
House vacation rentals in Leeward
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Top-rated house rentals in Leeward
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Leeward Landing Villa
Escape to paradise at Beach Landing Villa nestled in the heart of Leeward TCI. This luxurious villa is just minutes away from the pristine award-winning Grace Bay Beach offering a perfect blend of relaxation and adventure. Conveniently cruise your community with the provided pedal bikes. Lounge in the backyard in your private pool or relax indoors with the brilliant large screened TV equipped with all the latest streaming services. Book your villa now for an unforgettable experience in paradise!

Gated Villa + Private Pool• Walk to GraceBay Beach
Super Popular for Families, Couples & Group Vacations! PRIVATE Sun Drenched Pool. Walk to Famous GraceBay Beach shopping, dining, night-life, “Great space. Loved the outdoor/indoor living combo.” Jenny Bear, DE, USA The villa is tucked away in a peaceful setting on a private gated street with only 4 villas! Features a private plunge pool for kids & sunbathing or hanging out by the larger pool with some cocktails & your favorite music. The Ultimate Escape. Unpack, Relax, Enjoy... Reserve Now!

The Sapphire Villa. Tropical Oasis. Make memories
This is where an unscripted holiday begins. At our Villa, we provide the canvas for luxury and privacy for the perfect getaway. Where dreams are fulfilled, and precious memories are made to live forever. Whatever you desire is within reach. Our Villa combines with the extraordinary tranquility of Turks and Caicos Islands for sophisticated, low-key luxury. Here is where to create your story within the privacy of your own home away from home in an exceptional place that becomes uniquely yours.

~Villa Bonita~
Villa Bonita is a newly built 2-bedroom (King Beds), 2.5-bathroom home situated in the heart of Grace Bay. It features a private pool and is just a 10-minutes walk from the nearest beach access. It is conveniently located near all the top restaurants and the casino. Base price is for 2 persons each additional guest (4 max) is $45 USD/person/night. Villa Bonita is filled with love ❤️ where you can relax in peace during your holiday. We have all the essentials to quietly enjoy your stay.

Sea La Vie - Beachside 2 bdr Unit #4, Ocean views
Located in a secluded Beachside property, 500 ft from Long Bay Beach, and 5-minutes drive from Grace Bay Resorts and shops, this spacious, private, 2-Bedroom\2-Bathroom unit can accommodate up to 6 guests, with a king size bed, 2 full size beds, and a queen sofa bed. It occupies 2nd and 3rd floor of our middle building, roughly 15 yards from the pool, no pool view. With beautiful scenic views of the ocean and Long Bay Beach area, from its 3rd floor Livingroom and wrap-around balcony.

Villa Cocuyo Micro Villa with pool
"Discover a truly unique escape at our one-of-a-kind villa in the picturesque Blue Mountain. Crafted by a local architect, this exceptional residence is nestled on a half-acre of beautifully landscaped grounds, offering an exclusive retreat in a private and secure community. Admire the lush garden in the comfort of your own oasis. The villa boasts a distinctive design that is often imitated but never duplicated, showcasing the perfect blend of style, modern layout and local charm

PERIWINKLE | Charming Island Home|Near to Beach
Nestled in the Gated Upscale community of Leeward at the end of a quiet cul-de-sac is Periwinkle. Experience the true flavor of the Islands with us. Be cradled and relax in the lush native vegetation and enjoy the view from the many windows which decorate the home. Periwinkle is a short stroll away from the magnificent soul quenching Leeward Beach and a five minute drive to the heart of Grace Bay for great shopping and dining experiences. Escape to the quieter side of Paradise.

3 Bed Beach Oasis on Flamingo Lake w/Private Pool
Márohu is a stunning 3-bedroom modern Caribbean villa set within the exclusive neighbourhood of Turtle Tail, just a 10-minute drive from the world-renowned Grace Bay Beach. This spacious, well-equipped, and family-oriented villa offers expansive floor-to-ceiling views over Flamingo Lake from every room. You’ll experience the best of outdoor living with our own pool and sandy beach, ideal for lounging, a friendly game of cornhole, or exploring the lake with our included kayaks.

