed to see turtles. Fast WiFi lets you work from home if you must. Smart TVs with Netflix help you wind down after a day of fun.

Top guest favourite
Villa in The Bight Settlement
4.98 out of 5 average rating, 132 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.

Top guest favourite
A private pool is seen in this tranquil setting, featuring two lounge chairs positioned beside it. A small table holds a bottle of white wine, accompanied by two glasses. Lush greenery and a cloudy sky frame the serene view beyond the pool.
Cottage in Long Bay Hills
4.98 out of 5 average rating, 108 reviews

Seasage Cottage, 2bed 2bath, private pool & gazebo

Built in 2015 Seasage Cottage is a breezy 2 bedroom 2 bath home with a modest ocean view. Sleeps four adults comfortably but can accommodate up to six upon request. A quaint, quiet, clean and clutter free cottage with AC, private pool, BBQ and poolside gazebo. This 1200 square foot home is located in a friendly residential area, with neighbours nearby, but not right next door. The cottage is a 7 minute drive to Grace Bay Beach, 5 minutes to Long Bay beach, and 15 minutes from PLS airport.

Top guest favourite
A spacious living area is seen with comfortable seating arrangements, including a large sofa and armchairs. Natural light floods in through sliding glass doors that lead to a patio. A flat-screen TV is positioned on the wall, complemented by a welcoming décor.
Apartment in Providenciales
4.95 out of 5 average rating, 104 reviews

The Yacht Club-Relaxed Vibe-1 BR-Pool-Beach

This spacious, comfortable, well-designed one-bedroom poolside apartment is in a private gated community—The Yacht Club. Couples and small families will appreciate the gorgeous grounds, stunning multi-level saltwater pool, relaxed vibe, and local restaurants. A five-minute walk will take you to one of the best beaches on the island, which features a snorkeling reef. The property is next to one of the largest marinas on the island with boat cruises, fishing & a variety of water sports.

Top guest favourite
A panoramic view captures the ocean on the horizon, framed by swaying palm trees. The foreground features a spacious terrace with blue umbrellas providing shade. Below, a row of white-roofed buildings is nestled among lush greenery, enhancing the serene coastal atmosphere.
Flat in Providenciales and West Caicos
4.95 out of 5 average rating, 207 reviews

☀️🏖 Modern Luxury Ocean View Studio Suite 🏝☀️

☀️🏖 NEWLY RENOVATED, SPACIOUS STUDIO with an ocean view at La Vista Azul Condo Resort. Located hillside in the exciting area of Turtle Cove, Providenciales, the studio 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 ☀️🏖

Top guest favourite
A modern living area is presented with a spacious white sectional sofa, accented by decorative cushions. A sleek coffee table sits in the center, featuring a playful design. Wall art and a small plant add subtle touches to the minimalist decor.
Apartment in Leeward Settlement
4.94 out of 5 average rating, 102 reviews

Luxury 1Bed Large ModernCondo, close to Grace Bay

The perfect large 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 sq. ft. luxury one bedroom, freshly renovated in Feb 2023, provides all necessary amenities for your home away from home.

Superhost
Apartment 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.

Top guest favourite
An outdoor area features a swimming pool bordered by sun loungers and a shaded seating area. Umbrellas provide shade, while lush greenery and ocean views create a serene environment. The clear water of the pool reflects the blue sky, enhancing the inviting space.
Villa in Providenciales
4.99 out of 5 average rating, 115 reviews

Villa DelEvan 4B / 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 favourite
Home in Providenciales
4.96 out of 5 average rating, 362 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

Guest favourite
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.
Apartment in Providenciales
4.92 out of 5 average rating, 256 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 favourite
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, 124 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.

Guest favourite
A tranquil pool area is surrounded by lush tropical foliage, with palm trees and flowering plants presenting a vibrant backdrop. A pair of yellow lounge chairs is positioned near the water's edge, inviting relaxation under a bright blue sky dotted with clouds.
Flat in Leeward Settlement
4.95 out of 5 average rating, 281 reviews

Leisure in Paradise - steps from Beach, with pool

Wake up on a Mocking bird singing in the garden, sun rays sparkling through the lush green while you drink your cup of tea or coffee on your private screened patio. Take a walk in the topical garden and have a refreshing swim in crystal clear pool or take a short walk (3 minute) to the turquoise ocean and white sandy beach.

Popular amenities for Leeward rentals with a pool

Quick stats about holiday rentals with a pool in Leeward

  • Total holiday rentals

    Explore 270 holiday rentals in Leeward

  • Nightly prices starting at

    Leeward holiday rentals start at £103 per night before taxes and fees

  • Verified guest reviews

    Over 5,420 verified reviews to help you choose

  • Family-friendly holiday rentals

    210 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    270 of Leeward holiday rentals include wifi 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!