1. Jamaica
  2. Trelawny
  3. Windsor
  4. Holiday Homes

448+ Windsor Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Windsor

Planning a trip to Windsor, JM 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 Windsor . Online Reservations features 448 places to stay in Windsor with the amenities guests love, like private or indoor swimming pools, hot tubs, fitness centers, large bedrooms, and more.

Online Reservations helps large-sized groups planning to stay in Windsor find pitch-perfect premium stays, whether it’s for business trips, weddings, reunions, or multiple family getaways. Online Reservations 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 Windsor.

Online Reservations offers plenty of large group rental homes available in Windsor. 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 Windsor? We have many family-friendly vacation homes available to make your next trip a spectacular group experience. So, start browsing Online Reservations large vacation rental, resort, and hotel inventory and find the perfect home for your group.Plan Your Perfect Escape with Online Reservations.

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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 Online Reservations 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 448 self-catering family homes and holiday rentals in Windsor.
There are more than 448 luxury holiday homes in or near Windsor, according to 2025 data from Online Reservations. Consider these homes for your next holiday:
Yes, there are 448 pet friendly rentals that are available in Windsor.