
Family-friendly vacation rentals in Cupertino
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Top-rated family-friendly rentals in Cupertino
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Cupertino family-friendly rentals
Family-friendly home rentals with a hot tub

San Francisco Bay Area Ocean View, sleeps 10, 5 BR
First and foremost, thanks Julieta for allowing us to stay at your property. The photos truly don’t do the place and location justice. The views are incredible. The location is perched on a hill whereby its backyard is essentially an incredible hiking journey to several different peaks and vistas. Then, the convenience of having restaurants and grocery stores simply at the bottom of the hill. This is an absolute gem. Book it while you can!

TreeTops OceanView Retreat_HotTub_Month/LongTermOk
Had a lovely stay at Annette and Fred’s place - the location was great, the house was fully stocked and the hosts were extremely responsive when we had questions. Having a hot tub and gas fireplaces were an added bonus for spending the evenings admiring the views.

Tranquility Base Redwood Mountain Tree House
Tranquility Base…surely lived up to its name. So comfortable, so charming we felt like a part of the forest. The whole place had so much personality we felt right at home Magical and enchanting getaway Highly recommended We’ll be back

Half Moon Bay Coastal Home Walk Beach & Harbor SPA
Nancy’s place was beautifully decorated and thoughtfully arranged. Gathering areas were spacious and comfortable. Ample bathrooms made it a great place for our large family. There were plenty of linens and the kitchen was well supplied. Nancy took great care in providing extras such as water, coffee, snacks and robes that made our stay more comfortable. There’s a lovely parkway trail, with an ocean view in front of the home. Highly recommend, we had a fantastic time.

Private suite
Felt like it was just lke my home accept they have a hot tub that I used almost every night during my stay also had a beautiful garden. Is very quiet and relaxing.

3 BR Home on Vineyard nr Palo Alto & Stanford
I tell my local partners and friends in SF Bay they should send their visitors to stay. We have stayed multiple times and thankful for the pickleball, country walks on the property, stocked kitchen with utensils and cooking supplies, and clean linens. It was smaller than expected the first time, but we figured it out because the land and entertainment value of the courts and trails more than compensated the need for more bedroom space. We’ll be back again without a doubt.

G & M #1 Livermore Wine/ E-Bike Getaway (Pets ok)
Lori and Don raise the bar on how to welcome guests. This home away from home was warm and welcoming, gorgeously stocked with small kindnesses to ease in travelers showing up late. I loved seeing a small flock of sheep and goats graze the pasture behind the house in the early morning, and hearing the chickens cluck in the frontyard coop while getting some fresh morning air.

Gr8View-LrgDeck-BBQ-Spa-PoolTable-2xOven-Sleeps12
My family and I spent Christmas and New Year's at Justin's place, enjoying his beautiful decorated tree, thoughtful gifts, and delicious cake from a well known bakery and the stunning views of the mountains and city lights, including a firework show from the city. Justin‘s house is just big enough that we all have our own personal space but cozy enough that as a family we were all together.
Family- and pet-friendly home rentals

Comfortable Whole Home on two house lot
This was perfect for our specific needs. Wrich is a fabulous and responsive host. Friendly and helpful! Enjoyed our stay and the whole process was very easy to navigate. No complaints!

Modern, Clean, & Private in Silicon Valley
We stayed here for a month, and it was a great experience overall! What really stood out was Michael’s kindness and attentiveness - he was incredibly helpful, friendly, and welcoming. He provided lots of essentials for our toddler and even replaced the shower head, which made a huge difference for our extended stay. He was always quick to respond, sent someone to fix things the same day, and restocked kitchen and bathroom essentials whenever needed. The place is in a quiet, safe neighborhood and was spotless - seriously, one of the cleanest Airbnbs we've stayed in! The kitchen is well-stocked, which was perfect since we cooked a lot. You do hear some noise from upstairs during the day, but they keep quiet at night, so it wasn’t an issue for us. Thanks again, Michael, for making our stay so comfortable!

Caboose in the redwoods just outside of Cupertino
What an incredible place to stay! Nestled in picture perfect redwoods, the caboose is a magical place. Pat has done such an incredible job turning it into a warm and comfortable place to stay - he has really thought of everything! Highly recommend

Charming Entire Los Gatos Saratoga House
What you see is what you get! This really is a Fairy Palace. The house is located in a VERY peaceful setting well off the street in the forest. If the house were located in a normal subdivision it might seem a bit "weird". But given it's remote location and charming landscaping it somehow makes sense :) Rezan is very responsive and helpful. The home is larger than the pictures suggest and is very clean and functional. It would be great for a family exploring the area or like me, a traveler looking for peace and quiet to do a bit of business. Only things I would point out are that Rezan actually lives in the apartment below. So you don't have the entire property to yourself. And, I'm not sure what the outdoor cameras see, but one of them is aimed right at the large living room window. So you can't help but feel eyes are on you. Other than that, everything was as advertised. Enjoy!

Cottage near dwntwn Palo Alto, Stanford, Face-book
This was a perfect place to decompress during a busy work trip. The space is beautiful, and the attached gym is such a nice treat! Everything was exactly as described, clean and lovely. I would definitely stay again!

