366+ Vacation Rentals in Leeward Settlement |
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Leeward Settlement Vacation Rentals, Hotels, & Places to Stay

About Leeward Settlement Vacation Rentals

There are more than 366 places to stay that are available in Leeward Settlement. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in Leeward Settlement.

Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Varoom's places in Leeward Settlement, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in Leeward Settlement. Places to stay near Leeward Settlement are 3652.48 ft² on average, with prices averaging US $3,369 a night.

Varoom helps you discover places to stay and suggests things to do to create great travel memories in Leeward Settlement. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Rental Accommodation Types in Leeward Settlement

Type Count
Villas 218
Vacation Homes 70
Holiday Apartments 27
Cottages 10

Use these Quick Filters to Find a Vacation Rental in Leeward Settlement

★ Pro Tip: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in Leeward Settlement today.

Weather in Leeward Settlement, TC

View the weather forecast for Leeward Settlement before booking your Leeward Settlement Vacation Rentals to confirm your best time to go.

December - February
High 84°F       Low 71°F
March - May
High 86°F       Low 73°F
June - August
High 91°F       Low 80°F
September - November
High 89°F       Low 75°F

Top Attractions Around Leeward Settlement, TC

Varoom offers a large selection of top attractions around Leeward Settlement . Research things to do on your vacation before you visit Leeward Settlement.


Leeward Beach
Provo Conch Farm
Turtle Cove
Grace Bay Beach
Long Bay Beach
Sapodilla Bay
Providenciales Beaches
Pelican Beach
Taylor Bay Beach
Chalk Sound
The Regent Village Shopping Mall
Coral Gardens Reef
Salt Mills Plaza
Chalk Sound National Park
Pirate's Cove
Northwest Point National Park
Little Water Cay
Parrot Cay Beach
Three Mary Cays
The Hole

Other Places to Stay in Leeward Settlement, TC


Leeward Beach 1,102 Properties
Provo Conch Farm 948 Properties

Complexes around Leeward Settlement, TC


Checkers Leeward 4 Properties

Frequently Asked Questions About Leeward Settlement?

What are the top vacation rentals in Leeward Settlement?

We have scoured the web to find you options in Leeward Settlement. If you plan on staying near or in the Leeward Settlement area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the the Top Places to Stay in Leeward Settlement:

How many vacation rentals have private pools in Leeward Settlement?

We have found 155 places to stay that feature a private swimming pool in or near Leeward Settlement. Some of the best places to stay that feature or have access to a swimming pool are:

Which vacation homes in Leeward Settlement are best for families?

If you are looking for a place to stay that is family-friendly in Leeward Settlement, check out one of the following places as all are highly-rated options and have received excellent reviews for families or groups staying in Leeward Settlement:

How many Varoom vacation rentals are available in Leeward Settlement?

Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom in 2025 is over 366 in the Leeward Settlement area, and still growing every day. When we combine listings from multiple websites and travel providers, Varoom can provide you with a diverse amount of choice of the best places to stay in Leeward Settlement. 


People Also Ask

There are 366 Leeward Settlement, TC Vacation Rentals

Recently Booked Vacation Rentals in Leeward Settlement