363+ Vacation Rentals & Holiday Homes in Leeward Settlement |
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Leeward Settlement Accommodations - Hotels & Rentals

About Leeward Settlement Vacation Rentals

Discover More than 363 Incredible Getaway Rentals Available in Leeward Settlement. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Leeward Settlement.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Leeward Settlement, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Leeward Settlement. The Average Size of Places to Stay Near Leeward Settlement is 3577.2 ft², with Prices Averaging US $3,335 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Leeward Settlement. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Leeward Settlement

Type Count
Villas 216
Vacation Homes 71
Holiday Apartments 25
Cottages 10

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

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Leeward Settlement with Online Reservations.

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 SettlementGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World Leeward SettlementGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


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 & Vacation Rentals in these Cities and Neighborhoods


Leeward Beach 1,102 Properties
Provo Conch Farm 948 Properties

Frequently Asked Questions About Leeward Settlement?

What are the top hotels, lake houses & vacation rentals 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 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 Hotels & Vacation Rentals have private pools in Leeward Settlement?

We have 159 Hotels & Vacation 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 hotel, lake house, or vacation rental in Leeward Settlement is best for families?

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

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

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 363 in the Leeward Settlement area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Leeward Settlement.


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