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:

• 𝔾𝕦𝕝𝕗𝔽𝕣𝕠𝕟𝕥 Emerald Isle- "My Blue Heaven" 5-Star Reviews/Walk to All
• BEACHFRONT - 250+ 5 star reviews - Remodeled - Tiki Bar - 3 Pools - 2 Hot Tubs
• 4th Newest Beachfront Condo! 100% No Smoking
• 𝔾𝕦𝕝𝕗𝔽𝕣𝕠𝕟𝕥 𝑬𝒎𝒆𝒓𝒂𝒍𝒅 𝑰𝒔𝒍𝒆 9th Floor Stocked & Stellar Reviews!
• OceanFRONT LUXE Sleep with the waves Artist owned 9th FL breathtaking pano views
• SANDCASTLES OCEAN VIEW TOP FLOOR.DATES AVAILABLE (check Reviews)
• Luxury Beach Front- Top Floor Balcony Panoramic Gulf Views
• Regal Palms – Lazy River – Water Slide – Disney - Free Wifi - Baby Crib + FUN!
• Artist owned 7th floor paradise! DIRECT Oceanfront! Meet an Octopus! 🐙
• 20th floor 2nd Tower Views of both the Gulf & the Sound East Facing Highrise

The average cost for winter rentals in Florida is $442 per night. Unpluggedweekend 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
• Palms Retreat! Giant Heated Pool-HotTub-FirePit-5Min2Beach-Pets-EV Chgr
• Miami Highline- Sauna, Heated Pool, Cabanas
• BEAUTIFUL CONDO!PREMIER HOST! 5 STAR REVIEWS!GREAT PRICES/LOCATION FREEWIFI/PARK

See all pet-friendly vacation rentals in Florida on Unpluggedweekend

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 Unpluggedweekend shows that there are over 23601 private swimming pools or indoor pools accommodations near Florida along with other great amenities.