San Diego Winter Rentals & Holiday Homes

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

• Spacious Beach Studio
• The Seagull House - Steps away from Sail Bay - A/C - Ample Parking!
• Right On The Beach! Exquisitely Remodeled 3BR/3BA . Perfect For Families.
• Beautiful N. Mission Beach house, AC, Steps to the Ocean and bay, 250+ 5star
• Storybook Beach House 2 blocks from the Beach or Mission Bay with Pool & Hot tub
• Your Luxury Condo On The Ocean, Unobstructed Sunset And Ocean Views, Central Air
• Find your beach bliss!
• Adorable 1 bd cottage, heart of Old Town- WE LOVE PETS! Insta @oldtownvacay
• Perfect Location to Beach/SD Attractions, Parking, Beach Chairs, Boogie Boards!
• Right On The Beach! Exquisitely Remodeled 2BR/2BA . Perfect For Families.

The average cost for winter rentals in San Diego is $616 per night. Thiscityknows 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:

• Romantic Guest House, Spectacular Views, Close to everything , Private Hot Tub
• Homey Modern 2BR-15min to Gaslamp, SeaWorld, Beach
• Modern 4BR Haven with Fire Pit and Spacious Yard
• Ocean Views - SEAGIRT RETREAT- 4 BD/4 BTH - Air Conditioning - Family Getaway

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

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 2026, the data from Thiscityknows shows that there are over 6098 private swimming pools or indoor pools accommodations near San Diego along with other great amenities.