House vacation rentals in Leeward

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.

4.88 out of 5 average rating, 117 reviews

Gated Villa + Private Pool• Walk to GraceBay Beach

Super Popular for Families, Couples & Group Vacations! PRIVATE Sun Drenched Pool. Walk to Famous GraceBay Beach shopping, dining, night-life, “Great space. Loved the outdoor/indoor living combo.” Jenny Bear, DE, USA The villa is tucked away in a peaceful setting on a private gated street with only 4 villas! Features a private plunge pool for kids & sunbathing or hanging out by the larger pool with some cocktails & your favorite music. The Ultimate Escape. Unpack, Relax, Enjoy... Reserve Now!

The villa is pictured from above, showcasing a private outdoor space with a rectangular pool. Surrounding greenery enhances the tranquil setting, while loungers are placed beside the pool. The structure features large glass windows, allowing for ample natural light, and a covered area for relaxation.

5 out of 5 average rating, 25 reviews

Upper East Side Estates Gated Community Leeward

Escape to paradise at Waves of Blue Villa nestled in the heart of Leeward TCI. This luxurious villa is just minutes away from the pristine award-winning Grace Bay Beach offering a perfect blend of relaxation and adventure. Conveniently cruise your community in your 6 seater Golf Cart or pedal along with the (4) provided pedal bikes. Relax indoors with the brilliant large screened TVs equipped with all the latest streaming services. Book your villa now for an unforgettable experience in paradise!

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, 28 reviews

2 Bedroom Stunning Views

Kick back and relax in this calm, stylish space. This modern 2-bedroom, 2-bathroom home is nestled along the serene Chalk Sound, offering peaceful seclusion with breathtaking views. FAR from the hustle and bustle of Grace Bay, it caters to guests looking to relax and reset. Enjoy spacious living, stylish finishes, and stunning water views from almost every room—perfect for those seeking comfort and tranquility. 15 mins to airport 20 mins to Grace Bay 5 mins to Taylor Bay & Sapoddila Bay Beach

4.99 out of 5 average rating, 111 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.

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

Located in a secluded Beachside property, 500 ft from Long Bay Beach, and 5-minutes drive from Grace Bay Resorts and shops, this spacious, private, 2-Bedroom\2-Bathroom unit can accommodate up to 6 guests, with a king size bed, 2 full size beds, and a queen sofa bed. It occupies 2nd and 3rd floor of our middle building, roughly 15 yards from the pool, no pool view. With beautiful scenic views of the ocean and Long Bay Beach area, from its 3rd floor Livingroom and wrap-around balcony.

4.96 out of 5 average rating, 352 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 picturesque entrance leads to a light blue house surrounded by lush tropical vegetation. A smooth driveway, lined with palm trees and native plants, leads up to the home, providing a sense of privacy and tranquility. The clear sky enhances the inviting atmosphere.

4.95 out of 5 average rating, 85 reviews

PERIWINKLE | Charming Island Home|Near to Beach

Nestled in the Gated Upscale community of Leeward at the end of a quiet cul-de-sac is Periwinkle. Experience the true flavor of the Islands with us. Be cradled and relax in the lush native vegetation and enjoy the view from the many windows which decorate the home. Periwinkle is a short stroll away from the magnificent soul quenching Leeward Beach and a five minute drive to the heart of Grace Bay for great shopping and dining experiences. Escape to the quieter side of Paradise.

An overhead view reveals a private pool bordered by a patio with lounge chairs and outdoor seating, complemented by lush greenery. Nearby, a sandy beach leads to two kayaks resting beside the water, all under the shade of palm trees.

4.92 out of 5 average rating, 53 reviews

3 Bed Beach Oasis on Flamingo Lake w/Private Pool

Márohu is a stunning 3-bedroom modern Caribbean villa set within the exclusive neighbourhood of Turtle Tail, just a 10-minute drive from the world-renowned Grace Bay Beach. This spacious, well-equipped, and family-oriented villa offers expansive floor-to-ceiling views over Flamingo Lake from every room. You’ll experience the best of outdoor living with our own pool and sandy beach, ideal for lounging, a friendly game of cornhole, or exploring the lake with our included kayaks.

A spacious gazebo features a red and white picnic table, providing an ideal spot for relaxation. The surrounding views showcase the tranquil waters of Chalk Sound and lush greenery, creating a serene environment for enjoying nature.

4.76 out of 5 average rating, 129 reviews

Beach Cottage with Amazing Chalk Sound Views!

