Guest house holiday rentals in San Mateo

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Top-rated guest house rentals in San Mateo

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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.
Guest house in Redwood City
4.93 out of 5 average rating, 351 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
A modern kitchen is highlighted by a spacious granite countertop island with four wooden stools. Natural light pours in through a large window overlooking the garden, illuminating stainless steel appliances and cabinetry. Plants add a touch of greenery to the inviting space.
Guest house in Edgewood Park
4.99 out of 5 average rating, 114 reviews

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.

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.
Guest house in Belmont
4.92 out of 5 average rating, 112 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.

Guest favourite
A cozy sleeping area features a spacious bed with neutral-toned bedding. Two bedside lamps provide illumination, while a comfortable chair complements the room. Light wood flooring adds warmth to the space, contributing to a well-designed, inviting environment.
Guest house in San Mateo
4.92 out of 5 average rating, 164 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

Top guest favourite
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.
Guest house in Hillsdale
4.99 out of 5 average rating, 207 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 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.
Guest house in San Carlos
4.99 out of 5 average rating, 123 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 well-lit guestroom features a queen-size bed with floral bedding. A spacious loveseat sofa is positioned near a sliding glass door that opens to the backyard. A small coffee table rests in front of the sofa, and a portable air conditioner is visible in the corner.
Guest house in Park Pacifica
4.97 out of 5 average rating, 520 reviews

Elegant Guesthouse in Garden Close to SF/SFO/Beach

Built in 2020, our guesthouse is the perfect place for couples or solo travelers. It has a private entrance, smart lock, hotel-quality bedding, brand-new furniture, and the latest interior design selections. Staying in the sunbelt of beautiful Pacifica, there are a lot of fun activities nearby: spending your day on the beach, exploring the hiking trails, or road trip along Highway 1. Half Moon Bay, SF, and SFO are around 20 minutes away!

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.
Guest house 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.
Guest house in Hillsborough
4.95 out of 5 average rating, 980 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. Since the coronavirus pandemic, we have been 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.
Guest house 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 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.
Guest house in Redwood City
4.95 out of 5 average rating, 161 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 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.
Guest house in Emerald Hills
4.94 out of 5 average rating, 139 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.

Popular amenities for guest house rentals in San Mateo

When is the best time to visit San Mateo?

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Quick stats about guest house rentals in San Mateo

  • Total holiday rentals

    Explore 20 holiday rentals in San Mateo

  • Nightly prices starting at

    San Mateo holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 2,180 verified reviews to help you choose

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    20 of San Mateo holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi 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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