Guesthouse vacation rentals in Woodside

This beautiful Oakland Oasis was better than I imagined it would be! This place exceeded my expectations! Coming through the gate the first night, to a path of twinkling lights leading us to our adorable cabin took my breath away! It was the perfect location for peace and quiet right in the middle of Oakland. My only regret is that I didn’t spend more time on the property. We flew in from out of state to visit friends and spent a lot of time out and about. I definitely want to come back to spend more time hanging out in the backyard with the goats and chickens. My 13-year-old loved the backyard, the trampoline and the animals. The location was very walkable and within several blocks of many restaurants and shops. We rented a car and street parking was easily accessible. Reinhardt Redwood Regional Park was only an 8 minute drive away and we spent most mornings walking through the mountains enjoying the beautiful trees and views of San Francisco. Highly recommend this listing!

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!

This was an EXCELLENT Airbnb. Great value, beautiful property, plenty of privacy, exceptionally good instructions form the hosts. I can not recommend highly enough. Great place to recharge.

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!

Ray’s place is like a home away from home tor us and we appreciate especially his accommodating change that arose this trip - quiet house, convenient location, and everything we needed.

great ADU for a week long work trip! I was a solo traveler and the place was perfect for me. in a really cute neighborhood and felt completely safe the entire time. would definitely book this spot again!

Heidi's Casaluna is very nice! It was the perfect place for my weekend stay, peaceful with little distractions. The room opened up to a lovely back yard area with a garden and table and chairs. The bed was comfortable, the couch was a nice reading spot, and while the heaters did not blow, they were great at helping keep the room at the right temperature. Also of note, I was really happy with how calm and quiet the neighborhood felt day and night.

Kate’s place was great for our family of four while we visited San Francisco. The immediate area was clean and felt safe, and a variety of food and shops were within walkable distances. Access to the Caltrain was also close by. As for the house, it had everything our family needed but may be a bit tight for groups larger than 4, especially if they are all adults. Amenities were as listed and made the stay comfortable. Kate and Toni were responsive very quickly and helped us with everything we needed. Highly recommend!

Super cute place! Our kids loved the ducks and horses across the street. They couldn’t wait to explore! The house is very well stocked- games, kids toys, cookware, laundry soap… everything you can think of! We had a really great time, and it’s such a unique place to get to stay!

The host had a beautiful place and was quick to answer any questions we had. Would recommend to anyone staying in the San Jose area.

Marilynn has been great and very responsive when we have stayed there. The place is well-stocked and maintained, and San Carlos is a friendly town with good restaurants and boutique shopping.

This place was so beautiful, the pictures didn’t do it justice. Perfect location close enough to restaurants, and lil shops!! Just away enough out of the city, but not to far out. Would definitely recommend to anyone wanting a nice cozy easy place to get to. Also my wife’s 50th birthday and I asked him to do something special for her birthday and he put out a birthday banner and a bottle of champagne!!

We felt right at home in this cozy Air bnb. The garden areas surrounding the property are beautiful. We had everything we needed and more in the kitchen where we made breakfast every morning. Lots of cookware and cabinet full of spices. Super clean. Bed was comfortable. Walking distance to downtown San Carlos was about 23 minutes. The host checked in regularly with us online and we appreciated the attention. Was sad to leave when our time was up. We hope to return as we have family in the area.

This is an absolute hidden gem. It quickly became apparent why Carolyn is a super host. Not only is the property absolute perfection but Carolyn made it a point to go out of her way to welcome us, accommodate us, and go above and beyond customer service wise. This property radiates harmonious zen like energy from the community library, to its amenities and all its extra additives, to the garden. It’s graced with every bit of detail for guests to enjoy. I’ve loved traveling and have mostly been a hotel snob, until now. In short, Carolyn has carefully crafted a beautiful get away and decided to share it with the world. We will certainly be back when in town.

This place was spotless, and was a nice, private unit with a view of their beautiful garden. Instructions that were given were very detailed and easy to follow, and even had videos where applicable that were helpful. The area is quiet and peaceful, but still very convenient for getting around in San Jose.

The place was great exactly as shown on the pictures. I will say that in my car (thats is very low to the ground) struggled a little at the entrance/exit part of the air bnb so id recomend a vehicle has average ground clearance. When i told the host about my concern though they quickly responded with multiple solutions for my problem. All in all super great place and great host.

We thoroughly enjoyed our stay! The space was clean, comfortable, and exactly as described. It had everything we needed for a relaxing and enjoyable visit. Christina and her family were extremely kind and helpful, check-in was seamless and communication was easy. We’d happily stay here again and would definitely recommend it to others! Thank you for having us!

Our stay at Kyle’s was lovely and easy! It was a perfect home base for our adventures in the nearby state parks. The chickens are very cute, but if you’re a light sleeper looking for quiet, you may hear them in the morning. The eggs are amazing and such a wonderful addition to a comfortable stay. We had everything we needed and then some! Would definitely stay again during a trip to the Santa Cruz area.

My grandpa and grandma stayed here and they said this was the best bead and breakfast they have experienced in their life. huge thanks to Silvia for being responsive and making my grandparents feel at home!

Helen's place is roomy with a well-equipped kitchen and a nice bathroom. The dishwasher and washer/dryer provided added convenience. The location is just off busy Woodside Road with a Safeway market about 5 minutes away on foot.

Highly recommend. Central to the Bay Area and major freeways. Clean and quiet. Easy access and private parking. Everything was perfect. This is my second time staying and will be staying again! Thank you!!

Amazing stay at this cozy cabin by the sea. We enjoyed sitting on the balcony and listening to the sound of waves. The place is incredibly well-stocked with everything we needed — from kitchen supplies to dog blankets and groceries. Thank you!

Our stay was excellent. The place was very clean and well-maintained. Communication with the host was quick, and they were always available for any questions or recommendations. I would definitely recommend this place to other travelers and would stay here again in the future.

This was my second stay here with my dog and it was as great as the first time! David and Margaret are wonderful hosts.