Adorable cottage for an authentic Providenciales experience w/breathtaking views! - Quaint cottage w/amazing views of Chalk Sound & on clear days, West Caicos! - Silly Creek Mansion across the water - Minutes away from great restaurants from beach shacks to fine dining - Nearby beautiful beaches like Taylor Bay & Sapodilla Bay Beach. - Water sports abound like jet ski and kayak rentals. - Quiet area, So. Providenciales flanked by Chalk Sound & Atlantic Ocean!

A vibrant green house is surrounded by lush tropical plant life and colorful flowers. A white railing leads to the front steps, with a barbecue grill positioned nearby. Sunlight brightens the scene, enhancing the inviting exterior.

4.98 out of 5 average rating, 124 reviews

Charming Gecko House Island Vibes - Grace Bay

Perfect place for solo travelers and couples! Affordable and charming house situated in a quiet residential neighborhood in Grace Bay just a short 8 minute walk (less than a 3 minute ride) to the world famous Grace Bay Beach. And yes, we have a pool!!! Close to the beach and steps away from the very popular Coco Bistro Restaurant and Coco Van! Note: October-November: there is some construction in the area. Pls inquire. 😊

4.98 out of 5 average rating, 187 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!

A serene outdoor space features a private swimming pool reflecting the sky, surrounded by sun loungers and a cozy garden area. The modern home, with large sliding doors, sits in the background, providing access to the inviting interior and views of lush landscaping.

4.98 out of 5 average rating, 128 reviews

Modern Caribbean 2 - Amazing views & Private Pool

Stunning Contemporary Caribbean escape, with private swimming pool and private garden space, which is over 1100 ft.² in size has amazing views of Chalk Sound national park's crystal blue waters and Is located close to two of the islands best beaches Sapodilla beach and Taylor Bay beach

Popular amenities for Leeward house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious terrace is featured, furnished with a wooden dining table and matching chairs, suitable for six guests. The area is bordered by lush green shrubbery, while flowing curtains frame the openings to the indoor space under a clear blue sky.

4.92 out of 5 average rating, 52 reviews

2 BR Ocean View- Private Pool- Flame Tree Villa #1

5 out of 5 average rating, 11 reviews

Home in Richmond Commons

Beyond The Sea Cottage Turks and Caicos

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.

4.94 out of 5 average rating, 53 reviews

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, 33 reviews

NEW Water Access! Luxe Villa, Infinity Pool& Views

A spacious dining area is complemented by a glass table surrounded by eight light-colored chairs. The open-concept kitchen is visible in the background, featuring modern appliances and a decorative backsplash. Vaulted ceilings enhance the airy feel of the room.

4.88 out of 5 average rating, 67 reviews

SunSeaSand 3Bdrm Oceanview Home -Long Bay Hills

4.92 out of 5 average rating, 13 reviews

An aerial view of Eden House reveals a modern villa surrounded by lush greenery. A private swimming pool is visible in the foreground, alongside sun loungers and shaded seating. The nearby turquoise sea adds to the tranquil setting, promoting a sense of privacy.

Home in Caicos Islands

Two Bedroom Villa, Long Bay, Providenciales - Eden

A single-story home with a modern design is shown, featuring a swimming pool surrounded by a deck. Large glass doors allow natural light to fill the interior. The property is set within lush greenery, enhancing the serene ambiance of the outdoor space.

5 out of 5 average rating, 11 reviews

Sweet Escape 2 beds/baths W pool

A modern villa exterior is shown, featuring a large pool surrounded by lounge chairs. A screened-in porch is visible, along with a dining area in the background. The white painted structure is complemented by a light-colored roof and tropical greenery beyond the pool area.

4.65 out of 5 average rating, 49 reviews

Hummingbird Villa - Large pool steps from beach

Weekly house rentals

Home in Providenciales and West Caicos

A spacious wrap-around deck surrounds a private swimming pool, with tropical plants and colorful flowers adding natural beauty. Sun loungers and seating areas are available for relaxation. A shaded area with a hammock is visible, offering a serene spot to unwind.

5 out of 5 average rating, 66 reviews

Casa de Isle, Taylor Bay, Chalk Sound area

A private pool area is surrounded by sun loungers and tropical plants. A light blue sky is visible above, providing a bright atmosphere. The space features a covered seating area and outdoor dining table, complemented by a decorative planter nearby.

4.74 out of 5 average rating, 47 reviews

Sea Chelles Villa TCI

A tranquil pool with clear turquoise water is shown, reflecting sunlight. Nearby, a single blue lounge chair is positioned beside the pool, and a light-colored cottage is partially visible in the background. Lush greenery surrounds the area, enhancing the serene setting.

