House holiday 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!

Home in Leeward Settlement

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, 28 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!

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.

4.95 out of 5 average rating, 57 reviews

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

4.97 out of 5 average rating, 114 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.

A charming home is surrounded by lush palm trees and vibrant tropical landscaping. The exterior features a combination of stucco walls and a tiled roof under a clear blue sky. A gravel path leads to the entrance, adding to the welcoming ambiance.

4.92 out of 5 average rating, 116 reviews

Tropical Carabas Villa!

Peaceful Villa Near Grace Bay Beach 🌴 Escape to this serene villa just minutes from Grace Bay Beach and steps from Coco Bistro. Enjoy a private pool, air-conditioned bedrooms, a fully equipped kitchen, and an outdoor grill for relaxing meals. Lounge with beach towels and chairs, stay connected with strong Wi-Fi, and soak in the lush tropical surroundings. The perfect mix of comfort, convenience, and tranquility for your getaway! 🌴 12% government tax is included in the listed price.

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

2 BR Villa with Private Pool - Hill Top Ocean Views - Constant Breeze and 5 min drive to beach. Fully equipped and freshly designed in a simple Caribbean style, this 2 BR & 2 Bath Villa can accommodate 4 guests and offers unobstructed views of the surrounding areas with an ocean backdrop of Long Bay Beach - a world-class kiteboarding destination. An open floor concept comprising of the living room, dining area and kitchen opening up to a spacious exterior terrace seating 6 guests.

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 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, 133 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 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, 356 reviews

Private Villa Tropical Escape Close 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 including beach

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.

4.89 out of 5 average rating, 37 reviews

NEW Water Access! Luxe Villa, Infinity Pool& Views

Welcome to Maresia Villa — a luxury waterfront retreat in Turks & Caicos. ** NEW: direct water access with a kayak for guests use** Enjoy an infinity pool, rooftop terrace for stargazing, and breathtaking sunset views and Chalk Sound’s turquoise lagoon from every room. Just 1 minute drive from Sapodilla Bay beach, this villa is ideal for couples, families, or group of friends. SPECIAL OFFER: Stay 7+ nights and enjoy 10% off your booking!

4.98 out of 5 average rating, 191 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

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!

An aerial view captures the villa nestled among lush greenery, with the sparkling turquoise Caribbean Sea in the background. The property features a large front yard and a nearby road lined with modern buildings, providing a sense of privacy and connection to the surrounding landscape.

4.61 out of 5 average rating, 18 reviews

Luxury 4 BR Ocean View Villa

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.

4.97 out of 5 average rating, 34 reviews

Stunning Luxury Villa w/ Pool and Sunset 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, 16 reviews

White Coral Luxury Townhouse #4

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, 13 reviews

Sun and Sea

An aerial view captures the two villas nestled amidst lush greenery and tropical landscaping. A refreshing swimming pool is centered within the properties, surrounded by palm trees. The spacious outdoor area offers a blend of paved paths and greenery, providing an inviting atmosphere for relaxation.

4.67 out of 5 average rating, 9 reviews

Sun and Sea Villas (both) - Family friendly Villas

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, 71 reviews

SunSeaSand 3Bdrm Oceanview Home -Long Bay Hills

A serene outdoor space features a private pool surrounded by lounge chairs and a shaded seating area. A bicycle is parked nearby, and a barbecue area under a pergola is visible. Palm trees add greenery to the bright and inviting atmosphere.

4.97 out of 5 average rating, 33 reviews

3BDR Villa in Grace Bay

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.

4.75 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.

4.95 out of 5 average rating, 40 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

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, 61 reviews

Grace Bay/ New Luxurious home 3+ Bedrooms & Pool

5 out of 5 average rating, 8 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 Leeward Settlement

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.

4.86 out of 5 average rating, 35 reviews

Vista Blue Rental-Grace Bay Beach just 4 mins away

Private house rentals

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

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

The living area features high ceilings with exposed beams and natural light streaming through large windows covered by sheer curtains. A comfortable gray sectional sofa is arranged with a coffee table, and a television is mounted on the wall opposite a dining area.

Home in Cooper Jack Bay Settlement

4.75 out of 5 average rating, 4 reviews

Waterfront 2-bedroom Villa in Providenciales

4.67 out of 5 average rating, 3 reviews

Gabriella Luxury Villa - Opening Special Rates

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

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, 100 reviews

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

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.