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
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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
House
10.0(39 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $225/Night
7 Nights - CA $1,573
Apartment
10.0(23 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
Breakfast- Parking
- Pool
CA $380/Night
7 Nights - CA $2,658
Apartment
10.0(38 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $297/Night
7 Nights - CA $2,080
House
10.0(23 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $88/Night
7 Nights - CA $615
Condo
10.0(37 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $285/Night
7 Nights - CA $1,995
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(37 Reviews)
1 Bedroom
2 Guests
Private Pool- Hot Tub
- Parking
- Pool
CA $221/Night
7 Nights - CA $1,550
House
10.0(20 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
CA $294/Night
7 Nights - CA $2,060
House
10.0(36 Reviews)
1 Bedroom
13 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $622/Night
7 Nights - CA $4,358
House
10.0(35 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $380/Night
7 Nights - CA $2,659
House
10.0(34 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $489/Night
7 Nights - CA $3,422
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
Villa
10.0(30 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $231/Night
7 Nights - CA $1,619
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
About Florida Winter Rental on Casai.ca
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 236762 accommodations for your upcoming winter getaway, whether you're dreaming of azure waters and sun-kissed beaches or charming coastal towns.
At Casai, we present a diverse array of listings for holiday homes and villas nestled in the picturesque landscapes of the Mediterranean and the Caribbean. From luxurious villas overlooking crystal-clear waters to charming holiday homes nestled amidst palm-fringed shores, our curated selection caters to every preference and ensures an unforgettable retreat.
Indulge in the epitome of luxury with our Mediterranean and Caribbean villas, boasting opulent amenities such as private pools, spacious outdoor terraces, serene gardens, and breathtaking ocean views. Whether you're seeking a romantic escape, a family adventure, or a group getaway, our listings offer the perfect blend of comfort and sophistication.
Escape the winter chill and bask in the warmth of the Mediterranean or Caribbean sun. Explore our collection of holiday homes and villas, meticulously curated to provide the ultimate sanctuary for your winter retreat. With Casai, your dream vacation awaits.
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 $448 per night. Casai 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 Casai.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 Casai.ca shows that there are over 236762 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 236762 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.
