Book Luxury Winter Rentals in San Diego

We selected the 81 homes worth renting in this location

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Age 1 to 12

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Home spotlights in San Diego

California Coastal Retreat

California Coastal Retreat

  • 4 guests

  • 2 bedrooms

Solana Beach, San Diego County

If you’re in search of a blissful beachside escape, this apartment delivers a refreshing solution. Nestled on the picturesque cliffs of Solana Beach, you’ll have direct access to the shoreline as well as a community swimming pool, hot tub and sauna.

Ocean Roar

Ocean Roar

  • 7 guests

  • 3 bedrooms

Beach Barber Tract, San Diego

With ocean views from almost every room, this La Jolla home is something really special. The sound of the ocean sets the scene, rocking you to sleep each night and soothing you throughout your stay.

Blue Star

Blue Star

  • 8 guests

  • 5 bedrooms

Palacio Del Mar, San Diego

Located within the Palacio del Mar gated community, you’ll be able to live the country club dream at this home. Whether you choose to play a game of tennis on the courts, shoot some hoops or train in the fitness centre, it’ll be easy to keep in shape while staying here.

Sunny San Diego

Sunny San Diego

  • 8 guests

  • 3 bedrooms

Mountain View, San Diego

Perfect for getaways with friends, this Spanish-style home can be found in San Diego’s Mountain View neighbourhood. It’s close to the action, seven minutes from Downtown, and with Balboa Park eight minutes away.


We selected the top 3% holiday homes in San Diego Vacation Rentals for Winter

Explore the 81 most perfect homes in our collection

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Most popular homes in San Diego

Pacific Tranquillity

Pacific Tranquillity

  • 11 guests

  • 4 bedrooms

Sherman Heights, San Diego

The Ocean's Calling

The Ocean's Calling

  • 4 guests

  • 2 bedrooms

Sunset Cliffs, San Diego

Modern Retro

Modern Retro

  • 8 guests

  • 3 bedrooms

Hillcrest, San Diego

Hummingbird Dawn

Hummingbird Dawn

  • 8 guests

  • 5 bedrooms

Encinitas, San Diego County

Pacific Spirit

Pacific Spirit

  • 12 guests

  • 6 bedrooms

Lower Hermosa, San Diego

Fuschia Palms

Fuschia Palms

  • 9 guests

  • 4 bedrooms

La Jolla Shores, San Diego

Saltwater Breeze

Saltwater Breeze

  • 9 guests

  • 4 bedrooms

Pacific Beach, San Diego

Mellow Breeze

Mellow Breeze

  • 8 guests

  • 3 bedrooms

Pacific Beach, San Diego

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Check upcoming rates & availability for San Diego Vacation Rentals for Winter


Frequently asked questions

Browse our remarkable collection of luxury Vacation Rentals for Winter in San Diego, San Diego County, California, United States. As only the top 3% of homes go on to become Plum Award winners, you can be certain that your chosen home will be ideal for you. Each home in our range must pass 3 rounds of testing, and comes fully furnished with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Make the most of the chilly season, and wrap up warm in a comfortable Winter Holiday Rental in San Diego. Reach out to our caring team of experts, who love nothing more than helping you discover the perfect home for your trip.

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