House
10.0(45 Reviews)
2 Bedrooms
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
CA $237/Night
7 Nights - CA $1,657
Florida, US Winter Rentals & Holiday Homes
Discover winter rentals Florida - We found 237414 exact matches
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Compare Winter Rental in Florida
10.0
House
10.0(60 Reviews)
3 Bedrooms
8 Guests
Hot Tub- Parking
- Balcony/Terrace
View
CA $496/Night
7 Nights - CA $3,469
Condo
9.4(97 Reviews)
1 Bedroom
2 Guests
- Hot Tub
Pool
Ocean View- Balcony/Terrace
CA $417/Night
7 Nights - CA $2,916
House
10.0(40 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
CA $375/Night
7 Nights - CA $2,623
Apartment
10.0(45 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
EV Charge Station- Parking
- Pool
CA $232/Night
7 Nights - CA $1,628
Apartment
10.0(38 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $297/Night
7 Nights - CA $2,080
Apartment
10.0(23 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
Breakfast- Parking
- Pool
CA $380/Night
7 Nights - CA $2,658
Condo
10.0(37 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $285/Night
7 Nights - CA $1,995
House
10.0(23 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $88/Night
7 Nights - CA $615
House
10.0(35 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $380/Night
7 Nights - CA $2,659
Apartment
10.0(20 Reviews)
1 Bedroom
16 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $126/Night
7 Nights - CA $880
House
10.0(34 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $489/Night
7 Nights - CA $3,422
House
10.0(20 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
CA $294/Night
7 Nights - CA $2,060
Cottage
10.0(34 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
CA $254/Night
7 Nights - CA $1,780
Apartment
10.0(33 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $342/Night
7 Nights - CA $2,398
Apartment
10.0(32 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $381/Night
7 Nights - CA $2,670
Cottage
10.0(28 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
CA $480/Night
7 Nights - CA $3,359
House
10.0(28 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $304/Night
7 Nights - CA $2,131
Condo
10.0(27 Reviews)
1 Bedroom
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $445/Night
7 Nights - CA $3,116
Apartment
10.0(27 Reviews)
1 Bedroom
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $390/Night
7 Nights - CA $2,727
House
10.0(26 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
CA $369/Night
7 Nights - CA $2,585
House
10.0(26 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $274/Night
7 Nights - CA $1,920
Apartment
10.0(25 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $390/Night
7 Nights - CA $2,733
Condo
10.0(24 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
CA $231/Night
7 Nights - CA $1,619
About Florida Winter Rental on BedroomVillas.ca
At BedroomVillas, we feature a wide range of listings for accommodations in Florida, FL that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that travelers are sure to love. BedroomVillas winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you are escaping the snow or running to it, BedroomVillas helps connect you to the best cabins, bungalows, lodges, and villas, as well as the best places to stay in both sun and ski resorts. BedroomVillas will make your winter getaway an unforgettable experience.
BedroomVillas offers luxury finds for travelers planning on renting a place in Florida, to enjoy these benefits and to book your winter vacation homes, go to the BedroomVillas filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around Florida and unlock even more amazing deals. Relax with BedroomVillas.
Winter Rental: Explore Top Destinations
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:
- ~Sea Salt Sanctuary~Plush Beach Refuge~Bikes Kayaks SUPs Fire Pit~
- Quaint Private Cottage in Residential Mount Dora - 1/2 mile from downtown
- Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
- Beautiful Oceanfront Condo With Breathtaking Beach Views , 3RD floor, C117
- Immaculate Oceanfront on 7th floor See Description for renovation information.
- Across The Street From #1 Beach
- Little House on the River - on main river not canal,includes kayaks,paddle-board
- 4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192
- Seagrove Oasis — Dolphin Spot
- 115 p/nt Sun-Thur 'til end of Nov! Tax/fees extra. Phenomenal ratings! CLEAN!
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 $449 per night. BedroomVillas.ca 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:
- Bungalow on quiet street close to trendy cafes, pubs, and parks. Dogs welcome!
- Ambers Jensen Beachhouse with Hot Tub
- Cozy Coastal Studio | Near Pool & Beach
- Sunset Cove In the Village of St. John
See all pet-friendly vacation rentals in Florida on BedroomVillas.ca
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 BedroomVillas.ca shows that there are over 237414 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 237414 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.
