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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Superhost

Cabin in Los Gatos

4.9 out of 5 average rating, 444 reviews

The Coach House

The Coach House is located on our mountain top horse and lavender farm. We offer youth summer camps so are set up for fun outdoor adventures and activities. Have fun with our horses, goats, and chickens! You can take a 10 min walk over to Nonno's Restaurant for wine/pizza/BBQ and bacchi ball, or take an 8 min drive into Los Gatos, or 15 min to Santa Cruz for the beach and some of the best restaurants and spas around!. Good for couples, solo adventurers, business travelers, kids, & behaved dogs!

Top guest favorite

Home in Portola Valley

4.93 out of 5 average rating, 146 reviews

3 BR Home on Vineyard nr Palo Alto & Stanford

Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

Guest favorite

Home in San Mateo

4.84 out of 5 average rating, 207 reviews

Quiet 3ba/2ba HOUSE with backyard orchard. 🏡

For Business or Leisure. Comfortable place with easy check in with a team, smart choice over hotel. Beautiful 3 bedrooms home in nice neighborhood of San Mateo in the heart of Silicon Valley. 10 mins to SFO, 7 mins to Cal Trains, 11mins to BART train. A convenient location just a short hop to San Francisco and Palo Alto. Walk to the beach, running trail with breathtaking bay view, tennis court. Open to long term furnished rental. All 3 bedrooms with premium queen beds and mattresses. New Sofa

Superhost

Home in Foster City

4.86 out of 5 average rating, 179 reviews

❤️ Amazing! 2B/2B with a leisure garden.

Beautiful and comfortable end-unit, step-free, single-level townhouse with 2 bedrooms and 2 full baths. This corner unit opens up into a beautiful garden. located between San Francisco and Silicon Valley. A full kitchen, central heating, and washer/dryer are in the house. garage parking. backyard and patio. Few minutes walking distance to parks, restaurants, and the seaside walkway. It's excellent for vacations as well as business and professional stays. Check yourself in with the keypad code.

Superhost

Cabin in Felton

4.91 out of 5 average rating, 488 reviews

Tranquility Base Redwood Mountain Tree House

This 85 year old remodeled cabin is in Felton, close to Roaring Camp Railroad, Loch Lomond Rec Area, Henry Cowell's State Park, Mount Hermon Conference Center, Felton Covered Bridge Park. The Boardwalk and beaches of Santa Cruz are a 25 minute drive from the cabin. You will be deep in the heart of redwoods and ferns with sounds of a trinkling creek. A moonlit night in the hot tub tops it all off! Fun for couples, girlfriends getaways, writers, poets, solo adventurers, and families . NO PETS

Superhost

Home in Ben Lomond

4.93 out of 5 average rating, 135 reviews

Central Coast; Meadow, Hot Tub, Polite Pets Welcom

VR#111596 Seemingly remote & private yet so close to everything, single level home with massive deck on 2 1/2 acres backs to park and trails. The cook’s kitchen & herb garden overlook our meadow. The hot tub, outdoor living room & garden shower are just a few of the surprises you will uncover. The 350 heritage oak tree with 10,000 sq ft canopy is a magnet for wildlife. Ask about detached office if you need to work from home; the internet is great. Polite well trained pets OK.

Guest favorite

Home in East San Jose

4.93 out of 5 average rating, 247 reviews

Gr8View-LrgDeck-BBQ-Spa-PoolTable-2xOven-Sleeps12

Modern Kitchen w/Double Oven/Air-frier 10 Person & 4 Person Dining Table 2 master bdrms (1 CalKing & 2 Queen BunkBed) 2 standard rms (2 queens) & 1 sofa bed Double Sink in each x3 bath 2 Fridges & 3 Washer & Dryers Pool table 32x32 Foot Patio Elliptical Fitness Hot Tub Gas Grill AC Gourmet kitchen, large patio & fantastic accommodations. Amazing comfortable, quiet 4 bdrm w/breathtaking view & relaxing feel. Mattresses are top of the line Tempur-Pedic Cal-King & Queen (Master Rms)

Guest favorite

Home in Mountain View

4.98 out of 5 average rating, 379 reviews

Dolce Vita! Charming Downtown Bungalow Top Rated

Welcome! We are a favorite choice for comfort, convenience, & safety. Fully stocked with practical amenities. Clean, quiet, safe residential street just a 2 min walk to bustling downtown restaurants, bars, cafes, etc. Fully stocked kitchen, coffee, teas, cookware, spices, etc. Relax on the porch or inside with a 52" TV, fast WiFi, FireTV, Chrome Cast, A/C, Roche-Bobois, laundry, toiletries, baby gear, etc. Please, we have a strict no pets or smoking policy for health & safety.

Superhost

Guesthouse in Menlo Park

4.85 out of 5 average rating, 319 reviews

Spacious quiet cottage, next to Stanford, FaceBk

Our lovely cottage (~900+sf) with a park like setting, in a very nice neighborhood, is close to Stanford, FaceBk, Alphabet, Palo Alto and Menlo Park downtown. With ~200 roses, ~50 camellia under California sun, our beautiful garden blossom all year around. The 2 Br/1 ba cottage is great for solo traveler, couples, business, and families for a staycation or as a work-from-home alternative. NOTE: WE ONLY ACCEPT BOOKING/PAYMENT VIA AIRBNB; NEVER ASK FOR DIRECT PAYMENT.

Guest favorite

Guesthouse in Monte Sereno

4.9 out of 5 average rating, 206 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.

Superhost

Home in Mountain View

4.84 out of 5 average rating, 285 reviews

Cute two bedroom home in fantastic location!

Cute, cozy remodeled duplex in a great neighborhood with a fenced in yard and surrounded by parks. The amazing location...You have access to 3 freeways, and Central Expressway. This means in 15 minutes by car you can be in S tanford, Los Altos, Palo Alto, San Jose, Milpitas or the east bay. By foot or bike you can reach beautiful shoreline park, two public rail systems, and lovely downtown Mountain view with great food!

Top guest favorite

Guest suite in San Jose

4.91 out of 5 average rating, 232 reviews

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

Very large 1 bedroom. Heat/AC, Private entry, Loaded with Amenities. Private Patio, Garden View, parking in front. Nice, Quiet neighborhood; near trails, Pond, Freeways, Light Rail(VTA). 10 min walk to Westfield Oakridge Mall, Restaurants/Movies, Bowling, Mini golf, Walmart, Costco, Bass Pro, and much more. 1 HR to SFO/Monterey 30 Min to Santa Cruz Beach/Gilroy Outlets 20 Min Dwntwn SJ/SJSU