Winter Rentals for Professionals 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~
• 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 ⛱️
• Quaint Private Cottage in Residential Mount Dora - 1/2 mile from downtown
• 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

The average cost for winter rentals in Florida is $478 per night. Execstays 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:

• Brand New Butterfly Large Home Away
• Penthouse 7th floor with spectacular Ocean views! Immaculate, Beach Front Condo!
• Bungalow! Hot TUB! Games! 10 min to Beach!
• Oldfields Paradise

See all pet-friendly vacation rentals in Florida on Execstays

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 Execstays shows that there are over 222965 private swimming pools or indoor pools accommodations near Florida along with other great amenities.