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Surfside Winter Rentals & Holiday Homes

Discover winter rentals Surfside - We found 51 exact matches

About Surfside Winter Rental on Surfside Vacation Rental

Planning on a winter vacation in Surfside? Discover 51 places to stay in Surfside, for those traveling with their family, friends, in groups, or for a wedding retreat.

At Surfside Vacation Rental, we have a wide range of listings for accommodations in Surfside, FL that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. Surfside Vacation Rental winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Surfside winter accommodation starts at US $480, and the most popular properties in Surfside are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, Surfside Vacation Rental will make your winter trip memorable.

Surfside Vacation Rental offers a great deal for travelers planning on renting a place in Surfside, to enjoy these benefits and to book your winter vacation homes, go to Surfside Vacation Rental filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Surfside and unlock even more amazing deals.

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:

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 $480 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.

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.