Guesthouse holiday rentals in Los Gatos

The kitchenette features stylish white cabinetry and open shelving. A coffee maker is placed on a wooden tray, alongside bottles of wine and decorative accessories. A sink with modern fixtures is visible, while a microwave is discreetly housed beneath the counter.

4.97 out of 5 average rating, 559 reviews

Stylish, Light-filled Cottage

Eat breakfast on the secluded patio garden at a cozy studio in charming San Jose. Indulge in a relaxing soak in the all-white bathroom, unwind with a book in an antique chair under the sash window, or snuggle up in the carved wooden bed by the fire. The cottage has been fully remodeled. Relax in a brand new king bed and enjoy the all new full bath. Roku TV, AC/Heat and an electric fireplace to relax with. Fully equipped kitchenette and dining area. Private yard to enjoy and relax. Detached cottage, with private, well lit entry. A coded deadbolt lock allows safe entry into cottage. Enjoy a private patio that is also available for guests. We will be giving our guests privacy, but are available by phone or text if you have questions. Willow Glen is the South Bay’s hottest area within San Jose and the Silicon Valley. Downtown is two blocks away, with popular restaurants, banks, antique shops, beauty salons, and coffee houses all close by. Plenty of safe and well lit street parking available. A city bus stop is very close, with freeways, light rail, and Cal train a mile away. Willow Glen is a quaint neighborhood of San Jose, with its charming old homes, and vibrant downtown businesses. Many popular restaurants, banks, antique shops, beauty salons, and coffee houses, just to name a few...all just a short drive or walk away!

A light blue cottage is set amidst lush greenery and towering trees. The exterior features multiple windows, offering views of the surrounding landscape. A narrow pathway leads to the inviting front door, framed by flowering plants, enhancing the tranquil setting.

4.97 out of 5 average rating, 119 reviews

Mountain Retreat

Escape to the serene beauty of the Santa Cruz Mountains of Los Gatos! Our charming cottage rental is nestled amidst the towering redwoods, 30mins from Silicon Valley or Santa Cruz, and only 15mins from downtown LG, but feels isolated if you want get away from it all. The cottage features a living room (w/optional murphy bed) & full kitchen/dining area. Amenities like wifi, streaming and washing/dryer available in unit. Bedroom features king size bed and private backyard area. Pet friendly.

The exterior of the studio is framed by a stone facade, featuring large glass doors that open to reveal a cozy interior. Plush seating and a dining table are visible inside, with the gourmet kitchen in the background. Natural light brightens the space, enhanced by the greenery outside.

4.99 out of 5 average rating, 218 reviews

TheStudio in Willow Glen (San Jose) CA-95125

Vacationers, Extended Family, Work Travelers with Fast Internet! ALL the Comforts & Gourmet Kitchen!! Optional 2nd bed set-up fee collected after booking. I'll message options. Fully stocked gourmet kitchen, full-size appliances; small ones too! Full bathroom: large walk-in shower with 2 shower head fixtures! Bidet & every amenity. Patio, water fountain, Adirondack chairs, bistro table, outdoor shower-enjoy privately. Appointed to provide maximum functionality and relaxation!

Guesthouse in Monte Sereno

The cottage exterior features a charming design with a slate stone patio and a round dining table with two chairs. Glass double doors provide access, and large windows offer views of the surrounding greenery. The roof is intricately shaped, complementing the natural setting.

4.98 out of 5 average rating, 453 reviews

Quiet Poolside Cottage for Solitude

New construction 800 sq. ft. Cottage 1.1 miles to downtown Los Gatos. Off-street parking for one car. Cathedral ceilings with skylight (morning sun, nightly stars). Comfortable pillow top King bed. Single bed in same space for extra guest (extra $25 for third guest/night). Kitchenette with basics. Dining table for work spaces. Pool available for guests. Jacuzzi not available. Many quiet places on property to relax. We do not accept third party reservations. Add your guests on reservation.

