Florida Keys Winter Rentals & Holiday Homes
Discover winter rentals Florida Keys - We found 111 exact matches
About Florida Keys Winter Rental on Sell Off Cruises
Planning on a winter vacation in Florida Keys? Discover 111 places to stay in Florida Keys, for those traveling with their family, friends, in groups, or for a wedding retreat.
At Sell Off Cruises, we have a wide range of listings for accommodations in Florida Keys, FL that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. Sell Off Cruises winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Florida Keys winter accommodation starts at US $791, and the most popular properties in Florida Keys are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, Sell Off Cruises will make your winter trip memorable.
Sell Off Cruises offers a great deal for travelers planning on renting a place in Florida Keys, to enjoy these benefits and to book your winter vacation homes, go to Sell Off Cruises filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Florida Keys and unlock even more amazing deals.
Frequently Asked Questions About Florida Keys Winter Rental
What are the top rated Winter Rentals in Florida Keys?
There are a lot of options in Florida Keys. If you plan on staying in 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 Florida Keys:
- Floating Cottage: Roof Top Deck: Walk to Dining: Dock your Boat: Florida Keys
- Luxury 2 stateroom Yacht FREE TIME
- Strictly Pleasure : Unique Yacht Stay in the Keys : Marina & Sunset Views
- Antique trawler 2-bedroom boat in phenomenal Key West
- Eddie Griffiths Overnight Charters and Vacation Rentals!
- Island Sanctuary Islamorada
- 5 Cabin Catamaran Sailboat "Devine Sailing" at The Perry Hotel Marina & Resort
- SeaLab: 6 Cabin/6 Head 52 ft Catamaran with Hotel Pools and a Captains Lounge
- “ The Ultimate redneck” boat experience
- Accommodates 8 Guests 50% Discount! 3 bedroom boat with AC in amazing Key West
How much does it cost to rent a place to stay near Florida Keys in the wintertime?
The average cost for winter rentals in Florida Keys is $791 per night. Selloffcruises has a wide list of great winter places to stay near Florida Keys that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Florida Keys that allow pets?
Yes, here are the top cottage/chalet rentals in Florida Keys that allow you to bring your pet or dog:
- Florida Keys Houseboat - Rooftop Deck, Luxury & Adventure - Walk to Dining & Fun
- Waterfront Boat Stay & Resort Amenities
- Mangrove Marina and Resort Aqualodge Houseboats
- Living the Dream Key West Style
See all pet-friendly vacation rentals in Florida Keys on Selloffcruises
Do you have any winter rentals in Florida Keys that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Florida Keys to find what works for you.
Are there winter accommodations in Florida Keys that have indoor swimming pools?
As of 2026, the data from Selloffcruises shows that there are over 111 private swimming pools or indoor pools accommodations near Florida Keys along with other great amenities.
