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643+ Windsor Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Windsor

Discover more than 643 StayAndPlay accommodations in Windsor, perfect for your golf getaway. StayAndPlay offers luxury golf resorts, private villas, and vacation rentals with everything you need for a relaxing escape near Windsor, ON.

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 Windsor? 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 Windsor pet-friendly golf accommodations and easily book your dream golf resort or villa rental in Windsor with StayAndPlay.

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Frequently Asked Questions About Windsor Holiday Rentals

There are a lot of options in Windsor. If you plan on staying in the Windsor 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 Windsor:

There are many holiday rentals available in Windsor; however, here are a few of the most popular holiday homes listed in Windsor on our website:
At StayAndPlay most of our places to stay are perfect for families. Check out the complete list of holiday homes in Windsor to find one that works for you.
Yes, there are 643 self-catering family homes and holiday rentals in Windsor.
There are more than 643 luxury holiday homes in or near Windsor, according to 2025 data from StayAndPlay. Consider these homes for your next holiday:
Yes, there are 643 pet friendly rentals that are available in Windsor.