Guesthouse holiday rentals in San Mateo

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for San Mateo guesthouses

Family-Friendly guesthouses

Top Guest favourite
Guesthouse in Oakland
4.97 out of 5 average rating, 248 reviews

82 “ Pool, Jacuzzi , HOT SAUNA, VIEWS, Newer ADU!

MariaRating, 5 stars1 week ago
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.
Superhost
Guesthouse in Half Moon Bay
4.82 out of 5 average rating, 508 reviews

Coastal Cabin-outdoor Firepit near Trails & Harbor

JoannRating, 5 stars3 weeks ago
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!
Top Guest favourite
Guesthouse in Portola Valley
4.98 out of 5 average rating, 200 reviews

1 Bdr Cabana just west of Stanford

RickRating, 5 stars6 days ago
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.
Top Guest favourite
Guesthouse in Woodside
4.99 out of 5 average rating, 545 reviews

Guest House in the Woods

MaryRating, 5 stars3 weeks ago
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!
Guest favourite
Guesthouse in Menlo Park
4.97 out of 5 average rating, 150 reviews

Cottage near dwntwn Palo Alto, Stanford, Face-book

LanieRating, 5 stars6 months ago
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!
Top Guest favourite
Guesthouse in Atherton
5 out of 5 average rating, 209 reviews

Charming Cottage near Stanford in Lovely Garden

RobertRating, 5 stars1 week ago
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.
Guest favourite
Guesthouse in Sunnyvale
4.96 out of 5 average rating, 429 reviews

Private cottage in a garden

SukuntheaRating, 5 stars1 month ago
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!
Superhost
Guesthouse in Menlo Park
4.89 out of 5 average rating, 143 reviews

Tree-top studio--walk to Stanford

AlbertRating, 5 stars1 month ago
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

Top Guest favourite
Guesthouse in San Francisco
4.98 out of 5 average rating, 104 reviews

La Casita - a quiet studio, Crocker Amazon area!

AnthonyRating, 5 stars1 week ago
Very clean, quiet neighborhood, and had everything we needed! Would be happy to stay again.
Guest favourite
Guesthouse in Oakland
4.91 out of 5 average rating, 346 reviews

Guesthouse Garden Retreat

SangRating, 5 stars2 weeks ago
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.
Guest favourite
Guesthouse in Half Moon Bay
4.94 out of 5 average rating, 174 reviews

Boho beach bungalow- walk to Poplar Beach

MoeRating, 5 stars4 weeks ago
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!
Top Guest favourite
Guesthouse in Berkeley Hills
4.99 out of 5 average rating, 190 reviews

Berkeley Bitty House - a little bit of home

AaronRating, 5 stars2 weeks ago
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
Guest favourite
Guesthouse in Palo Alto
4.93 out of 5 average rating, 127 reviews

Palo Alto Cottage: Privacy, Comfort & Convenience

RuoyingRating, 5 stars1 week ago
Host was super friendly and responsive. Highly recommend!
Guest favourite
Guesthouse in Menlo Park
4.93 out of 5 average rating, 221 reviews

Charming, modern, restorative, private studio

ErinRating, 5 stars1 month ago
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!
Top Guest favourite
Guesthouse in Mill Valley
4.99 out of 5 average rating, 102 reviews

The Bathhouse: Boho Modern + Hot Tub + Water View

ShaunaRating, 5 stars1 week ago
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!
Guest favourite
Guesthouse in Felton
4.96 out of 5 average rating, 191 reviews

Redwood Cottage & Hot Tub

SarahRating, 5 stars1 week ago
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

Top Guest favourite
Guesthouse in La Honda
4.95 out of 5 average rating, 440 reviews

Bicycle Shack @ La Honda Pottery

YevgineRating, 5 stars6 days ago
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.
Top Guest favourite
Guesthouse in Menlo Park
4.99 out of 5 average rating, 131 reviews

Quaint Cottage Near Downtown Palo Alto

VivianRating, 5 stars6 days ago
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
Guest favourite
Guesthouse in Half Moon Bay
4.9 out of 5 average rating, 296 reviews

Stylish Spacious Seaside Retreat, Walking to Beach

SarahRating, 5 stars1 week ago
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.
Guest favourite
Guesthouse in Downtown San Jose
4.98 out of 5 average rating, 211 reviews

Private Abodu Guesthouse in Downtown San Jose

JohnRating, 5 starstoday
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.
Top Guest favourite
Guesthouse in San Jose
4.98 out of 5 average rating, 342 reviews

Private unit close to Santa Clara University

ShoaibRating, 5 stars2 weeks ago
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.
Top Guest favourite
Guesthouse in Redwood City
4.99 out of 5 average rating, 113 reviews

Private Cottage near Redwood City and San Carlos Downtowns

ShaneRating, 5 stars9 months ago
Great experience in every way. Nico was response and friendly. Place was just as described. Would definitely stay again
Guest favourite
Guesthouse in San Lorenzo
4.89 out of 5 average rating, 137 reviews

16017-Private 2BR Guest Unit near HWY, BART & Mall

DarioRating, 5 stars2 weeks ago
Great place to stay.
Guest favourite
Guesthouse in Sunnyvale
4.89 out of 5 average rating, 275 reviews

Tranquil and Charming 1-Bedroom Guest house w/bath

LillianRating, 5 stars1 week ago
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

Destinations to explore