Winter Rentals for Professionals in Florida Keys

There are a lot of options in Florida Keys. If you plan on staying in the Florida Keys 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 Keys:

• Almond Tree Inn Hotel - Adults Only
• Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
• Oceanfront Key Largo Paradise~Private Beach~Pool~Tennis~Marina~Cafe/Bar
• Summer Fun Awaits! Clean and Cozy w TOP FLOOR VIEWS.Your Home Away From Home!
• Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
• Heated Pool, Views, Vaca Cut , Gulf & Atlantic Access. Availability Nov + Dec
• Key Lime Kottage- Waterfront Home on Gulf of Mexico w/Private Pool, Dock & More
• 🌴 Coco Plum Paradise 🌴 Private Bayfront Home Pool Hot Tub Dock View
• Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
• Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

The average cost for winter rentals in Florida Keys is $632 per night. Execstays has a wide list of great winter places to stay near Florida Keys 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 Keys that allow you to bring your pet or dog:

• Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - WITH Boat Slip!
• Amsterdam's Curry Mansion Inn
• Casita de Catherine by Avantstay 1 Block to Duval St w/Hot Tub!
• Paradise Bay - 4 Bedrooms [with 2 Master Suites] & 4 Bathrooms - sleeps 10

See all pet-friendly vacation rentals in Florida Keys on Execstays

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Florida Keys to find what works for you.

As of 2026, the data from Execstays shows that there are over 8060 private swimming pools or indoor pools accommodations near Florida Keys along with other great amenities.