Florida Winter Rentals & Holiday Homes
Discover winter rentals Florida - We found 259 exact matches
About Florida Winter Rental on Cruise Vacations
Planning on a winter vacation in Florida? Discover 259 places to stay in Florida, for those traveling with their family, friends, in groups, or for a wedding retreat.
At Cruise Vacations, we have a wide range of listings for accommodations in Florida, 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. Cruise Vacations winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Florida winter accommodation starts at US $935, and the most popular properties in Florida 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, Cruise Vacations will make your winter trip memorable.
Cruise Vacations offers a great deal for travelers planning on renting a place in Florida, to enjoy these benefits and to book your winter vacation homes, go to Cruise Vacations 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 and unlock even more amazing deals.
Frequently Asked Questions About Florida Winter Rental
What are the top rated Winter Rentals in Florida?
There are a lot of options in Florida. If you plan on staying in the Florida 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:
- BAYDREAM - Peaceful! Inviting! Clean! Floating quiet getaway! Dock your boat!
- DOCK HOLIDAY - The View! Hidden Gem! Pristine! Quiet! Go fish! Dock a boat!
- Banana Boat! Moored at Private Dock on the Carrabelle River
- Floating Cottage: Roof Top Deck: Walk to Dining: Dock your Boat: Florida Keys
- 3 Level Luxury Yacht, 3 Bedrooms With 3 Baths.
- Luxury 2 stateroom Yacht FREE TIME
- Serene 3-bedroom yacht walking distance to beautiful Coconut Grove, Coral Gables
- Strictly Pleasure : Unique Yacht Stay in the Keys : Marina & Sunset Views
- Luxury Yacht on Las Olas Riverwalk, Full Resort & Spa Access, downtown Location
- Seafari Miami
How much does it cost to rent a place to stay near Florida in the wintertime?
The average cost for winter rentals in Florida is $935 per night. Cruisevacations has a wide list of great winter places to stay near Florida 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 that allow pets?
Yes, here are the top cottage/chalet rentals in Florida 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
- Sailing catamaran vacation rentals in Pensacola Beach
See all pet-friendly vacation rentals in Florida on Cruisevacations
Do you have any winter rentals in Florida 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 to find what works for you.
Are there winter accommodations in Florida that have indoor swimming pools?
As of 2026, the data from Cruisevacations shows that there are over 259 private swimming pools or indoor pools accommodations near Florida along with other great amenities.