Beach Cottage with Amazing Chalk Sound Views!
Adorable cottage for an authentic Providenciales experience w/breathtaking views! - Quaint cottage w/amazing views of Chalk Sound & on clear days, West Caicos! - Silly Creek Mansion across the water - Minutes away from great restaurants from beach shacks to fine dining - Nearby beautiful beaches like Taylor Bay & Sapodilla Bay Beach. - Water sports abound like jet ski and kayak rentals. - Quiet area, So. Providenciales flanked by Chalk Sound & Atlantic Ocean!

Moonrise, Turks and Caicos
Kick back and relax in this calm, stylish space. This Long Bay beach villa featuring 1800 sq feet of A/C space with views of the Caicos bank. Enjoy two spacious ensuite bedrooms and a large open living, dinning, kitchen area. The outdoor space features 3 sun decks, covered dinning, and a relaxing pool. It's a short 5 minute walk to the Long Bay beach access via a path. A 2 minute drive to South Bank and 10 minutes to Grace Bay beaches. Managed by Ski2Sea

“The Lighthouse”, Private Pool, Ocean Views, Beach
The Lighthouse private cottage features a tower fashioned after a lighthouse affording stellar ocean views Private pool just outside living room doors! Deck & patio lounge w/ BBQ for fun & sun Nestled in the Thompson Cove Canal area and just a 3-minute walk to the beach WiFi, Smart TV with Netflix. Book now for a relaxing yet adventurous getaway! Kayaks, SUPs & snorkel gear included!

Charming Gecko House Island Vibes - Grace Bay
Affordable and charming house situated in a quiet residential neighborhood in Grace Bay just a short 8 minute walk (less than a 3 minute ride) to the world famous Grace Bay Beach. Very popular with solo travelers and couples. Close to the beach and steps away from the very popular Coco Bistro Restaurant and Coco Van.
Popular amenities for Leeward house rentals
House rentals with a pool

2 BR Ocean View- Private Pool- Flame Tree Villa #1

Beyond The Sea Cottage Turks and Caicos

Grace Bay/ New Luxurious home 3+ Bedrooms & Pool

1 BR Apt w/pool - Long Bay Hills #2

NEW Water Access! Luxe Villa, Infinity Pool& Views

2 Bedroom Stunning Views

Caya Villa 2 - 2 Bedroom - Island Fusion Home

LUXURy Villa: Ocean View. Private Pool! Chef avail
Weekly house rentals

Casa de Isle, Taylor Bay, Chalk Sound area

Brighter Days Villa

@Villa 360! Private, Gorgeous Views Near airport

Colibri Oasis - Gated Villa w Pool, Walk to Beach

Colibri Gardens Villa - Great value in Grace Bay

Charming CoCo Gardens -2 bedroom island hideaway

White Coral Luxury Townhouse #4

Vista Blue Rental-Grace Bay Beach just 4 mins away
Private house rentals

Secluded Escape, Ocean Views, Pool and Hot Tub

Tropical Oasis | Patio | Walk to Grace Bay Beach

ParadiseONE 2 Suites 3 Bedrooms

Tropical Chalk Sound Cottage with Pool and Kayak!

#10 The Enclave

Blue Tang Villa (2 Bedroom)

3bd ~ Private Pool ~ Kayak to the Mangroves

Peaceful 1BR Private Cottage w/ HotTub Beach Front
Quick stats about house rentals in Leeward

Total vacation rentals
Explore 80 vacation rentals in Leeward

Nightly prices starting at
Leeward vacation rentals start at ﺩ.ﺇ624 per night before taxes and fees

Verified guest reviews
Over 1,290 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
80 of Leeward vacation 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!
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