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San Diego Winter Rentals & Holiday Homes

Discover winter rentals San Diego - We found 5226 exact matches

About San Diego Winter Rental on PickleTrip

Planning on a winter vacation in San Diego? Discover 5226 places to stay in San Diego, for those traveling with their family, friends, in groups, or for a wedding retreat.

At PickleTrip™, we have a wide range of listings for accommodations in San Diego, CA 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. PickleTrip™ winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

San Diego winter accommodation starts at US $582, and the most popular properties in San Diego 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, PickleTrip will make your winter trip memorable.

PickleTrip™ offers a great deal for travelers planning on renting a place in San Diego, to enjoy these benefits and to book your winter vacation homes, go to PickleTrip™ 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 San Diego and unlock even more amazing deals.

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Frequently Asked Questions About San Diego Winter Rentals

The average cost for winter rentals in San Diego is $582 per night. PickleTrip has a wide list of great winter places to stay near San Diego 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 San Diego that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in San Diego on PickleTrip

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in San Diego to find what works for you.
As of 2025, the data from PickleTrip shows that there are over 5226 private swimming pools or indoor pools accommodations near San Diego along with other great amenities.

About 5226 holiday rentals in San Diego 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 San Diego for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near San Diego with all the best amenities for your next trip.