San Jose Holiday Homes with Staff

We selected the 140 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in San Jose

The Viticulturalist

The Viticulturalist

  • 4 guests

  • 2 bedrooms

Paso Robles, San Luis Obispo County

In the centre of downtown Paso Robles, this stylish apartment puts you close to shops, restaurants and, of course, wine tasting rooms. The hills around Paso are filled with California’s best wineries where Zinfandel and Petit Sirah grapes grow plump on the vine.

Pinewood & Prints

Pinewood & Prints

  • 6 guests

  • 3 bedrooms

Golden Rectangle, Carmel-by-the-Sea

The host of this renovated beach hut in downtown Carmel-by-the-Sea has done a stellar job in retaining the home's historical character while also ensuring it belongs well and truly in the twenty-first century. Pinewood flooring, original windows and the stone fireplace are accompanied by industrial-inspired lighting, furnishings in an angelic shade of white and pops of colour from prints hanging on the wall.

Run Russian River Run

Run Russian River Run

  • 4 guests

  • 2 bedrooms

Guerneville, Sonoma County

Surrounded by redwoods and boasting vertiginous valley vistas, this gorgeous Guerneville home is the ultimate California crib. Featuring a fully equipped kitchen and open plan living cum dining room complete with gas fireplace – think traditional river cabin – and French doors out onto a barbecue, dining and lounging deck, not to mention a hot tub and festoon light strewn relaxation area, this stunning Sonoma County home is truly magical.

Black Walnut Cove

Black Walnut Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

Tucked away in the serene coastal community of Pedro Point, this modern cabin offers the perfect escape to the shores of the Pacific Ocean. Located just a nine-minute walk from Pacifica State Beach and a six-minute stroll from Shelter Cove Beach – you'll be blown away by the bay's beauty, making it a popular spot for photographers.


We selected the top 3% holiday homes in San Jose Holiday Homes with Staff

Explore the 140 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

Californian Cosy

Californian Cosy

  • 8 guests

  • 4 bedrooms

Sonoma County, California

Redwood Hideaway

Redwood Hideaway

  • 8 guests

  • 4 bedrooms

Mill Valley, Marin County

Amidst The Vines

Amidst The Vines

  • 6 guests

  • 3 bedrooms

Sonoma County, California

Rose Mandala

Rose Mandala

  • 6 guests

  • 2 bedrooms

Grand Lake, Oakland

The Valley Stream

The Valley Stream

  • 2 guests

  • 1 bedrooms

Healdsburg, Sonoma County

The Curve of the Moon

The Curve of the Moon

  • 10 guests

  • 4 bedrooms

El Granada, San Mateo County

Academic Pursuits

Academic Pursuits

  • 8 guests

  • 4 bedrooms

College Terrace, Palo Alto

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Check upcoming rates & availability for San Jose Holiday Homes with Staff


Frequently asked questions

Are you hoping for a stay in one of the best holiday homes with staff in San Jose? If so, you've definitely come to the right place. Reach out to our expert team who will happily arrange for staff to be present at your home in San Jose as an addition to your booking. Our Plum Guide homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short extended stay. Should you need anything, our friendly team is on hand 24/7, so just ask.

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