Holiday rentals with a pool in Leeward

Villa in The Bight Settlement

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.

4.98 out of 5 average rating, 143 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.

4.99 out of 5 average rating, 112 reviews

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

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.

Apartment in Providenciales

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.

4.92 out of 5 average rating, 248 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 (under consrtuction until mid-Nov) • 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

4.95 out of 5 average rating, 192 reviews

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.

Apartment in Turtle Cove

🏖🏝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 🏝

Flat in Leeward Settlement

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.

4.95 out of 5 average rating, 243 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.

4.99 out of 5 average rating, 118 reviews

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

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.

4.92 out of 5 average rating, 129 reviews

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

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!!

Guest house in Long Bay Hills

The infinity edge pool reflects the vibrant colors of the sunset, overlooking Juba Sound. Lush greenery surrounds the area, enhancing the serene atmosphere. The horizon features a calm waterway and the setting sun, creating a picturesque evening view.

4.99 out of 5 average rating, 179 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.

A modern kitchen features stainless steel appliances, including a refrigerator and stove. A central island with a marble countertop is complemented by three bar stools. Brightly colored decorative flowers are arranged on the counter, accentuating the contemporary design.

4.98 out of 5 average rating, 166 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.

4.96 out of 5 average rating, 354 reviews

Private Villa Tropical Escape wPool Near GB Beach

Villa Cocuyo offers complete privacy, comfort, and consistent 5-star 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

4.95 out of 5 average rating, 119 reviews

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

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.

4.98 out of 5 average rating, 189 reviews

The image captures the exterior of a cottage at dusk, highlighting a lighthouse-shaped tower with softly illuminated windows. A poolside area is visible, featuring lounge seating and a dining area, all surrounded by white walls and a well-maintained patio space.

Home in TC

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

The Lighthouse private cottage features a tower fashioned after a lighthouse affording stellar ocean views Private pool just outside living room doors! Deck & patio lounge w/ BBQ for fun & sun Nestled in the Thompson Cove Canal area and just a 3-minute walk to the beach WiFi, Smart TV with Netflix. Book now for a relaxing yet adventurous getaway! Kayaks, SUPs & snorkel gear included!

Popular amenities for Leeward rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Leeward Settlement

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.

4.94 out of 5 average rating, 18 reviews

Leeward Landing Villa

5 out of 5 average rating, 11 reviews

Home in Richmond Commons

Beyond The Sea Cottage Turks and Caicos

4.88 out of 5 average rating, 117 reviews

A bright outdoor pool area is framed by lush greenery and features comfortable seating under a shaded gazebo. The sunlight reflects off the water, creating a serene atmosphere, while the clear sky adds to the inviting environment.

Home in Grace Bay

Gated Villa + Private Pool• Walk to GraceBay Beach

4.95 out of 5 average rating, 56 reviews

A shaded outdoor space is visible, featuring a sleek grill and comfortable seating arranged on a deck. In the distance, a serene pool reflects the sky under soft lighting, surrounded by tropical greenery. The landscape displays sandy textures and scattered rock formations.

Home in Long Bay Hills

1 BR Apt w/pool - Long Bay Hills #2

An infinity pool glistens under a clear blue sky, with lounge chairs positioned elegantly at the water's edge. The tranquil waters of Chalk Sound are visible in the background, reflecting the vibrant hues of the ocean and the distant shoreline.

4.88 out of 5 average rating, 34 reviews

NEW Water Access! Luxe Villa, Infinity Pool& Views

The living room features a neutral color palette with light wood accents and high ceilings. Two sets of sliding glass doors provide access to the wrap-around balcony. Seating options include a leather sofa and two wooden chairs beside a glass coffee table, with a television mounted on a console.

4.89 out of 5 average rating, 113 reviews

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

An outdoor patio features a private pool complemented by two orange lounge chairs and a shaded seating area. Lush greenery surrounds the space, offering a view of the tranquil waters beyond. The sky is bright with fluffy clouds, enhancing the serene atmosphere.

5 out of 5 average rating, 29 reviews

2 Bedroom Stunning Views

4.88 out of 5 average rating, 128 reviews

A comfortable bedroom is highlighted by a spacious bed with a patterned duvet and decorative pillows. Soft curtains frame a window, allowing natural light to fill the room. A bedside lamp adds a warm touch, while a door offers access to the adjoining bathroom.

