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.

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Guest favorite

Guesthouse in Redwood City

4.93 out of 5 average rating, 300 reviews

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.

Guest favorite

Guesthouse in San Carlos

4.99 out of 5 average rating, 642 reviews

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.

Guest favorite

Guesthouse in San Bruno

4.95 out of 5 average rating, 137 reviews

Detached private cozy studio ~ 5 mins to SFO

Welcome to our private & detached studio with its own separate entrance. Enjoy this remodeled cozy 175 square feet space. It is located next to our home. We have put in lots of love to make your stay pleasant. We take pride in cleanliness. Please take time to review pictures and size before booking. We are located in a safe & friendly neighborhood that is walking distance to many restaurants and grocery stores. 5 minutes to SFO 1 mile to BART Walking distance to caltrain Only street parking

Guest favorite

Guesthouse in San Bruno

4.95 out of 5 average rating, 222 reviews

❤️Newly remodeled SFO Guesthouse, Private entrance

Detached, and perfectly situated cute guesthouse with a private entrance. Ideal for a vacation to explore San Francisco bay area/Silicon valley while staying in a safe and quiet neighborhood. Conveniently located 8 min drive from SFO Airport! 5 min drive to BART/Caltrain station, 2 min walking distance to bus stop and 4 min to EV charging station. Close access to 101, 280 freeway. 15 mins to San Francisco and 20 mins to Silicon Valley. 10 mins to the beautiful Highway 1, Pacifica.

Superhost

Guesthouse in San Mateo

4.92 out of 5 average rating, 156 reviews

Cozy Studio 1B/1B w A/C No Pet in San Mateo

This cozy studio is good for a couple vacation. It is also suitable for business trip with high speed WIFI. It is well equipped with all the amenities you need to enjoy your stay! 15 minutes walk to San Mateo Downtown. 11 minutes walk to Cal Train Station, which takes you to San Francisco in 30 min, and San Jose 45 min. If you have a car, you can reach those popular destinations easily: Hwy 101: 3 min San Francisco Airport: 9 min Apple Palo Alto: 12 miles Stanford: 17 miles

Guest favorite

Guesthouse in San Mateo

4.99 out of 5 average rating, 135 reviews

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

Guest favorite

Guesthouse in San Carlos

4.99 out of 5 average rating, 118 reviews

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.

Guest favorite

Guesthouse in San Mateo

4.93 out of 5 average rating, 209 reviews

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. *

Guest favorite

Guesthouse in Hillsborough

4.94 out of 5 average rating, 862 reviews

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.

Guest favorite

Guesthouse in Belmont

4.83 out of 5 average rating, 218 reviews

Charming Cottage Studio

Our place is small but comfy for solo adventurers and business travelers. Very safe neighborhood. Is close to public transportations CalTrains station, bus stops, restaurants and malls. Plenty of parking on the street. We are 30 min to San Jose, and 30 min to San Francisco. Very close to Oracle and to the 101 & 92 Highways. Only 20 min to the Ocean in Half Moon Bay.

Guest favorite

Guesthouse in Burlingame

4.98 out of 5 average rating, 302 reviews

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!

Guest favorite

Guesthouse in Burlingame

4.95 out of 5 average rating, 138 reviews

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.