Family-friendly holiday rentals in Woodside

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…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

We loved this home. The area was great and near everything and the street was nice and quiet for the area. The home was immaculate, the care to maintain this home is obvious! Next time we are in San Francisco, this will be our first choice for lodging.

Quiet, peaceful, beautiful garden, responsive host, ample street parking. Definitely worth the price. Plus there's a hot tub you can use after the end of a long day or before the start of one like how we used. MINUTES away from bars, restaurants, and shopping in Oakland. Great location. Thank you so much for the comfortable stay!

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.

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.

Home is filled with everything you need, beds are comfortable, neighborhood is adorable, and it was fun to put bits and pieces of information together about our hosts from what they had displayed in their home (books, mementos, family photos). It feels like you’re welcomed into a shared space and someone’s home not just some perfectly polished and stale Airbnb. The high ceilings, hot tub, and bathroom made our stay feel luxurious. Thanks so much!

Charming and peaceful getaway. Enjoyed soaking in the hot tub, walking around the neighborhood, petting the cats, even being offered some Meyer lemons for my dinner. Very comfy bed, too! Just what I needed. Grateful for the respite.

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!

overall we really liked ramils place. it is very spacious and we loved sitting out on the front porch while the kids enjoyed drawing with chalk on the sidewalk. it was in walking distance to lots of great things including a great little coffee shop (lazy bird) and a playground. they had lots of amenities for people with kids including a stroller for us to use for longer walks. parking was really easy. the kitchen is huge and was a nice place to drink our coffee while the kids ate breakfast. kitchen was decently stocked but we ate out most nights. the only downside was the noise from upstairs. towards the end we were used to it but the first few days it woke us up/surprised us and felt very bothersome. however, I think we would stay here again despite that (and I'm sure we were plenty loud downstairs too). ideally there would be no upstairs noise but for the size, comfort and cost of this Airbnb I'd say it's worth it.

Nancy's place was beautiful and perfect for a family vacation! She was very communicative, providing recommendations for local eats, and very responsive whenever we needed help with anything. Her home is very comfortable with lots of amenities (tea, coffee, snacks, water bottles) and a fully stocked kitchen. The home is in a peaceful neighborhood and nearby to lots of restaurants. A wonderful stay overall!

The house is in a great location and perfectly suited for a relaxing visit to the area. Great walks right out the front door and downtown Half Moon Bay is a quick drive or even a walk.

I enjoyed my time at Audrey’s place. They are centrally located and the backyard is a beautiful place to work or unwind. Audrey, Jordie, and the pups were very friendly and hospitable. I would highly recommend their place for any guest visiting Oakland.

I stayed here for a month and it was great, I highly recommend! As described and seen in the pictures. Annie was helpful and ensured I had everything I needed. I think this apartment is perfect for 1-2 people with a child or small/medium-sized pet. Clean and cozy with nice, warm lighting. The bed was comfy, kitchen was small but well-equipped, living room was roomy with a medium-sized couch, and bathroom more than sufficient. I loved relaxing on the deck as well! The neighborhood is hilly and beautiful, close to bus/ferry/restaurants/stores. Touristy downtown, but not as much in the immediate vicinity. I walked A LOT with my dog and enjoyed it, but the hills can be steep! Definitely a very safe area. The only “con” is, in my opinion, it’s just a bit expensive for the size. However, I understand it’s in a pretty wealthy neighborhood and am sure Airbnb fees/taxes account for a decent part of the cost. Suffice to say, this is a once-in-a-long-while stay for me. Hopefully that’s fair.

I was in Danville to visit friends. I had time and easy opportunity to walk Iron Horse trail out their back gate to the downtown area and to enjoy the shops, restaurants and ambiance. The area is desirable for so many reasons and John's home and guest house is another pleasant part of that attraction. Thanks.

It was the perfect place for our family to gather over the holidays. Cozy but spacious with that back cottage providing a separate space for separate couple.

Amy's place was wonderful - one of the few places we've ever stayed that was even better in person than in pictures. It was clean, spacious, and very comfortable for the 2 of us. The outdoor space was amazing, plenty of quiet spaces to lounge in the sun and walk around. The area was great as well, quiet but close to downtown, and Amy was a thoughtful and responsive host, we really appreciated her thoughtfulness. The one thing to note is that the Wi-fi could be unreliable - we both worked from the Airbnb, and made it work for the week, but something to note for future visitors. We'd definitely recommend this place and plan to come back next time we visit. Thank you Amy!

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.

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.

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.

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...

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

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.

This place is such a gem that I’m inclined to be selfish and not tell everyone about it! Modern appliances, close to grocery and mass department, clean and recently renovated. Very happy and will book this again!!