4.95 out of 5 average rating, 111 reviews

A modern workspace is highlighted by a wooden desk and clear chair, accompanied by a lamp. A wall-mounted television displays an ocean scene. A kitchenette with a microwave and mini-fridge is visible, while a bathroom area with a sink and mirrors is seen in the background.

Guesthouse in San Jose

Luxe Suite with Private Yard & AC

Perfect for solo travelers or those with pets, this centrally located San Jose suite combines luxury and comfort. Sleep like royalty on a queen bed, start your day with a Nespresso, and enjoy a mini-fridge, microwave, and 45" TV at your workspace. Indulge in premium toiletries, AC, and use the hair dryer and steamer for a polished look. Easy self-check-in/out. The trendy wood panel wall adds style, creating your private cocoon. Plus, enjoy a private yard to relax and feel the outdoor breeze.

The exterior of the townhome is softly illuminated by outdoor lighting, highlighting the welcoming front entrance. A large oak tree provides natural coverage, while lush greenery surrounds the pathway, offering a sense of privacy and tranquility in a serene nighttime setting.

4.95 out of 5 average rating, 101 reviews

Five Star Smart Home Living Experience

SUPER BOWL CLOSE LOCATION!! Nestled beneath a century old oak tree and only a 5-10 minute walk to downtown Los Gatos or Vasona Park sits a newly constructed 900 square foot 1 BR, 1.5 bath loft style luxury townhome with a private front entrance and backyard. This exclusive experience in downtown Los Gatos is ideal for someone (or a couple) looking for the comfort, quiet and privacy of a detached home in the center of one of the San Francisco Bay Area’s most desirable communities.

A private stone patio is adorned with wooden chairs, overlooking a garden filled with plants. The sunset illuminates the sky with soft hues of pink and orange, creating a serene backdrop against the rolling hills and trees.

4.97 out of 5 average rating, 106 reviews

Oak&Bloom cottage - Los Gatos, 2 bedrooms, private

Beautifully remodeled, sparkling clean, and cozy private two-bedroom cottage with sweeping canyon and mountain views, located less than 2 miles from charming Downtown Los Gatos. Enjoy mornings with Nespresso coffee in the peaceful private yard, explore nearby parks, and access scenic hiking and biking trails just minutes away. Inside, the cottage offers a fully equipped kitchen, air conditioning in every room, and fast fiber internet. Santa Cruz Beach is a scenic 30-minute drive.

A spacious bed is adorned with decorative pillows, set against a light-colored wall. The bed’s canopy features soft draping, while nearby furniture includes a dark dresser and a decorative lamp. Artistic wall hangings contribute to the room's unique character.

4.87 out of 5 average rating, 275 reviews

An Adventurer's Private Cottage Paradise

*Any stay 30+ days requires a background check(50$), a signed lease and a strong and consistent positive review history. Wifi speeds: 67 Mbps download, 11 Mbps upload. You don't have to be named Indiana Jones to enjoy the Far East touches of this private and fun studio and bath. Everything is provided: a work space, a cooking/eating place, and even an outdoor space with BBQ. Whether you are traveling for work or play, this cottage will make your stay more fun and memorable!

Guesthouse in Almaden Valley

An outdoor area features a serene pool surrounded by blooming flowers and lush greenery. The distant horizon showcases a sparkling view of the city lights below, under a clear evening sky transitioning from dusk to night.

4.97 out of 5 average rating, 1,013 reviews

Cabana in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

Guesthouse in Monte Sereno

A vibrant garden is showcased, featuring blooming red flowers and lush green plants. A stone patio leads to a tranquil blue pool, framed by greenery and distant hills. Decorative pottery is placed among the flora, adding charm to the natural setting.

4.91 out of 5 average rating, 230 reviews

Greenwood Guest House, a Peaceful Oasis

Welcome to Greenwood Guest House, a 1 bedroom, 1 bath private house situated in a peaceful and expansive backyard with a pool, tennis court, and beautiful scenery. Our space is a good fit for business trips, couple vacations, and family visits. The kitchenette and laundry room make longer stays quite enjoyable. Easy access to Highway 17 and 85, 15 minute drive to San Jose airport (SJC) and 2 minute drives to either downtown Los Gatos or Saratoga.

