Florida Winter Rentals & Holiday Homes

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:

• Amazing villa close to Disney with 5* Reviews
• Conservation View - Hot Tub - Free Pool Heat - Very Private
• Our DisneyDreamVilla - minutes to DisneyWorld!
• BEST HOUSE! StarWars Theater, HarryPotter, Princess, Pirates! Disney 8-10 min!
• Mickeys Magical Villa Disney Five Star Pool Villa Home at Windsor Hills
• Magical Getaway - 4BR/3BA with Pool/Spa, Wifi, Games Room
• Beautiful 6 Bedroom Home, 6 Miles from Disney World, South Facing Pool
• Adventure Villa - WOW Pool & SPA - All Vacation Themed + Beauty & Beast Dining
• 1 BEDROOM 2 BATHROOM GOLF VILLAnEDGEWATER BEACH RESORT
• Stunning 3BR 2BA 1700 sq ft Penthouse Villa - Fully Upgraded, Fantastic Location

The average cost for winter rentals in Florida is $577 per night. Luxurysicilyvilla 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.

Yes, here are the top cottage/chalet rentals in Florida that allow you to bring your pet or dog:

• 4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192
• Florida Celebrity Millionaire Mansion
• Dreams Come True
• NEW - Luxury decorated villa with amazing view, private pool and spa

See all pet-friendly vacation rentals in Florida on Luxurysicilyvilla

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.

As of 2026, the data from Luxurysicilyvilla shows that there are over 13610 private swimming pools or indoor pools accommodations near Florida along with other great amenities.