Vacation rentals with a pool in Leeward

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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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Superhost

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, 139 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.

Superhost

A private pool is set against a backdrop of lush greenery under a clear blue sky. The water appears inviting and reflects the surrounding environment, enhancing the tranquil outdoor space. A deck bordered by a wooden railing offers a place to relax and enjoy the view.

Cottage in Long Bay Hills

4.94 out of 5 average rating, 108 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!

Superhost

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, 246 reviews

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

• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access *Pool under construction Sept & Oct • Hot tub • Highest Rated Spa on Island • 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 • Onsite full service spa • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

Superhost

A tranquil pool area is surrounded by lush greenery and palm trees, with blue lounge chairs positioned nearby. The clear water reflects the blue sky, creating a serene atmosphere. A single umbrella offers shade adjacent to the pool, providing a comfortable spot to relax.

Condo in Turtle Cove

4.95 out of 5 average rating, 190 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 🏝

Superhost

A serene pool area is surrounded by lush greenery and vibrant tropical flowers. Four yellow lounge chairs are positioned beside the pool, which is shaped in a natural design. Tall palm trees frame the scene, creating a tranquil oasis for relaxation.

Apartment in Leeward Settlement

4.95 out of 5 average rating, 239 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

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, 348 reviews

Villa Cocuyo Micro Villa with pool

"Discover a truly unique escape at our one-of-a-kind villa in the picturesque Blue Mountain. Crafted by a local architect, this exceptional residence is nestled on a half-acre of beautifully landscaped grounds, offering an exclusive retreat in a private and secure community. Admire the lush garden in the comfort of your own oasis. The villa boasts a distinctive design that is often imitated but never duplicated, showcasing the perfect blend of style, modern layout and local charm

Superhost

A private plunge pool is framed by wooden decking and landscaped greenery. Two lounge chairs are positioned nearby, offering a relaxing spot to enjoy the serene surroundings. Large glass doors provide a view into the interior space, enhancing the connection between indoor and outdoor areas.

Villa in Long Bay Hills

4.92 out of 5 average rating, 126 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!!

Superhost

A serene pool area is framed by lush palm trees, with clear blue waters inviting relaxation. Lounge chairs are positioned around the pool, and several umbrellas provide shade. The condominium structure in the background adds a welcoming touch to the tropical setting.

Condo in Providenciales

4.88 out of 5 average rating, 141 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.

Superhost

A heated pool is surrounded by a wood deck, featuring lounge beds and seating areas. Lush greenery borders the pool area, enhancing the outdoor ambiance. The modern condo building is visible in the background against a bright blue sky.

Condo in Grace Bay

4.99 out of 5 average rating, 156 reviews

1 Bedroom Luxury Grace Bay Condo in Best Location

The perfect location, and only a 5 minute walk to world famous Grace Bay Beach! Located in the heart of Grace Bay near Seven Stars Resort and the Ritz Carlton Resort. 5 minute walk to the beach. 2 minute walk to the best grocery store, and 10 minute walk to the best restaurants and shopping on the island. No rental car is needed. This 790 sq. ft. luxury one bedroom, newly built condo (Nov 2020), provides all necessary amenities for your home away from home.

Superhost

A wooden deck surrounds a clear swimming pool, with two sun chairs positioned for relaxation. Lush greenery is visible in the background, enhancing the private feel of the space. The pool's steps invite easy access for a refreshing swim.

Guesthouse in Providenciales

5 out of 5 average rating, 135 reviews

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

Our Sail Loft home features two separate but identical efficiency suites, each one equipped with a King Sized bed. This side of the duplex is called Sail Loft Starboard. 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.

Superhost

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, 118 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.

Superhost

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

4.84 out of 5 average rating, 121 reviews

Elegant Villa 5 mins from Long Bay Beach Paradise

Escape to your private paradise in this stunning 2-story villa with pool, minutes from pristine Long Bay Beach. You'll love the spacious bedrooms, modern kitchen, and secure gated entrance, perfect for family getaways or friend celebrations. Fast Wi-Fi keeps you connected while you unwind in luxury. Add our VIP airport transfer (additional cost) for the ultimate arrival experience. Book your Caribbean dream today!