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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 suite in Cupertino

4.82 out of 5 average rating, 245 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

Guest favourite

Home in Sunnyvale

4.97 out of 5 average rating, 294 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!

Guest favourite

Loft in San Jose

4.94 out of 5 average rating, 464 reviews

Santana Row Luxury Executive 2 Story Loft

Beautiful, luxury and clean 2 story open plan loft on the top floor at Margo building right on Santana Row. 2 bedroom 1,5 bath. Panoramic view of the mountains, downtown San Jose and the planes landing at SJC. Your favorite restaurants and shops downstairs. Valley Fair Mall is across the street. Brand new king size bed in the Master Bedroom, walk-in closet, kitchen, Nespresso coffee, teas. Underground parking with EV/Tesla hookup. Security on site 24/7. Ideal for business travelers and families.

Treehouse in East San Jose

4.93 out of 5 average rating, 699 reviews

Treehouse , San Jose

250 sq ft treehouse with stairs leading to 2 lofts with beds overlooking the most gorgeous view of the Silicon Valley. The treehouse opens to a deck 14 foot high nestled in between 3 sycamore trees.Custom made stained glass window and spiral staircase leads up into the tree. Includes full functioning bathroom , kitchenette w sink , cooking stove, mini fridge . Sleeps 4 people. ( 1 queen bed in each open loft) You are living with a live tree in nature so think glamping - an amazing experience .

Guest favourite

Rental unit in Downtown San Jose

4.93 out of 5 average rating, 196 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

Guest favourite

Loft in Rose Garden

4.86 out of 5 average rating, 601 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.

Guest favourite

Guest suite in Sunnyvale

4.97 out of 5 average rating, 153 reviews

Entire Guest Suite, Entrance@ House of Chauncey

Attention Travelers: Please inquire about availability before booking/instant booking. Thank you! Hello there! Vicky and I have a nice, comfortable newly renovated room with attached private bath and separate entrance in our home for you to stay in. It's in a quiet neighborhood in Sunnyvale, bordering Mountain View. We are super close to Apple, LInkedIn, NASA and G00gle, with a G00gle shuttle and Facebook shuttle stops a few blocks away. We are also close to downtown Sunnyvale.

Guest favourite

Guest suite in Cupertino

4.95 out of 5 average rating, 401 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.

Guest favourite

Guesthouse in Monte Sereno

4.89 out of 5 average rating, 199 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.

Guest favourite

Train in Cupertino

4.92 out of 5 average rating, 378 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.

Home in Mountain View

4.95 out of 5 average rating, 246 reviews

Perfect Location, No Cleaning Fees or Checkout Cho

You couldn't get a more perfect location for this cozy, quiet, comfy, well-appointed cottage: just blocks from Mountain View's bustling downtown area centered on Castro Street, and a 5 minute walk to Caltrain and VTA. Perfect for visiting G00ogel and other local tech companies. That's right -- no separate cleaning fees, no checkout chores! On your way out, just lock the door and have a safe trip!

Home in Mountain View

4.74 out of 5 average rating, 460 reviews

Spacious Mt View 1B/1B In-law Suite

Beautifully furnished 1B/1B private entrance in-law suite very close to downtown Mountain View. - Queen bed in bedroom - Spacious living room w/ sofa & TV - Twin bed in living room for the convenience of the 3rd guest (e.g. your child or a friend) - Dining room & kitchenette w/ fridge & microwave - Private full bathroom - High speed internet and smart TV - Great discount weekly and monthly

Vacation rentals for every style

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Popular amenities for Cupertino family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest suite in San Carlos

4.81 out of 5 average rating, 185 reviews

Sweet Studio -SF Peninsula

Cabin in Felton

4.91 out of 5 average rating, 489 reviews

Tranquility Base Redwood Mountain Tree House

Guest favourite

Home in Redwood City

4.97 out of 5 average rating, 297 reviews

Private suite

Home in Berryessa

4.62 out of 5 average rating, 126 reviews

Serene, Large 4BR/2.5BA Home in San Jose

Guest favourite

Home in East San Jose

4.93 out of 5 average rating, 243 reviews

Luxe w/Gr8View-LGDeck-BBQ-Hottub-Billiard-2xOven

Guest favourite

Condo in Mountain View

4.95 out of 5 average rating, 124 reviews

Spacious Top Floor Condo Retreat

Guest favourite

Condo in Santa Clara

4.94 out of 5 average rating, 289 reviews

La Casa de Alpaca

Guest favourite

Home in Fremont

4.94 out of 5 average rating, 197 reviews

The White Rose Ranch (Sleeps 10 or 10+ with Annex)

Family- and pet-friendly home rentals

Guest favourite

Home in San Jose

4.92 out of 5 average rating, 371 reviews

Comfortable Whole Home on two house lot

Guest favourite

Cabin in Los Gatos

4.9 out of 5 average rating, 434 reviews

The Coach House

Guest favourite

Townhouse in San Jose

4.86 out of 5 average rating, 100 reviews

Santana Row Luxury Condo 2 Story 1100 Sq Feet

Guest favourite

Guesthouse in Menlo Park

4.97 out of 5 average rating, 148 reviews

Cottage near dwntwn Palo Alto, Stanford, Face-book

Guest favourite

Rental unit in Campbell

4.89 out of 5 average rating, 225 reviews

Victorian Paradise Downtown Campbell intelliBed

Guest favourite

Guesthouse in Monte Sereno

4.84 out of 5 average rating, 158 reviews

Private Cozy suite Los Gatos -Saratoga

Condo in San Jose

4.88 out of 5 average rating, 209 reviews

Santana Row Properties #2 - Silicon Valley Getaway

Guest favourite

Guest suite in San Jose

4.91 out of 5 average rating, 224 reviews

Cozy,Quiet”Home Away from Home”.attached cottage

Family-friendly home rentals with a pool

Home in Union City

4.88 out of 5 average rating, 103 reviews

Impressive Exec. Luxury Home, Pool & SPA, Central

Guest favourite

Home in Menlo Park

4.9 out of 5 average rating, 52 reviews

Entire Home: Pool, Hot tub, walk downtown/Stanford

Guest suite in Boulder Creek

4.93 out of 5 average rating, 67 reviews

Magical Huckleberry Woods Sanctuary w/Pool and Spa

Guest favourite

Guesthouse in Menlo Park

4.95 out of 5 average rating, 222 reviews

Private Cottage near Stanford / FB

Home in Santa Clara

4.86 out of 5 average rating, 36 reviews

Modern Retreat in the Heart of Silicon Valley

Home in Santa Clara

4.67 out of 5 average rating, 3 reviews

Modern Rivermark Home near tech companies

Guest suite in Los Altos Hills

4.78 out of 5 average rating, 156 reviews

A private hillside suite nestled among oaks

Guest favourite

Guesthouse in Los Altos

4.98 out of 5 average rating, 371 reviews

Splendid - Resort Style

Quick stats about vacation rentals that are family-friendly in Cupertino

Total rentals
120 properties
Nightly prices starting at
$55 CAD before taxes and fees
Total number of reviews
3.4K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace

Destinations to explore