Leeward vacation rentals

We found 1,549 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of 72 homes, 65 apartments, and other vacation rentals in Leeward that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a washer and dryer. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including accessible or non-smoking choices.

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Choose a vacation rental for your Leeward getaway

Experience the unique character of Leeward with a stay in a vacation home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Exploring the natural landscape of Leeward

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Leeward is a great spot to appreciate mother nature. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Flamands Beach (0.5 mi / 0.8 km)
  • Colombier Beach (1.1 mi / 1.7 km)
  • St. Jean Beach (1.1 mi / 1.8 km)
  • Lorient Beach (2.1 mi / 3.4 km)
  • Gouverneur Beach (2.5 mi / 4 km)
  • Saline Beach (2.8 mi / 4.5 km)

Transportation options to and around Leeward

The nearest airport is in Gustavia (SBH-Gustaf III), located 1 mi (1.6 km) from the city center.

Frequently asked questions

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

Villas are the most popular style of vacation rental in Leeward, according to our data. Even if you've got a different idea about what you want, Vrbo has vacation homes in loads of shapes and sizes. Filter our options to find your perfect Leeward pad.

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

Length of stay, property type and time of year are some factors that can affect the price of a vacation home. Simply enter your travel dates to find your ideal escape. From cozy chalets to expansive villas, all Vrbo vacation rentals offer amazing value.

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

When you travel and the style and size of the property will influence how much you'll pay for your beachside vacation rental. Enter your Leeward travel dates to view your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use our filters to choose the amenities and features you want in your vacation home.

What are popular rental amenities in Leeward?

A fridge, a private pool and a microwave oven are rated the most popular rental amenities in Leeward. Whether you're traveling alone, with your significant other or a group of family members, Vrbo will help you find a vacation rental that fits your style with all the conveniences you're looking for.

Are there large group vacation rentals in Leeward?

Take your pick of 104 vacation homes in Leeward that can accommodate a group of 10 or more people. Whether you're organizing a trip with the family or a special event like a birthday party, there's plenty of space to get your loved ones together under the same roof.

Can I find two-bedroom vacation rentals in Leeward?

You can select from 341 two-bedroom vacation homes in Leeward. Settle the kids into the second room or fill it with a couple of your best friends. There's plenty of space for whoever's fortunate enough to be coming along for the ride.

Are there vacation rentals with WiFi in Leeward?

There are 182 vacation rentals with WiFi in Leeward. If you want to disconnect from the world during your escape, but still need to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How old do you have to be to rent a vacation rental in Leeward?

Age restrictions can differ between properties on Vrbo, so double-check the rules of the vacation rental in Leeward you're considering. But typically, it's 16, 18 or 21.

How long can I rent a vacation rental in Leeward for?

The length of time you can book a vacation rental in Leeward is up to the property. Just enter your selected dates to display a list of options offering extended stays. With tons of features such as air conditioning and laundries, 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.

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