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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.

Guesthouse · 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.
Oct 5 – 12
$199 per night
Superhost
Cottage · 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.
Oct 5 – 12
$169 per night
Superhost
Private room · Leeward Settlement
Halcyon Nest, relax close to the beach in serenity
Halycon Nest, in the secure residential community of Leeward is situated at the end of a quiet cul d sac. Only three mins from the Beach, 2 mins from the golf course, tennis courts and restaurants and 5 mins from Grace Bay shopping area. My home is nestled in the shade of a luscious garden. The one bedroom suite adjoins the main house and has a separate entrance which opens to a lovely shaded screened patio where the hammock sways in the gentle breeze . From the patio the pool beckons.
Jan 28 – Feb 4
$153 per night
Superhost

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Leeward Settlement beach vacation rentals

Private room · Long Bay Hills
Private en-suite close to Grace Bay & Long Bay
Oct 4 – 11
$65 per night
Superhost
Home · Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
Jun 24 – Jul 1
$895 per night
Superhost
Apartment · Caicos Islands
Coco apartment (Grace Bay beach 2 min walk)
May 11 – 18
$151 per night
Superhost
Villa · Long Bay Hills
VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY
Feb 23 – Mar 2
$475 per night
Villa · Providenciales
Closest villa to the ocean on island!
Apr 30 – May 7
$491 per night
Superhost
Guesthouse · Long bay
Villa Kendara~$100/NITE~10/1-10/8~Private~SeaFront
Sep 30 – Oct 7
$262 per night
Superhost
Apartment · Leeward Settlement
Romantic Vacation at La Casita
Jul 10 – 17
$281 per night
Superhost
Loft · Long Bay Hills
Ponciana House Studio Loft: Ocean View, Pool
Oct 4 – 11
$90 per night
Guesthouse · Leeward Settlement
Pelican Cottage -Mins. to the Beach!! Car 4 Rent!
Oct 27 – Nov 3
$160 per night
Superhost
Home · Leeward Settlement
Aloe Vera Villa..
Mar 10 – 17
$215 per night
Superhost
Villa · Providenciales
Khaya | Newly Built Luxury Waterfront Villa
May 20 – 27
$922 per night
Superhost
Condo · Providenciales
★★★★★ Modern Condo | Amazing Pool | On Site Spa
Sep 19 – 26
$354 per night
Superhost