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Vacation rentals with a pool in Leeward Settlement

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Top-rated rentals with a pool in Leeward Settlement

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Top guest favorite

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, 133 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.

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, 339 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

A modern two-story villa is depicted, featuring a light grey exterior with large windows. A covered balcony is visible on the upper floor, adorned with decorative railing. Lush greenery surrounds the property, and a spacious driveway provides access to the entrance.

Home in Grace Bay

4.94 out of 5 average rating, 162 reviews

Follow Your Dreams Villa!

Follow Your Dreams – Private Villa Escape to this stylish villa designed for one couple. Enjoy a private pool surrounded by palms, a 65" TV, and a fully equipped kitchen with dishwasher and laundry. Located behind Coco Bistro/Coco Van and just 2 minutes by car to Grace Bay Beach, it offers a mix of privacy and convenience. This totally private villa is perfect for two guests seeking a serene and unforgettable tropical getaway. Book now to make your dream vacation a reality!

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, 119 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!!

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, 137 reviews

*Balcony View* Renovated 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 favorite

An infinity edge pool is set against a scenic backdrop of Juba Sound National Park. The pool area features a sun shade overhead and is surrounded by tiled flooring. Lush greenery is visible in the distance, providing a tranquil and relaxing environment.

Guesthouse in Long Bay Hills

4.99 out of 5 average rating, 173 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.

Top guest favorite

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, 148 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.

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, 239 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 • 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

A private villa exterior is displayed, featuring a modern design with a rectangular pool surrounded by lounge chairs. A shaded outdoor area includes a dining table and seating arrangements under large windows, while tropical plants enhance the serene environment.

Villa in Caicos Islands

4.95 out of 5 average rating, 114 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 pool after a day at the beach! 2 bedrooms (K&Q) 2.5 bathroom. Each room has its own AC as well as the downstairs living space. Construction 🚧 in the neighborhood.

A tranquil outdoor area features a heated swimming pool, surrounded by lounge chairs and umbrellas. The ocean view is visible in the background, with lush greenery framing the space, enhancing the relaxing atmosphere of the resort.

Condo in Turtle Cove

4.9 out of 5 average rating, 108 reviews

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED

Our cool and comfortable one bedroom condo offers tranquility and relaxation. Sitting on the balcony you can feel the tropical breezes and see the magnificent view of Grace Bay. The pool and hot tub are only steps away. If the rental car is not needed, we will reduce the price by $40.00 per night. Note: Stays of either 1 or 2 nights will not include the car rental, and a refund of $40.00 for each night will be applied after booking.

Apartment in Leeward Settlement

4.95 out of 5 average rating, 263 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.

A spacious swimming pool is surrounded by lush tropical landscaping, featuring numerous lounge chairs positioned under palm trees. The soft blue tiles of the pool reflect sunlight, while a well-maintained building with balconies is visible in the background.

Condo in Providenciales and West Caicos

4.87 out of 5 average rating, 441 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

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Popular amenities for Leeward Settlement rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A charming home is surrounded by lush palm trees and vibrant tropical landscaping. The exterior features a combination of stucco walls and a tiled roof under a clear blue sky. A gravel path leads to the entrance, adding to the welcoming ambiance.

Home in Grace Bay

4.92 out of 5 average rating, 113 reviews

Tropical Carabas Villa!

A private swimming pool is surrounded by a spacious wooden deck and lush tropical greenery. Sun loungers are positioned near the pool, offering a place to relax under the sun. Clear blue water reflects the bright sky, creating a serene outdoor retreat.

Home in Grace Bay

4.88 out of 5 average rating, 110 reviews

Gated Villa w Pool. Walk to GraceBay Beach & Shops

Top guest favorite

An aerial view showcases the modern home surrounded by lush greenery and the serene waters of Chalk Sound. The property features a spacious rooftop area and outdoor living space, emphasizing its connection to the natural landscape.

Home in Providenciales

5 out of 5 average rating, 22 reviews

2 Bedroom Spectacular Views

Top guest favorite

A private pool with clear blue water is visible just outside the living area. Large glass doors create a seamless connection between the indoor and outdoor spaces. Light-colored lounge chairs sit nearby on the patio, along with a few sparse trees in the background.

