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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
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 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, 102 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.

Guest favourite
Villa in The Bight Settlement
4.97 out of 5 average rating, 134 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
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.
Apartment in Turtle Cove
4.95 out of 5 average rating, 201 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 🏝

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, 104 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.

Top guest favourite
A serene outdoor space features a sparkling pool surrounded by lush tropical plants and palm trees. Soft lighting illuminates the area, enhancing the inviting atmosphere. A shaded lounge chair rests nearby, offering a comfortable spot to relax and enjoy the peaceful surroundings.
Flat in Leeward Settlement
4.96 out of 5 average rating, 250 reviews

Romantic Apartment few steps from beach

Wake up to the soothing melody of a mockingbird in the garden, as gentle sunlight filters through the lush greenery. Sip your morning coffee on the balcony, overlooking the tropical garden and sparkling crystal-clear pool, where the peaceful ambiance sets the tone for a romantic escape. Afterward, take a leisurely stroll through the vibrant garden or wander just a few minutes to the nearest beach with turquoise waters and soft white sands, perfect for a tranquil start to your day.

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, 146 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! 🏠🌴

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, 116 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, 364 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 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, 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 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, 126 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.

Top guest favourite
A vibrant green house is surrounded by lush tropical plant life and colorful flowers. A white railing leads to the front steps, with a barbecue grill positioned nearby. Sunlight brightens the scene, enhancing the inviting exterior.
Home in Grace Bay
4.98 out of 5 average rating, 130 reviews

Charming Gecko House with porch & pool - Grace Bay

Affordable and charming house situated in a quiet residential neighborhood in Grace Bay just a short 8 minute walk (less than a 3 minute ride) to the world famous Grace Bay Beach. Very popular with solo travelers and couples. Close to the beach and steps away from the very popular Coco Bistro Restaurant and Coco Van.

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 £104 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!