Key West Historic District Winter Rentals & Holiday Homes

Discover winter rentals Key West Historic District - We found 1710 exact matches

About Key West Historic District Winter Rental on SunSkiResorts

Planning a winter vacation in Key West Historic District? Discover 1710 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Key West Historic District, 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 Key West Historic District start at US $752. The most popular properties in Key West Historic District 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 Key West Historic District, 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 Key West Historic District and unlock incredible deals.

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Frequently Asked Questions About Key West Historic District Winter Rentals

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

The average cost for winter rentals in Key West Historic District is $752 per night. SunSki has a wide list of great winter places to stay near Key West Historic District 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 Key West Historic District that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Key West Historic District on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Key West Historic District to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 1710 private swimming pools or indoor pools accommodations near Key West Historic District along with other great amenities.

About 1710 holiday rentals in Key West Historic District 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 Key West Historic District for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Key West Historic District with all the best amenities for your next trip.