House vacation rentals in Leeward

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

Escape to paradise at Beach Landing 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 with the provided pedal bikes. Lounge in the backyard in your private pool or relax indoors with the brilliant large screened TV equipped with all the latest streaming services. Book your villa now for an unforgettable experience in paradise!

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!

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.

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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 exterior of the villa is highlighted by a private pool, surrounded by lounge chairs under palm trees. The two-story structure features large glass doors, offering views of the pool area and landscaped surroundings.

5 out of 5 average rating, 15 reviews

~Villa Bonita~

Villa Bonita is a newly built 2-bedroom (King Beds), 2.5-bathroom home situated in the heart of Grace Bay. It features a private pool and is just a 10-minutes walk from the nearest beach access. It is conveniently located near all the top restaurants and the casino. Base price is for 2 persons each additional guest (4 max) is $45 USD/person/night. Villa Bonita is filled with love ❤️ where you can relax in peace during your holiday. We have all the essentials to quietly enjoy your stay.

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.

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, 86 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.

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.

4.77 out of 5 average rating, 132 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!

An expansive outdoor deck surrounds a gleaming pool. Sun loungers are positioned at one side, while a shaded dining area is visible at the far end, providing ample space for relaxation and gatherings. The clear sky enhances the inviting atmosphere of the villa.

4.97 out of 5 average rating, 38 reviews

Moonrise, Turks and Caicos

Kick back and relax in this calm, stylish space. This Long Bay beach villa featuring 1800 sq feet of A/C space with views of the Caicos bank. Enjoy two spacious ensuite bedrooms and a large open living, dinning, kitchen area. The outdoor space features 3 sun decks, covered dinning, and a relaxing pool. It's a short 5 minute walk to the Long Bay beach access via a path. A 2 minute drive to South Bank and 10 minutes to Grace Bay beaches. Managed by Ski2Sea

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.

4.96 out of 5 average rating, 355 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

4.98 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.

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“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 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

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. Very popular with solo travelers and couples. Close to the beach and steps away from the very popular Coco Bistro Restaurant and Coco Van.

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 wide view of a sandy beach stretches along the shoreline, where gentle waves meet the turquoise water. A wooden pier extends into the sea, with fluffy white clouds dotting the bright blue sky.

4.86 out of 5 average rating, 22 reviews

Fairway House

A private pool is featured in a spacious outdoor area, surrounded by lush greenery. Comfortable lounge chairs are arranged under a shaded pergola, providing an inviting space for relaxation. The clear blue water of the pool reflects the bright sky, enhancing the serene atmosphere.

4.88 out of 5 average rating, 8 reviews

Villa Keppel- panoramic views!

A serene pool area features inviting blue water, bordered by steps leading into the pool. Two lounge chairs are positioned nearby on a wooden deck, with a dining table and chairs visible in the background, providing a tranquil outdoor setting.

5 out of 5 average rating, 14 reviews

White Coral Luxury Townhouse #4

A private pool is surrounded by a spacious deck with loungers and parasols under a clear blue sky. The modern villa is visible in the background, showcasing a blend of indoor and outdoor living spaces. A vibrant landscape with tropical plants frames the property.

4.98 out of 5 average rating, 42 reviews

Caribbean Villa with Pool and Beach Access

An aerial view of a coastal villa is presented, featuring a light-colored exterior with a pitched roof. The property is surrounded by lush greenery and crystal-clear waters. A private dock with sun loungers extends into the water, complemented by a circular seating area nearby.

5 out of 5 average rating, 12 reviews

Sun and Sea

A bright living space displays a dining table with dark wood and plush seating. In the background, expansive glass doors frame a stunning view of turquoise waters and lush landscapes. A potted floral arrangement adds a touch of color to the serene setting.

4.96 out of 5 average rating, 48 reviews

Coastal Vibes Villa Near Sapodilla Beach

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.

4.89 out of 5 average rating, 70 reviews

SunSeaSand 3Bdrm Oceanview Home -Long Bay Hills

An open-plan living area is showcased, featuring natural light from multiple windows. A comfortable sofa with decorative cushions is positioned next to a coffee table. The kitchen area is furnished with modern appliances and a dining table set for two, complemented by a bowl of oranges.

4.96 out of 5 average rating, 23 reviews

Peaceful 1BR Private Cottage w/ HotTub Beach Front

Weekly house rentals

Home in Venetian Road Settlement

A two-story villa is positioned at the edge of Flamingo Lake, surrounded by lush greenery. A wrap-around deck extends around the upper level, providing a panoramic view of the water. The clear blue sky reflects in the tranquil lake, enhancing the serene landscape.

4.77 out of 5 average rating, 35 reviews

Brighter Days Villa

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

Aerial view of a villa surrounded by lush greenery, featuring a private hot tub on the deck. The exterior showcases a blend of white walls and a sloped metal roof, with large windows and doors inviting natural light. Outdoor seating beneath an umbrella is visible.

4.98 out of 5 average rating, 45 reviews

@Villa 360! Private, Gorgeous Views Near airport

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.

4.75 out of 5 average rating, 48 reviews

Sea Chelles Villa TCI

4.86 out of 5 average rating, 36 reviews

Secluded Escape, Ocean Views, Pool and Hot Tub

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, 36 reviews

Colibri Oasis - Gated Villa w Pool, Walk to Beach

A view of the property reveals a central pool surrounded by lush greenery and palm trees. Sandy paths connect the surrounding buildings with bright blue roofs. Colorful lounge chairs are arranged near the pool, promoting a relaxed outdoor environment.

4.81 out of 5 average rating, 16 reviews

Chez Moi Villa, Beach & Pool

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

A bright and airy living room features a comfortable sofa and stylish armchairs. Large windows provide abundant natural light, complemented by ceiling fans. A modern TV stands on a wooden console, with tropical plants adding a touch of greenery to the space.

4.86 out of 5 average rating, 7 reviews

Tropical Oasis | Patio | Walk to Grace Bay Beach

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

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

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, 99 reviews

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

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 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.

4.93 out of 5 average rating, 14 reviews

#10 The Enclave

The exterior features a modern villa surrounded by landscaped greenery. Lounge chairs are positioned near a swimming pool, while palm trees provide a tropical backdrop. Large glass windows reflect the bright sky, enhancing the villa's contemporary design.

5 out of 5 average rating, 8 reviews

Blue Tang Villa (2 Bedroom)

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.