
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🌴

Stunning Villa - short walk to Sapodilla Beach
The Villa is located just a 5 min walk for Sapodilla beach. A stylish two bedroom villa, both with ensuite bathrooms and Balinese bathtubs. The Villa has its own private swimming pool in its own garden space. Located near Las Brises restaurant on Chalk Sounds. Chalk Sound is a stunning Sea glass blue, Aqua) I’m sure you’ll find your own words to describe the color. The property is located approximately quarter of a mile from Taylor Bay beach and approximately 300 feet from sapodilla Beach.

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!

Townhome Villa – Steps to Grace Bay (Sleeps 4)
Escape to your own luxurious villa in Grace Bay! This spacious 2-bedroom, 2.5-bath retreat sleeps 4 and features a full kitchen, large living area, washer/dryer, SMART TVs, and private patios and balconies. Enjoy resort-style amenities including hotel check-in, concierge service, on-site gym, saltwater pool, complimentary bikes, and beach shuttle. Just steps from Grace Bay Beach, shops, cafés, and restaurants—perfect for families, friends, or groups seeking privacy and comfort in paradise.

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.

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).

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!

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!!

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.

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!
Popular amenities for villa rentals in Leeward
Private villa rentals

Contemporary 3 Bed 2.5 Bath Villa minutes from the

Kokoon at Oceanside PrivatePool OceanView SunSet

Private Pool Villa w/ Firepit/Outdoor Dining

3bd/2.5ba for 6-Pool-90 steps to Grace Bay Beach

Private Villa w/Pool, Ideal Family w/Teens, Beach

White Osprey Villa

100 Steps to Beautiful Grace Bay Beach!

Gorgeous Waterfront Villa w/ HUGE Outdoor Patio
Luxury villa rentals

Hilltop Hideaway Entire Villa Second level bedroom

Caya Villa 1 - 2 Bedroom - Modern Island Home

Our Home on the Water - I Land Time Villa

Luxury Modern villa with pool

Modern 2BR Villa | Pool, Basketball & Pickleball

Blue Flamingo Villa - Paradise Is a Lifestyle!

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

Gated 1 bd Villa | Pool | Ocean View | Near Beach
Villa rentals with a pool

Amalfi- Luxury Beach front villa

Luxury Bungalow - Private Infinity Pool - Firepit

Sapodilla Bay - Walk to the Beach!

Sugar Cube

Peaceful island getaway in Long Bay (New 2BR)

Nirvana's Nest

Turks & Caicos Oceanfront Villa w/Pool and Dock

Cheerful 3bedroom Villa with Private Pool and View
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 $269 SGD 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
- House rentals Leeward
- Beachfront rentals Leeward
- Rentals with a washing machine and dryer Leeward
- Waterfront rentals Leeward
- Rentals with pools Leeward
- Rentals with a hot tub Leeward
- Rentals with a patio Leeward
- Rentals with beach access Leeward
- Family-friendly rentals Leeward
- Rentals with a firepit Leeward
- Rentals with outdoor seating Leeward
- Rentals with a kayak Leeward
- Fitness-friendly rentals Leeward
- Flat rentals Leeward
- Luxury rentals Leeward
- Pet-friendly rentals Leeward
- Villa rentals Providenciales
- Villa rentals Caicos Islands
- Villa rentals Turks and Caicos Islands