4.94 out of 5 average rating, 34 reviews

3Bed Gated Villa w Pool, Easy Walk to Beach, Shops

5 out of 5 average rating, 3 reviews

An inviting living space is shown, featuring a cozy sofa with decorative cushions. A dining table with four stools complements the area, while a large window allows natural light to fill the room, providing a view of the surrounding green landscape.

Home in Bottle Creek

Relaxing Lagoon Stay | Watersports Haven

4.84 out of 5 average rating, 79 reviews

A semi-private pool is framed by a wooden deck, featuring two blue lounge chairs positioned nearby. Lush greenery and tropical plants surround the pool area, enhancing the outdoor ambiance. A villa is visible in the background, with a screened-in verandah and steps leading up to it.

Home in Caicos Islands

Colibri Gardens Villa - Great value in Grace Bay

A shaded cabana features a thatched roof and is furnished with bright turquoise seating, accompanied by colorful striped pillows. A glass-topped table sits at the center, surrounded by lush greenery and decorative accents. The space offers a relaxing outdoor living area for guests.

5 out of 5 average rating, 4 reviews

Charming CoCo Gardens -2 bedroom island hideaway

5 out of 5 average rating, 7 reviews

The exterior of a spacious villa is seen, featuring a white roof and light-colored walls. Tropical greenery surrounds the property, which is situated near the ocean. The vibrant blue waters of the sea create a striking backdrop, providing a serene coastal view.

Home in Caicos Islands

ParadiseONE 2 Suites 3 Bedrooms

A single-story rental unit is visible, featuring a warm-toned exterior and a sloped roof. Lush greenery and a palm tree with coconuts frame the entrance, which is marked by a covered porch and multiple windows. A gravel pathway leads to the front door.

4.85 out of 5 average rating, 34 reviews

Vista Blue Rental-Grace Bay Beach just 4 mins away

Private house rentals

Home in blue hills millennium highway

A spacious bedroom is depicted with a large, comfortable bed in white linens. A mirrored wall reflects the soft glow from two bedside lamps. A doorway leads to a full bathroom with a double vanity, while an additional door indicates access to another room.

4.88 out of 5 average rating, 42 reviews

Island Turquoise Rental- Two Bedroom house

Home in Cooper Jack Bay Settlement

A calm canal view showcases lush greenery along the water's edge, with smooth rocky formations partially submerged. The serene turquoise water reflects the sky, while the distant structure is surrounded by trees, offering a glimpse of natural beauty in a tranquil setting.

4.94 out of 5 average rating, 36 reviews

Waterfront House - Upstairs

A charming villa exterior is framed by lush green foliage and vibrant flowers. A covered entryway, supported by wooden beams, leads to the front door. The light-colored façade contrasts beautifully against the clear blue sky, providing a welcoming appearance.

4.76 out of 5 average rating, 25 reviews

Fleur de Mer ii - Gracebay, TCI

Home in The Bight Settlement

The exterior of the bungalow is shown, featuring a welcoming entrance with a covered porch. Tropical plants and vibrant flowers surround the pathway, while a clear blue sky adds to the serene setting. The driveway leads to the front door, enhancing accessibility.

5 out of 5 average rating, 98 reviews

2b/2b BEACH HOUSE STEPS to GRACE BAY! WiFi,AC,Pool

A private pool is situated on a wooden deck, showcasing clear blue water that shimmers in the sunlight. The surrounding area features well-maintained greenery and scenic views of the tranquil lagoon and natural landscape beyond.

4.84 out of 5 average rating, 25 reviews

Tropical Chalk Sound Cottage with Pool and Kayak!

A light and airy living space features a comfortable seating area with white sofas adorned with soft gray pillows. A sleek coffee table sits at the center, while built-in shelves and a television enhance the room's functionality. Natural light fills the area through large windows.

5 out of 5 average rating, 12 reviews

#10 The Enclave

A charming villa is set against a bright blue sky, featuring a metal roof and landscaped gardens. The property is framed by tall palm trees and presents a waterfront view with crystal-clear turquoise water. A wooden pergola is visible near the entrance.

4.71 out of 5 average rating, 14 reviews

3bd ~ Private Pool ~ Kayak to the Mangroves

An aerial view of Callaloo Cottage reveals a spacious outdoor area featuring a central swimming pool surrounded by sun loungers. A gazebo provides shade, while vibrant tropical foliage frames the property. Nearby, a beach and turquoise waters are visible, enhancing the tranquil setting.