South San Mateo Winter Rentals & Holiday Homes

Discover winter rentals South San Mateo - We found 149 exact matches

About South San Mateo Winter Rental on SunSkiResorts

Planning a winter vacation in South San Mateo? Discover 149 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in South San Mateo, CA perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in South San Mateo start at US $246. The most popular properties in South San Mateo include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.

To book your winter vacation homes in South San Mateo, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around South San Mateo and unlock incredible deals.

Show more
Show less

Frequently Asked Questions About South San Mateo Winter Rentals

There are a lot of options in South San Mateo. If you plan on staying in the South San Mateo area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in South San Mateo:

The average cost for winter rentals in South San Mateo is $246 per night. SunSki has a wide list of great winter places to stay near South San Mateo 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 South San Mateo that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in South San Mateo on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in South San Mateo to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 149 private swimming pools or indoor pools accommodations near South San Mateo along with other great amenities.

About 149 holiday rentals in South San Mateo boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in South San Mateo for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near South San Mateo with all the best amenities for your next trip.