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Leeward Settlement vacation rentals

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Top-rated vacation rentals in Leeward Settlement

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Villa in Leeward Settlement
Villa La Palma
Villa La Palma is located in the gated community of Leeward, just a 2 minute drive and 10 minute walk to Sunset Beach, on Grace Bay Beach. This 2 Bed, 2 Bath villa has a private pool, screened patio, enclosed backyard, gated entry, and golf cart! Kitchen is fully equipped, and also comes will all your gear for the beach. Built for indoor and outdoor living, this villa is the perfect home away from home for your friends and family. Stay comes w. a beach photo shoot with photos for purchase!
$167 per night
Rental unit in Leeward Settlement
Luxury Large 1 Bed Condo close to Grace Bay Beach
Just renovated: The perfect condo, and only 3 minutes from the famous Grace Bay Beach! Located in the exclusive Leeward area, a gated, secure residential area where all the major luxury villas are. The beach is a short stroll away & the main Grace Bay shopping / resort area is 5 minutes by car. The condo boasts a large pool, stunning modern finish and appliances. This 925 sqft luxury 1 bedroom, newly renovated (Jan 2023), provides all necessary amenities for your home away from home.
$168 per night
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
Kick back and relax in this delightful modern one bedroom cottage in the high end residential gated community of Leeward. Grace Bay Beach, most recently voted “The best in the world” is only a 4 minute walk away! This cozy cottage is perfect for a couple, wanting to relax and have some downtime. Complete with full kitchen, washer/dryer/ BBQ, high speed internet with cable TV and all amenities needed for the perfect getaway.
$197 per night

Stay near Leeward Settlement's top sights

Photo of Caicos Conch Farm
Caicos Conch Farm12 locals recommend
Photo of Provo Golf Club
Provo Golf Club14 locals recommend
Photo of TCI Ferry
TCI Ferry8 locals recommend
Photo of Big Blue Collective
Big Blue Collective17 locals recommend
Photo of Blue Haven Resort
Blue Haven Resort10 locals recommend
Photo of Blue Haven Marina
Blue Haven Marina5 locals recommend

Other great vacation rentals in Leeward Settlement

Private room in Leeward Settlement
Halcyon Nest, relax close to the beach in serenity
$124 per night
Loft in Providenciales and West Caicos
Cozy Loft Condo Great Location w/Pool, Reno Sept22
$135 per night
Condo in Grace Bay
22 Middle of Gracebay, Heated Pool, Gated Condo.
$265 per night
Condo in Grace Bay
Middle of Gracebay, Heated Pool, Gated Condo.
$292 per night
Rental unit in Leeward Settlement
Romantic Vacation at La Casita
$311 per night
Home in Leeward Settlement
Charming Garden cottage on the canal in Leeward
$194 per night
Townhouse in Providenciales
BirdsofParadise, Golf Course, 5mins walk to beach!
$358 per night
Home in Leeward Settlement
Sea Shell Villa 2.
$252 per night
Guest suite in Leeward Settlement
The Sandbox
$150 per night
Guesthouse in Leeward Settlement
"The Nest Cozy Cottage"
$250 per night
Rental unit in Caicos Islands
Swan Studio Waterfront
$280 per night
Condo in Grace Bay
Luxury 1 Bedroom Condo - In the heart of Grace Bay
$282 per night