Waterside Village Winter Rentals & Holiday Homes

Discover winter rentals Waterside Village - We found 310 exact matches

About Waterside Village Winter Rental on SunSkiResorts

Planning a winter vacation in Waterside Village? Discover 310 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Waterside Village, 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 Waterside Village start at US $391. The most popular properties in Waterside Village 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 Waterside Village, 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 Waterside Village and unlock incredible deals.

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Frequently Asked Questions About Waterside Village Winter Rentals

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

The average cost for winter rentals in Waterside Village is $391 per night. SunSki has a wide list of great winter places to stay near Waterside Village 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 Waterside Village that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Waterside Village on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Waterside Village to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 310 private swimming pools or indoor pools accommodations near Waterside Village along with other great amenities.

About 310 holiday rentals in Waterside Village 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 Waterside Village for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Waterside Village with all the best amenities for your next trip.