Beach Cottage Near Coastal Trail & Ritz
Great location, walking distance to go watch the sunset from the bluff of the ocean. The house being at the end of the street was a plus. Home felt very private and you can hear the waves crashing…Both Guliz and Matt were very helpful and quick to respond to our needs.🥰 My partner is in a wheelchair, but easy to bump him up the one step into the house. Our lab loved the doggy friendly home and the large yard to play fetch! 🐶 We will be back~

Cottage - bedroom, living, bath and small kitchen
Vijeta and Meenu were wonderful hosts. We enjoyed staying in their beautiful suite and we had a lovely time while in the Campbell, Los Gatos area. It was a delight to stay with them. They were very helpful and very kind. We would love to come back again!

Stay Nestled in Ancient Redwoods in Silicon Valley
I hate to say how wonderful our stay was because then everyone will go and I might never be able to get another reservation. Rick and his wife Heather were amazing hosts, giving us space to do what we wanted but also being available if we needed anything. The apartment we stayed in was perfect for my 2 year old granddaughter and I to spend an amazing week exploring and having fun together. The property itself is amazing! I hope to go back sometime when I’m not with a toddler so I can explore further and spend more time amongst the beautiful trees. They had a wonderful play area that was perfect and the host, Heather, pointed out that there were some extra toys in the apartment that would be perfect, and she was correct. We have family nearby and I don’t want to stay anywhere else when we visit again. They had reasonable requests for us given the location of the property but didn’t have huge expectations for check out. Their place is amazing and I can’t wait to go back. Seriously.
Family-friendly home rentals with a pool

Impressive Exec. Luxury Home, Pool & SPA, Central
Everything was perfect the house was amazing with its pool and hot tub… Everything mentioned was there but unfortunately the Air-conditioning wasn’t available for the first floor and the fans in the rooms where not enough for cooling. Lastly, Rahel the host was very welcoming and we had an easy check-in. Great communication she was very responsive to our notes…

Silicon Valley Executive home in Santa Clara
Beautiful home; comfortable and cozy. Walter was very responsive and answered all of our questions. Everything we needed was provided. Thoroughly enjoyed our stay and would highly recommend it to anyone looking.

Mission style, w. Pool, Hot tub, walk to downtown
We stayed at Sara's while visiting family nearby, but her home felt like a vacation in itself. The backyard is magical - we spent a fair amount of time there, swimming, grilling/dining, reading/napping. The backyard (and its myriad diversions) even lured our tech-obsessed teenagers away from their devices for extended periods. Everything was well maintained, no detail overlooked. We also enjoyed the access to a peloton bike and workout equipment. The interior was clean, organized, stylish but comfortable. The sunroom and small courtyard off of the bedrooms were great for yoga or stealing a quiet moment with a cup of coffee or book. Sara was responsive and attentive. Instruction booklet was clear and helpful. The stay exceeded our expectations. We hope to be back.

Magical Huckleberry Woods Sanctuary w/Pool and Spa
EJ and Nancy have such a lovely property. We easily felt we had our own space. You can tell that they've been doing this for years, and have a great way of making everything comfortable for guests. Our two kids had space to spread out, the playground is not directly next to the front door of the apartment, but you can see it through the yard's trees & hear them more or less within ear shot. Kitchen was amply supplied and set up, & there are plenty of storage spaces and creature comforts to make the stay feel like home. Beds were comfortable & clean, super comfortable pillows. The unit itself doesn't get a ton of natural light, but to be expected in redwoods. The hosts were incredibly friendly, welcoming, and helpful, we had a nice time chatting with them. Wonderful hosts, they felt like family. Their little dog is so so sweet and friendly as well, my kids loved the dog. Great location, easy to get to surrounding areas and Santa Cruz proper. Would return!

A private hillside suite nestled among oaks
A perfect stay for professionals. Vara’s place is cozy, peaceful, and tucked away in the beautiful Los Altos Hills - far from the noise yet still conveniently located. The space was clean, comfortable, and had everything I needed for a relaxing stay. Waking up to the quiet surroundings and fresh air was a great way to start the day. Vara was a wonderful host, responsive and welcoming. Highly recommend for anyone looking for a quiet retreat!

2 BR/2 full bath Modern Santana Row Condo sleeps 6
Great location on Santana Row with cafes and restaurants within a short walk. We only used the kitchen for breakfast. It was suitable for other meals, too. The two BRs and two BAs were useful. Note that the 3rd bed is upstairs next to the master. We enjoyed relaxing on the couch and watching TV.

Serene, Large 4BR/2.5BA Home in San Jose
all great accept there were only one trash bag... I had buy some trash bag.. and need to upgrade fry pan. we couldn't do egg fry due to stuck on the pan. other than that need little touch up with paints... hahaha 😆 😂 Great location and great house...

Private & clean STUDIO 580/680 Tri-Valley
If I could give a rating of 6 stars, I would. This is my go-place when I have to be in the Bay Area.....if it is available. Peaceful is amazing to work with. It has a great location, gated parking, very comfortable bed and more
Quick stats about vacation rentals that are family-friendly in Cupertino
Total rentals
130 properties
Nightly prices starting at
$55 CAD before taxes and fees
Total number of reviews
3.5K 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
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- Golden Gate Park
- Monterey Bay Aquarium
- Stanford University
- Washington Square
- Capitola State Beach
- Sumner Beach
- Joaquin Miller Park
- Children’S Fairyland
- Corcoran Beach
- Muir Woods National Monument
- Oracle Park
- Golden Gate Bridge
- El Granada Beach
- Surfers Beach
- The Forest of Nisene Marks State Park
- Glen Canyon Park
- Big Basin Redwoods State Park
- SAP Center
- Mission Dolores Park
- Oakland Zoo
- California’S Great America
- Henry Cowell Redwoods State Park
- Pacifica State Beach
- Painted Ladies