Book a stay in one of the best homes in Cupertino

We selected the 122 homes worth renting in this location

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Home spotlights in Cupertino

Redwood & Palm

Redwood & Palm

  • 6 guests

  • 3 bedrooms

Santa Cruz County, California

Surrounded by hiking trails, golf courses, and stretches of Pacific coast, this home in Santa Cruz not only has an enviable location, but it’s bursting with the potential for plenty of memories made. The backyard, alone, has a private swimming pool, tiki bar, and a swath of green turf that the kids will love running around on – especially when they’re hiding from the dinosaur.

Wonder of the Waves

Wonder of the Waves

  • 4 guests

  • 2 bedrooms

Moss Beach, San Mateo County

Enjoy mesmerising views and direct beach access from this Pacific Ocean retreat. You’ll also find a private hot tub overlooking the water, a putting green and a fire pit for magical evenings under the stars.

Large Glass of Red

Large Glass of Red

  • 24 guests

  • 8 bedrooms

Napa County, California

Just outside of the village of Calistoga in the northernmost tip of the Napa Valley, you'll encounter this rustic yet refined retreat surrounded by acres of verdant vineyards and lush gardens. With no nearby neighbours, enjoy that all-too-rare feeling of seclusion, yet the convenience of only being a mile and a half from downtown Calistoga.

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.


We selected the top 3% holiday homes in Cupertino

Explore the 122 most perfect homes in our collection

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Most popular homes in Cupertino

The Valley Stream

The Valley Stream

  • 2 guests

  • 1 bedrooms

Healdsburg, Sonoma County

Life in the Valley

Life in the Valley

  • 16 guests

  • 6 bedrooms

Sonoma County, California

Run Russian River Run

Run Russian River Run

  • 4 guests

  • 2 bedrooms

Guerneville, California

Sycamore Cove

Sycamore Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

Black Walnut Cove

Black Walnut Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

Willow Cove

Willow Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

The Viticulturalist

The Viticulturalist

  • 4 guests

  • 2 bedrooms

Paso Robles, San Luis Obispo County

The White Cloud

The White Cloud

  • 4 guests

  • 1 bedrooms

Sonoma County, California

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