San Jose Holiday Homes with Staff

We selected the 138 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in San Jose

Redwood Hideaway

Redwood Hideaway

  • 8 guests

  • 4 bedrooms

Mill Valley, Marin County

It’s easy to see why this beautiful home has been featured in magazines including Martha Stewart Living – it’s stunning. The professional pastry chef homeowner has designed the kitchen as the heart of the home, and there’s a real focus on the shared living spaces.

A Life On the Water

A Life On the Water

  • 6 guests

  • 3 bedrooms

Lake County, California

Perched on a private ridge, we invite you to take a lungful of some of the purest air in mainland USA and step inside this charming single-storey home, which enjoys spectacular views over its 14-acre vineyard and the pristine waters of Clear Lake. Everything about this elegantly designed building aims to accentuate the natural beauty on the doorstep.

Redwood Riverside

Redwood Riverside

  • 6 guests

  • 3 bedrooms

Sonoma County, California

Gain peace and perspective at this stunning Californian riverside home. This serene sanctuary is tucked away in a wooded knoll on North Fitch Mountain, and sits amongst the towering redwoods of this area, with its own direct path to the Russian River.

Taylor Ridge Retreat

Taylor Ridge Retreat

  • 8 guests

  • 4 bedrooms

Sonoma County, California

Surrounded by acclaimed vineyards and a short drive from the rugged beauty of the Sonoma coast, this welcoming home offers a spectacular retreat for anyone looking to spend a week or so discovering everything Wine Country has to offer or simply get away from it all for the weekend. Inside, an open layout offers a wonderful flow throughout the home.


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

Explore the 138 most perfect homes in our collection

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Most popular homes in San Jose

Academic Pursuits

Academic Pursuits

  • 8 guests

  • 4 bedrooms

College Terrace, Palo Alto

Californian Cosy

Californian Cosy

  • 8 guests

  • 4 bedrooms

Sonoma County, California

Komorebi

Komorebi

  • 5 guests

  • 2 bedrooms

Upper Rockridge, Oakland

Echo of the River

Echo of the River

  • 6 guests

  • 4 bedrooms

Industrial Area West, Roseville

The White Cloud

The White Cloud

  • 4 guests

  • 1 bedrooms

Sonoma County, California

Life in the Valley

Life in the Valley

  • 16 guests

  • 6 bedrooms

Sonoma County, California

Redwood & Palm

Redwood & Palm

  • 6 guests

  • 3 bedrooms

Santa Cruz County, California

Under the Fruit Trees

Under the Fruit Trees

  • 4 guests

  • 2 bedrooms

Professorville, 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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