Guest house holiday 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 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.

SkyHigh Redwoods Retreat with Bay Views

Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.

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.

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. *

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.

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 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.

Private Garden Cottage Belmont Hills*Pool*HotTub*

Charming, fully equipped cottage in a quiet Bay Area retreat. Enjoy a newly renovated backyard with blooming gardens, fruit trees, hot tub, and pool. Frequent deer visits and soft evening lighting create a magical forest-like escape. Multiple patios for relaxing, plus a fun treehouse for kids.