1. St. Barthelemy
  2. Leeward
  3. Holiday Homes

1539+ Leeward Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Leeward

Planning a trip to Leeward, BL with a group and need a place to stay? We have a selection of hotels, family resorts, and vacation rentals for small or large groups, friends, or large families. Whether you're looking for luxury or budget-friendly holiday rentals, condos, villas, or cabins in Leeward . Cabinns.com features 1539 places to stay in Leeward with the amenities guests love, like private or indoor swimming pools, hot tubs, fitness centers, large bedrooms, and more.

Cabinns.com helps large-sized groups planning to stay in Leeward find pitch-perfect premium stays, whether it’s for business trips, weddings, reunions, or multiple family getaways. Cabinns.com makes it an easy and hassle-free booking process for your next incredible travel accommodations, giving you a memorable trip with the people you love. Houses, family resorts, and villas are some of the most popular options for staying in Leeward.

Cabinns.com offers plenty of large group rental homes available in Leeward. Whether you need accommodation for a large family or group event, we have an array of holiday rentals that will meet your needs. Want to stay in or near Leeward? We have many family-friendly vacation homes available to make your next trip a spectacular group experience. So, start browsing Cabinns.com large vacation rental, resort, and hotel inventory and find the perfect home for your group. Stay Close to Nature with Cabinns.com.

Show more
Show less

Frequently Asked Questions About Leeward Holiday Rentals

There are a lot of options in Leeward. If you plan on staying in the Leeward area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Leeward:

There are many holiday rentals available in Leeward; however, here are a few of the most popular holiday homes listed in Leeward on our website:
At Cabinns.com most of our places to stay are perfect for families. Check out the complete list of holiday homes in Leeward to find one that works for you.
Yes, there are 1539 self-catering family homes and holiday rentals in Leeward.
There are more than 1539 luxury holiday homes in or near Leeward, according to 2025 data from Cabinns.com. Consider these homes for your next holiday:
Yes, there are 1539 pet friendly rentals that are available in Leeward.