Family-friendly holiday rentals in Cupertino

Sparkling Clean Brand New Luxury House w Parkings

*If you have trouble booking please message the host*BUILT in 2019. New, charming, beautiful, quiet, safe, and comfortable 5 bedroom/3 bathroom house (2400+ sq. ft.) that sleeps 20 people and has ocean view and a free parking minutes of driving from San Francisco, San Francisco airport, BART, CalTrain, and freeways. It is also in the walking distance to groceries, supermarket and restaurants. The house is wheelchair friendly and has high speed internet (150+ Mbps), cookware, and microwave, oven!

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

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.

Great Townhouse in charming Pleasanton

3 bed 1.5bath townhouse with 1 car garage. Fully furnished with beautiful high end but cozy furnishings. Max guests are 6 adults 1 infant no extra guests. 1 cal-king, 1 queen, 2 twin beds. Please be advised there are stairs and some people say they are steep. Smart TVs YouTube TV Netflix etc. High speed Wi-Fi internet is included. The house has central heating and air conditioning and is professionally cleaned before every booking. Home comes fully stocked with everything you need.

Luxurious Bayview Treehouse: Hot Tub, 15 min to SF

Immerse yourself in an architectural gem that balances modern elegance and rustic allure. Our four-bedroom, three-bathroom sanctuary is your secluded escape amidst expansive greenery, a canvas for unforgettable moments. Just 10 minutes from SFO Airport and 15 minutes from dynamic San Francisco, our home is your launchpad to exploration. The Bay Bridge graces the view from your private balcony and hot tub, framing your stay with an awe-inspiring vista.

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.

Victorian Experience Downtown Campbell King Bed

Light streams through the picture window, bathing the room in a golden glow. As you bask in the sun’s warm gift, the taste of morning's first cup of coffee kisses your lips, awakening your senses. You take a deep breath, feeling grateful to have found the perfect oasis—a thoughtfully designed retreat in the heart of downtown Campbell. Whether you’re here for work or relaxation, this space invites you to unwind and savor the moment.

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!

Urban retreat + Garage, minutes to UCSF MB & more

Top Floor Unit (upstairs) • Walk Score 90 ("Very Walkable") • Transit Score 91 ("Excellent Transit") • Outdoor private patio • Garage parking for 1 vehicle • 5 min walk to grocers • 10 min walk to Balboa Park BART • 15 min drive to downtown SF • Fully equipped & stocked kitchen • Safe residential neighborhood • Shared on-site washer/dryer + supplies for guests