
Guesthouse holiday rentals in San Mateo
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Top-rated Guesthouses in San Mateo
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for San Mateo guesthouses
Family-Friendly guesthouses

82 “ Pool, Jacuzzi , HOT SAUNA, VIEWS, Newer ADU!
simply Laura's family are so wonderful hostess, beautiful persons and the house is very nice place, peaceful, beautiful and for my wife and I will be thinking to return again soon.

Coastal Cabin-outdoor Firepit near Trails & Harbor
Really cool and thoughtful garden Joshua and his dad built! We had a chill and relaxed stay. Also appreciated their recommendations for nearby cycling routes!

1 Bdr Cabana just west of Stanford
David’s place was well appointed, clean and thoughtfully furnished and organized. There were power strips with electrical outlets and USB ports wherever they might be needed — a nice touch. Coffee was plentiful and the kitchen well supplied. David and Goldie went out of their way to make us feel at home. We will definitely return.

Guest House in the Woods
Such a serene location! Nestled amongst the trees, this Airbnb will have you feeling like you’re a world away without being far from amenities at all. My husband and I enjoy staying here tremendously. The place was spotless and has everything you could need for a comfortable stay. Lea was one of the friendliest hosts I’ve ever come across and made us feel warm and welcomed. Can’t wait to visit again!

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!

Charming Cottage near Stanford in Lovely Garden
Julie and I had a wonderful time at Margaret and Phils. It was near a neighborhood I grew up. The accommodations were great, private cottage and beautiful gardens. They have a dog, Sadie, who was a delight. We hope to go back in the future.

Private cottage in a garden
Was a great option for close proximity to the Google campus which is where we needed to be. Neighborhood seemed to be safe and walkable. It’s evident they are very involved with the beautiful landscaping and gardening on/around the property therefore notable tree pollen/allergens during the spring time. Overall a cute, cozy, and darling stay!

Tree-top studio--walk to Stanford
The apartment is ideally located for visiting Stanford and is in a quiet neighborhood surrounded by trees and flowers, and lots of birds. The host is very friendly and responsive
Guesthouses with a patio

La Casita - a quiet studio, Crocker Amazon area!
Very clean, quiet neighborhood, and had everything we needed! Would be happy to stay again.

Guesthouse Garden Retreat
Overall, a very nice stay. Michelle was very responsive and quick to answer any questions I had. There was a bit of a hiccup but was all on our end and we enjoyed our stay there. Michelle and Victoria are very friendly and kind people.

Boho beach bungalow- walk to Poplar Beach
Our stay at this Airbnb was fantastic! The space is beautifully decorated, very clean, and thoughtfully equipped. One of the highlights was the bed, it even has a built-in massager, which was such a relaxing treat after a day of exploring. The kitchen is fully equipped with everything you need to cook or just enjoy a cozy night in. If you’re planning a trip to Half Moon Bay, make sure to stop by Sam’s Chowder House, it’s an absolute must. The food there is unbelievable! The only small issue we ran into was with the shower. The water tends to splash out, even reaching into the bedroom area. It wasn’t a deal-breaker for us, but just something to be aware of. Overall, we had a wonderful experience and would definitely come back. Highly recommend this place!

Berkeley Bitty House - a little bit of home
Eugenia’s place and Eugenia and her husband are fantastic… One of the most comfortable organic cotton beds I’ve ever slept on, the most enchanting, beautiful property, and every appliance state of the art, efficient and intentional with the touch of love. Eugenia brought me teas, and various unconventional items I asked for. And the natural light and airflow were wonderful. And very healing and the most peaceful and healing neighborhood I’ve stayed at in the East Bay. For anyone looking for a healing retreat, Book this place as soon as possible

Palo Alto Cottage: Privacy, Comfort & Convenience
Host was super friendly and responsive. Highly recommend!

Charming, modern, restorative, private studio
We loved our stay at Julie’s studio. It was such a beautiful space and perfect for our needs. The outdoor area is beautiful and the inside is cozy and so well put together. We enjoyed walking in the neighborhood to get delicious food. Would definitely stay again!

