
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.

Soak up the Serenity on the Patio of a Charming Cottage
Light the fire pit and dress for dinner in the vine-covered garden at a peaceful retreat with a soothing waterfall. Zen beachy decor and coastal paintings set the scene indoors, with abundant natural light enhancing easy open-plan living. Pets are welcome with a small cleaning fee of a $50 (one time fee) and additional pets $25 (one time fee). The main room is 12'x17'. Closet is 6 1/2' long. Bathroom 4'x5 1/2' + shower 3'3" x 3'3". kitchen 4 1/2' x 8". Simple breakfast served. Your own private entrance, plenty of parking on the street, nice neighborhood. We are available if you have any questions or need information on the area. 2 night minimum please. The cottage is tucked away off the street in a quiet, safe neighborhood where residents walk their dogs in pleasant weather. Nearby downtown Redwood City is home to shops and groceries and freeways and public transportation are within easy reach. There is a bus that runs at the corner of our block, it would take you to downtown Redwood City or travel down the El Camino Real. There is a train depot downtown as well. Pets - 2 small dogs in the main house, 2 outdoor cats.

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

Silicon Valley Oasis
Experience elegance and comfort in our spacious, 500 sq ft studio cottage, located in the heart of Silicon Valley. Newly built in a classic Craftsman style, it features wooden casement windows, a private garden with Adirondack chairs, and a fully-equipped kitchen with an Italian range. Enjoy a plush queen-sized bed, a cozy sectional for cinema-like experiences on a 65" TV with in-ceiling speakers, and lightning-fast Wi-Fi. Perfect for a luxurious and memorable stay.

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.

Private Garden Cottage in Belmont Hills
A fully accessorized cottage in a private and quiet setting at the heart of the San Francisco Bay Area. Newly renovated backyard with always blooming flowers, fruit trees, hot tub, and pool. Regular visits from deer, and professional night illumination make this place feel like a magical forest getaway, quiet and secluded from the surrounding city. Enjoy the multitude of patios for reading and relaxation. We even have a tree house for the kids.

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.

Clean&Cozy Cottage near downtown Burlingame & SFO
Our sunny backyard cottage, with outdoor private entry, is centrally located in Burlingame between Burlingame Avenue and Broadway and is a great spot suited to a business traveler in search of a home away from home while also being ideal for vacationers looking to live like a local, only miles from SF. Enjoy and unwind!
Popular amenities for San Mateo guesthouse rentals
Family-friendly guest house rentals

Enchanted redwood treehouse: Spring bloom escape

Cozy bedroom in the heart of Silicon Valley

Charming Cozy Cottage in Eco-Garden Oasis

Guesthouse in Serene Neighborhood

Bicycle Shack @ La Honda Pottery

Stylish Spacious Seaside Retreat, Walking to Beach

Elegant & Convenient RWC Studio

Cabana in Sierra Azul Open Space Preserve
Guest house rentals with a patio

Guesthouse Garden Retreat

Berkeley Bitty House - a little bit of home

Detached Cozy Studio w/ private patio garden & BBQ

Palo Alto Cottage: Privacy, Comfort & Convenience

Adorable 2 bed guesthouse walk to Willow Glen DWTN

Santa Clara Guest House w/King Bed and Parking

Quiet guesthouse near SJ airport with EV charger

Cozy redwood cottage by the bay
Guest house rentals with a washer and dryer

Redwood Heights Cottage with Stunning Bay Views

Cottage near downtown Palo Alto

Quaint Cottage Near Downtown Palo Alto

Cozy Home + Garden in the Hills

Woodsy Silicon Valley Cottage

Fabulous Guesthouse next to Stanford w/ Kitchen

Charming Studio Garden Cottage near Stanford

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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