
Guesthouse vacation rentals in San Mateo
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Top-rated guesthouse rentals in San Mateo
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Popular amenities for San Mateo guesthouse rentals
Family-friendly guest house rentals

Farm in the city & sweeping bayview
I had a magic few days at Lori and Mike's. I drive a VW passat and I found the drive up the mountain to be non-challenging and even very fun by the end. The hosts are cool and easy to get along with. A+ doggo. Hot tub was great. Pool was fun. I usually stay in SF when I'm in the Bay Area. This was much more lovely and relaxing, with SF close enough that going in for dinner or a show felt like it wasn't a big deal. 100% would recommend this place. I brought my cat and had my lady friend with me for a night. Everyone loved it.

Stand-alone cottage in garden setting, parking.
Very friendly and proactive host. Praceful and quiet location. Several pieces of lovely fruit were provided, as well as flavored sparkling water, milk, and granola/muesli, which was really convenient. Showerhead can be adjusted for angle and whether you want a straighter stream straight down, or a wider spray. I appreciated that there was a screen on the window so it was easy to get fresh air when I wanted while keeping bugs out. I suggest trying to time your arrival the first day during daylight hours, as that will make it easier to see the signs, especially when Google Maps is off by a few yards in terms of where it tells you to turn.

Eco-Cottage Sanctuary in Garden Oasis
Lovely cottage in a lush backyard urban garden, goats and chickens included. Relaxing nighttime water babbling. Lots of great little details in the cottage. Claw foot tub shower, tidy kitchen, quartersawn redwood surfaces, sleeping spaces just right for my family and me. Super cool loft over kitchen, daybed surrounded by windows, easy to use folding sofa.

Greenwood Guest House, a Peaceful Oasis
The lodging is in the back, in a garden and near the swimming pool and tennis court. The backdrop is beautiful, and the host and hostess were friendly and accommodating. There is privacy and the area offers much in terms of restaurants and shopping. The internet is broadband, so one can work in the lodging. Amy and Lou are wonderful people----worthy of friendship in any circumstance.

Little Cottage on the Hill
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.

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!

Backyard Beach House (BBH)
Barbara and her Backyard Beach House were wonderful. Best stocked Air B & B we've ever stayed at. Clean, comfortable, and relaxing. Especially convenient for us because we were visiting family a mile away. We'll definitely stay again. Thanks!

Modern 2Bed/1Bath suite in San Jose
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.
Guest house rentals with a patio

Newly built stylish guesthouse
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.

Private garden retreat
Cozy apartment with immaculate and comfortable living space--perfect for a couple. Bonus is the beautifully landscaped enclosed backyard space with a courtyard in front of the apartment. The kitchen is thoughtfully equipped and fully functional. Short walk to local restaurants and shopping. Mary Lee was a friendly, flexible and responsive host, who even before we booked went out of her way to clock the distance between the apartment and our son's home which was much appreciated. Great place, great host, great experience--highly recommend!.

Delightful Hideaway in San Carlos
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.

Garden Cottage w/ Hot Tub • 3 mi. to SJC
I stay here whenever I'm in town absolutely my fav. Host is amazing and love her house! Thanks, Taylor!!

Sausalito Garden Stay
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!!

1-bedroom guesthouse w/ full kitchen near DTSJ/SAP
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 Creole Cottage
This is our fourth stay at Creole Place. Both Susan and her husband Gerald are very accommodating, kind, and responsive in every way without ever interfering in any way. The quiet location is easily accessed plus it is a quick walk to Safeway, CVS, and shops and restaurants at Red Hill Shopping Center. Our grandson has stayed with us and loves visiting. There is a beautiful very large screen TV with multiple kid friendly programs. A park with a ball diamond and playground, and a nice hill for exploration are both close by. Nice restaurants close by, but I really also enjoy cooking in the lovely kitchen. We celebrated Christmas** here with our family, and have made reservations to return to Creole Cottage in late April. **We were not able to find Christmas wrapping paper (last minute gifts) and the stores were SOLD OUT. I ran into Susan and mentioned going back to get bags when I really wanted/needed paper. She was there in 5 minutes with her wrapping paper.♥️

Entire guesthouse Santa Clara smart lock entrance.
Fabulous! Darling little studio ADU. Sparking clean and beautifully appointed. Loved staying here and will again.
Guest house rentals with a washer and dryer

Evergreen Valley Hillside retreat
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!

Adorable renovated guest cottage near downtown
First off I want to publicly say Thank Betsey for everything!! Great location, easy freeway access. Very close to downtown for restaurants and entertainment. For extended stays it is the best!!

TheStudio in Willow Glen (San Jose) CA-95125
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!

Easy commute Private guest suite
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.

Private Entry Adorable 1 bed 1 bath
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!!

Tranquil and Charming 1-Bedroom Guest house w/bath
Very nice to find a affordable place to stay With my schnauzer Winston. He is a low impact dog (doesn't shed, well behaved), but most charge more regardless. The local area has lots of places open late, which turned out a boon for me as I work as a stage manager and get home after 10p. Many thanks Margret and David!

Mission Casita, Walking Distance to DT San Rafael
We stayed at Matthew's place for 2 weeks and had a great stay. We highly recommend it to anyone visiting Marin! The location is incredibly convenient—right off the highway in central Marin—making it easy to explore the area. The house felt spacious for our family of 4 and everyone had enough room to work & relax. The kitchen was fully stocked and both the bedrooms & bathrooms were clean and comfortable. It's a well-maintained home so we had no complaints. Matthew and Tim were always available if we had questions and we highly recommend their house to anyone!

Convenient 3 bedroom guest house near SFO, highway
A group of us stayed here for a wedding and it was an amazing house. Highly recommended!
Quick stats about guesthouse rentals in San Mateo
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
Total number of reviews
2.1K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Santa Cruz Beach
- Capitola Beach
- Rio Del Mar Beach
- Seacliff State Beach
- Golden Gate Park
- Stanford University
- Twin Peaks
- Oracle Park
- Washington Square
- Davenport Beach
- Bolinas Beach
- Montara State Beach
- Twin Lakes State Beach
- Pescadero State Beach
- Rodeo Beach
- Capitola State Beach
- New Brighton State Beach
- Rockaway Beach
- Bonny Doon Beach
- China Beach, San Francisco
- Black Sands Beach
- Sumner Beach
- Drakes Beach
- Joaquin Miller Park