Home in TC

Sea More Getaway

Apartment rentals with a pool

4.91 out of 5 average rating, 116 reviews

A spacious living area is equipped with a comfortable sofa adorned with patterned cushions. A wooden coffee table sits in the center, while a large flat-screen TV is mounted on the wall. Floor-to-ceiling glass doors lead to a balcony with ocean views, framed by light blue drapes.

Apartment in Turtle Cove

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED

A spacious living area includes a striped sofa and a light-colored coffee table atop a patterned rug. Natural light fills the space through glass doors, which open to a patio with outdoor seating. A small plant is placed on the table, enhancing the decor.

4.94 out of 5 average rating, 71 reviews

Inn at Grace Bay - Casa Jardin

Apartment in Providenciales

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.

4.89 out of 5 average rating, 148 reviews

*Balcony View* Modern Studio C202

Apartment in Providenciales and West Caicos

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.

4.87 out of 5 average rating, 453 reviews

🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞

Apartment in Wheeland Settlement

A serene beach scene features soft white sand leading to calm waters, with lounge chairs placed under umbrellas. The tranquil sky displays a gradient of pastel colors as the sun sets, illuminating the nearby condominium and surrounding palm trees.

4.92 out of 5 average rating, 128 reviews

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

Apartment in Providenciales

A serene pool area is surrounded by lush greenery and palm trees. Blue sun loungers with rolled towels are positioned alongside the inviting turquoise water of the private pool, under large blue umbrellas. The setting offers a relaxing outdoor space for guests.

4.76 out of 5 average rating, 104 reviews

**Premium Grace Bay Beach condo**

4.98 out of 5 average rating, 111 reviews

A serene pool area is surrounded by lush tropical landscaping and palm trees. Blue umbrellas provide shade over lounge chairs positioned near the clear water. The resort architecture features multiple levels, with balconies framed by vibrant flowers and greenery.

Apartment in Turtle Cove

Shore to Please - Large Studio Condo with Patio

A modern three-story building features spacious balconies with outdoor seating. Expansive glass windows reflect the sky, while an inviting lawn with well-maintained greenery surrounds the structure, creating a serene environment.

4.81 out of 5 average rating, 133 reviews

Gated Condo in Grace Bay/ Short Walk to Everything

Other holiday rentals with a pool

5 out of 5 average rating, 9 reviews

A tranquil seating area is presented on the screened-in lanai, featuring wooden chairs and a coffee table. A softly glowing lantern offers warm illumination amidst lush greenery. The surrounding foliage creates a serene and private atmosphere, ideal for relaxing evenings.

Flat in Grace Bay

1 BR Couples boutique stay, the heart of GraceBay

4.94 out of 5 average rating, 33 reviews

A tranquil pool area is surrounded by lounge chairs and umbrellas, offering ample relaxation space. The villa's exterior features large windows and a backdrop of lush palm trees under a bright blue sky. A waterfall feature adds a serene touch to this inviting outdoor setting.

Villa in Grace Bay

Passionflower 1BR Villa | Grace Bay | Dec DEAL!

A modern living area features a light gray sectional sofa with blue and white cushions, accompanied by an ottoman. A circular dining table with four chairs is set nearby. A large window opens to a view of the patio and pool area, complemented by a beach-themed artwork.

4.98 out of 5 average rating, 57 reviews

Grace Bay modern 2 bedroom poolside condo

Villa in Leeward Settlement

The image captures a serene outdoor setting, featuring a private pool surrounded by lush palm trees. The sun sets in the background, creating a warm glow. A staircase leads from the villa to the pool area, enhancing the inviting atmosphere of the retreat.

4.73 out of 5 average rating, 52 reviews

Delightful Family Villa with Pool in Leeward

5 out of 5 average rating, 13 reviews

A hanging chair is positioned beside a sparkling swimming pool, surrounded by lounge chairs and sunbeds. The modern villa features large glass doors that open to the outdoor area, allowing for seamless integration of indoor and outdoor spaces.

Villa in Long Bay Hills

Dreamy Suite Paradise with Pool and Beach Access

5 out of 5 average rating, 5 reviews

Townhouse in Grace Bay

Luxury 4Bed/4.5Bath/Pool Townhome

4.95 out of 5 average rating, 63 reviews

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.

Flat in Providenciales

Caicos Retreat Apt#3

A central pool surrounded by lounge chairs reflects the bright blue sky above. Lush palm trees frame the area, creating a serene atmosphere. Modern white buildings with large windows stand on either side, providing a contemporary backdrop to this inviting space.