Discover winter rentals Florida - We found 213425 exact matches
About Florida Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Florida, FL perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in Florida. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Florida and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Florida Winter Rentals
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:
- Carlisle Inn
- Almond Tree Inn Hotel - Adults Only
- ~Sea Salt Sanctuary~Plush Beach Refuge~Bikes Kayaks SUPs Fire Pit~
- HARBOR ISLAND - A GEM IN THE HISTORIC DISTRICT.
- Family friendly summer fun 🦀 sleep 6 in beds ☀️heated pool & hot tub ⛱️ beach gear
- Casa Dolphina: 6BR Waterfront Mini-Resort—Pool & Spa, Sunsets, Dock, St. Pete FL
- Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
- Tranquil Waterfront Cottage. 1 Bedroom, 1 Bathroom. Sleeps 2
- Across The Street From #1 Beach
- Penthouse 7th floor with spectacular Ocean views! Immaculate, Beach Front Condo!
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 $454 per night. Vacation Cottage 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:
- Quaint Private Cottage in Residential Mount Dora - 1/2 mile from downtown
- Palms Retreat! Giant Heated Pool-HotTub-FirePit-5Min2Beach-Pets-EV Chgr
- Relaxing Cozy Beach Condo + Hot Tub ~ Maravilla 4109
- Tahiti Style 5 STAR OVER-WATER BUNGALOW + Lake House Blue + YouTube Video's PETS
See all pet-friendly vacation rentals in Florida on Vacation Cottage
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 Vacation Cottage shows that there are over 213425 private swimming pools or indoor pools accommodations near Florida along with other great amenities.
Do any winter holiday rentals in Florida have hot tubs?
About 213425 holiday rentals in Florida boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Florida?
Yes, there are many luxury places to stay in Florida for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Florida with all the best amenities for your next trip.
