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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.

Superhost
Condo in Providenciales
★★★★★ Modern Condo | Amazing Pool | On Site Spa
• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access • Hot tub • Highest Rated Spa on Island • Fully equipped kitchen • Private front patio + grill • Garage parking for 1 car • Onsite washer + dryer • Fitness center access • Queen sofa bed with extra linens in living room • Onsite full service spa • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance
$290 per night
Superhost
Villa in Grace Bay
Cottonflower BoutiqueVilla at Grace Shore Villa
The Cottonflower Suite at Grace Shore Villas is a private villa located just minutes from Grace Bay. FOLLOW: @graceshorevillas Grace Shore Villas also has the Passionflower Suite and the Sageflower Suite listed on AirBnB. Check them out! NOTE: Grace Shore Villas has a designated spot at Grace Bay Beach with beach chairs and umbrellas for our guests only. When filling out TCI Assured info you will need to provide our email address: info@graceshorevillas.com
$418 per night
Superhost
Condo in Grace Bay
Luxury 1 Bedroom - Central Grace Bay
The perfect location, and only a 5-7 minute walk to world famous Grace Bay Beach! Located in the heart of Grace Bay near Seven Stars Resort and the Ritz Carlton Resort. 5-7 minute walk to the beach. 4 minute walk to the grocery store, and 10 minute walk to the best restaurants and shopping on the island. No rental car is needed. This 790 sq. ft. luxury one bedroom, newly built condo (Nov 2020), provides all necessary amenities for your home away from home.
$277 per night

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials
Gym
BBQ grill
Laptop-friendly workspace
Wifi
Air conditioning

Stay near Leeward Settlement's top sights

Caicos Conch Farm12 locals recommend
Provo Golf Club14 locals recommend
Big Blue Collective17 locals recommend
Blue Haven Resort7 locals recommend
Caicos Catalyst3 locals recommend
Talbot's Adventures5 locals recommend

Other great vacation rentals in Leeward Settlement

Superhost
Villa in Providenciales
Gardenia Villa
$559 per night
Superhost
Home in Leeward Settlement
Charming Garden cottage on the canal in Leeward
$207 per night
Superhost
Condo in Grace Bay
Inn by the Beach, Grace Bay
$253 per night
Superhost
Condo in Leeward Settlement
New! Luxury 1Bed Large Condo
$224 per night
Superhost
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
$250 per night
Superhost
Condo in Grace Bay
Royal Tropical Studio
$339 per night
Superhost
Villa in Long Bay Hills
VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY
$524 per night
Superhost
Guesthouse in Long bay
VillaKendara~BK 3/23 & 4/27~Gated~SeaFront GH~View
$265 per night
Superhost
Villa in The Bight Settlement
Idyllic getaway villa | 250 yds to the beach
$509 per night
Superhost
Apartment in Grace Bay
Gracebay, Heated Pool, Gated.
$280 per night
Superhost
Condo in Leeward Settlement
Grace’s Condo In Leeward Settlement
$264 per night
Superhost
Cottage in Leeward Settlement
Aqua Del Rose 1 Br Beachfront Cottage
$627 per night
Show all

Frequently Asked Questions

  • How much does it cost to stay in condo rentals in Leeward Settlement?

    Experience the best of Leeward Settlement with our condo rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Leeward Settlement house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 house rentals with pools in Leeward Settlement, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there apartment rentals with a dedicated workspace in Leeward Settlement?

    Yes! Work meets play with ease at over 10 apartment rentals in Leeward Settlement featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Leeward Settlement have a bbq area?

    Absolutely! We offer over 130 house rentals with a bbq area in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Leeward Settlement?

    Leeward Settlement has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do condo rentals in Leeward Settlement have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Leeward Settlement have a gym?

    Absolutely! We offer over 20 villa rentals with a gym in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Leeward Settlement have air conditioning?

    Absolutely! We offer over 10 condo rentals with air conditioning in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly house rentals in Leeward Settlement?

    Four-legged friends are welcome in Leeward Settlement. Choose from more than 10 house rentals for guests traveling with pets.

  • What are the most popular amenities for Vacation Home Rentals in Leeward Settlement?

    Enhance your stay in our Vacation Home Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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