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:

• Carlisle Inn
• Almond Tree Inn Hotel - Adults Only
• ~Sea Salt Sanctuary~Plush Beach Refuge~Bikes Kayaks SUPs Fire Pit~
• Relaxing Oceanfront Condo -Seaglass Spectacular Ocean Views from every room
• HARBOR ISLAND - A GEM IN THE HISTORIC DISTRICT.
• Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
• Family Oceanfront Retreat-Private Beach~Spa~Pool View~Ground floor~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
• Beautiful Oceanfront Condo With Breathtaking Beach Views

The average cost for winter rentals in Florida is $477 per night. Ownerdirect 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:

• TOPS'L Tides III
• Quaint Private Cottage in Residential Mount Dora - 1/2 mile from downtown
• Family Condo Near Disney w Pool & Gym—Pets Welcome
• Palms Retreat! Giant Heated Pool-HotTub-FirePit-5Min2Beach-Pets-EV Chgr

See all pet-friendly vacation rentals in Florida on Ownerdirect

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 Ownerdirect shows that there are over 223788 private swimming pools or indoor pools accommodations near Florida along with other great amenities.