
Guesthouse vacation rentals in San Mateo County
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in San Mateo County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for San Mateo County guesthouse rentals
Family-friendly guest house rentals

Cottage near downtown Palo Alto
Very quiet and well appointed suite, though personally I prefer cotton bed linens and a firmer mattress. Wished we had allowed time to enjoy the beautiful surroundings, and the swinging garden bench.

Near harbor & coastal trails-walk to Surfers beach
Small, cute, quite space. Great price for the location. Close to all Half Moon Bay and Pacifica has to offer! Close great restaurants, surfing and lots of nature. I didn't meet Shirley but I did meet Olive her dog, Husband and son. All very nice. I enjoyed my stay and would stay again!

Quiet , Private Studio / Cottage
Chris's place was spotless, comfortable, private and well equipped. Everything you might need and hope to find was available. The location is quiet and easily accessible from downtown Redwood City. We would definitely stay here again if space is available when we visit the area.

Simplistic Crocker Suite
Very good stay at Mai's, very nice comfortable accommodation and carefully decorated, the little extra is the Japanese garden which offers a nice view of the Californian hills. An hour from San Francisco by transport that is very easy to access and inexpensive, I recommend this listing for a couple or with a child.

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.

Elegant & Convenient RWC Studio
The place was convenient to stay, clean, quiet, and felt safe. The kitchen was much bigger than a typical in-law unit and pretty much equipped, so it made cooking convenient. The closet was big enough to stay for a month. Washer and dryer were right behind the unit, big enough, and not shared with others. Shower booth was a bit small, but that was ok. The place was easy to access and parking was always easy. Easy access to 101. Walking to the downtown redwood city took only a few minutes. Delivery was always done correctly, and I’ve never lost any package. The hosts were easy to reach out and very helpful.

Charming Cottage near Stanford in Lovely Garden
Margaret’s cozy little place was serene and warm. She herself was welcoming and responsive. Plenty of nice little touches, including Sasha the dog to greet you upon arrival. Well stocked and very comfortable. Peaceful and serene setting, not walkable to any business really, but perfect for my need for a little retreat at end of the day while my husband was at Stanford Hospital.

Spacious cottage near downtown & Stanford with AC
I was surprised when we arrived that the space was a converted Garage. I was a little worried when we drove up but the space is beautiful. They did an amazing job it was spacious , clean and safe. The neighborhood is peaceful and serene. My girls and I loved walking through the neighborhood in the mornings and evenings. Communication was great the host was very responsive.We will absolutely be staying here again.
Guest house rentals with a patio

Poolhouse in woodside
Lola truly goes above and beyond expectation to make my stay enjoyable. Thank you

Beautiful Guesthouse in Woodside, 1 Bedroom + Loft
Very cozy place. Beautiful home & beautiful area. Cath was very responsive, helpful and nice. We will definitely be coming back here

Adorable 1-bed independent guesthouse in Palo Alto
We recently had the pleasure of staying at Kirupa's Airbnb, and it was an absolutely wonderful experience. Kirupa was incredibly kind, friendly, and communicative throughout our stay. He always responded quickly to any questions or requests, which made our stay even more comfortable. The unit itself was beautiful and very well decorated, creating a cozy and inviting atmosphere. Every detail was thoughtfully considered, making it a perfect home away from home. It was even stocked with many convenient essentials (all kitchen equipment, spices, oils, tea/coffee, toiletries, etc.). Additionally, the location in Palo Alto was fantastic. The neighborhood and surrounding areas were beautiful and we really enjoyed walking around. We highly recommend Kirupa's place to anyone looking for a great stay in Palo Alto. Thank you, Kirupa, for being such a fantastic host!

A freestanding casita in a delightful grape garden
Thank you Maria. We were there for work but had a day off in between. We were planning on spending our day off doing something off property but we were already in the most beautiful place we could imagine. We felt like we were in our own private spa. Pool, Hot Tub, Spectacular flowers, grapevines, dining table on the patio and more outdoor space. The beds were comfortable and the bath & kitchen were both very nice. Hope to come back again and spend more time off at your Casita. Thanks again!!

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.

Sunny Cottage in Redwood City
This was our second stay at Rebeka's place since we visit family nearby. The cottage is very cute and very functional.

Boho beach bungalow- walk to Poplar Beach
Very cozy and private. I brought my family of four and we had a lovely time. The only tricky part is figure out how to lock the door, but if that’s the worst of it, then I’d say it was pretty amazing. It’s about a 15 minute walk to the beach along nature paths and side streets. Definitely worth it!

