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Pinellas County Winter Rentals & Holiday Homes

Discover winter rentals Pinellas County - We found 10925 exact matches

About Pinellas County Winter Rental on SunSkiResorts

Planning a winter vacation in Pinellas County? Discover 10925 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Pinellas County, 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 Pinellas County start at US $401. The most popular properties in Pinellas County 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 Pinellas County, 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 Pinellas County and unlock incredible deals.

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Frequently Asked Questions About Pinellas County Winter Rentals

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

The average cost for winter rentals in Pinellas County is $401 per night. SunSki has a wide list of great winter places to stay near Pinellas County 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 Pinellas County that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Pinellas County on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Pinellas County to find what works for you.
As of 2026, the data from SunSkiResorts shows that there are over 10925 private swimming pools or indoor pools accommodations near Pinellas County along with other great amenities.

About 10925 holiday rentals in Pinellas County 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 Pinellas County for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Pinellas County with all the best amenities for your next trip.