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Leeward Settlement vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Leeward Settlement

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

Villa in Long Bay Hills
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 dip pool that can create amazing instagramable moments . Located in long bay , 5 minute walk to long bay beach . 5 minute drive to IGA gourmet and 6 minute drive to grace bay beach KING SIZE BED QUEEN SIZE SOFA BED Famous Tiki bar pick up 2min away
$489 per night
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Guesthouse in Leeward Settlement
"The Nest Cozy Cottage"
“The Nest” Spacious and modern 1 bedroom cottage sits amongst a well-manicured garden with majestic swaying palms. Less than 150 steps away from the famous Grace Bay Beach. This cozy sanctuary is quiet and bears the true beauty of itself, it’s perfect for honeymooners or if you’re just seeking for some quiet and down time. Complete with high-speed internet, cable TV and all amenities one need for the perfect vacation, The Nest is where you want to be.
$320 per night
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Rental unit in Leeward Settlement
Leisure in Paradise
Wake up on a Mocking bird singing in the garden, sun rays sparkling through the lush green while you drink your cup of tea or coffee on your private screened patio. Take a walk in the topical garden and have a refreshing swim in crystal clear pool or take a short walk (3 minute) to the turquoise ocean and white sandy beach.
$251 per night
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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 Big Blue Collective
Big Blue Collective17 locals recommend
Photo of Blue Haven Resort
Blue Haven Resort10 locals recommend
Photo of Caicos Catalyst
Caicos Catalyst3 locals recommend
Photo of Talbot's Adventures
Talbot's Adventures5 locals recommend

Leeward Settlement beach vacation rentals

Rental unit in Caicos Islands
Swan Villa water-front Studio
$277 per night
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Condo in Grace Bay
Royal Tropical Studio
$333 per night
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Rental unit in Leeward Settlement
Romantic Vacation at La Casita
$299 per night
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Private room in Leeward Settlement
Halcyon Nest, relax close to the beach in serenity
$173 per night
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Loft in Providenciales and West Caicos
Cozy Loft Condo Great Location w/Pool, Reno Sept22
$166 per night
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Vacation home in Venetian Road Settlement
Lovely studio apartment, with pool
$149 per night
Home in Leeward Settlement
A private Airbnb house nearby beaches and Marinas
$120 per night
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Guesthouse in Long bay
VillaKendara~BK 6/24 &ON~Private~Seafront~Gated GH
$280 per night
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Guesthouse in Leeward Settlement
Pelican Cottage -Mins. to the Beach!! Car 4 Rent!
$169 per night
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Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
$229 per night
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Condo in Providenciales
★★★★★ Modern Condo | Amazing Pool | On Site Spa
$374 per night
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Rental unit in Grace Bay
Crescent #2 Grace Bay (beach 2 min walk)
$185 per night