Painters Hill Winter Rentals & Holiday Homes

Discover winter rentals Painters Hill - We found 44 exact matches

About Painters Hill Winter Rental on SunSkiResorts

Planning a winter vacation in Painters Hill? Discover 44 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Painters Hill, FL 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 Painters Hill start at US $608. The most popular properties in Painters Hill 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 Painters Hill, 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 Painters Hill and unlock incredible deals.

Show more
Show less

Frequently Asked Questions About Painters Hill Winter Rentals

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

The average cost for winter rentals in Painters Hill is $608 per night. SunSki has a wide list of great winter places to stay near Painters Hill 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 Painters Hill that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Painters Hill on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Painters Hill to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 44 private swimming pools or indoor pools accommodations near Painters Hill along with other great amenities.

About 44 holiday rentals in Painters Hill 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 Painters Hill for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Painters Hill with all the best amenities for your next trip.