Guest house holiday rentals in San Mateo

A rustic cabin is situated among tall redwood trees. A wooden deck extends towards a tranquil pool, which is surrounded by greenery and flower beds. The warm tones of the cabin's exterior complement the natural surroundings, enhancing the serene atmosphere.

4.99 out of 5 average rating, 353 reviews

Rustic Cabin in the Redwoods

Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

Guest house in Edgewood Park

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.

4.99 out of 5 average rating, 117 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.

A cozy living area features a gas fireplace, providing warmth. A television is mounted above, and natural light enters through two windows. A round red rug is positioned on the hardwood floor, with a light-colored sofa and a dark chair visible, creating an inviting space.

4.98 out of 5 average rating, 452 reviews

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those who are inclined to have an active lifestyle, We are close to Purisima Creek, Huddart Park, and El Corte De Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space) 20 minutes away from Half Moon Bay with beautiful beaches and 30 min. from Stanford, Palo Alto. We are adjacent to The Mountain House Restaurant. Res recommended. Short drive to local breakfast place. NO PETS!

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.

4.97 out of 5 average rating, 335 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 house in Mt. Carmel

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.

4.97 out of 5 average rating, 233 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.

4.99 out of 5 average rating, 214 reviews

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

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 house in San Carlos

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.

4.99 out of 5 average rating, 168 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 house in San Carlos

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.

4.99 out of 5 average rating, 131 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.

Guest house in Portola Valley

An outdoor deck features two green cushioned chairs and a wooden table at its center. A potted plant is placed on the table, complementing the natural setting. The entrance door, framed in black, leads into the guesthouse, surrounded by tall trees.

4.94 out of 5 average rating, 216 reviews

Woodsy Silicon Valley Cottage

Discover a laid-back side of Silicon Valley in a cozy, cedar-shake guesthouse surrounded by mature trees. Walking distance from a great network of destination hiking and biking trails. 15-30 minutes from Stanford, Sand Hill Road, and major tech companies. This 400 square foot space is on top of our garage and next to our home. There is no public transportation nearby and ride share services are available but not always reliable so you'll need a car.

A spacious bedroom features vaulted wooden ceilings and large glass sliding doors leading to an outdoor deck. A comfortable bed is flanked by two bedside tables with lamps. A decorative painting hangs above the bed, and a wooden dresser adds functional storage.

4.99 out of 5 average rating, 571 reviews

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

4.93 out of 5 average rating, 242 reviews

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

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 house in Hillsborough

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.

4.95 out of 5 average rating, 995 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.

Popular amenities for guest house rentals in San Mateo

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guest house in Emerald Hills

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.

4.94 out of 5 average rating, 142 reviews

Cozy bedroom in the heart of Silicon Valley

Guest house in Redwood Heights

A cozy interior of a cabin is showcased, featuring a lofted sleeping area accessed by a wooden ladder. Below, a spacious bed is positioned near windows that invite natural light. A small dining table with chairs and bookshelves add functionality to the warm wooden space.

4.96 out of 5 average rating, 253 reviews

Charming Cozy Cottage in Eco-Garden Oasis

The exterior of the guesthouse is showcased, featuring a light-colored facade with large windows. A well-maintained garden displays various shrubs and plants. The driveway includes a garage door and the surrounding area is paved and neatly landscaped.

4.89 out of 5 average rating, 112 reviews

Guesthouse in Serene Neighborhood

Superhost

A sunset casts vibrant orange and purple hues across the sky, reflecting on the ocean's surface. Waves gently lap against a sandy shore, where several birds can be seen near the water's edge. A distant lighthouse is visible on the horizon.

Guest house in Half Moon Bay

4.91 out of 5 average rating, 469 reviews

Stylish Seaside Cottage - Walking to Beach

4.99 out of 5 average rating, 112 reviews

The open living area features a spacious leather sofa facing a wall-mounted television. Natural light fills the room through large windows overlooking the yard. A dining table is positioned nearby, and a cozy seating area includes blue chairs and a round coffee table, complemented by wood flooring.

Guest house in Stanford

Fabulous Guesthouse next to Stanford w/ Kitchen

Guest house in Redwood City

A modern kitchen features dark cabinetry complemented by a striking granite countertop. Stainless steel appliances, including a refrigerator, microwave, and dishwasher, are visible. Ample storage is provided by cabinets and shelves, with natural light filtering through a nearby window.

4.92 out of 5 average rating, 130 reviews

Elegant & Convenient RWC Studio

Guest house in Menlo Park

A welcoming entrance to the studio is framed by wooden fencing and highlighted by a sign that reads 'Park Studio.' Large terracotta pots with blooming flowers and lush greenery add a touch of nature, creating an inviting atmosphere.

4.94 out of 5 average rating, 246 reviews

Charming, modern, restorative, private studio

Guest house in Edgewood Park

A shaded porch area features stone flooring and is bordered by lush greenery. Two outdoor chairs and a small table are positioned on the left side, providing a serene spot for relaxation. The entrance to the studio is visible through large glass doors.

