Guesthouse holiday 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.

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Top Guest favourite
A charming cottage entrance is framed by natural wood shingles and surrounded by lush greenery. A small porch is adorned with a wicker chair and colorful cushion, inviting guests to enjoy the serene outdoor space. Sunlight filters through the trees, illuminating the pathway.
Guesthouse in Redwood City
4.93 out of 5 average rating, 347 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.

Top Guest favourite
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, 780 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 favourite
A spacious living area features a light grey couch adorned with patterned cushions, situated in front of a glass-topped table. A small succulent plant and coasters are placed on the table, with glimpses of a neat kitchen and a dedicated sleeping area visible in the background.
Guesthouse in Belmont
4.93 out of 5 average rating, 108 reviews

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.

Top Guest favourite
An inviting outdoor patio is displayed, featuring a round table surrounded by six cushioned chairs. A vibrant red front door complements the neutral siding of the cottage, while lush greenery and colorful plants frame the entrance, enhancing the welcoming atmosphere.
Guesthouse in San Carlos
4.99 out of 5 average rating, 160 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.

Top Guest favourite
A spacious deck features two wooden directors' chairs positioned around a small circular table. Lush greenery lines the perimeter, creating a natural backdrop. A sunshade is partially visible, offering protection from the sunlight.
Guesthouse in San Carlos
4.99 out of 5 average rating, 120 reviews

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.

Top Guest favourite
A white trellis adorned with vibrant flowers stands against a sunny garden backdrop. A mix of colorful blooms, including tulips and daisies, creates a lively display in a brick planter, inviting guests to enjoy the natural beauty of the surroundings.
Guesthouse in Atherton
5 out of 5 average rating, 222 reviews

Charming Studio Garden Cottage near Stanford

Come and relax in our light and airy studio cottage situated in a beautiful garden setting, the perfect get-away after a day of business meetings or visiting with family. We are close to major Silicon Valley destinations as well as Stanford Hospital, 45 minutes' drive from San Francisco, San Jose and the beach in Half Moon Bay — easy access to Highways 101 and 280. Our quiet neighborhood full of mature oak trees beckons you to take a walk.

Top Guest favourite
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, 238 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 favourite
A spacious room features vaulted ceilings with wooden beams. A queen-sized bed, draped in a geometric patterned blanket, sits next to a sleek fireplace. A dining table and chairs are visible, along with a large TV and two closets that provide storage options.
Guesthouse in Hillsborough
4.95 out of 5 average rating, 971 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.

Top Guest favourite
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, 338 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 favourite
A light-filled sleeping area features a spacious bed dressed in white linens, complemented by dark pillows. A skylight brings natural light into the room, highlighting a workspace with a desk and chair. Mirrored surfaces add depth to the design.
Guesthouse in Emerald Hills
4.93 out of 5 average rating, 136 reviews

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.

Guest favourite
Guesthouse in South San Francisco
4.89 out of 5 average rating, 620 reviews

Savor the Peace at a Comfy Cottage Minutes from Downtown SF

Head out to the patio for some me-time in the hanging chair at this zen hideaway within easy reach of all the action. This sunny spot features private gated parking, soothing gray interiors, and marble worktops in the glossy dark wood kitchen.

Top Guest favourite
A spacious bedroom features a comfortable bed with dark gray bedding, flanked by matching bedside tables and lamps. Two large windows allow natural light to fill the room, highlighting the textured wallpaper and organized bookshelf in the corner.
Guesthouse in Hillsdale
4.98 out of 5 average rating, 465 reviews

A Comfortable, Clean, & Private Guest House

Beautiful, Secluded, Safe, Fully Stocked, Comfortable, Newly Renovated, & Close to Public Transportation. In the heart of Silicon Valley with its own private entrance. It's 30 mins. N of San Jose, and 30 mins. of San Francisco.

Popular amenities for San Mateo guesthouses

When is the best time to visit San Mateo?

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Avg. price$202 NZD$200 NZD$197 NZD$200 NZD$200 NZD$211 NZD$214 NZD$211 NZD$209 NZD$192 NZD$197 NZD$200 NZD
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Quick stats about guesthouse rentals in San Mateo

  • Total holiday rentals

    Explore 20 holiday rentals in San Mateo

  • Nightly prices starting at

    San Mateo holiday rentals start at $120 NZD 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

  • Wi-Fi availability

    20 of San Mateo holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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