Vacation rentals with a pool in Leeward

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Leeward

  • Total vacation rentals

    Explore 280 vacation rentals in Leeward

  • Nightly prices starting at

    Leeward vacation rentals start at G$22,994 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,160 verified reviews to help you choose

  • Family-friendly vacation rentals

    220 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    280 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!

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
A modern living area features a sectional leather sofa and a glass coffee table. Large sliding doors lead to a patio surrounded by tropical foliage. Light-colored walls and tile flooring enhance the spacious feel of the room.
Apartment in Leeward Settlement
4.97 out of 5 average rating, 117 reviews

Large Luxury Modern Condo + pool + close to beach

*Pool closed 09/11 to 10/03 2026 for maintenance* This 925 sqft luxury 1 bedroom, recently renovated condo provides all necessary amenities. 3 minutes drive 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. We recommend renting a car.

Top guest favorite
A modern living area features a plush sectional sofa and a coffee table, complemented by a flat-screen TV and decorative shelving. Large sliding glass doors lead to a balcony with outdoor seating and lush greenery in the background. A vase of colorful flowers adds a fresh touch to the scene.
Condo in Grace Bay
4.98 out of 5 average rating, 117 reviews

Grace Bay Luxury Gated 1400 sq ft 2 Bedroom Condo

Welcome to your own peaceful, safe and secure luxury condo in the heart of Grace Bay, Providenciales! This contemporary two bedroom suite on the second floor facing NW enjoys gorgeous sunsets. Located in the heart of Grace Bay means you are a very short walk to every amenity you could possibly need on your vacation. Three minutes to a full service grocery store, a multitude of restaurants and shops, pharmacy and casinos, not to mention a five minute walk to the worlds #1 ranked Grace Bay Beach!

Guest favorite
A bright dining area overlooks the marina, featuring a table with chairs positioned for scenic views. Lush greenery frames the outdoor space, while the tranquil blue water reflects the clear sky. The room is designed with floor-to-ceiling glass doors that enhance the open layout.
Apartment in Venetian Road Settlement
4.94 out of 5 average rating, 122 reviews

OCEAN ORCHID

This fabulous penthouse apartment is located within the exclusive Turtle Tail Marina and next to the late singer Prince's house. This newly built 3 large en suite bedroom apartment offers beautiful ocean and marina views from every room and balconies. The outdoor BBQ area has views of the ocean and Flamingo Lake where you can socialize, chill and spot the odd pink flamingo. There is a large pool with loungers and a hammock for relaxing, kayaks are available to explore the small cays and beach.

Top guest favorite
Villa in The Bight Settlement
4.97 out of 5 average rating, 151 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.

Superhost
A shaded seating area is created beneath a wooden pavilion, featuring two spherical rattan chairs. A large dining table is also present, surrounded by white chairs, set within a lush garden filled with vibrant tropical plants.
Condo in Grace Bay
4.83 out of 5 average rating, 113 reviews

Island Club Supreme 2 bedroom

A Hidden Oasis in the Heart of Grace Bay. Stand on your private balcony and overlook a beautiful inner courtyard which features palm trees, lush tropical vegetation and a newly renovated pool; an amazing spot to just escape and relax! Since Island Club Turks is close to various amenities, you really don't need to rent a vehicle. But if you did want to get out there and explore, there are several options available for car, scooter, bicycle or boat rentals all within walking distance of ICT.

Top guest favorite
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, 116 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.

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, 222 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 favorite
An aerial view showcases the surrounding area of Grace Bay, highlighting a mix of residential and commercial buildings along with lush greenery. The vibrant blue ocean is visible in the background, contrasting with the sandy terrain and roads that connect the community.
Apartment in Grace Bay
5.0 out of 5 average rating, 99 reviews

Grace Bay Studio

Welcome to an exquisite studio in the heart of Grace Bay. Step inside and you'll be greeted by an open-concept layout with a well-equipped kitchen. Head to the private balcony and savor your morning coffee, dine al fresco, or unwind with a good book. Afterwards, take a dip in the sparkling pool. With its prime location, you'll have access to Grace Bay Beach and a plethora of dining and shopping options within easy walking distance. Book your stay and let the island adventure begin!

Guest favorite
Condo in Grace Bay
4.82 out of 5 average rating, 153 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.

Luxe
An outdoor area features a rectangular swimming pool with clear water, surrounded by a deck area with lounge chairs. A striped umbrella provides shade, while views of the ocean and sandy beach create a serene backdrop. Lush greenery frames the space, enhancing the coastal ambiance.
Villa in Providenciales
4.99 out of 5 average rating, 144 reviews

Villa DelEvan 4A / 1-bedrm Beach front 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.

Superhost
A modern villa is showcased, with its sleek design complemented by lush tropical landscaping. A private plunge pool is visible, surrounded by wooden decking and lounge chairs. A small outdoor dining area and a barbecue grill are also present, creating a relaxing outdoor living space.
Villa in Long Bay Hills
4.9 out of 5 average rating, 150 reviews

VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY

Take it easy at this dreamy, unique and tranquil getaway. Villa Infini brings privacy and relaxation all in one. Tropical oasis landscaping that will bring you connected with nature and amplify the commencement of your personal getaway. Bali like plunge pool that can create amazing insta-worthy moments. Located in Long Bay! A 5 minute walk to Long Bay Beach, a 5 minute drive to the nearest grocery store and a 5 minute drive to Grace Bay Beach. Everything is 5 minutes away!!

Top guest favorite
An aerial view of a modern villa surrounded by lush greenery. The exterior features large glass windows and a private pool, accompanied by sleek lounge chairs on the deck. The open layout invites natural light, showcasing the villa's seamless connection to its outdoor surroundings.
Home in Providenciales
4.96 out of 5 average rating, 384 reviews

Private Luxury Villa with Pool 5 Min to GB 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

Popular amenities for Leeward rentals with a pool