Family-friendly holiday rentals in Cupertino

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.

Had a great and comfortable visit! Very quiet with a private entrance. Close to downtown in a great neighborhood. Friendly hosts. Definitely will stay here again in the future!

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

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.

A lovely property to relax in and enjoy. Just what we needed after doing all the sightseeing in the first part of the holiday

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.

During my stay at Joann’s place, I felt safe and very comfortable. The whole home is bright and spotlessly clean, with greenery visible outside the windows. Parking was very convenient, and communication with her was smooth throughout. The kitchen was fully equipped, allowing me to cook and enjoy a good glass of red wine. The sofa was cozy and the bed was spacious. I was pleasantly surprised to find such a wonderful place—thank you!

The Aerie is definitely a hidden gem, we had such a relaxing time. I didn’t even realize a spot like this was available and affordable in Oakland. It was definitely worth hiking up those 108 stairs. Im definitely coming back!

Close to San Jose Convention center, so it was super simple to get to the events nearby and if I needed to stop by the Airbnb to grab anything it was easy to head there and back. Every amenity I could need was there, and overall a very lovely stay.

⸻ I had such a wonderful two-week stay at the farm. From the moment I arrived, everyone was incredibly friendly—especially the sweet little black cat named Teva, who wore a green collar and quickly became a favorite companion. Toni was so kind and responsive, always making sure everything was just right. The farm felt very safe and peaceful throughout my stay. Being in a cabin on a farm, a few bugs are to be expected, but it wasn’t an issue—I came prepared with essential oils, which worked well to keep them at bay. The cabin itself is cozy and compact, but the many windows let in so much natural light that it felt bright and open. The shower was great too—good water pressure and ventilation, though it might be a bit snug for some. Overall, it’s a lovely little escape—close enough to San Jose for convenience, but with a feeling of peaceful seclusion that makes it feel like a true retreat.

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!

We really enjoyed our time at Rezan's place! It allowed us to experience peaceful holidays in a stunning environment rich in nature. Rezan and her sister, Nazan, were really friendly and always ready to help whenever we needed support. We are deeply grateful for all that you have done, Rezan and Nazan – we look forward to seeing you again!

This was the absolute perfect place for my family to stay while in SF. Kimberly and her husband were both so friendly and great to work with. We had a slight issue with fobs but it was taken care of quickly and easily. The location was wonderful with lots to do but not too noisy. Kimberly provided everything we could've wanted which made us feel right at home.

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!

Very cute and homey space, the beds were very comfortable. Thanks!

Very comfortable place for our family. Lots of space. Was great to have 3 full bathrooms. Loved spending time on the patio. Place was equipped with everything we needed. Only thing to be aware of if you need a very quiet place to sleep is that, given that you are in Santana Row, it can sometimes be loud at night. The owners gave very detailed instructions which made the check in process easy.

A recent stay at Robert’s home in Ben Lomond was exceptional. The property felt like home from the pictures on the wall to the books in the bookcase. The fully equipped kitchen, comfortable beds and toiletries was like walking into our personal family vacation home with everything clean and organized. Upon our arrival, we contacted the owner to let them know we arrived. We enjoyed a welcoming orientation of the property. The location was ideal with convenient access to stores and restaurants. We could not have selected a better place to enjoy quality family time and celebrate a graduation from UC Santa Cruz. This was a super stay and gets our highest recommendation.

I half expected to see Jay Gatsby on the balcony when I pulled in. Instead I found Lou very welcoming. The location is convenient to Santa Cruz and Los Gatos. Very peaceful.

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…

Sara and Nic were gracious and very responsive hosts. Their home is spacious, clean, comfortable, and suited our needs perfectly. The outdoor space also looked wonderful but we didn't use it much because our visit was during winter.

it's a wonderful house and the location is great too! walk to shops, parks, playground....etc also they provided lots of toys and kid books, my kids were so happy stay in there. Walter was really helpful and easy to communicate with.

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!

As expected, a gorgeous place. Location is great—right across the Tesla shop, walking distance to everywhere in Santana Row. Highly recommended.

Phu and the other hosts were amazing and kind. They accommodated us in every way that was possible. The house was spacious and felt safe, mainly because the neighborhood was filled with friendly people! We had some trouble with our flights (as most people can with flying and traveling), but Phu and the other hosts constantly communicated with us when possible. We requested a rice cooker because we wanted to potentially save on our trip by cooking homemade meals. Although we didn’t use it, they delivered one to the house. I felt so comfortable being in the house. Now, if you were to stay, I have to say that because the house is so well lit with new LED lights and other technology, some of my family had a hard time telling if the lights were turned off completely. Some of the light switches didn't seem to have a purpose. But they had so many pros that outweighed the minor cons. Instructions were clear and easy!