Photo by Shannon Maya

Downtown Winter Garden holiday homes

We found 33 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Downtown Winter Garden to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the amenities that you need and want, including parking and a TV. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value