362+ Luxury Vacation Rentals & Cabins in Leeward Settlement |
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Leeward Settlement Cabin Rentals

About Leeward Settlement Vacation Rentals

There are more than 362 incredible getaway rentals that are available in Leeward Settlement. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.ca and uncover great stays in Leeward Settlement.

Cabinns.ca features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. 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 Cabinns.ca in Leeward Settlement, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.ca vacation rentals, resorts, and Airbnb-style properties in Leeward Settlement. Places to stay near Leeward Settlement are 3578.4 ft² on average, with prices averaging CA $4,569 a night.

Cabinns.ca helps you find the ideal holiday rental to create a lifetime of travel memories in Leeward Settlement. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Leeward Settlement

Type Count
Villas 215
Vacation Homes 71
Holiday Apartments 25
Cottages 10
B&B 3
Unique Vacation Rentals 2

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

★ Pro Tip: Cabinns.ca is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Leeward Settlement with Cabinns.ca.

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

Activities Leeward Settlement Guest Reviews Local Attractions

A Large Selection of Cabins and Vacation Rentals from Around the World Leeward Settlement. Discover Top Attractions For Your Next Outdoor Adventure.


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 Nearby Cabin Rentals 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 cabins, lake houses & summer homes in Leeward Settlement?

We provide an array of great vacation destinations in Leeward Settlement. If you are looking to stay in or around the Leeward Settlement area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Leeward Settlement:

How many cabin rentals and resorts have private pools in Leeward Settlement?

We have 151 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Leeward Settlement. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Leeward Settlement is best for families?

Searching for a family-friendly cabin in Leeward Settlement? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

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

Cabinns.ca offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.ca in 2025 is over 362 in the Leeward Settlement area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.ca can provide you with a diverse amount of choices of the best luxury stays in Leeward Settlement.


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Cabins in Leeward Settlement 16 resorts, and 311 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Leeward Settlement