Guesthouse vacation rentals in San Mateo

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in San Mateo

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

The exterior of a cozy cottage is visible, surrounded by a lush garden filled with various plants and flowers. A stone path leads to the entrance, framed by vibrant greenery. Large windows allow glimpses of the inviting interior, enhanced by a seasonal wreath on the door.

Guesthouse in San Carlos

4.99 out of 5 average rating, 734 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.

Top guest favorite

A light and airy living area features a neutral-toned sofa adorned with patterned cushions. A wooden coffee table with magazines sits in front of the couch, while a modern dining area is visible in the background, showcasing stylish bar stools and large windows.

Guesthouse in Redwood City

4.97 out of 5 average rating, 216 reviews

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. Vaccinated Hosts.

Top guest favorite

Tall redwood trees rise from the forest floor, creating a serene canopy. A distant view of the bay is visible through the trees, with a blanket of clouds resting over the landscape. The sky is clear, contrasting with the lush greenery of the forest.

Guesthouse in Woodside

4.97 out of 5 average rating, 283 reviews

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.

Guest favorite

A cozy living area features a sectional sofa and coffee table, complemented by a 55" smart TV mounted on the wall. A standing desk with dual monitors and a small kitchenette, including a microwave and refrigerator, provide convenience. Three nature-themed artworks adorn the walls.

Guesthouse in San Mateo

4.99 out of 5 average rating, 166 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

Top guest favorite

The entrance of the two-story cottage is framed by neatly maintained greenery. A solid blue front door is centered between two windows, allowing natural light to enter. A brick path leads from the garden, guiding guests to the doorway.

Guesthouse in Menlo Park

4.99 out of 5 average rating, 133 reviews

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.

Top guest favorite

The entrance to the studio features double glass doors framed by potted plants and flowers in various sizes. A welcome mat is positioned at the threshold, and small wall-mounted lights provide illumination. Natural light can be seen streaming through the doors.

Guesthouse in San Mateo

4.93 out of 5 average rating, 227 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. *

Top guest favorite

The cottage entrance is shown, featuring a green door framed by a screen door. A small outdoor seating area with two chairs and a table is visible on a gravel path, surrounded by lush greenery and trees.

Guesthouse in Hillsborough

4.95 out of 5 average rating, 924 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.

Superhost

A cozy outdoor seating area is visible, featuring a round table and a chair shaded by a large umbrella. A small cottage with a black door and decorative wreath is set against a backdrop of wooden fencing and greenery, creating a peaceful atmosphere.

Guesthouse in Belmont

4.83 out of 5 average rating, 224 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.

Top guest favorite

A cozy sleeping space features a queen bed with white linens and colorful decorative pillows. A light fixture stands beside the bed, and a wall art piece composed of natural materials adds interest. A closet with sliding doors is visible in the background.

Guesthouse in Burlingame

4.98 out of 5 average rating, 321 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

A spacious bed is positioned in the foreground, adorned with decorative pillows. A soft throw is draped across the bed. The bathroom is visible through an open door, featuring a shower and light tiles. A closet with hangers is also accessible, alongside a small kitchenette.

Guesthouse in Redwood City

4.96 out of 5 average rating, 130 reviews

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.

Guest favorite

The cozy sleeping area features a large bed adorned with a geometric pattern comforter. Natural light filters through sheer curtains, illuminating the room. A wall mirror reflects the space, and a laundry basket is positioned near the window, providing functional convenience.

Guesthouse in Burlingame

4.95 out of 5 average rating, 166 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.

Guest favorite

A loft bedroom features a spacious bed with a white wooden frame and plush bedding. A small dining table sits in one corner. The room is illuminated by a hanging light fixture and natural light streaming through a window, creating a cozy atmosphere.

Guesthouse in Redwood City

4.95 out of 5 average rating, 546 reviews

Stylish Separate Loft/Cottage Walk to Redwood City

* Automated, simple, quick self check in! * Located in a quaint and desirable neighborhood in Redwood City * 15 minutes from Stanford * 5 minutes to the 101 and 280 freeways * Easy walking distance to fun and lively downtown Redwood City/Train * No pets, no pets, no pets