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

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 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.
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 stars5 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!
Top Guest favourite
Guesthouse in Alameda
4.95 out of 5 average rating, 223 reviews

Cute, backyard Cottage w/ close access to all!

AlexRating, 5 stars1 week ago
Cozy, quiet atmosphere in a great location! The studio cottage is just the right size for one person, and probably no more than two. The little yard area is beautifully manicured and provides a tranquil setting when you walk in and out of the studio cottage. I instantly felt right at home. Alzira was kind enough to demonstrate how to lock the side gate behind me - and this after I knocked on her front door for help! (I'm not tech-savvy AT ALL, as I had to explain.) Alzira is not only friendly in person, but her text message communication was also extremely prompt and polite. I would stay here again and again.
Guest favourite
Guesthouse in Berkeley
4.94 out of 5 average rating, 481 reviews

Sunny studio near UCB

DavidRating, 5 stars1 week ago
It was a great stay. They have a beautiful property and garden. Berkley is a great walking city. It was fun to explore. This was my 2nd time to Berkeley, and my wife and kid's first. She loved the city. Thanks for a great stay.
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!
Guest favourite
Guesthouse in Palo Alto
4.96 out of 5 average rating, 125 reviews

Spacious cottage near downtown & Stanford with AC

FlaviaRating, 5 stars1 month ago
This is the third time we stay in Tracy's place, and it's always a great pleasure. The location is great, the house is very well equipped, clean and very comfortable. Tracy responds quickly to any messages and really makes us feel at home. Will keep coming back :)

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 stars6 days ago
Very clean, quiet neighborhood, and had everything we needed! Would be happy to stay again.
Guest favourite
Guesthouse in Downtown San Jose
4.96 out of 5 average rating, 104 reviews

Cozy Private 1B1B Cottage near Japantown

KathleenRating, 5 stars1 month ago
The cottage was absolutely beautiful! Very accommodating and very clean and quiet. Arthur was the perfect host! Our only issue was the parking. We were in San Jose for a church conference that took place off of 1st Street near 237. We wouldn't get back to the cottage until after 10 p.m. so had to park a block or so away both nights. But, it won't stop us from returning. We will be back for next year's conference. Thanks again Arthur!
Top Guest favourite
Guesthouse in Point Richmond
4.98 out of 5 average rating, 117 reviews

Private garden retreat

RayRating, 5 stars3 weeks ago
When we entered Mary Lee’s backyard where the unit is located, we were instantly pleased with how beautiful and well landscaped it is. The studio is well built, with attention to detail and the use of quality materials. The décor was also pleasant and well thought out. In addition, we were satisfied with the fact that they provide 100% cotton towels and linen for the bed. The kitchen was well stocked with stainless steel cookware and everything we needed. Mary Lee and her husband David were friendly and responsive to all our requests. We would be happy to stay at their place again.
Guest favourite
Guesthouse in Oakland
4.91 out of 5 average rating, 345 reviews

Guesthouse Garden Retreat

MadalynRating, 5 stars3 weeks ago
This was our first time staying in a guesthouse, and sharing a space with the owners, and I was completely blown away, we both felt right at home, so much so we didn’t wanna leave haha. Victor and Michelle gave us our privacy but also complete freedom to play music, relax on the patio, and roam around their absolutely beautiful backyard. We were able to come and go as we please and always know our things would be safe. The kitchen had everything you could need, the bed was extra comfy and the shower was a DREAM, the whole experience was incredibly cozy and peaceful. This was truly the best place we both have ever stayed, 1000% would recommend!!!
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 San Rafael
4.96 out of 5 average rating, 161 reviews

Hillside Oasis Btwn SF, Napa w/ Big Views + Pool!

EmmaRating, 5 stars5 days ago
The Casita in the Trees was the perfect getaway and Melodie and family were amazing hosts. The space has a very nice layout, the kitchen and other rooms are lovely with charming ambiance and thoughtfully stocked, you have everything you need and more. The soft morning birdsong was so pretty amongst the oak trees, the view is spectacular, and Melodie was such a thoughtful and kind host. I would absolutely recommend!

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 stars5 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 stars5 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 Portola Valley
4.94 out of 5 average rating, 202 reviews

Woodsy Silicon Valley Cottage

GregRating, 5 stars1 month ago
This is the ONLY home I will stay in when visiting my sister in Menlo Park. Beautiful setting, quiet, tastefully designed, responsive hosts 10/10!
Guest favourite
Guesthouse in Downtown San Jose
4.98 out of 5 average rating, 210 reviews

Private Abodu Guesthouse in Downtown San Jose

LouiseRating, 5 stars1 week ago
Excellent stay as always. Walkable distance into town. Lovely garden to chill out in. Flora always on hand to help out. I love her doggy Honey x
Top Guest favourite
Guesthouse in Albany
4.93 out of 5 average rating, 210 reviews

Cozy backyard cottage

ChristianRating, 5 stars5 days ago
This apartment has a lovely garden, which makes a stay very special. People should know that the apartment does not provide much space for cooking and clothes, especially for two guests, since it is just a tiny house. Raquel is very supportive, friendly, helps where she can very quickly and is flexible with the check-in and check-out times, which helped us a lot. It also great that a washer and dryer is included.
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 stars1 week 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 Sunnyvale
4.89 out of 5 average rating, 274 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

    $108 AUD 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