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 where pets are allowed? We have a selection of dog-friendly 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. PetFriendly features 448 places to stay in Windsor with the amenities that guests like, such as private or indoor swimming pools, hot tubs, fitness center, large bedrooms, and more.

In addition to helping you plan things to do and places to stay, PetFriendly welcomes large-sized groups planning to stay in Windsor, whether it’s for business trips, weddings, reunions, or multiple family getaways. PetFriendly makes it an easy and hassle-free booking for your next trip accommodation, giving you a memorable trip with your group. Houses, family resorts, and villas are the most popular options for staying in Windsor.

PetFriendly offers plenty of large group rental homes available in Windsor. Whether you're needing accommodation for a large family or a large group event, we have many holiday rentals that accept pets 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 enjoyable & spectacular. So, start searching PetFriendly's large vacation rental, resort, and hotel inventory and find the perfect home for your group. Bring the whole family with PetFriendly.

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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 PetFriendly 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 PetFriendly. Consider these homes for your next holiday:
Yes, there are 448 pet friendly rentals that are available in Windsor.