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

1539+ Leeward Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Leeward

Discover more than 1539 holiday rentals in Leeward. PickleTrip™ holiday homes has everything you need to find a place to stay near Leeward, .

Whether you are looking for luxury villas in Leeward, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place with private pickleball courts or nearby facilities. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Leeward with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Leeward for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in Leeward with PickleTrip™. Stay and play pickleball when you travel.

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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 PickleTrip 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 PickleTrip. Consider these homes for your next holiday:
Yes, there are 1539 pet friendly rentals that are available in Leeward.