Villa holiday rentals in Leeward

Villa in Providenciales and West Caicos

An aerial view captures the villa nestled among tropical vegetation, with the serene turquoise waters of Taylor Bay and a pristine white sand beach stretching along the coastline. The surrounding landscape features a winding road and nearby villas, offering a sense of seclusion.

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, 47 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🌴

The modern villa features a two-story design with a spacious ground-level patio. A private pool reflects the blue sky, surrounded by tropical landscaping. Comfortable outdoor seating is visible on the terrace, offering a quiet space for relaxation.

4.98 out of 5 average rating, 140 reviews

Grace Bay villa | Pool | 3min walk to Beach & Reef

A modern beach villa with its own private pool. Sleeps up to 4 adults in separate rooms. Just 250 steps from the azure blue waters and soft white corals sands of Grace Bay beach. In a quiet off-street location. Perfect for a romantic getaway. With its quiet secluded garden and pool area, many of our guests come to celebrate birthdays, anniversaries, and honeymoons in full privacy. Walk to coral reef snorkeling in 3 mins plus several restaurants. Large grocery supermarket & shops are nearby.

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.

4.88 out of 5 average rating, 138 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.

4.95 out of 5 average rating, 21 reviews

Villa in TC

Live Villa

Modern Triple Townhome Rentals:🌴 "Live, Love, Laugh" Live Villa is a luxurious 2-bedroom, 3-bathroom rental in Grace Bay, located just behind Coco Bistro and a short walk to Grace Bay Beach. This newly built villa features en-suite bathrooms, AC in every room, fast internet, and a private pool for ultimate relaxation. Perfect for up to 4 guests, it combines modern amenities with a prime location and Super Host service to ensure an unforgettable stay. Book now for a dream getaway!🌴

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!

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 serene beachfront scene showcases two yellow lounge chairs positioned under white umbrellas. The calm turquoise waters are framed by a clear blue sky, with fluffy white clouds dotting the horizon. Native greenery and sandy pathways lead to the water's edge.

4.95 out of 5 average rating, 124 reviews

Villa DelEvan 4D / 1-bedrm 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 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, 100 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, 15 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 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 Leeward villa rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Private villa rentals

A spacious outdoor seating area features plush turquoise cushions on a white-framed sofa, set against a backdrop of vibrant greenery and the serene, turquoise waters of Chalk Sound. Two glasses sit on a small white table, inviting relaxation and enjoyment of the view.

4.99 out of 5 average rating, 69 reviews

Modern Cottage with Chalk Sound Views

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

An outdoor view features a private infinity pool with a deck and sun loungers. Umbrellas provide shade, and the surrounding landscape includes lush greenery and a turquoise lagoon in the background. The scene is framed by elegant columns and a second-floor balcony.

4.82 out of 5 average rating, 33 reviews

Sunset Soaked Retreat Where Two Waters Meet

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

An aerial view showcases the expansive property, featuring lush tropical landscaping and a shared pool surrounded by palm trees. Two distinct single-story buildings can be seen, with a driveway leading to both. The serene setting is complemented by the vibrant greenery.

4.98 out of 5 average rating, 46 reviews

Sea Villa - Cozy Family Villa Steps From the 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.

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

A modern villa is highlighted by a serene swimming pool reflecting the night sky. Comfortable lounge chairs and umbrellas are arranged around the pool area, providing space for relaxation. The expansive glass doors of the villa create a seamless transition between the outdoors and indoors.

5 out of 5 average rating, 11 reviews

3 Bedrooms Villa Near The Beach

Luxury villa rentals

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

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.

4.94 out of 5 average rating, 33 reviews

Caya Villa 1 - 2 Bedroom - Modern Island Home

A sunny pool area features a clear blue pool surrounded by comfortable lounge chairs. Palm trees sway gently nearby, and umbrellas offer shaded seating. The villa is visible in the background, showcasing a charming design under a bright sky.

5 out of 5 average rating, 37 reviews

1 BR Villa | Island Escape | October DEAL!

A modern, white two-story building is surrounded by lush palm trees. The exterior showcases a sleek design, with a spacious balcony on the roof and a well-defined entrance door. A light gravel pathway leads to the front of the structure, creating a clean and open atmosphere.

4.75 out of 5 average rating, 8 reviews

Sugar Kube

The outdoor area features a swimming pool surrounded by lounge chairs, with soft lighting illuminating the space. Glass doors lead to a villa interior, creating a seamless connection between outdoor and indoor relaxation. The evening sky showcases calming hues of purple and pink.

5 out of 5 average rating, 13 reviews

Dreamy Suite Getaway with Pool and Beach Access

The exterior of the villa showcases a modern design with a white façade. Lush tropical plants and palm trees surround the property, contributing to a serene ambiance. A stone pathway leads to the entrance, framed by vibrant greenery and flowering shrubs.

4.89 out of 5 average rating, 70 reviews

1 Bedroom Cottage - near beach

The entrance to the villa is showcased, featuring a set of stairs leading to a white front door framed by lush greenery and vibrant flowering plants. A clear blue sky complements the inviting atmosphere of the property's exterior.

4.96 out of 5 average rating, 46 reviews

Newly Renovated - 2 Minute Walk to Grace Bay Beach

4.88 out of 5 average rating, 66 reviews

Villa in Long Bay

Hakuna Matata Villa + Golf Cart!

Villa rentals with a pool

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!

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.

4.97 out of 5 average rating, 29 reviews

Hang Five Surf Villa in Long Bay

A bright bedroom features large windows that provide expansive views of the turquoise ocean. A spacious bed with light linens is centered in the room, complemented by a white dresser and a cozy chair near the window. Natural light enhances the airy atmosphere.

Villa in Turtle Cove

4.81 out of 5 average rating, 70 reviews

Nirvana's Nest

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 panoramic view reveals a sparkling pool surrounded by lush palm trees, leading to the turquoise waters of Long Bay Beach. The clear blue sky complements the vibrant landscape, offering a serene backdrop for relaxation and outdoor activities.

5 out of 5 average rating, 3 reviews

1BR Ocean "Paradise Found" on Best Beach in Turks!

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.