We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation 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.

0 of 0 items showing

1 of 3 pages

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, 135 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.

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, 110 reviews

The Sapphire Villa. Tropical Oasis. Make memories

This is where an unscripted holiday begins. At our Villa, we provide the canvas for luxury and privacy for the perfect getaway. Where dreams are fulfilled, and precious memories are made to live forever. Whatever you desire is within reach. Our Villa combines with the extraordinary tranquility of Turks and Caicos Islands for sophisticated, low-key luxury. Here is where to create your story within the privacy of your own home away from home in an exceptional place that becomes uniquely yours.

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, 186 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

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.

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, 345 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

4.95 out of 5 average rating, 167 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, 123 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 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, 176 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, 151 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, 244 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 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, 117 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.

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

This exquisite 2-story villa offers an unparalleled getaway and a private pool. Ideal for families or groups, it boasts high ceilings, expansive windows, and a fully-equipped kitchen. Just minutes from Long Bay Beach, enjoy ultimate relaxation in a gated, secure space. With spacious bedrooms, modern amenities, and fast Wi-Fi, it's your perfect luxury escape. Book now for an unforgettable stay!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Popular amenities for Leeward rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

The image showcases a modern villa with a private pool in the foreground. Lounge chairs are arranged around the pool, while an outdoor dining area and BBQ are visible under a shaded structure. Large glass doors lead into the bright interior space.

Home in Leeward Settlement

4.94 out of 5 average rating, 18 reviews

Leeward Landing Villa

A modern house is depicted with a covered patio area and a private pool. Two lounge chairs are positioned beside the pool, while a seating arrangement with cushions offers a relaxing spot. Lush greenery surrounds the property, creating a serene outdoor environment.

Home in Long Bay Hills

5 out of 5 average rating, 4 reviews

1 BR Apt w/pool - Long Bay Hills #1

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, 114 reviews

Gated Villa w Pool. Walk to GraceBay Beach & Shops

An open-concept living area is visible, featuring a modern kitchen island with a sink and fruit bowl. A comfortable seating arrangement is positioned near large glass doors that offer stunning water views. The space is complemented by greenery and contemporary furnishings.

Home in Providenciales

5 out of 5 average rating, 27 reviews

2 Bedroom Spectacular Views

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, 108 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, 127 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, 116 reviews

Sunny Paradise Long Bay

The exterior of a modern two-story house features a spacious balcony on the upper level. A private infinity pool glimmers under the sun, surrounded by lounge chairs. A barbecue grill is positioned nearby, with lush greenery adding to the tranquil atmosphere.

4.91 out of 5 average rating, 23 reviews

Harbour House - 2 Bed Waterfront; 7 Min to Beach

Condo rentals with a pool

Top guest favorite

Condo in Turtle Cove

4.93 out of 5 average rating, 117 reviews

Allies Rest - Seaflowers townhome

A serene pool area is depicted, featuring clear blue water that reflects the sky. Two lounge chairs beneath a blue umbrella are positioned beside the pool, with palm trees swaying gently in the background. A well-maintained deck surrounds the pool, enhancing the tranquil setting.

Condo in Providenciales

4.94 out of 5 average rating, 195 reviews

Amazing Ocean views -Modern Condo -Balcony - Pool

A sleek salt-water pool is framed by stylish day beds and loungers, surrounded by tropical greenery. The modern building exteriors feature clean lines, with blue skies and scattered clouds creating a serene backdrop.

Condo in Grace Bay

5 out of 5 average rating, 18 reviews

Grace Bay Luxury Gated 900sqft 1 Bdrm 2 Bath Condo

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, 445 reviews

🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞

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, 126 reviews

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

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

An outdoor recreation area is featured, showcasing a swimming pool surrounded by lounge chairs and shaded cabanas. Lush greenery is present alongside the pool. A paved walkway connects the pool area to the building, which is illuminated by natural sunlight.

Condo in Grace Bay

4.8 out of 5 average rating, 128 reviews

Gated Condo in Grace Bay/ Short Walk to Everything

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, 196 reviews

Sea Dreams - Jr 1 bdrm with Panoramic Ocean views!

Other vacation rentals with a pool

A modern villa showcases a bright exterior against a clear blue sky. A refreshing pool features a floating yellow swim platform, surrounded by a spacious terrace with several lounge chairs. Lush landscaping adds greenery, creating a relaxing outdoor space.

Villa in Long Bay Hills

5 out of 5 average rating, 3 reviews

Private Villa w/Pool,Resort Amenities and Beach 1

Top guest favorite

A modern pool area is surrounded by palm trees and lounge chairs, providing a relaxing space for guests. A covered seating area is located at one end of the pool. The clear blue water reflects the bright sky, enhancing the inviting atmosphere.

Condo in Grace Bay

4.98 out of 5 average rating, 52 reviews

Grace Bay modern 2 bedroom poolside condo

A clear blue pool is surrounded by lush greenery and palm trees. A shaded seating area with a trellis is positioned at one end, and several lounge chairs are arranged along the poolside. The sky is bright and sunny, adding to the inviting atmosphere.

Villa in Providenciales

4.98 out of 5 average rating, 44 reviews

Sea Villa - Cozy Family Villa Steps From the Beach

Two lounge chairs are positioned by a private infinity pool, with views overlooking the calm turquoise waters of Chalk Sound. Lush greenery and distant islands are visible in the background, while sunlight creates playful shadows on the poolside terrace.

Home in Providenciales

4.86 out of 5 average rating, 28 reviews

Luxe Villa | Infinity Pool, Rooftop & Sunset Views

A vibrant two-story home features a spacious terrace supported by columns, overlooking a private pool. Bright yellow walls contrast with deep blue shutters and trim. Lush greenery surrounds the property, creating a serene atmosphere for relaxation and enjoyment of the outdoor space.

Villa in Leeward Settlement

4.97 out of 5 average rating, 66 reviews

Cocodemer, a short walk to secluded Pelican Beach.

Top guest favorite

A modern bedroom features a spacious bed adorned with turquoise and white bedding. Two light fixtures hang above the bed, complemented by a decorative wall art piece that reads 'LOVE.' Nightstands are placed on either side of the bed, enhancing the room's design.

Apartment in Providenciales

4.95 out of 5 average rating, 61 reviews

Caicos Retreat Apt#3

The living area features a neutral-colored sofa facing a wall-mounted Smart TV. Large glass sliding doors lead to the outdoor pool area. A colorful accent chair adds a pop of color, while natural light fills the space, complemented by soft grey curtains and a woven area rug.

Villa in Caicos Islands

4.84 out of 5 average rating, 68 reviews

Private Pool Luxury Villa, 5min to Grace Bay beach

A spacious living area features two white sofas positioned around a wooden coffee table adorned with green apples. Soft lighting from a nearby lamp complements a large artwork of a serene seascape hanging on the wall, creating a relaxed environment.

Condo in Providenciales

5 out of 5 average rating, 15 reviews

Darcy's place at Golf Course

Quick stats about vacation rentals with a pool in Leeward

Total rentals
290 properties
Nightly prices starting at
G$22,988 GYD before taxes and fees
Total number of reviews
5.2K reviews
Family-friendly rentals
230 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
100 properties have a dedicated workspace

Destinations to explore