Family-friendly holiday 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 favourite

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!

8–15 Jul

$189 SGD 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

18–25 Dec

$314 SGD per night

Guest favourite

Cabin in Los Gatos

4.99 out of 5 average rating, 788 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.

9–16 Apr

$240 SGD per night

Guest favourite

Flat in San Jose

4.92 out of 5 average rating, 183 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

23–30 Jun

$165 SGD per night

Guest favourite

Guest suite in Santa Clara

4.89 out of 5 average rating, 225 reviews

Clean remodeled private suite w/ separate entrance

Remodeled from floor to ceiling and located in the heart of Santa Clara, between the 101 & 280. Separate outdoor entry to a deep cleaned, quiet, and private in-law suite with large, modern bedroom, private bathroom, kitchenette, and laundry room with washer and dryer. This space was designed for the discerning business traveler and features Cal King bed, ample closet space, wall-mounted HDTV, dedicated 5.0GHz WiFi, refrigerator/freezer, glass desk, reclaimed wood accent wall, and Keurig.

13–20 Jan

$168 SGD per night

Guest favourite

Loft in San Jose

4.87 out of 5 average rating, 564 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.

18–25 Jul

$188 SGD per night

Guest favourite

Cottage in Santa Clara

4.94 out of 5 average rating, 187 reviews

Manzanita Cottage in the Heart of Silicon Valley

*We respond to inquiries quickly! We use CDC cleaning guidelines. Smoking is not permitted on the premises* The Manzanita Cottage is a perfect getaway for business or vacation travelers. The cottage is well appointed and has everything you need for an extended or short stay. This private & inviting cottage is big on amenities: stove, oven, microwave, coffee maker, dishwasher, washer & dryer, etc. We have two other units on our property: The Orchard tiny house and The Manzanita cottage.

2–9 Apr

$186 SGD per night

Guest favourite

Guest suite in Cupertino

4.96 out of 5 average rating, 376 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.

14–21 Jul

$197 SGD per night

Guest favourite

Guest house in Monte Sereno

4.9 out of 5 average rating, 186 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.

30 Dec – 6 Jan

$259 SGD per night

Guest favourite

Train in Cupertino

4.92 out of 5 average rating, 344 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.

3–10 Apr

$303 SGD per night

Superhost

Guest suite in Mountain View

4.9 out of 5 average rating, 275 reviews

2-bedroom suite in peaceful neighborhood

Newly remodeled garden level (partially below ground) private unit. Fully furnished with 2 bed, 1 bath, kitchen, and living room/dining area. Ceiling a bit low. One block from major shopping, restaurants, and parks. Very private living space in a quiet neighborhood. About 650 sq ft.

16–23 Oct

$189 SGD per night

Guest favourite

Guest house in Sunnyvale

4.96 out of 5 average rating, 386 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.

30 Mar – 6 Apr

$163 SGD per night