Book Luxury Holiday Rentals in San Jose

Award-winning homes from £98

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Home spotlights in San Jose

Amidst The Vines

Amidst The Vines

  • 6 guests

  • 3 bedrooms

Sonoma County, California

If you love wine, this award-winning home is what dreams are made of. Located down an idyllic, oak tree-lined country road and nestled amongst the vines of a working vineyard in Sonoma, this place is utter bliss.

Rose Mandala

Rose Mandala

  • 6 guests

  • 2 bedrooms

Grand Lake, Oakland

There’s an unmistakably bohemian vibe to this character home outside Oakland. With acoustic guitars on the walls, sprawling houseplants and sixties style bedspreads, it’s the kind of place where creativity rules.

Baby It's Cold Outside

Baby It's Cold Outside

  • 8 guests

  • 3 bedrooms

Truckee, Nevada County

With its dark wooden frames and surrounding woodland, this home makes for a cosy stay despite its large size. Spread across a few floors, this impressive and innovative spot is somewhere between a townhouse and a lodge.

Fair of Face

Fair of Face

  • 4 guests

  • 2 bedrooms

Menlo Park, San Mateo County

In the business hub of Fair Oaks, near the Facebook HQ, this flash apartment sits in a building filled with amenities. If you’re not hitting the building’s private gym, perhaps take a jog through Bedwell Bayfront Park, a five-minute walk away.


We selected the top 3% holiday homes in San Jose Holiday Rentals

Explore the 136 most perfect homes in our collection

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Most popular homes in San Jose

Under the Fruit Trees

Under the Fruit Trees

  • 4 guests

  • 2 bedrooms

Professorville, Palo Alto

Cali Vista

Cali Vista

  • 8 guests

  • 4 bedrooms

Polo Grounds, Bakersfield

Vineyard Views

Vineyard Views

  • 12 guests

  • 4 bedrooms

Amador County, California

A Song For You

A Song For You

  • 5 guests

  • 3 bedrooms

Kensington, California

If You Come Back to California

If You Come Back to California

  • 6 guests

  • 3 bedrooms

Sonoma County, California

Wonder of the Waves

Wonder of the Waves

  • 4 guests

  • 2 bedrooms

Moss Beach, San Mateo County

The Idyllic

The Idyllic

  • 12 guests

  • 4 bedrooms

East Foothills, California

Black Walnut Cove

Black Walnut Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in San Jose. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that San Jose has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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