Winston Waterways Winter Rentals & Holiday Homes

Discover winter rentals Winston Waterways - We found 441 exact matches

About Winston Waterways Winter Rental on SunSkiResorts

Planning a winter vacation in Winston Waterways? Discover 441 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Winston Waterways, 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 Winston Waterways start at US $404. The most popular properties in Winston Waterways 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 Winston Waterways, 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 Winston Waterways and unlock incredible deals.

Show more
Show less

Frequently Asked Questions About Winston Waterways Winter Rentals

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

The average cost for winter rentals in Winston Waterways is $404 per night. SunSki has a wide list of great winter places to stay near Winston Waterways 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 Winston Waterways that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Winston Waterways on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Winston Waterways to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 441 private swimming pools or indoor pools accommodations near Winston Waterways along with other great amenities.

About 441 holiday rentals in Winston Waterways 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 Winston Waterways for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Winston Waterways with all the best amenities for your next trip.