Winter Garden Winter Rentals & Holiday Homes

Discover winter rentals Winter Garden - We found 342 exact matches

About Winter Garden Winter Rental on SunSkiResorts

Planning a winter vacation in Winter Garden? Discover 342 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Winter Garden perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in Winter Garden start at US $210. The most popular properties in Winter Garden include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.

To book your winter vacation homes in Winter Garden, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around Winter Garden and unlock incredible deals.

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Frequently Asked Questions About Winter Garden Winter Rentals

There are a lot of options in Winter Garden. If you plan on staying in the Winter Garden area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Winter Garden:

The average cost for winter rentals in Winter Garden is $210 per night. SunSki has a wide list of great winter places to stay near Winter Garden that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Winter Garden that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Winter Garden on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Winter Garden to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 342 private swimming pools or indoor pools accommodations near Winter Garden along with other great amenities.

About 342 holiday rentals in Winter Garden boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Winter Garden for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Winter Garden with all the best amenities for your next trip.