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

1530+ Leeward Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Leeward

Discover more than 1530 StayAndPlay accommodations in Leeward, perfect for your golf getaway. StayAndPlay offers luxury golf resorts, private villas, and vacation rentals with everything you need for a relaxing escape near Leeward, .

Whether you're seeking upscale golf-front resorts, private luxury villas, spacious vacation homes, or family-friendly golf retreats, we can help you find the ideal stay. Our rentals feature top-tier amenities such as private pools, fully equipped kitchens, outdoor patios, hot tubs, and Wi-Fi, ensuring your group enjoys a comfortable and memorable stay.

Planning a group golf trip to Leeward? StayAndPlay guarantees a unique and unforgettable experience with plenty of options for families, large groups, or private rentals for long or short stays. Explore our Leeward pet-friendly golf accommodations and easily book your dream golf resort or villa rental in Leeward with StayAndPlay.

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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 StayAndPlay 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 1530 self-catering family homes and holiday rentals in Leeward.
There are more than 1530 luxury holiday homes in or near Leeward, according to 2025 data from StayAndPlay. Consider these homes for your next holiday:
Yes, there are 1530 pet friendly rentals that are available in Leeward.