4.98 out of 5 average rating, 182 reviews

“The Lighthouse”, Private Pool, Ocean Views, Beach

A bright living area showcases white furniture accented with cushions in soothing shades of blue and grey. An elegant glass coffee table sits in the center, reflecting natural light from expansive windows, while a glimpse of the kitchen and dining area can be seen in the background.

Home in Islands

4.99 out of 5 average rating, 107 reviews

The Sapphire Villa. Tropical Oasis. Make memories

The outdoor area features a large swimming pool surrounded by lounge chairs with soft cushioning. The property is set within a lush, tropical garden, and the spacious patio is equipped with tables and umbrellas for shade. A covered outdoor dining area is also visible.

Home in Providenciales

4.91 out of 5 average rating, 107 reviews

Sea La Vie - Beachside 2 bdr Unit #4, Ocean views

A spacious deck surrounds a swimming pool, complemented by outdoor furniture under a shaded umbrella. The yellow structure features multiple windows, allowing natural light. Lush greenery is visible, enhancing the outdoor setting.

4.88 out of 5 average rating, 126 reviews

Sea More Getaway

A clear blue pool is set within a spacious deck, surrounded by lush greenery. The pool's inviting water reflects the sky, enhancing the outdoor area. A white pool ladder is positioned for easy access, and the vibrant wooden decking offers ample space for relaxation.

Home in Providenciales

4.96 out of 5 average rating, 114 reviews

Sunny Paradise Long Bay

Condo rentals with a pool

Top guest favorite

Condo in Turtle Cove

4.93 out of 5 average rating, 114 reviews

Allies Rest - Seaflowers townhome

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, 180 reviews

🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝

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

4.99 out of 5 average rating, 88 reviews

Grace Bay Luxury Gated 1400 sq ft 2 Bedroom Condo

A large swimming pool is surrounded by lush palm trees and vibrant landscaping. The tranquil water reflects the clear blue sky, while a nearby condominium is visible, providing an inviting backdrop. The area appears well-maintained and spacious, ideal for relaxation and enjoyment.

Condo in Wheeland Settlement

4.95 out of 5 average rating, 124 reviews

Couple’s Retreat with ocean view,pool and hot tub!

The image displays a serene swimming pool surrounded by lush greenery and decorative plants. A poolside lounge area is visible in the background, while a paved pathway leads towards the parking area, which accommodates multiple vehicles. Bright sunlight illuminates the tranquil setting.

Condo in Grace Bay

4.85 out of 5 average rating, 74 reviews

Middle of Gracebay, Heated Pool, Gated Condo.

An aerial view presents a large, inviting pool surrounded by lush greenery and vibrant flowers. Blue lounge chairs are positioned around the pool area, offering a relaxed setting. The roofs of nearby buildings feature distinctive red tiles, enhancing the tropical atmosphere.

Condo in Turtle Cove

4.98 out of 5 average rating, 110 reviews

Shore to Please - Large Studio Condo with Patio

The outdoor area features a large swimming pool surrounded by palm trees and white lounge chairs. Bright blue umbrellas offer shade, while the resort's two-story white building showcases multiple balconies. Lush tropical landscaping enhances the inviting atmosphere.

Condo in Turtle Cove

4.81 out of 5 average rating, 132 reviews

Paradise Stay Studio-Beaches-Nature-Relax-Central

A sparkling swimming pool features built-in steps leading into the water, surrounded by lounge chairs and umbrellas. Palm trees provide gentle shade. The backdrop showcases a clear blue sky with scattered clouds, and the ocean is visible in the distance.

Condo in Providenciales

4.89 out of 5 average rating, 193 reviews

Sea Dreams - Jr 1 bdrm with Panoramic Ocean views!

Quick stats about vacation rentals with a pool in Leeward Settlement

Total rentals
280 properties
Nightly prices starting at
€ 95 before taxes and fees
Total number of reviews
4.9K reviews
Family-friendly rentals
230 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
110 properties have a dedicated workspace

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