
Guesthouse vacation rentals in San Mateo
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Top-rated guesthouses in San Mateo
Guests agree: these guesthouses 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 Garden Cottage
Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

A private and quaint gateway on Belmont Hills
Welcome to our cozy Belmont studio! This charming retreat offers a comfortable stay with its stylish design, fully equipped kitchen, and a comfortable bed. Conveniently located in Belmont, CA, you'll be close to vibrant San Mateo downtown, the scenic coastline of Half Moon Bay, and the airport. This quaint studio is tucked away on a small hill, surrounded by greenery. As a delightful bonus, you'll find a lovely lemon tree in the driveway, providing complimentary lemons for your stay.

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

🌼Modern guesthouse w private patio and ♨️ hot tub
New and modern guesthouse, built in 2018, 20 min walk to downtown Redwood City. The kitchen comes fully equipped with high-end appliances, quartz countertops, Keurig coffee maker, and an eat-in island. In the living room, enjoy the 55" 4K TV with Bose sound on a sectional sofa that doubles as a pull-out bed. Rest well on a premium cal king size bed and enjoy a relaxing dip in the hot tub on your tranquil backyard patio. Unit has washer/dryer, heat/AC, and ensuite bath.

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.

Quaint Cottage Near Downtown Palo Alto
This charming, quiet 2-story cottage includes a bedroom, bathroom, kitchen and spacious common room with a couch, working desk, fast wifi and a large flat-screen TV. Located in a family-friendly neighborhood in Menlo Park, you'll enjoy your own private space with a separate entrance and tranquil, sunny patio area. The cottage is nestled in the rear of our backyard, detached from the main house.

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. Due to the coronavirus, we are 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!

Cozy bedroom in the heart of Silicon Valley
Unwind at this cozy, peaceful oasis when visiting Silicon Valley. This miniature cottage/bedroom is located less than 10 minutes away from highways and downtown amenities, but is surrounded by the peace of the hills that oversee the San Francisco Bay.
Popular amenities for San Mateo guesthouses
Family-friendly guesthouses

Private, Detached, Urban Creekside Studio.

Charming Cozy Cottage in Eco-Garden Oasis

Private Garden Cottage in Belmont Hills

Bicycle Shack @ La Honda Pottery

Redwood Sanctuary Oakland Hills

Guesthouse Garden Retreat

Elegant & Convenient RWC Studio

Rustic Cottage *****Hiking & Biking
Guesthouses with a patio

La Casita - a quiet, Crocker Amazon area studio!

Near Japantown & SJC ARPT, King Bed, Fast Internet

Palo Alto Cottage: Privacy, Comfort & Convenience

Charming, modern, restorative, private studio

Quiet guesthouse near SJ airport with EV charger

Guest House w/King Bed and Parking in Santa Clara

Private and serene studio with full kitchen

Private Oasis Btwn SF, Napa. Big Views + Pool!
Guesthouse rentals with a washer and dryer

Redwood Heights Cottage with Stunning Bay Views

Cottage near downtown Palo Alto

Guest House in the Woods

Woodsy Silicon Valley Cottage

Private cottage in the heart of Silicon Valley

Fabulous Guesthouse next to Stanford w/ Kitchen

Charming Peaceful New Studio in Mtn View

Cozy backyard cottage
When is the best time to visit San Mateo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $166 CAD | $165 CAD | $162 CAD | $165 CAD | $165 CAD | $173 CAD | $176 CAD | $173 CAD | $172 CAD | $158 CAD | $162 CAD | $165 CAD |
| 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 $99 CAD per night before taxes and fees

Verified guest reviews
Over 2,010 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of San Mateo vacation rentals include wifi 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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