Book Luxury Vacation Rentals in Cupertino

Award-winning homes from £98

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Home spotlights in Cupertino

Coffee Shop Soundtrack

Coffee Shop Soundtrack

  • 4 guests

  • 2 bedrooms

Menlo Park, San Mateo County

Set in Menlo Park within the San Francisco Bay Area of California – you'll be just a fifteen-minute drive away from the world-renowned Silicon Valley, home to the iconic Meta headquarters. Blending city living with an abundance of local nature, you'll find plenty of things to do here, come day and night.

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.

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.

The Curve of the Moon

The Curve of the Moon

  • 10 guests

  • 4 bedrooms

El Granada, San Mateo County

With the magic of the sea, sun, and stars surrounding you at Half Moon Bay, this incredible home is the perfect weekend retreat for a family, only twenty minutes away from San Fransisco. Charge the Tesla at the EV charging station and then explore the trails of the National Forest backing the house or pack your beach bag and stop by the Pacific Ocean, a fifteen-minute stroll away.


We selected the top 3% holiday homes in Cupertino Vacation Rentals

Explore the 128 most perfect homes in our collection

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Most popular homes in Cupertino

Wonder of the Waves

Wonder of the Waves

  • 4 guests

  • 2 bedrooms

Moss Beach, San Mateo County

Black Walnut Cove

Black Walnut Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

Willow Cove

Willow Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

Large Glass of Red

Large Glass of Red

  • 24 guests

  • 8 bedrooms

Napa County, California

The Valley Stream

The Valley Stream

  • 2 guests

  • 1 bedrooms

Healdsburg, Sonoma County

Amidst The Vines

Amidst The Vines

  • 6 guests

  • 3 bedrooms

Sonoma County, California

Down by the Shoreline

Down by the Shoreline

  • 8 guests

  • 4 bedrooms

Placer County, California

A Life On the Water

A Life On the Water

  • 8 guests

  • 3 bedrooms

Lake County, California

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in Cupertino. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect Cupertino Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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