A cozy living area features two leather sofas positioned around a rustic coffee table. Natural light filters through large windows, illuminating the space. A rocking chair adds a touch of charm beside an accent lamp, and a soft area rug adds warmth to the flooring.

5 out of 5 average rating, 162 reviews

Orchard Cottage in convenient countryside location

Orchard Cottage is a newly refurbished historical home in a rural neighborhood 10 minutes from downtown Los Gatos. Lots of wildlife and beautiful scenery make this location in the Santa Cruz Mountains a peaceful retreat from city life. Enjoy your private deck and yard or visit our ducks for a mini-farm experience. Lots of nearby hiking and wineries, and only 25 minutes to Santa Cruz beaches. Please contact me with any questions!

A tranquil Watsu pool is surrounded by lush greenery and vibrant plants. A fabric shade cover is suspended overhead, providing protection from the sun. Natural stone flooring complements the pool's serene ambiance, creating a peaceful retreat atmosphere.

4.97 out of 5 average rating, 629 reviews

Cabana with Warm Watsu Pool

Our guests best describe it as: ‘Like luxury hotel meets Zen retreat meets Day Spa meets Bali rain forest meets mom and pop warm hospitality’. A private cabana close to shops and restaurants in downtown Willow Glen. You’ll love our place because of the tranquil setting, warm watsu pool, Finlandia sauna, hot plunge, and beautiful gardens. Our place is good for couples, solo adventurers, and business travelers.

Popular amenities for Los Gatos guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Superhost

Tall redwoods provide a natural canopy, creating a serene atmosphere with dappled sunlight filtering through the leaves. A forest floor of soft mulch and green undergrowth complements the tranquil setting, inviting exploration and reflection.

4.82 out of 5 average rating, 585 reviews

Rustic Cottage, Redwoods, Beaches.

4.9 out of 5 average rating, 124 reviews

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.

Guesthouse in Palo Alto

Guesthouse in Serene Neighborhood

4.95 out of 5 average rating, 479 reviews

The interior of the cabin features a single bed dressed in a blue and white plaid coverlet alongside two soft pillows. A kitchenette area with wooden cabinets and a small fridge is visible, complemented by a round mirror and decorative wall art of a forest scene.

Guesthouse in La Honda

Bicycle Shack @ La Honda Pottery

Guesthouse in Portola Valley

A spacious living and dining area showcases large glass doors that invite natural light and views of the surrounding greenery. A wooden dining table rests on soft carpeting, surrounded by modern chairs. The open space flows into the kitchen area, enhancing the inviting atmosphere.

4.98 out of 5 average rating, 221 reviews

1 Bdr Cabana just west of Stanford

Superhost

The living area features a cozy sofa with decorative cushions, a coffee table, and a large flat-screen TV. A colorful area rug enhances the space, while natural light enters through the windows. A door leads to the sleeping area, providing a seamless flow between rooms.

4.83 out of 5 average rating, 230 reviews

1BR beautiful, cozy guest cottage in Willow Glen

4.96 out of 5 average rating, 218 reviews

The cottage is framed by lush greenery and tall trees, featuring a welcoming entrance with steps leading to a porch. A gravel walkway and landscaped areas with plants create a serene outdoor setting, inviting guests to explore.

Guesthouse in Felton

Felton Forest Cottage Near Henry Cowell State Park

4.99 out of 5 average rating, 136 reviews

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

Delightful Hideaway in San Carlos

4.88 out of 5 average rating, 425 reviews

A spacious living room features comfortable seating, including a cream-colored leather sofa and armchairs. Warm yellow walls create a cheerful atmosphere, while a large window allows natural light to brighten the space. A wooden coffee table sits on a patterned area rug, complemented by decorative plants.

Guesthouse in Gilroy

Back-to-Eden Guest House on a Farm

Guesthouses with a patio

4.99 out of 5 average rating, 106 reviews

A contemporary living area is depicted, featuring light-colored furniture and a flat-screen TV mounted on the wall. A round coffee table with a decorative item is placed in front of two sofas. A dining area with curved chairs complements the space, all illuminated by natural light.