4.95 out of 5 average rating, 208 reviews

Charming Studio

Guest house rentals with a patio

Guest house in West Oakland

A bright living room features large windows allowing natural light, framed with sheer white curtains. The space includes a comfortable white sofa, a round coffee table, and decorative accents like a geometric art piece and sunflowers placed on the table.

4.94 out of 5 average rating, 112 reviews

Charming Victorian Retreat | Minutes to SF

4.92 out of 5 average rating, 184 reviews

A bright living area features a dark leather sofa adorned with decorative pillows, accompanied by a wooden coffee table. A small table with two chairs is positioned beside a large window, allowing natural light to illuminate the space. A floor lamp and decorative plant enhance the room's inviting feel.

Guest house in San Jose

Newly built stylish guesthouse

4.92 out of 5 average rating, 382 reviews

The image depicts a serene garden pathway leading to two adjacent cabins, framed by vibrant greenery and flowering plants. A wooden trellis is visible, providing shelter, while soft lighting from the cabins enhances the calm atmosphere. A mixture of stone and mulch surfaces directs attention toward the entrance.

Guest house in Oakland

Guesthouse Garden Retreat

4.99 out of 5 average rating, 221 reviews

The inviting interior of the studio features a spacious bed with white linens and decorative pillows. A kitchenette is visible with modern appliances, complemented by a small dining table and chairs. Natural light filters through windows, highlighting the warm wood accents and brick wall.

Guest house in Berkeley

Berkeley Bitty House - a little bit of home

4.91 out of 5 average rating, 109 reviews

A spacious studio is showcased with a large bed and a serene wall mural of trees. Natural light fills the room through sliding glass doors, which lead to the outside garden. A comfortable chair and side table create a cozy seating area.

Guest house in Alameda

Detached Cozy Studio w/ private patio garden & BBQ

A spacious studio is displayed, featuring a light-filled sleeping area with a cozy bed, adorned with crisp white linens and decorative pillows. A small dining table with two chairs is positioned nearby, along with a stylish desk and chair. Soft lighting enhances the overall warmth of the space.

4.9 out of 5 average rating, 153 reviews

Palo Alto Cottage: Privacy, Comfort & Convenience

Guest house in El Granada

A serene beach scene at sunset is captured, featuring gentle waves reflecting the hues of orange and blue in the sky. Silhouettes of people can be seen walking along the shoreline, while lights from the distant marina twinkle against the darkening landscape.

4.96 out of 5 average rating, 114 reviews

Coastal Cottage Guest House

Guest house in Santa Clara

A spacious living area is highlighted by a comfortable sofa adorned with decorative pillows. The open kitchen is visible, featuring modern appliances and a dining table. Large windows allow natural light to fill the room, enhancing the airy atmosphere.

4.95 out of 5 average rating, 116 reviews

Santa Clara Guest House w/King Bed and Parking

Guest house rentals with a washing machine and dryer

Guest house in Redwood Heights

A cozy living area is presented with a gray sofa adorned with orange accent pillows. Natural light enters through two upper windows, highlighting a rustic wooden table and shelves displaying decorative items. A flat-screen television sits on a wooden stand, contributing to the space's inviting ambiance.

4.99 out of 5 average rating, 226 reviews

Redwood Heights Cottage with Stunning Bay Views

Guest house in Walnut Creek

A charming guest house is set against a backdrop of green hills. A stone pathway leads to a welcoming front porch with multiple seating areas. Lush grass surrounds the home, and trees provide natural shade, enhancing the serene setting.

4.98 out of 5 average rating, 213 reviews

Gorgeous Guest House with a Farmhouse Flair

A private patio area is featured, furnished with two seating areas and a central table. An umbrella provides shade, while potted plants add greenery to the space. The wooden fence offers privacy, and the stone floor is complemented by a textured outdoor rug.

4.99 out of 5 average rating, 160 reviews

Quaint Cottage Near Downtown Palo Alto

5 out of 5 average rating, 231 reviews

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.

Guest house in Atherton

Charming Studio Garden Cottage near Stanford

Guest house in Downtown San Jose

A cozy living area features a stylish brown leather sofa and a round dining table accompanied by black chairs. Large glass doors invite natural light and provide views of the shared backyard. A modern kitchen is situated in the background, enhancing the open layout.

4.98 out of 5 average rating, 239 reviews

Private Abodu Guesthouse in Downtown San Jose

Guest house in Allied Arts

A combined living and kitchen area is shown, featuring a brown leather sofa and a wooden coffee table. A plaid patterned chair adds a pop of color. A flat-screen TV is mounted on the wall, and natural light fills the space through doorways leading outside.

4.91 out of 5 average rating, 140 reviews

Menlo Park 2 Bedr Cottage

Guest house in Redwood City

The exterior of a recently renovated guest unit showcases a light grey wooden façade with white trim. A small porch area is visible, leading to the entrance. An air conditioning unit is mounted on the side wall, and a fenced area provides privacy.

4.96 out of 5 average rating, 170 reviews

Redwood Casita

A neatly designed guesthouse exterior is presented, featuring a light gray façade and a welcoming white door. The pathway is paved with stone, bordered by fresh greenery and landscaping, under a clear blue sky. A sense of tranquility is underscored by the surrounding trees.