House holiday 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!

4.95 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

Great views of Long Bay Hills towards the ocean and 3-8 minute drive to either Long Bay Beach or Grace Bay beaches. Gentle breezes keep you relaxed and cool by the pool. House is situated on a private lot with shared pool deck with an adjacent unit ( also for rent https://www.airbnb.com/l/SI1O0xog ) Take a break and unwind at this peaceful oasis. Full kitchen with everything you have at home. King size bed is the only way to go with en-suite bathroom Car rental is advisable for groceries etc

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.

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, 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.

4.93 out of 5 average rating, 55 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, 130 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!

4.96 out of 5 average rating, 354 reviews

Modern Villa W Pool 5 Minutes to 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.

4.98 out of 5 average rating, 188 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 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.

Popular amenities for house rentals in Leeward

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 47 reviews

An outdoor dining area is highlighted by a large table surrounded by wooden chairs, situated beneath a pergola. Light curtains softly flutter in the breeze, providing shade and enhancing the open view of the surrounding greenery and ocean. The clear blue sky complements the serene setting.

Home in Long Bay Hills

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

5 out of 5 average rating, 11 reviews

Home in Richmond Commons

Beyond The Sea Cottage Turks and Caicos

4.97 out of 5 average rating, 34 reviews

A collage of the luxury villa showcases a spacious outdoor pool area with sun loungers, expansive sunset views from the balcony, a cozy bedroom with a king-sized bed adorned with decorative pillows, and a modern living room featuring a comfortable sofa with a Smart TV.

Home in Long Bay Hills

Stunning Luxury Villa w/ Pool and Sunset Views

The image captures a tranquil outdoor space featuring a private pool surrounded by a wooden deck. Two white lounge chairs are positioned for relaxation, while palm trees are visible in the background. A modern building is partially seen, creating a serene atmosphere.

5 out of 5 average rating, 60 reviews

Grace Bay/ New Luxurious home 3+ Bedrooms & Pool

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

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

The villa features a spacious outdoor area with a private pool surrounded by lounge chairs. Large glass doors open to the living space, providing a seamless transition to the patio. A modern roof deck offers additional scenic views of the surrounding landscape.

4.83 out of 5 average rating, 42 reviews

Caya Villa 2 - 2 Bedroom - Island Fusion Home

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

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

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

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, 44 reviews

@Villa 360! Private, Gorgeous Views Near airport

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

An outdoor dining table equipped with four chairs is positioned on a patio, offering expansive views of lush greenery and turquoise waters. A centerpiece bowl with candles and a decorative shell adds to the setting, framed by a balustrade and clear skies.

4.97 out of 5 average rating, 35 reviews

Secluded Escape, Ocean Views, Pool and Hot Tub

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 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

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

A spacious living room is featured, furnished with comfortable leather seating and a wooden dining table. Large windows allow natural light, showcasing views of the outdoors. The walls are adorned with art, and a television is positioned for entertainment.

4.86 out of 5 average rating, 7 reviews

June Plum Hideaway Cottage in Grace Bay, TCI

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

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

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

Home in Cooper Jack Bay Settlement

Two white lounge chairs are positioned by the water's edge, surrounded by lush greenery and rocky terrain. The calm canal reflects the clear sky, creating a serene atmosphere. The buildings in the background hint at the proximity to the duplex accommodations.

4.88 out of 5 average rating, 26 reviews

Waterfront House - Downstairs

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

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.