Photo by Staci Partlo

Leeward Settlement vacation rentals

We found 1,128 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 59 homes, 159 villas, and vacation rentals in Leeward Settlement that are perfect for your trip. Whether you're staying in a vacation rental with family or friends, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. You're sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
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  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Book a vacation rental for your Leeward Settlement getaway

Learn about the unique charm of Leeward Settlement with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Exploring the natural features in Leeward Settlement

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Leeward Settlement is a great spot to appreciate mother nature. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Leeward Beach (1 mi / 1.6 km)
  • Long Bay Beach (1.1 mi / 1.8 km)
  • Grace Bay Beach (2.6 mi / 4.2 km)
  • Providenciales Beaches (4.7 mi / 7.6 km)
  • Pelican Beach (5.6 mi / 8.9 km)
  • Sapodilla Bay (10.1 mi / 16.3 km)

Transportation options to and around Leeward Settlement

Fly into Providenciales Intl. Airport (PLS), the closest airport, located 8.3 mi (13.4 km) from the city center.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Leeward Settlement?

Based on our research, villas are the most desirable property type in Leeward Settlement. But of course, everyone's idea of an awesome trip can vary. Vrbo has vacation rentals in a variety of sizes and shapes, so you're sure to find the perfect fit.

How much does it cost to rent a vacation rental in Leeward Settlement?

Different things determine what you'll pay for your vacation rental in Leeward Settlement, such as the season, type of property and length of stay. But, all Vrbo homes have one thing in common — amazing value. Just add your travel dates to find your home away from home.

How much does it cost to rent a beach house in Leeward Settlement?

The average price for a vacation rental near the beach in Leeward Settlement will depend on when you're going and the style and size of property you want. You can easily find prices on Vrbo by entering the dates you'll be traveling. Then use the filter tool to choose the number of bedrooms and amenities that you need, like a pool, WiFi and air conditioning.

Are there pet-friendly vacation rentals in Leeward Settlement?

Pack up a suitcase for your pup because Leeward Settlement has 160 vacation homes that throw open their doors to pets. Let your four-legged pal have fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check our "Pets allowed" filter box.

Can I rent a house with a pool in Leeward Settlement?

Mark the "pool" box in our handy filter tool and choose from 124 houses with private pools in Leeward Settlement on Vrbo. Morning swim, afternoon splash or midnight soak? Free time is up to you when your Vrbo vacation property has a swimming pool.

What are popular rental amenities in Leeward Settlement?

When it comes to rental amenities that people are looking for in Leeward Settlement, a firepit, a water view and a fireplace rank the highest. With Vrbo vacation rentals, there are options to suit your style and taste, whether you're taking a trip with your partner, your friends or even pets.

Are there large group vacation rentals in Leeward Settlement?

Leeward Settlement has 60 vacation properties that can fit 10 or more people. These properties come with enough space to share good times with your favorite people.

Are there vacation rentals in Leeward Settlement that welcome kids?

With 150 family-friendly vacation homes to pick from in Leeward Settlement, now is a superb time to introduce your children to the thrills of travel. Check our "Properties good for families" filter box to browse stays loaded with amenities ideal for traveling families, like multiple bedrooms, backyards, entertainment areas and bunk beds.

What are the top attractions for families in Leeward Settlement?

Keep the kids busy at these awesome family-friendly attractions in Leeward Settlement:

  • Grace Bay Beach
  • Turtle Cove
  • Providenciales Beaches

Are there one-bedroom vacation rentals in Leeward Settlement?

Leeward Settlement has 20 one-bedroom rentals available. Often located in prime spots due to their smaller size, a one-bedroom property is great if you're traveling with a buddy or your partner. And with plenty of home comforts like laundry facilities and more privacy than a standard hotel, you'll be able to kick back while enjoying this fabulous destination.

Can I find two-bedroom vacation rentals in Leeward Settlement?

Gather your family and experience complete comfort and privacy in one of the 18 two-bedroom vacation properties Leeward Settlement has to offer.

Are there vacation rentals with WiFi in Leeward Settlement?

You'll find 64 vacation rentals with WiFi in Leeward Settlement. If you'd like to disconnect from daily life on your trip, but still want to be connected to the internet, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

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