Surfside Winter Rentals & Holiday Homes
Discover winter rentals Surfside - We found 51 exact matches
When do you want to travel?
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Frequently Asked Questions About Surfside Winter Rental
What are the top rated Winter Rentals in Surfside?
There are a lot of options in Surfside. If you plan on staying in the Surfside area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Surfside:
- Grand Beach Hotel Surfside West
- Grand Beach Hotel Surfside
- Surfside Retreat: 1BR Work-From-Home Oasis
- Alluring Solara Surfside, 2 Bedroom Oceanfront Resort
- Beautiful 1 bedroom unit at resort, sleeps 4
- Beautiful studio unit at resort, sleeps 2
- Beautiful studio unit at resort, sleeps 2
- 4 Cozy Studios in Surfside | Walk to Beach, Shops, and Restaurants
- Steps from Ocean, Dining & Shopping – Breakfast & Outdoor Pool - 4 Unit
- Walk to Surfside Beach from This Well-Appointed Suites w/Kitchenette - 3 Units
How much does it cost to rent a place to stay near Surfside in the wintertime?
The average cost for winter rentals in Surfside is $490 per night. Surfsidevacationrental has a wide list of great winter places to stay near Surfside that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Surfside that allow pets?
Yes, here are the top cottage/chalet rentals in Surfside that allow you to bring your pet or dog:
- Spectacular Oceanfront Views in Miami's Safest Beachfront Community
- Sun Harbour Boutique Hotel
- Sun Harbour Boutique Hotel
- Luxury Home Walk to Beach Near Miami Beach Family Friendly
See all pet-friendly vacation rentals in Surfside on Surfsidevacationrental
Do you have any winter rentals in Surfside that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Surfside to find what works for you.
Are there winter accommodations in Surfside that have indoor swimming pools?
As of 2026, the data from Surfsidevacationrental shows that there are over 51 private swimming pools or indoor pools accommodations near Surfside along with other great amenities.