Guesthouse in San Jose

MolivuHomes 2BR: King Bed, Backyard, Pet-friendly

4.95 out of 5 average rating, 122 reviews

A bright kitchen area features white cabinetry and modern appliances, including a stove, refrigerator, and washer/dryer unit. A small rug adds a touch of warmth to the space. Countertops are clear and equipped with essential cooking items, creating a functional and inviting cooking environment.

Guesthouse in Japantown

Cozy Private 1B1B Cottage near Japantown

4.96 out of 5 average rating, 124 reviews

A newly constructed guest house is displayed, featuring a modern design with a sloped roof and solar panels. The exterior includes a combination of white stucco and dark accents. A landscaped area with grass and gravel pathways leads to the entrance, complemented by a tree and outdoor seating.

Guesthouse in San Jose

Garden Cottage w/ Hot Tub • 3 miles to SJC

Guesthouse in Downtown San Jose

An outdoor patio area is shown beneath a wooden pergola adorned with warm string lights, creating a cozy ambiance at night. A large 65-inch TV is mounted on the wall, while comfortable dining and lounging furniture is arranged for relaxation and socializing.

4.99 out of 5 average rating, 132 reviews

Near Japantown & SJC ARPT, King Bed, Fast Internet

4.9 out of 5 average rating, 158 reviews

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.

Guesthouse in Palo Alto

Palo Alto Cottage: Privacy, Comfort & Convenience

4.94 out of 5 average rating, 258 reviews

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.

Guesthouse in Menlo Park

Charming, modern, restorative, private studio

Guesthouse in Naglee Park

The exterior of a charming studio is featured, surrounded by lush greenery and landscaped paths. A light fixture with multiple globes stands near the entrance, which is framed by a decorative door. Sunlight casts a gentle glow on the white facade.

4.92 out of 5 average rating, 147 reviews

Guest studio in Naglee Park

4.99 out of 5 average rating, 173 reviews

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

Silicon Valley Oasis

Guest house rentals with a washing machine and dryer

4.99 out of 5 average rating, 138 reviews

The light blue Victorian carriage house is shown from the exterior, featuring an upper balcony and white trim. The sloped roof is adorned with a weather vane, while planters with greenery add to the inviting entrance. The surrounding area is open and airy.

Guesthouse in Santa Cruz

Carriage House on West Cliff Drive 18-0090

4.93 out of 5 average rating, 363 reviews

The guesthouse entrance is framed by a neatly landscaped area, featuring a spacious path made of stone tiles leading to the front door. Elegant wrought iron railings and manicured greenery enhance the inviting setting under clear blue skies.

Guesthouse in Evergreen

Evergreen Valley Hillside retreat

Guesthouse in La Selva Beach

The entrance of the home features a set of brick steps leading to a welcoming door. Flanking the entrance are two potted plants. A small wooden table and two chairs are placed on the porch, surrounded by decorative landscaping with flowering plants.

4.83 out of 5 average rating, 156 reviews

1 bedroom attached guesthouse

Guesthouse in The Willows

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, 168 reviews

Quaint Cottage Near Downtown Palo Alto

Guesthouse in Downtown San Jose

The kitchen features dark wood cabinetry complemented by a light grey tile backsplash. A white electric stove and microwave are positioned above a spacious countertop with a sink. A mini-dishwasher and coffee maker are also present, providing essential appliances for convenience.

4.91 out of 5 average rating, 127 reviews

Private, stylish, clean detached studio

Superhost

A welcoming living space is displayed, featuring a black couch and a wooden coffee table. A colorful flower arrangement brightens the area, while a vintage-style poster adds character to the wall. Natural light enters through the windows, enhancing the inviting atmosphere.

4.86 out of 5 average rating, 188 reviews

Modern 2Bed/1Bath suite in San Jose

4.97 out of 5 average rating, 234 reviews

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 Mt. Carmel

Mt Carmel Cottage Charmer-Bright, Stylish & Clean