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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
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.
Apartment in Grace Bay
4.98 out of 5 average rating, 102 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!

Top guest favourite
The modern villa features a two-story design with a spacious ground-level patio. A private pool reflects the blue sky, surrounded by tropical landscaping. Comfortable outdoor seating is visible on the terrace, offering a quiet space for relaxation.
Villa in The Bight Settlement
4.98 out of 5 average rating, 148 reviews

Grace Bay villa | Pool | 3min walk to Beach & Reef

A modern beach villa with its own private pool. Sleeps up to 4 adults in separate rooms. Just 250 steps from the azure blue waters and soft white corals sands of Grace Bay beach. In a quiet off-street location. Perfect for a romantic getaway. With its quiet secluded garden and pool area, many of our guests come to celebrate birthdays, anniversaries, and honeymoons in full privacy. Walk to coral reef snorkeling in 3 mins plus several restaurants. Large grocery supermarket & shops are nearby.

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 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
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.

Guest favourite
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.
Apartment 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 favourite
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.

Top guest favourite
An infinity edge pool is visible on a spacious deck, overlooking stunning views of Juba Sound. The sunset casts warm hues across the sky, reflecting on the calm waters below. Lush greenery surrounds the area, enhancing the natural beauty of the landscape.
Guest house in Long Bay Hills
4.99 out of 5 average rating, 187 reviews

Juba Sunset

Waterfront Private apartment that is fully furnished. Private deck. fantastic views overlooking Juba Sound. within 7mins to Grace Bay, world famous Grace Bay Beach and shops. Very quiet and safe area. Infinity edge pool included. Glorious sunsets. BBQ on the waterfront. Only a couple of mins away from popular Kite Surfing spot. There is also a Kayak available for guests use down on the waterfront. This is the only rental unit on property, you will be the only guests.

Guest favourite
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

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, 257 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 serene view of Turtle Cove Marina features glistening blue waters framed by lush green palm trees. Several boats are docked in the marina, and a clear sky stretches above, creating a peaceful coastal atmosphere.
Apartment in Providenciales and West Caicos
4.87 out of 5 average rating, 462 reviews

🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞

Welcome to this immaculate 'piece of paradise' at the exclusive 'Yacht Club' Turks and Caicos..Enjoy the beautiful Caribbean sun setting over Turtle cove marina any day of the year from the comfort of your own terrace. Please note this is a strictly - NO SMOKING apartment even on the terrace . Thank you

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!