Palo Alto Cottage: Privacy, Comfort & Convenience
Thanks for the stay! The bed was very comfortable, and the space was private and quiet. The room is quite large and nicely divided into the sleeping area, sitting area, and eating area. And parking on the street was aplenty.
Guest house rentals with a washer and dryer

Quaint Cottage Near Downtown Palo Alto
It was another great stay at Jess‘ and Louis‘ place! We enjoyed every minute of it and were very impressed that they had actually updated various things since our last stay. Cannot recommend enough! We hope to have a chance to come back!

Woodsy Silicon Valley Cottage
My second stay at Hilary’s was as peaceful as my first. The apartment is a beautiful treehouse, with lovely outdoor space. Loved listening to the frogs in the evening! So peaceful. Appreciated access to hiking trails, too. Super nice spot!

Cozy Professorville Cottage
The decor is lovely and the place has everything you need. It has a separate couch TV viewing area which can be a rarity in one bedroom accommodation. It also has a separate kitchen. It is in walking distance to restaurants. Gary is a responsive host and kindly allowed me to have a later check out. Great place to stay!

Charming Peaceful New Studio in Mtn View
Great! This was my third stay in the studio, this time I stayed for 2 months. Highly recommend staying here. The studio is located in a quite area within a beautiful garden (with fresh oranges). The San Antonio Caltrain station is 10min walk, and the closest bus station is 6min if you’re quick. It’s stocked with everything needed for a short or long stay. During my stay the internet was upgraded, so now it’s even better than in previous stays 🙌 Eric and Rebecca are very friendly and great hosts and were very flexible when i extended my stay.

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.

Menlo Park 2 Bedr Cottage
This was an amazing place and I will definitely try to stay here again every time we come to this area for baseball tournaments! This was the perfect spot, Richard and Amanda were amazing hosts, and it made my stay the easiest ever. 5-stars! Thanks and I’ll be back!

16017-Private 2BR Guest Unit near HWY, BART & Mall
Enjoyed my stay again! Friendly and responsive host, place is clean and as described. Looking forward to booking in the future!

Luxury 4BR House at Westlake near BART, Beach Golf
Was a good option for our group of 7 to stay. The hosts were prompt in helping out.
Destinations to explore
- Kid-friendly rentals San Mateo County
- Condo rentals San Mateo County
- Pet-friendly rentals San Mateo County
- Rentals with pools San Mateo County
- Family-friendly rentals San Mateo County
- Rentals with breakfast San Mateo County
- Rentals with a fireplace San Mateo County
- Rentals with outdoor seating San Mateo County
- Rentals with a patio San Mateo County
- Rentals with a hot tub San Mateo County
- Waterfront rentals San Mateo County
- Rentals with an EV charger San Mateo County
- Townhouse rentals San Mateo County
- Fitness-friendly rentals San Mateo County
- Rentals with beach access San Mateo County
- Beachfront rentals San Mateo County
- Apartment rentals San Mateo County
- Private suite rentals San Mateo County
- Tiny house rentals San Mateo County
- Serviced apartment rentals San Mateo County
- Villa rentals San Mateo County
- Rentals with a washer and dryer San Mateo County
- Rentals with a fire pit San Mateo County
- House rentals San Mateo County
- Rentals with lake access San Mateo County
- Guesthouse rentals California
- Guesthouse rentals United States
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Golden Gate Park
- Stanford University
- Oracle Park
- Washington Square
- Capitola State Beach
- Sumner Beach
- Joaquin Miller Park
- Children’S Fairyland
- Corcoran Beach
- Muir Woods National Monument
- Mission Dolores Park
- Golden Gate Bridge
- El Granada Beach
- The Forest of Nisene Marks State Park
- Surfers Beach
- Glen Canyon Park
- Six Flags Discovery Kingdom
- California’S Great America
- Pasatiempo Golf Club
- SAP Center
- Big Basin Redwoods State Park
- Henry Cowell Redwoods State Park
- Painted Ladies
- Oakland Zoo
- Things to do San Mateo County
- Things to do California
- Tours California
- Sightseeing California
- Wellness California
- Sports activities California
- Art and culture California
- Food and drink California
- Entertainment California
- Nature and outdoors California
- Things to do United States
- Food and drink United States
- Art and culture United States
- Sightseeing United States
- Tours United States
- Wellness United States
- Nature and outdoors United States
- Entertainment United States
- Sports activities United States
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes