Guesthouse vacation rentals in San Mateo

Mt Carmel Cottage Charmer-Bright, Stylish & Clean

Beautifully well-appointed cottage with a private entrance, designed for comfort, style, and privacy—ideal for couples, solo travelers, and business stays. The space is meticulously maintained to provide a clean, relaxing, and comfortable experience. Located within walking distance to Caltrain (0.9 miles) and downtown Redwood City (0.6 miles), offering access to boutiques, cafes, restaurants, parks, and a movie theater. Seamless access to Palo Alto, San Francisco and the greater Silicon Valley.

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 inclined toward an active lifestyle, we are close to Purisima Creek, Huddart Park, and the El Corte de Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space)Note 20 minutes from Half Moon Bay with beautiful beaches and 30 min from Stanford in Palo Alto. We are adjacent to The Mountain House Restaurant. (note) The bed is a Murphy bed in the living area. NO PETS!

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.

Treehouse w/ Canyon Views · King · Workspace · SFO

Wake up to canyon and oak-tree views from your private Belmont treehouse cottage—a quiet 2-bedroom guesthouse perched above the neighborhood with a deck, full kitchen, 360 Mbps wifi for remote work, and in-unit laundry. Self check-in via smart lock. ~15 min to SFO, 5 min to Belmont Caltrain. Great for Silicon Valley business trips, longer stays for relocators or remodels, and Bay Area event trips toward San Francisco, Palo Alto, and San Jose.

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. *

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!

Beautiful private guest studio

Clean, new construction guest studio with private entrance centrally located in a residential neighborhood near downtown Redwood City. Queen bed with full bathroom, A/C, and fridge/coffee/microwave. Small desk next to bed great for remote work or studies. Easy self check-in with smart lock and easy parking.

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.