PADDLE! the Florida Keys Winter Rentals & Holiday Homes

Discover winter rentals PADDLE! the Florida Keys - We found 759 exact matches

About PADDLE! the Florida Keys Winter Rental on SunSkiResorts

Planning a winter vacation in PADDLE! the Florida Keys? Discover 759 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in PADDLE! the Florida Keys, 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 PADDLE! the Florida Keys start at US $429. The most popular properties in PADDLE! the Florida Keys 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 PADDLE! the Florida Keys, 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 PADDLE! the Florida Keys and unlock incredible deals.

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Frequently Asked Questions About PADDLE! the Florida Keys Winter Rentals

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

The average cost for winter rentals in PADDLE! the Florida Keys is $429 per night. SunSki has a wide list of great winter places to stay near PADDLE! the Florida Keys 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 PADDLE! the Florida Keys that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in PADDLE! the Florida Keys on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in PADDLE! the Florida Keys to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 759 private swimming pools or indoor pools accommodations near PADDLE! the Florida Keys along with other great amenities.

About 759 holiday rentals in PADDLE! the Florida Keys 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 PADDLE! the Florida Keys for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near PADDLE! the Florida Keys with all the best amenities for your next trip.