
Villa holiday rentals in Leeward
Find and book unique villas on Airbnb
Top-rated villa rentals in Leeward
Guests agree: these villas are highly rated for location, cleanliness and more.

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🌴

Gated Villa + Private Pool• Walk to GraceBay Beach
Popular for Families, Couples & Group Vacations! PRIVATE Sun Drenched Pool. Walk to Famous GraceBay Beach + shopping, dining, night-life, “Incredible space! Loved the outdoor/indoor living combo and comfy veranda.” Sarah Burton, OH, USA The villa is tucked away in a peaceful setting on a private gated street with only 4 villas! Features a PRIVATE pool perfect for relaxation, sunbathing, enjoying some cocktails & your favorite music. The Ultimate Escape. Unpack, Relax, Enjoy... Reserve Now!

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.

Canal Front 3BR Villa and dock+ Pool+Sups+Kayaks
Classic Caribbean 3 Bedroom canal front villa in Leeward. Cotton House has been designed in the timeless, traditional Caribbean aesthetic and is solar powered. Located in the gated Leeward community (25 min from PLS airport - 8 min to Grace Bay), this canal front home exudes an easy living elegance. Each bedroom opens to a central courtyard, the serene heart of the home featuring fountain, ferns, climbing vines, and tropical trees. *Ask us about our 4 and 5 Bedroom options for this villa.

Hakuna Matata Villa + Golf Cart!
Hakuna Matata Villa is a three-bedroom, three-bath home located in Long Bay on the south side of Providenciales. Our stylish 2-person golf cart offers a quick and fun way to access Long Bay Beach, located just two minutes away from Hakuna Matata Villa. The giant swimming pool of the Caicos Bank features miles of shallow warm turquoise water. Hakuna Matata Villa offers fantastic value for your money with close proximity to the shops and amenities of Grace Bay and Blue Haven Marina where

Sea Sun Relax - villa 5 min walk to Grace Bay
Location, location, location! Stay at this recently renovated 1,650 sq. feet, 2 bedrooms, 2 baths Caribbean house with a large private pool, close to the beach, in the prestigious Leeward gated community at the eastern tip of Providenciales island, in the beautiful Turks and Caicos. Also, another queen bed is inside a mini-cottage. The house is within 0.5 KM / 5-6 min. walk from Sunset beach and Perlican beach ( as well as the Grace Bay beach that is one of the best in the world).

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 a bright and inviting getaway, ideal for relaxing moments and quality time during your stay. 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. 🚧 in the neighborhood.

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.

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!!

NEW *2 BR Villa Maya- BBQ- Golf- Pool in Grace Bay
This stunning 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 with golf course views, it offers modern luxury and tranquility. Just 5 min from Grace Bay beach, 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!

Golden Palms – Lotus Villas #2 Privacy, Pool, BBQ
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!

The Caicos House -5 mins to the Beach & Dining!
Daily Housekeeping included! …… Nestled in the tranquil gated community of Leeward, on the heels of the Grace Bay and the Grace Bay Beach, regularly ranked as the “The Best Beach in the World!”. The upscale Leeward community is within a 5-8 minute drive to the Grace Bay shopping and restaurant district, with over two dozen businesses, including a large grocery store and bank.
Popular amenities for villa rentals in Leeward
Private villa rentals

Boutique Villa | Private Beach Chairs on GraceBay

Stunning Villa - short walk to Sapodilla Beach

Townhome Villa – Steps to Grace Bay (Sleeps 4)

‘My Little Hideaway’ at Lucayan Cays

Delightful Family Villa with Pool in Leeward

Perfect Oceanside Haven for Honeymooners!

Sun Villa-Family friendly Villa Close to the Beach

Grace House Amazing home in the heart of Grace Bay
Luxury villa rentals

Villa Bashert

Contemporary 3 Bed 2.5 Bath Villa minutes from the

BeachHaus Villa with ocean view and private pool

The Retreat, Spacious 1-Bed, 1-Bath Villa

Walk to Grace Bay Beach ~ 3 bedroom en-suite

TC Villas | Sea Edge Villa | Heated Pool, Beach

White Osprey Villa

White Villas - Oceanview, Pool & Beach Access (1)
Villa rentals with a pool

Sapodilla Bay - Walk to the Beach!

Private Pool Villa w/ Firepit/Outdoor Dining

Our Home on the Water - I Land Time Villa

Blue Flamingo Villa - Paradise Is a Lifestyle!

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

*NEW* Complimentary Golf Cart - Villa Seabatical

Cocodemer, a short walk to secluded Pelican Beach.

T'PII Villa: Brand New Villa in Turtle Creek
Quick stats about villa rentals in Leeward

Total holiday rentals
Explore 140 holiday rentals in Leeward

Nightly prices starting at
Leeward holiday rentals start at £157 per night before taxes and fees

Verified guest reviews
Over 2,320 verified reviews to help you choose

Family-friendly holiday rentals
130 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
130 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
140 of Leeward holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Leeward rentals

4.8 Average rating
Leeward stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Santo Domingo Holiday rentals
- Las Terrenas Holiday rentals
- Santiago De Los Caballeros Holiday rentals
- Santo Domingo Este Holiday rentals
- Puerto Plata Holiday rentals
- Sosúa Holiday rentals
- Cabarete Holiday rentals
- Juan Dolio Holiday rentals
- Jarabacoa Holiday rentals
- Boca Chica Holiday rentals
- Río San Juan Holiday rentals
- Bonao Holiday rentals
- Rentals with a washing machine and dryer Leeward
- Rentals with a firepit Leeward
- Rentals with outdoor seating Leeward
- Waterfront rentals Leeward
- House rentals Leeward
- Rentals with beach access Leeward
- Beachfront rentals Leeward
- Flat rentals Leeward
- Rentals with a patio Leeward
- Family-friendly rentals Leeward
- Fitness-friendly rentals Leeward
- Rentals with a kayak Leeward
- Luxury rentals Leeward
- Rentals with pools Leeward
- Rentals with a hot tub Leeward
- Pet-friendly rentals Leeward
- Villa rentals Providenciales
- Villa rentals Caicos Islands
- Villa rentals Turks and Caicos Islands





