361+ Private Villas and Holiday Rentals in Leeward Settlement |
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Leeward Settlement Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Leeward Settlement

Discover more than 361 vacation rentals available in Leeward Settlement. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Leeward Settlement.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Leeward Settlement, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Leeward Settlement. On average, places to stay near Leeward Settlement offer 3616.24 ft², with nightly prices averaging $3,317.

With Casai, finding and comparing holiday rentals in Leeward Settlement is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Leeward Settlement

Type Count
Villas 217
Vacation Homes 69
Holiday Apartments 24
Cottages 10

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

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation 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

Top Attractions Around Leeward Settlement, TC

Casai 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

Frequently Asked Questions About Leeward Settlement?

What are the top holiday rentals in Leeward Settlement?

With numerous options available in Leeward Settlement, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Leeward Settlement:

How many holiday rentals have private pools in Leeward Settlement?

Discover a selection of holiday rentals with private pools near Leeward Settlement with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Leeward Settlement are best for families?

If you're searching for a family-friendly holiday home in Leeward Settlement, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Leeward Settlement:

How many Casai.com holiday rentals are available in Leeward Settlement?

As of 2025, Casai boasts over 361 properties listed in the Leeward Settlement area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Leeward Settlement.


People Also Ask

There are 361 Leeward Settlement, TC Holiday Rentals

Recently Booked Holiday Rentals in Leeward Settlement