Guesthouse vacation rentals in San Mateo

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Popular amenities for San Mateo guesthouse rentals

Family-friendly guest house rentals

Superhost
A full moon illuminates the night sky over the bay, casting a soft glow on the water below. The view captures the city lights and distant mountains, along with the silhouette of a bridge spanning the bay, creating a serene nighttime landscape.
Guesthouse in San Rafael
4.84 out of 5 average rating, 164 reviews

Farm in the city & sweeping bayview

JesseRating, 5 stars1 week ago
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.
Top guest favorite
The exterior of a detached guesthouse is showcased, featuring rustic brick walls and large glass doors that invite natural light. A few potted plants are placed near the entrance, which includes a small set of steps leading up to the door.
Guesthouse in Kensington
4.99 out of 5 average rating, 335 reviews

Stand-alone cottage in garden setting, parking.

AnnaRating, 5 stars2 weeks ago
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.
Guest favorite
A sunlit dining area features a wooden table surrounded by six chairs, providing ample space for gatherings. Large windows allow natural light to flow in, creating a bright ambiance. A cozy sitting area with cushions is situated beside the windows, offering a comfortable spot to relax.
Guesthouse in Oakland
4.93 out of 5 average rating, 230 reviews

Eco-Cottage Sanctuary in Garden Oasis

PatrickRating, 5 stars1 month ago
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.
Guest favorite
A sunlit corner showcases a decorative chair draped with a soft green throw. A small black table holds a vase with fresh flowers. Light flows through large glass doors, leading to a deck surrounded by greenery.
Guesthouse in Monte Sereno
4.9 out of 5 average rating, 208 reviews

Greenwood Guest House, a Peaceful Oasis

RobertRating, 5 stars1 month ago
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.
Top guest favorite
A kitchenette is featured with white countertops and wooden cabinets. A coffee maker, toaster, and microwave are visible alongside a sink, while a poster of the Rolling Stones decorates the wall. Natural light enters through a window fitted with a floral curtain, showcasing greenery outside.
Guesthouse in Hillsborough
4.95 out of 5 average rating, 908 reviews

Little Cottage on the Hill

IanRating, 5 stars2 weeks ago
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.
Guest favorite
The exterior of the guest house features a modern gray facade with the number '440' displayed prominently. A green succulent plant in a white pot adds a touch of greenery beside a paved patio area, leading towards a wooden fence and lush landscaping in the background.
Guesthouse in Menlo Park
4.97 out of 5 average rating, 150 reviews

Cottage near dwntwn Palo Alto, Stanford, Face-book

LanieRating, 5 stars4 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 favorite
The exterior of the house is shown with a pink surfboard leaning against the wall. Bright green foliage frames the image, contrasting against the house's neutral-colored walls and multiple windows that allow natural light to enter.
Guesthouse in Concord
4.96 out of 5 average rating, 168 reviews

Backyard Beach House (BBH)

LeeRating, 5 stars1 week ago
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!
Superhost
A living area features a black leather sofa adorned with colorful cushions and a wooden coffee table with a bowl of green apples. Natural light enters through large windows, while a laundry machine is visible near the kitchen area, complemented by a dining table set for four.
Guesthouse in Willow Glen
4.87 out of 5 average rating, 172 reviews

Modern 2Bed/1Bath suite in San Jose

RuthRating, 5 stars2 months ago
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

Guest favorite
A bright living area features a dark leather sofa adorned with decorative pillows, accompanied by a wooden coffee table. A small table with two chairs is positioned beside a large window, allowing natural light to illuminate the space. A floor lamp and decorative plant enhance the room's inviting feel.
Guesthouse in San Jose
4.94 out of 5 average rating, 130 reviews

Newly built stylish guesthouse

BrettRating, 5 stars2 weeks ago
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.
Top guest favorite
A private outdoor patio features two white lounge chairs and a table with four black metal chairs, all arranged among lush greenery and colorful plants. A large green umbrella provides shade, creating a serene space for relaxation or dining.
Guesthouse in Point Richmond
4.98 out of 5 average rating, 114 reviews

Private garden retreat

JudyRating, 5 stars2 days ago
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!.
Top guest favorite
A spacious deck features two wooden directors' chairs positioned around a small circular table. Lush greenery lines the perimeter, creating a natural backdrop. A sunshade is partially visible, offering protection from the sunlight.
Guesthouse in San Carlos
4.99 out of 5 average rating, 100 reviews

Delightful Hideaway in San Carlos

ThomasRating, 5 stars2 weeks ago
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.
Top guest favorite
A modern outdoor patio area features a stone-paved surface surrounded by neatly trimmed bushes and potted plants. A large round table with multiple chairs is situated in the center. In the background, a guesthouse and additional outdoor features can be observed.
Guesthouse in Rose Garden
4.96 out of 5 average rating, 112 reviews

