Photo by Staci Partlo

Leeward Settlement holiday rentals

We found 1,193 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Leeward Settlement by choosing from 49 houses, 25 apartments and other holiday rentals. Whether you're staying in a holiday rental with a group or just with your pet, you'll have the amenities that you expect and more, which might include cable TV and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Book a holiday rental for your Leeward Settlement getaway

Learn about the unique charm of Leeward Settlement with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway 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 looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Leeward Settlement. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Grace Bay Beach (2.6 mi / 4.2 km)
  • Leeward Beach (1 mi / 1.6 km)
  • Long Bay Beach (1.1 mi / 1.8 km)
  • Coral Gardens Reef (4.1 mi / 6.5 km)
  • Providenciales Beaches (5.3 mi / 8.5 km)
  • Pelican Beach (5.6 mi / 8.9 km)

Transport options to and around Leeward Settlement

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

Frequently asked questions

What is the most popular type of holiday home 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. Stayz has holiday homes in a variety of sizes and shapes, so you’re sure to find the perfect fit.
How much does it cost to rent a holiday home in Leeward Settlement?
Different things determine what you’ll pay for your holiday home in Leeward Settlement, such as the season, type of property and length of stay. But, all Stayz 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 holiday home 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 Stayz by entering the dates you’ll be travelling. 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 holiday homes in Leeward Settlement?
Pack up a suitcase for your pup because Leeward Settlement has 160 holiday homes that throw open their doors to pets. Let your four-legged pal have fun with the family at one of our pet-friendly holiday homes on Stayz. 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 Stayz. Morning swim, afternoon splash or midnight soak? Free time is up to you when your Stayz holiday property has a swimming pool.
What are popular home amenities in Leeward Settlement?
When it comes to home amenities that people are looking for in Leeward Settlement, a firepit, a water view and a fireplace rank the highest. With Stayz holiday homes, 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 holiday homes in Leeward Settlement?
Leeward Settlement has 60 holiday properties that can fit 10 or more people. These properties come with enough space to share good times with your favourite people.
Are there holiday homes in Leeward Settlement that welcome kids?
With 150 family-friendly holiday 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 travelling 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 holiday homes in Leeward Settlement?
Leeward Settlement has 20 one-bedroom homes available. Often located in prime spots due to their smaller size, a one-bedroom property is great if you’re travelling 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 holiday homes in Leeward Settlement?
Gather your family and experience complete comfort and privacy in one of the 18 two-bedroom holiday properties Leeward Settlement has to offer.
Are there holiday homes with WiFi in Leeward Settlement?
You’ll find 64 holiday homes 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 Stayz.
How can I find holiday homes with air conditioning in Leeward Settlement?
Leeward Settlement has 142 holiday homes where you can kick back in air-conditioned comfort. To locate a property on Stayz that provides this amenity, enter your travel dates and use the handy filter tool to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Leeward Settlement?
You should check with the Leeward Settlement holiday home you’re considering on Stayz as the minimum age differs. However, typically it’s 16, 18 or 21.
How long can I rent a holiday home in Leeward Settlement for?
The length of time you can book a holiday home in Leeward Settlement is up to the property. Just enter your selected dates to view a list of options offering extended stays. With tons of creature comforts such as washing machines and kitchens, as well as some offering weekly or monthly discounts, you’re sure to find the perfect place to call your home away from home in Leeward Settlement.

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