Upper Sugarloaf Key Winter Rentals & Holiday Homes

Discover winter rentals Upper Sugarloaf Key - We found 101 exact matches

About Upper Sugarloaf Key Winter Rental on SunSkiResorts

Planning a winter vacation in Upper Sugarloaf Key? Discover 101 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Upper Sugarloaf Key, 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 Upper Sugarloaf Key start at US $546. The most popular properties in Upper Sugarloaf Key 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 Upper Sugarloaf Key, 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 Upper Sugarloaf Key and unlock incredible deals.

Show more
Show less

Frequently Asked Questions About Upper Sugarloaf Key Winter Rentals

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

The average cost for winter rentals in Upper Sugarloaf Key is $546 per night. SunSki has a wide list of great winter places to stay near Upper Sugarloaf Key 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 Upper Sugarloaf Key that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Upper Sugarloaf Key on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Upper Sugarloaf Key to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 101 private swimming pools or indoor pools accommodations near Upper Sugarloaf Key along with other great amenities.

About 101 holiday rentals in Upper Sugarloaf Key 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 Upper Sugarloaf Key for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Upper Sugarloaf Key with all the best amenities for your next trip.