
Guesthouse vacation rentals in San Mateo
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Top-rated guesthouse rentals in San Mateo
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Rustic Cabin in the Redwoods
Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

Private Cottage near Redwood City and San Carlos Downtowns
Quiet, private two-level garden cottage ideal for business travelers and visiting family. Gig+ high-speed Wi-Fi, workspace, central AC & heat, king-size bed, private entry (24/7), 50” 4K TV, fully equipped kitchen with granite countertops, and guest-exclusive washer and dryer. Bedroom, living area, kitchen, bathroom, and dining / work space. Shared garden with BBQ, teak table and hot tub. Walkable to transit, downtown areas, and a popular breakfast café. Some train and light traffic noise.

Kings Mountain Studio Cabin
Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those who are inclined to have an active lifestyle, We are close to Purisima Creek, Huddart Park, and El Corte De Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space) 20 minutes away from Half Moon Bay with beautiful beaches and 30 min. from Stanford, Palo Alto. We are adjacent to The Mountain House Restaurant. Res recommended. Short drive to local breakfast place. NO PETS!

Mt Carmel Cottage Charmer-Bright, Stylish & Clean
Beautiful cottage constructed with its own entry, offering beauty, comfort and privacy for your travel needs. Great location for couples, solo & business travelers alike. Cottage well appointed with many travel needs. Expertly maintained and cleaned. Walking distance to Caltrain (.9 mile), bustling downtown Redwood City (.6 mi), boutiques, coffee, restaurants, parks, movies (1.1 mi) & 5 miles to Palo Alto. Easy access to San Francisco, San Jose and the Silicon Valley.

Modern guest house in great location
Private 1 bedroom + 1 bathroom with your own entrance. Highlights: • self-checkin with code on digital lock • free parking + additional free street parking • professional cleaning and sanitizing • king size bed with premium mattress and linens • located at end of cul-de-sac in a safe and quiet neighborhood • standing desk with monitor and docking station • high speed WiFi • 55” smart TV • Rainfall shower, bidet toilet with heated seat, heated towel rack, makeup mirror

Delightful Hideaway in San Carlos
Fully equipped executive studio in the heart of Silicon Valley. This studio is ideal for accommodating executives, visiting doctors and nurses and other professions that might require long term stays. Visitors will enjoy the warm family-friendly environment and delightful garden setting. It is also well-suited for those on vacation who delight in visiting the nearby cities, as well as those who have families close by and want to have their own private spot.

Coastal Cottage Guest House
Guest house is attached to our primary residence but has a separate exterior entrance. The interior is separated by double doors that lock from both sides, similar to adjoining hotel rooms. The backyard is shared by us, the owners. There’s a very real chance you’ll be greeted by our friendly Australian Shepherd, Gracie, during your stay! You may see us in the yard during your stay. Feel free to say hi! Otherwise, we like to give our guests privacy.

Guest House in the Woods
Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

Charming Private Quiet Backyard Studio
This charming, sunny, secluded backyard studio is located in the heart of San Mateo, near public transportation, freeways, restaurants, shopping, and 15 minutes to SFO. Private entrance, quiet backyard setting, plenty of street parking. Less than a 5-min walk to Safeway, CVS, Starbucks and restaurants. * To my regular guests, the rate increase is due to SM County increasing the tax rate. *

Little Cottage on the Hill
Enjoy a peaceful stay at this charming, secluded detached garden cottage great for a stay-cation or as a work-from-home alternative. Since the coronavirus pandemic, we have been taking extra care to disinfect frequently touched surfaces between reservations. The cottage features a queen-sized bed, a fireplace, private bathroom and kitchenette. Perfect for both leisure and Business travelers.

Stylish Urban Escape Close to SFO & Many Amenities
Step into this stylish, light-filled loft in the heart of South San Francisco—minutes from SFO and easy Bay Area access. Designed with modern comfort and cozy touches, it fits 4 guests comfortably but can host up to 6. Whether for work or leisure, unwind after a day of exploring in this serene retreat featuring clean design, thoughtful details, and all the essentials for a memorable stay.

Cozy private studio near SFO & Downtown Burlingame
This cozy studio apartment is on the ground floor of a two-story building with private entrance and on site laundry. It is in a nice residential neighborhood within walking distance of Burlingame Ave., Broadway, CalTrain and convenient to Hwy 101 and within 10 minutes from SFO. Free street parking.
Popular amenities for San Mateo guesthouse rentals
Family-friendly guest house rentals

Charming Cozy Cottage in Eco-Garden Oasis

Private Garden Cottage in Belmont Hills

Cozy Home + Garden in the Hills

Immaculate Vintage Airstream in Mill Valley
Lulu's Place: a safe gated retreat min to Downtown

Elegant Garden Studio w/ AC | Near SF/SFO/Beach

Sunnyvale2B/1B/Family/Free EV Charging/AC/WiFi/PKG

Charming Guest House
Guest house rentals with a patio

Charming Victorian Retreat | Minutes to SF

Guesthouse Garden Retreat

Berkeley Bitty House - a little bit of home

Detached Cozy Studio w/ private patio garden & BBQ

Santa Clara Guest House w/King Bed and Parking

Private and serene studio with full kitchen

Quiet guesthouse near SJ airport with EV charger

Charming, modern, restorative, private studio
Guest house rentals with a washer and dryer

Guesthouse in Serene Neighborhood

Quaint Cottage Near Downtown Palo Alto

Cozy Alameda Garden Cottage

Woodsy Silicon Valley Cottage

Private cottage in the heart of Silicon Valley

Charming Studio Garden Cottage near Stanford

Spacious 4B2B Levis/GreatAmerica/ConventionCtr

Private in-law unit cute and cozy
When is the best time to visit San Mateo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ433 | ﺩ.ﺇ430 | ﺩ.ﺇ422 | ﺩ.ﺇ430 | ﺩ.ﺇ430 | ﺩ.ﺇ452 | ﺩ.ﺇ459 | ﺩ.ﺇ452 | ﺩ.ﺇ448 | ﺩ.ﺇ441 | ﺩ.ﺇ437 | ﺩ.ﺇ422 |
| Avg. temp | 11°C | 12°C | 13°C | 14°C | 16°C | 17°C | 18°C | 18°C | 19°C | 17°C | 14°C | 11°C |
Quick stats about guesthouse rentals in San Mateo

Total vacation rentals
Explore 20 vacation rentals in San Mateo

Nightly prices starting at
San Mateo vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 2,180 verified reviews to help you choose

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of San Mateo vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across San Mateo rentals

4.9 Average rating
San Mateo stays are highly rated by guests—averaging 4.9 out of 5!
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- Moscone Center
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