Villa holiday rentals in Leeward

Villa in Providenciales and West Caicos

4.85 out of 5 average rating, 144 reviews

Secluded 3 BR Villa on Taylor Bay -Place De La Sol

The luxury of privacy is what this villa is all about. A few steps through a private tropical path takes you to the pristine waters and powder sand beach that is Taylor Bay. This Villa is split between the main villa which hosts 2 bedrooms, living room, bathroom and kitchen/dining. The Master Suite is located across the patio with it's private bathroom and outdoor/indoor shower. Sunsets are 2nd to none and should be done at least once beachside since the villa faces west. **12% TCI Tax Included

The villa's modern architecture is highlighted by multiple levels and a rooftop terrace. Lush greenery surrounds the property, with palm trees framing the outdoor seating area. Soft lighting emanates from the interior, creating a welcoming atmosphere as dusk falls.

4.96 out of 5 average rating, 48 reviews

Ideal Honeymoon Villa

Luxurious Gated Villa near Grace Bay Beach– Private Pool & Jacuzzi♨️ Escape to this luxury villa, just 2 minutes by car or a 10-min walk from Grace Bay Beach. Relax in your private infinity pool or rooftop jacuzzi with ocean view. The villa features 2 outdoor balconies, a modern kitchen with new appliances, and fast fiber internet. Perfect for 2 guests, this private retreat offers comfort, style, and Super host service. Close to dining, shopping, and activities. Book your dream vacation today🌴

4.98 out of 5 average rating, 128 reviews

Ideal private getaway villa | 250 yds to the beach

The perfect getaway villa, just 250 yards from Grace Bay beach, Gracehaven Getaway is tucked away from passing traffic in a little garden oasis of its own. It is an ideal venue to celebrate anniversaries, birthdays, or honeymoons, or just for a couple seeking a romantic, private setting. Enjoy your own private pool hidden away from main roads and just a 2-minute walk to the Grace Bay beach and Coral Gardens Reef. Easily walk to local restaurants or visit the nearby supermarket for groceries.

An outdoor dining area features a rectangular table surrounded by chairs, with a grill nearby. Lounge chairs are positioned alongside a sparkling pool, set against a backdrop of lush greenery and a clear blue sky. Pendant lights hang from the ceiling, enhancing the space.

4.87 out of 5 average rating, 140 reviews

Gardenia Villa a Private Escape

Gardenia Villa. This contemporary Oasis is perfect for a small family or couples, located steps away from the world’s #1 Grace Bay Beach. The villa entrance opens to a bright entryway leading to the living room area with a spectacular view through a wall of sliding doors to the covered deck and pool. The open plan is perfect for entertaining with the dining and kitchen area all part of the living space. The upstairs consist a master King and second queen sized bedrooms both ensuite baths.

The outdoor area features a private saltwater pool surrounded by a sun deck with lounge chairs. Tropical plants are positioned nearby, and a shaded seating area is created by a white umbrella. The villa’s modern architecture complements the serene outdoor setting.

4.82 out of 5 average rating, 102 reviews

BeachHaus Villa with ocean view and private pool

Newly renovated Villa. Enjoy breathtaking panoramic ocean views from your private terrace, or from your second floor master suite balcony in our bright and modern villa. Fully-equipped open concept kitchen featuring a gas range, and dishwasher. Reliable wifi. Master with , ensuite with rainforest and hand-shower, wood barn doors, and private balcony with outshower. Pool and outdoor living. Ideal for families. Safe, quiet and central neighborhood, 3 minute walk to the beach!

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.

4.99 out of 5 average rating, 118 reviews

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.

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.

4.92 out of 5 average rating, 129 reviews

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!!

A modern terrace featuring a private plunge pool extends towards breathtaking ocean views. Comfortable outdoor seating is provided nearby, allowing for relaxation while surrounded by lush greenery and pristine blue skies. The design creates an inviting atmosphere overlooking the vibrant landscape.

4.93 out of 5 average rating, 102 reviews

Blanca: Taylor Bay Beach-Ocean View

Get away from it all on a beautiful white powdery half-moon shaped beach! The villa offers spectacular turquoise ocean views and dreamy sunsets from the terrace & pool. A private/gated path brings you to the beach in 30 steps where your loungers await you. Located in the prestigious Sunset Bay Community, offering nightly private security patrol & guards. The Island Escapes Villa Managers will meet & greet you and offer an unparalleled level of service during your stay.

The exterior of the villa is shown, highlighting its modern design with crisp white walls. Lush palm trees are flanked on both sides, and the entrance is illuminated by soft lighting. A gravel driveway leads to the garage, framed by well-maintained landscaping.

