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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
Apartment in Leeward Settlement
NEW! Large Luxury Modern condo
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 890 sq. ft. luxury one bedroom, newly renovated condo (in May 2023), provides all necessary amenities for your home away from home.
$150 per night
Superhost
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.
$180 per night
Superhost
Apartment 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.
$168 per night

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape
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 Resort8 locals recommend
Caicos Catalyst3 locals recommend
Talbot's Adventures5 locals recommend

Other great vacation rentals in Leeward Settlement

Superhost
Home in Leeward Settlement
Charming Garden cottage on the canal in Leeward
$180 per night
Superhost
Guest suite in Leeward Settlement
Erisa Private Studio near Grace Bay Beach
$101 per night
Apartment in Grace Bay
Crescent #3 Grace Bay (beach 2 min walk)
$154 per night
Superhost
Guesthouse in Leeward Settlement
"The Nest Cozy Cottage"
$130 per night
Superhost
Guest suite in Leeward Settlement
The Sandbox
$137 per night
Superhost
Loft in Providenciales and West Caicos
Cozy Loft Condo Great Location w/Pool, Reno Sept22
$175 per night
Superhost
Private room in Leeward Settlement
Halcyon Nest, relax close to the beach in serenity
$164 per night
Superhost
Villa in Leeward Settlement
Langley - Caribbean Style Waterfront Villa
$420 per night
Superhost
Condo in Grace Bay
22 Middle of Gracebay, Heated Pool, Gated Condo.
$230 per night
Superhost
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
$155 per night
Home in Leeward Settlement
Charming Cottage
$165 per night
Superhost
Villa in Long Bay Hills
VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY
$493 per night
Show all

Frequently Asked Questions

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

    Yes! We have over 50 homes with more than 2 bedrooms perfect for families looking for a comfortable and convenient stay in Leeward Settlement.

  • How much does it cost to stay in a villa in Leeward Settlement?

    Experience the best of Leeward Settlement with our villa vacation rentals, averaging about $2,760 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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

    Yes! Four-legged friends are welcome too! Select from over 20 pet-friendly vacation rentals in Leeward Settlement, so your furry family members can join in on the adventure.

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

    Yes! Work meets play with ease at over 110 vacation rentals in Leeward Settlement featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Yes! Dive into the perfect getaway at one of over 240 vacation homes with pools in Leeward Settlement, available on Airbnb. Make a splash and soak up the sun in style!

  • Do houses in Leeward Settlement have a Gym?

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

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