The Bathhouse: Boho Modern + Hot Tub + Water View
The bathhouse is incredible! I’m an Airbnb superhost of 2 properties and I’ve stayed in Airbnbs globally. This is one of the best Airbnbs I’ve stayed in! It’s gorgeous and serene. The jacuzzi under the redwood is incredible. It had everything I needed to feel right at home. I walked into the town of Mill Valley which is picturesque, has great shopping and amazing food. I highly recommend!

Redwood Cottage & Hot Tub
This was a sweet get away in the quiet redwoods and while the road to get there is a classic windy way, staying up in the trees was so beautiful and peaceful. I loved it! cute chickens who were unobtrusive and in general, a very peaceful experience close to many incredible outdoor adventures and the town of Felton with excellent cafes, health food stores and yoga!
Guest house rentals with a washing machine and dryer

Bicycle Shack @ La Honda Pottery
Stayed here for a weekend to attend a wedding. Devora was very helpful and friendly and made sure my stay was comfortable and seamless. The neighborhood is absolutely gorgeous and I found lots of things to do in the area. The space had everything I needed, couldn’t have asked for better hosts! 100% would come return.

Quaint Cottage Near Downtown Palo Alto
Charming cottage! Louis was a great host (didn’t get a chance to meet Jess!). The neighborhood is quiet and very peaceful! There’s a very nice private patio, great place to have your morning coffee and just relax

Stylish Spacious Seaside Retreat, Walking to Beach
We had a delightful stay here! It was a great location - easy to walk to the beach and drive downtown. The stay was comfortable, clean, and quiet.

Private Abodu Guesthouse in Downtown San Jose
Flora’s place was great for our recent visit to San Jose. The unit was lovely and well equipped with everything we needed. Floras was a wonderful host and provided clear instructions and assistance as needed. We would definitely stay there again.

Private unit close to Santa Clara University
This is our first Airbnb experience and we were glad we chose this place for our first stay. Rahil was a very-very responsive and kind host. We had a tiny bit of trouble first entering the property due to the locking system. I messaged Rahil and he quickly responded and fixed the lock and we were good to go for the rest of our stay. The place was spotless and very clean when we first entered. It is like having your own mini house with all the amenities you need even for a long stay. Everything was professional, instructions were clear, bed and sofa bed were comfortable. The area is super nice and private. It is like a 5 minute drive to Santana Row, Valley Fair Mall, and multiple restaurants. I had no problem keeping my car parked in front of the property and never felt like it was going to be a problem. Overall I would definitely recommend staying at this Airbnb and you are in good hands with Rahil.

Private Cottage near Redwood City and San Carlos Downtowns
Great experience in every way. Nico was response and friendly. Place was just as described. Would definitely stay again

16017-Private 2BR Guest Unit near HWY, BART & Mall
Great place to stay.

Tranquil and Charming 1-Bedroom Guest house w/bath
This place was a very cute and peaceful retreat from the daily grind. I only stayed one night but it was everything I needed and expected. Clean and with all the amenities, great stay and I’d stay here again!
Quick stats about guesthouse rentals in San Mateo
Total rentals
20 properties
Nightly prices starting at
$117 NZD before taxes and fees
Total number of reviews
2.1K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
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- Santa Cruz Beach
- Capitola Beach
- Rio Del Mar Beach
- Golden Gate Park
- Stanford University
- Oracle Park
- Seacliff State Beach
- Twin Peaks
- Bolinas Beach
- Davenport Beach
- Montara State Beach
- Pescadero State Beach
- Twin Lakes State Beach
- Capitola State Beach
- New Brighton State Beach
- Muir Woods National Monument
- Rodeo Beach
- Mission Dolores Park
- China Beach, San Francisco
- Rockaway Beach
- Bonny Doon Beach
- Sumner Beach
- Black Sands Beach
- Joaquin Miller Park