Family-friendly vacation rentals in Cupertino

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Cupertino

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Sunnyvale

4.97 out of 5 average rating, 274 reviews

Comfortable, Modern, Bright w/Patio

A completely separate private guest suite in a beautiful house, furnished with love and all the amenities you'd need. Also, super walkable & safe location, fast wifi, comfy beds, friendly experienced hosts ready to help you with whatever you need. Look forward to soaking in the sun on the patio, and enjoying the park across the street. It's a 10min walk to the great bars & restaurants downtown SV, or to the Caltrain station for a hassle-free trip to SF or SJ. We love living here and so will you!

Aug 14 – 21

G$27,503 GYD per night

Superhost

Guest suite in Cupertino

4.82 out of 5 average rating, 226 reviews

Luxury 2 Room Private Bunglow - Executive Suite

- GUESTs' SAFETY 1st: Cleaners sanitizes every surface and point of contacts - Separate access to 2 room bungalow Executive Suite - full privacy - Easy access to restaurants, shopping and transport - Lovely San Francisco Bay - Executive Mediterranean Retreat home - New modern 2 room bungalow with bedroom, living room-equipped kitchen combo - comfortable, clean & serene. - Close to Apple and @heart of silicon valley companies & Amenities - Latest improvement pictures are pending to be uploaded

Nov 12 – 19

G$45,871 GYD per night

Guest favorite

Cabin in Los Gatos

4.99 out of 5 average rating, 791 reviews

Private Guest-House in the Redwoods

Our custom built guesthouse was completed in 2016. It is situated on 5 redwood-covered acres, 10 minutes south of Los Gatos and 20 minutes from Santa Cruz. We have easy access to hiking and biking trails, world-class wine-tasting, microbreweries, shops, amazing dining, and more! There is something for everyone in our area! We are surrounded by a 35 acre tree farm, so it's very private, yet close to the silicon valley! Our property has a standby generator so we are not affected by power outages.

Oct 23 – 30

G$38,921 GYD per night

Guest favorite

Apartment in San Jose

4.92 out of 5 average rating, 184 reviews

❤️of Downtown San Jose Cozy Studio Free Parking

Our cozy studio is at heart of downtown San Jose and features onsite parking, washer/dryer, and fully stocked kitchenette (NO STOVE) with a toaster oven, microwave, Keurig, electric kettle, mini fridge, strong WiFi. Enjoy the quality linens & cozy touches. Walk to Convention Center, 5 min drive to SAP Center, Diridon Station, SJC & Japantown. next to I-280/87. Wi-Fi TV, Youtube TV subscription only, login to your own Netflix, Hulu etc. Sorry, no portable hotplate can be brought in,1 person only

Jul 9 – 16

G$23,623 GYD per night

Guest favorite

Loft in San Jose

4.87 out of 5 average rating, 566 reviews

Rose Garden Cottage

A private free standing guest cottage on our property in San Jose's historic Rose Garden. 5 min to SJC airport, 1.5 miles to Diridon Station and VTA light rail. Walkable to restaurants, coffee shops, nightlife, parks and public transit. One mile to the SAP Center (Shark Tank) and Santa Clara University. 2 miles to Santana Row and Westfield Shopping Center. You’ll love our place because of it's tranquil setting. Kuerig coffee maker, Britta water filter small refrigerator and microwave.

Aug 22 – 29

G$28,225 GYD per night

Guest favorite

Guest suite in Cupertino

4.96 out of 5 average rating, 379 reviews

Modern Suite in Cupertino

Nice quiet location. Bright, tranquil, and comfortable unit in a private house with a separate entrance and private yard. Unit consists of one bedroom, one bathroom, and a kitchen and living area. House is within walking distance of Cupertino Library, De Anza College, and top Cupertino schools. Very close to nearby Silicon Valley high-tech companies. Prime Bay Area location with high accessibility to public transporation, eateries, and entertainment.

Jul 21 – 28

G$30,394 GYD per night

Guest favorite

Guesthouse in Monte Sereno

4.9 out of 5 average rating, 187 reviews

Greenwood Guest House, a Peaceful Oasis

Welcome to Greenwood Guest House, a 1 bedroom, 1 bath private house situated in a peaceful and expansive backyard with a pool, tennis court, and beautiful scenery. Our space is a good fit for business trips, couple vacations, and family visits. The kitchenette and laundry room make longer stays quite enjoyable. Easy access to Highway 17 and 85, 15 minute drive to San Jose airport (SJC) and 2 minute drives to either downtown Los Gatos or Saratoga.

Jan 7 – 14

G$38,556 GYD per night

Guest favorite

Train in Cupertino

4.91 out of 5 average rating, 347 reviews

Caboose in the redwoods just outside of Cupertino

This rustic caboose is just 10 minutes from Cupertino and downtown Saratoga, perfect for both business travelers, outdoor adventurers, and everything in between. There are lots of nearby hiking and biking trails, as well as other exciting outdoor activities. Being so close to Silicon Valley, yet feeling so far from it all is a truly unique experience unlike anywhere else. Pets generally ok. Check with hosts. Pets must not be left alone.

Nov 9 – 16

G$45,510 GYD per night

Guest favorite

Guest suite in Campbell

4.95 out of 5 average rating, 356 reviews

Cottage - bedroom, living, bath and small kitchen

The cottage has separate entrance for the independent bedroom, living-cum-dining area and a small kitchen for our guests. Cottage has queen bed in the bedroom and comfortable sectional sofa and dining table in the living-cum-dining area. Cottage is connected to rest of the house through adjoining wall.

Jul 22 – 29

G$28,170 GYD per night

Guest favorite

Guesthouse in Sunnyvale

4.96 out of 5 average rating, 387 reviews

Private cottage in a garden

Charming, private backyard studio cottage nestled in a fenced garden in a quiet Sunnyvale neighborhood. Private, clean and cozy, this 240-sq ft space has a kitchenette, bathroom with shower, full-size bed, Wifi, A/C. Short walk to cafes, groceries. Ample parking.

Dec 27 – Jan 3

G$24,476 GYD per night

Guest favorite

Guesthouse in San Jose

4.93 out of 5 average rating, 301 reviews

Cozy Guest Cottage in Willow Glen

Studio apartment in converted garage behind main house featuring king sized bed, Cable TV, WiFi, private bathroom, kitchenette, patio, and parking near front door. Convenient location near shopping center at Bird and Minnesota Avenues in Willow Glen.

Jun 29 – Jul 6

G$22,364 GYD per night

Guest favorite

Guest suite in San Jose

4.92 out of 5 average rating, 116 reviews

Quiet and Comfortable Studio

This studio has a private entrance and is located in the back of the property. It has a private bathroom and a kitchenette with fridge, microwave oven, toaster, single-serve coffee, kettle, stove and oven. Off-street parking for 1 car included.

May 22 – 29

G$13,878 GYD per night