5 out of 5 average rating, 16 reviews

NEW *2 BR Villa Kiwi- BBQ- Pool in Grace Bay Beach

This crisp and clean newly built Grace Bay villa is perfect for a family trip, girls' getaway, or couples' retreat on honeymoon. Featuring 2 king bedrooms, 2.5 baths, a private pool and a balcony, it offers modern luxury and tranquility. Just 5 min from Grace Bay beach (0.8 mile), restaurants, and shops, the villa boasts stylish interiors, premium amenities, and a lush backyard with palm trees, bougainvillea, and poolside chilling. Book your dream escape today!

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.

An inviting outdoor space features a modern swimming pool surrounded by tropical landscaping. Lounge chairs provide a comfortable spot for relaxation. Large glass doors open to the villa, enhancing the connection between indoor and outdoor areas. Shade is offered by a large umbrella.

5 out of 5 average rating, 9 reviews

Golden Palms – Private Pool & Beach Nearby

Our Lotus Villa is an Oasis in the heart of the Caribbean and escape to a tropical haven in our stunning 3-bed room, perfectly nestled in the heart of Turks and Caicos. This Luxurious retreat promises an unforgettable Island experience, with its pool and garden views, and lavish amenities. The villa is newly built and thoughtfully designed to make your visit unique, comfortable and unforgettable!

An aerial view showcases a circular villa with a natural-shaped pool at its center, surrounded by lush tropical landscaping. The villa is positioned near clear turquoise waters, with a dock visible along the water's edge, providing access to outdoor activities.

5 out of 5 average rating, 19 reviews

2BR Waterfront Villa- Piccolo Ponte+Sups+Pool+ BBQ

Waterfront 2 BR villa with BBQ grill, private pool and dock close to the beach. Great for couples and families! Piccolo Ponte is an elegant 2 bedroom waterfront Caribbean villa that sits on an acre of private tropical garden where friends and family gather together by the pool to relax and enjoy a laid-back vacation island-style. If you need 3 bedrooms, just ask, we can open up the guest house!

Popular amenities for villa rentals in Leeward

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

A private patio area features a sparkling pool framed by lush greenery. Two lounge chairs are positioned under an umbrella, offering shaded seating. Beyond the pool, the serene turquoise waters and palm trees create a tranquil coastal view.

4.97 out of 5 average rating, 29 reviews

Amalfi- Luxury Beach front villa

Villa in Chalk Sound, Providenciales

A semi-outdoor sitting area features four comfortable chairs and a central fire pit. Bright blue pillows add a pop of color against the natural tones of the furniture. Lush tropical plants and water views create a serene backdrop under a partially cloudy sky.

4.88 out of 5 average rating, 24 reviews

Villa Waterloo - Waterfront on Silly Creek

A brightly lit living room features a striped sofa, two armchairs, and a wooden coffee table. A ceiling fan adds to the airy atmosphere, while a piece of colorful artwork hangs above the sofa. Natural light enhances the neutral tones of the decor.

4.83 out of 5 average rating, 47 reviews

3b/2.5b for 7/Pool/AC/90 steps to Grace Bay Beach

The dining area features a wooden table surrounded by four upholstered chairs with intricate designs. A ceiling fan is mounted above, and light fills the space from large windows, while a light-colored cabinet stands against the wall to the right.

4.83 out of 5 average rating, 18 reviews

3bd/2ba Villa in the Bight

4.97 out of 5 average rating, 35 reviews

Shades of Blue Grace Bay Beach

A vibrant two-story home features a spacious terrace supported by columns, overlooking a private pool. Bright yellow walls contrast with deep blue shutters and trim. Lush greenery surrounds the property, creating a serene atmosphere for relaxation and enjoyment of the outdoor space.

4.96 out of 5 average rating, 67 reviews

Cocodemer, a short walk to secluded Pelican Beach.

A modern retreat is set within a tropical landscape, featuring lush palm trees and a welcoming entrance. Large windows highlight the architecture of the spacious building, while a clear blue sky with textured clouds creates a serene backdrop.

4.86 out of 5 average rating, 29 reviews

The Haven

A bright studio bedroom features a queen bed with crisp white bedding positioned against a vibrant yellow wall. Nearby, a plush armchair and large glass doors lead to outdoor views, allowing natural light to fill the room.

4.76 out of 5 average rating, 51 reviews

Peaceful island getaway in Long Bay (New Studio)

Luxury villa rentals

A private swimming pool is shown, featuring clear water reflecting the sky. Surrounding the pool are smooth stone surfaces and a palm tree providing shade. The backdrop includes a modern white structure and a serene garden area.

