
Villa holiday rentals in Leeward
Find and book unique villas on Airbnb
Quick stats about villa rentals in Leeward

Total holiday rentals
Explore 150 holiday rentals in Leeward

Nightly prices starting at
Leeward holiday rentals start at $254 NZD per night before taxes and fees

Verified guest reviews
Over 2,620 verified reviews to help you choose

Family-friendly holiday rentals
130 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
150 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
150 of Leeward holiday rentals include Wi-Fi 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!
Top-rated villa rentals in Leeward
Guests agree: These villas are highly rated for location, cleanliness and more.

Cheers 🥂 Villa 🌴
Beautiful private Villa in a superb location,surrounded with🌴.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.
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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🌴
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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!
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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.
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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).
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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.
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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!!
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3BR Villa | Pool | 100 Steps to Pelican Beach
Slow down and enjoy your own private island retreat, just 100 steps from beautiful Pelican Beach. Surrounded by lush tropical gardens and the gentle island breeze, our 3-bedroom, 3-bathroom villa offers a private pool, outdoor shower, spacious covered outdoor dining area and BBQ. Relax by the pool, spend the day at the beach, and gather together for long dinners under the stars. Our family retreat is designed for making memories and enjoying the best of Turks & Caicos.
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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.
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Gated Long Bay Villa Near Grace Bay with Pool
Gated two-story villa in Long Bay Hills with a private pool, sea-view balconies, and optional private chef and yacht experiences arranged through your host. Long Bay Beach is a 5-minute drive; Grace Bay Beach is 10 minutes away. Complimentary airport transfers for stays of 5+ nights. Designed for groups and families seeking a fully exclusive property with concierge-level service in Turks and Caicos.
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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.
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Spacious contemporary private villa
This beautiful and well appointed property was constructed in 2011. It has contemporary appliances, over 1400sq/ft of internal space with high '"loft" ceilings along with two large external deck areas and a private garden / yard. Located in walking distance to the main supermarket and gracebay west beaches (Bight Park), it makes the perfect island getaway.
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Popular amenities for Leeward villa rentals
Private villa rentals

NEW Luxury Grace Bay villa|Pool | 2 min>Beach|Reef
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NEW *2 BR Villa Kiwi- BBQ- Pool in Grace Bay Beach
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Perfect for 1 Couple - Pool & Beach access
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Hakuna Matata Villa - 5 Minutes to Long Bay Beach
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Caya Villa 1 - 2 Bedroom - Modern Island Home
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Stunning Villa - short walk to Sapodilla Beach
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Private Pool Stay with Ocean Views & Near Beach
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Romantic Villa -Private Pool, Steps from the Beach
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Luxury villa rentals

Vista Cove - Entire Property
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Villa Blu - Contemporary 3 BDR close to Grace Bay
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Private Pool Villa w/ Firepit, Outdoor Dining
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Townhome Villa – Steps to Grace Bay (Sleeps 4)
LocationBikingLaundry

The Retreat, Spacious 1-Bed, 1-Bath Villa
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Fall Specials on now. 25% off regular rates
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WOW! Waterfront Chalk Sound Oasis w/ Infinity Pool
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Villa Bianca walk to #1 Grace Bay Beach Pool Gated
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Villa rentals with a pool

Kokoon 60% OFF Summer PrivatePool OceanView SunSet
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HopeWell Villa West - 5 Minutes to Grace Bay Beach
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T'PII Villa: Brand New Villa in Turtle Creek
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‘My Little Hideaway’ at Lucayan Cays
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Waterfront Villa with Plunge Pool and Ocean Views
ValueFamilyAccuracy

Walk to Sapodilla Bay | Stunning Chalk Sound Views
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Blue Flamingo Villa - Paradise Is a Lifestyle!
PoolDecorCleanliness

Cocodemer, a short walk to secluded Pelican Beach.
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