Garden Cottage w/ Hot Tub • 3 mi. to SJC

ChristinaRating, 5 stars1 month ago
I stay here whenever I'm in town absolutely my fav. Host is amazing and love her house! Thanks, Taylor!!
Superhost
A serene garden setting is presented, featuring a wooden seating arrangement surrounded by lush greenery and vibrant flowers. A pathway leads through the gravel, while a multi-level structure is partially visible in the background, blending harmoniously with the natural surroundings.
Guesthouse in Sausalito
4.87 out of 5 average rating, 123 reviews

Sausalito Garden Stay

CynthiaRating, 5 stars2 weeks ago
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!!
Top guest favorite
A view from the window features a small outdoor table with a round, stone top, surrounded by greenery. The backyard is lined with plants and includes a path leading to a wooden fence, providing a sense of privacy.
Guesthouse in San Jose
4.99 out of 5 average rating, 169 reviews

1-bedroom guesthouse w/ full kitchen near DTSJ/SAP

GraceRating, 5 stars1 week ago
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.
Top guest favorite
Guesthouse in San Anselmo
4.97 out of 5 average rating, 102 reviews

The Creole Cottage

SuzanneRating, 5 stars4 months ago
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.♥️
Guest favorite
A cozy guestroom features a spacious bed covered with a vibrant teal bedspread. A white kitchenette is visible, equipped with essential appliances, while a small dining area is present nearby. Natural light filters through sheer curtains, illuminating the modern decor.
Guesthouse in Santa Clara
4.92 out of 5 average rating, 144 reviews

Entire guesthouse Santa Clara smart lock entrance.

KatrinaRating, 5 stars1 month ago
Fabulous! Darling little studio ADU. Sparking clean and beautifully appointed. Loved staying here and will again.

Guest house rentals with a washer and dryer

Guest favorite
The guesthouse entrance is framed by a neatly landscaped area, featuring a spacious path made of stone tiles leading to the front door. Elegant wrought iron railings and manicured greenery enhance the inviting setting under clear blue skies.
Guesthouse in Evergreen
4.92 out of 5 average rating, 309 reviews

Evergreen Valley Hillside retreat

RizwanRating, 5 stars5 days ago
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!
Top guest favorite
A well-maintained cottage is showcased with a welcoming front porch and a bright red door. A concrete path leads from the sidewalk to the entrance, flanked by manicured lawns and trees providing shade. Numerous windows allow natural light to fill the interior.
Guesthouse in Morgan Hill
5 out of 5 average rating, 17 reviews

Adorable renovated guest cottage near downtown

PaulRating, 5 stars2 months ago
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!!
Top guest favorite
The exterior of the studio is framed by a stone facade, featuring large glass doors that open to reveal a cozy interior. Plush seating and a dining table are visible inside, with the gourmet kitchen in the background. Natural light brightens the space, enhanced by the greenery outside.
Guesthouse in Willow Glen
4.99 out of 5 average rating, 200 reviews

TheStudio in Willow Glen (San Jose) CA-95125

CalebRating, 5 stars2 weeks ago
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!
Guest favorite
The exterior of the home showcases a welcoming entrance with a covered porch and a set of wooden stairs leading to the front door. Vibrant flowers in various colors line the path and the yard, surrounded by a wooden fence and green foliage.
Guesthouse in Redwood City
4.96 out of 5 average rating, 24 reviews

Easy commute Private guest suite

ArthurRating, 5 stars2 months ago
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.
Guest favorite
Guesthouse in Campbell
4.93 out of 5 average rating, 164 reviews

Private Entry Adorable 1 bed 1 bath

ChristineRating, 5 stars5 days ago
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!!
Guest favorite
A spacious backyard is visible, featuring a manicured lawn with artificial turf and paved stepping stones arranged in a grid pattern. Several potted plants are placed near the building, with two decorative lamps standing amidst the greenery. The area is well-lit and inviting.
Guesthouse in Sunnyvale
4.89 out of 5 average rating, 260 reviews

Tranquil and Charming 1-Bedroom Guest house w/bath

GregRating, 5 stars3 days ago
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!
Guest favorite
The spacious living room features a large, dark blue sectional sofa with plush cushions, complemented by a wooden coffee table. A decorative area rug in neutral tones lies beneath, while large windows allow natural light to fill the space. A dining table for four and a modern electric wall fireplace add warmth.
Guesthouse in San Rafael
4.91 out of 5 average rating, 100 reviews

Mission Casita, Walking Distance to DT San Rafael

AnnieRating, 5 stars1 month ago
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!
Guest favorite
A contemporary kitchen area features warm wood cabinetry and sleek stainless steel appliances. A spacious countertop provides seating for two. Washing machine and dryer units are conveniently located beside the kitchen, contributing to the functional layout.
Guesthouse in South San Francisco
4.86 out of 5 average rating, 137 reviews

Convenient 3 bedroom guest house near SFO, highway

AreebaRating, 5 stars3 weeks ago
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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