4.98 out of 5 average rating, 46 reviews

Stunning Villa - short walk to Sapodilla Beach

A covered patio area features a comfortable seating arrangement with blue-patterned cushions. Large sliding doors open to reveal unobstructed views of Grace Bay Beach, showcasing clear turquoise waters and a partially cloudy sky. Lush greenery is visible along the shoreline.

5 out of 5 average rating, 10 reviews

TC Villas | Sandcastle | Dining, Bars, Snorkeling

A private salt-water pool features clear blue water, surrounded by a spacious patio. Comfortable seating areas, including lounge chairs and a shaded area with a red umbrella, are set amid lush tropical vegetation and decorative plants, enhancing the inviting atmosphere of the outdoor space.

4.92 out of 5 average rating, 59 reviews

Sea Sun Relax - villa 5 min walk to Grace Bay

Villa in Providenciales, Long Bay Beach

A spacious outdoor area features a shimmering private pool surrounded by lounge chairs. The villa displays modern architecture with large glass doors and ample sunlight. Tropical plants add greenery, while the upper balcony offers seating, providing a relaxing atmosphere against a clear blue sky.

4.88 out of 5 average rating, 33 reviews

Top-Rated Seaside Villa with Pool - White Villas

A modern villa features a private pool surrounded by a spacious patio area, with lounge chairs positioned nearby. A spiral staircase is seen leading to the upper deck, offering additional outdoor seating. Large glass doors provide views of the interior living spaces.

4.88 out of 5 average rating, 34 reviews

Caya Villa 1 - 2 Bedroom - Modern Island Home

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.

5 out of 5 average rating, 13 reviews

Dreamy Suite Paradise with Pool and Beach Access

Luxe

An infinity pool surrounded by a stone deck is depicted, with a sunbed positioned nearby. Lush greenery frames the area, and wooden seating can be seen under a pergola. A view of the tranquil ocean and sky filled with clouds is visible in the background.

4.89 out of 5 average rating, 9 reviews

Beach Shack

Villa in Providenciales Turks and Caicos Islands

A spacious studio layout features a queen bed with a patterned duvet. The room opens to a balcony through large glass doors, providing a view of the ocean and surrounding greenery. A small dining table is positioned near the window, complemented by a ceiling fan.

4.8 out of 5 average rating, 49 reviews

Serene Oceanfront - Beach Front Junior Suite

Villa rentals with a pool

A spacious outdoor deck overlooks tranquil waters and lush mangroves, with vibrant turquoise hues reflecting the sky. The surrounding vegetation includes tropical palms, providing a natural frame to the picturesque scene. The area suggests a peaceful retreat with scenic views.

Villa in Cooper Jack Bay Settlement

4.56 out of 5 average rating, 52 reviews

Tropical Waterfront Cooper Jack Bay Villa

A light-filled living area features a large, contemporary sectional sofa facing a wall-mounted television. Built-in shelves display various decorative items and framed photos. The space is complemented by soft lighting and an adjacent dining area, creating a welcoming environment for relaxation.

4.6 out of 5 average rating, 25 reviews

The White House TCI Guests house

4.75 out of 5 average rating, 16 reviews

Our Home on the Water - I Land Time Villa

The modern villa features a sleek, two-story facade with large windows and a wooden balcony. Lush palm trees frame the entrance, complemented by a clean concrete pathway leading to the front door. The property is situated in a bright outdoor setting under clear blue skies.

Villa in Discovery Bay Settlement

4.87 out of 5 average rating, 60 reviews

Modern two-bedroom Villa with pool!

An aerial view of Beach Please Villa is shown, highlighting its proximity to Grace Bay Beach. The villa is surrounded by lush greenery, with a clear pathway leading to the beach access. The vibrant blue ocean is visible in the distance, enhancing the tranquil setting.

5 out of 5 average rating, 24 reviews

Walk to Grace Bay Beach ~ 3 bedroom en-suite

Villa in Cooper Jack Bay Settlement

The exterior of a two-story villa is presented, featuring a white façade and a wide staircase. Lush greenery surrounds the property, while a seating area is visible on the patio. Large windows allow natural light into the upper levels, set against a clear blue sky.

5 out of 5 average rating, 8 reviews

Waterfront 3BR Villa w/ Pool, Canal View , Parking

A modern villa is set against a vibrant blue sky, featuring a well-manicured front garden adorned with tropical flowers. A welcoming entrance with a wooden door leads to the interior, complemented by a spacious driveway paved with light-colored stones.