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Leeward Settlement Hotels, Resorts, and Rentals

About Leeward Settlement Vacation Rentals

There are more than 363 places to stay in Leeward Settlement that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Leeward Settlement.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Leeward Settlement, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Leeward Settlement. Places to stay near Leeward Settlement are 3669.09 ft² on average, with prices averaging US $3,335 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Leeward Settlement with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Leeward Settlement

Type Count
Villas 215
Vacation Homes 71
Holiday Apartments 26
Cottages 10
B&B 3
Unique Vacation Rentals 2

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

★ Pro Tip: Hotala has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Leeward Settlement.

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

Stay Near Leeward Settlement's Top Attractions

Hotala can help you find hotels, resorts, and rentals near many of Leeward Settlement's top attractions, neighborhoods, and points of interest.


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

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


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 hotels or resorts in Leeward Settlement?

You have a lot of choices in or near Leeward Settlement. If you need a hotel in the Leeward Settlement area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Leeward Settlement:

How many vacation rentals have private pools in Leeward Settlement?

There are 181 accommodation options with private pools in or near Leeward Settlement. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

How many hotels, resorts, or rentals are available in Leeward Settlement?

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 363 in the Leeward Settlement area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Leeward Settlement.


People Also Ask

Hotels in Leeward Settlement 16 resorts, and 312 rentals

Recently Booked Hotels, Resorts, or Rentals in Leeward Settlement