Book Family Friendly Rentals in Cupertino

We selected the 116 homes worth renting in this location

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Home spotlights in Cupertino

The Smiling Poet

The Smiling Poet

  • 4 guests

  • 2 bedrooms

Golden Rectangle, Carmel-by-the-Sea

Like a warm hug, this classic cottage-style home presents a soothing space to relax between discovering the serene beaches, sought-after restaurants, impressive art galleries and sophisticated wine tasting locations of Carmel-by-the-Sea. Furnished with style, homely features pave the way to a comfortable and practical stay here.

Face the Music

Face the Music

  • 5 guests

  • 2 bedrooms

Menlo Park, San Mateo County

With the Facebook HQ your neighbour, this stylish apartment is ideal for any business trip to Fair Oaks. It’s the perfect mix of business and downtime, with Bedwell Bayfront Park just across the road for a morning jog or leisurely stroll, and plenty of trendy eateries in the area.

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.

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 Family Friendly Rentals

Explore the 116 most perfect homes in our collection

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Most popular homes in Cupertino

Utmost Taste

Utmost Taste

  • 4 guests

  • 2 bedrooms

Healdsburg, Sonoma County

Red Robles

Red Robles

  • 3 guests

  • 1 bedrooms

San Luis Obispo County, California

Sonoma Sanctuary

Sonoma Sanctuary

  • 8 guests

  • 4 bedrooms

Healdsburg, Sonoma County

The Art of Wine

The Art of Wine

  • 8 guests

  • 3 bedrooms

Angwin, Napa County

The Valley Stream

The Valley Stream

  • 2 guests

  • 1 bedrooms

Healdsburg, Sonoma County

Willow Cove

Willow Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

Vineyards & Verandas

Vineyards & Verandas

  • 6 guests

  • 3 bedrooms

Healdsburg, Sonoma County

Cabernet Cottage

Cabernet Cottage

  • 6 guests

  • 2 bedrooms

Sonoma County, California

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Check upcoming rates & availability for Cupertino Family Friendly Rentals


Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Cupertino. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Cupertino Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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