Book Luxury Winter Rentals in San Diego County

We selected the 89 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights in San Diego County

California Boardin'

California Boardin'

  • 7 guests

  • 3 bedrooms

San Clemente, Orange County

A home for California swell chasers to search out, this home will have you in the water in no time, with the sands of San Clemente a five-minute drive from your front door and some of SoCal's best beach breaks within an hour's drive. However, that's not to say that if you're not a surf pro, you won't find something for you here.

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.

El Camino

El Camino

  • 2 guests

  • 1 bedrooms

San Clemente, Orange County

Treat yourself to a romantic getaway and escape from everyday life at this beautiful home, ideally located a two-minute drive away from downtown San Clemente. Enjoy your morning coffee on the private roof deck while you admire the outstanding ocean views.

The Ocean's Smile

The Ocean's Smile

  • 10 guests

  • 5 bedrooms

La Jolla Shores, San Diego

Perfect for a coastal family getaway, this home boasts enviable views across La Jolla Shores beach. With two living rooms and all five bedrooms offering en-suites, there’s plenty of space for the whole family to spread out and relax here – we particularly love the upstairs family room, with ocean views and doors onto the terrace to enjoy a spot of sunshine over a glass of wine.


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

Explore the 89 most perfect homes in our collection

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Most popular homes in San Diego County

The Crystal Pillow

The Crystal Pillow

  • 16 guests

  • 6 bedrooms

Carlsbad Village, Carlsbad

Mossflower

Mossflower

  • 6 guests

  • 3 bedrooms

Bird Rock, San Diego

Rockin' in the Roundabout

Rockin' in the Roundabout

  • 10 guests

  • 5 bedrooms

Village of La Jolla, San Diego

Ocean Roar

Ocean Roar

  • 7 guests

  • 3 bedrooms

Beach Barber Tract, San Diego

Blue Star

Blue Star

  • 8 guests

  • 5 bedrooms

Palacio Del Mar, San Diego

The Ocean's Calling

The Ocean's Calling

  • 4 guests

  • 2 bedrooms

Sunset Cliffs, San Diego

Sunny San Diego

Sunny San Diego

  • 8 guests

  • 3 bedrooms

Mountain View, San Diego

Pacific Tranquillity

Pacific Tranquillity

  • 11 guests

  • 4 bedrooms

Sherman Heights, San Diego

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


Frequently asked questions

Browse our remarkable collection of luxury Vacation Rentals for Winter in 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 County. 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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