Guesthouse holiday rentals in Los Gatos

Guesthouse in Willow Glen

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, 566 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!

Guesthouse in Willow Glen

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, 223 reviews

TheStudio in Willow Glen (San Jose) CA-95125

Vacationers, extended family, work travelers needing 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!

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, 125 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.

4.99 out of 5 average rating, 311 reviews

A cozy, dark green cabin is nestled among towering trees, showcasing a large window and a glass-paneled door. Three steps lead to the entrance, surrounded by a natural landscape of redwoods.

Guesthouse in Felton

Cozy Coastal Redwood Cabin

Rest and connect in this warm, cozy, and private cabin that is nestled in the redwoods. Only minutes away from Henry Cowell State Park, where you can enjoy world class mountain biking trails, hiking, or swimming in the river. Or, enjoy the beach 15 minutes away. This is a perfect place to refresh in the magic of the Coastal Redwoods. Music fills most nights either from the Felton Music Hall or from the chorus of frogs. And wake up in the mornings to the mist in the trees when the fog rolls in.

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, 460 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.

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.

4.96 out of 5 average rating, 115 reviews

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.

4.92 out of 5 average rating, 195 reviews

Guesthouse in Campbell

Private Entry Adorable 1 bed 1 bath

Kick back and relax in this calm, stylish, and serene space. The unit features 1 bedroom with a queen bed, a full kitchen, a sofa bed, and a queen pull-out bed. Enjoy the convenience of in-unit washer and dryer. Located close to the highway yet tucked in a quiet, safe, and convenient neighborhood. Parking is available in front of the house, and the property is private, gated, and secure. • EV charger onsite • Ambient LED lighting in the bedroom • PS4 gaming system in the living room

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, 114 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.

Guesthouse in Scotts Valley

A spacious sleeping area is highlighted by a large bed featuring white bedding. Two windows allow natural light to fill the room, offering views of greenery. A small table with two stools is positioned near the windows, and modern lighting fixtures complement the overall design.

4.92 out of 5 average rating, 209 reviews

The Hen House Haven

Welcome to The Hen House Haven, a charming retreat where comfort meets modern amenities. Enjoy fresh eggs from our ten friendly hens, though egg availability may vary, especially in winter. Located near the Santa Cruz Beach Boardwalk, Henry Cowell Redwoods, and scenic hiking trails, our cozy studio is perfect for a relaxing getaway or adventure-filled stay. Embrace the serenity and warmth of staying with us, and make yourself at home. We can't wait to host you!

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, 1,020 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, 233 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.

An open living space features a light-colored sofa adorned with colorful cushions, complemented by a plush area rug. A wall-mounted television is positioned opposite the seating. Natural light filters through sheer curtains, illuminating the room with a view of the private yard through glass doors.

4.88 out of 5 average rating, 131 reviews

Los Gatos Cozy 2BD 2BA Private Guesthouse

Enjoy a peaceful stay in this brand-new guesthouse in Los Gatos. Nestled in a safe, tranquil, upscale neighborhood. Private side yard, assigned parking, separate entrance. Open-concept living area, spacious bedrooms, and full kitchen. Exterior security cameras and systems. 20 min to SJ Airport, 6 min to Netflix, 6 min to Downtown Los Gatos, <5 min to Vasona Park, 3 min to Good Samaritan Hospital, 25 min to Stanford Hospital, 3 min to Whole Foods

Popular amenities for Los Gatos guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

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.

4.83 out of 5 average rating, 590 reviews

Rustic Cottage, Redwoods, Beaches.

A modern studio features a spacious bed with light bedding and a decorative pillow reading 'relax'. Built-in cabinets flank the bed, while a stylish chair and a small table are positioned nearby. A woven wall hanging adds texture, and a large mirror reflects the natural light.

4.92 out of 5 average rating, 417 reviews

Los Gatos/Cambrian COTTAGE-HOT TUB/pvt.parking

4.97 out of 5 average rating, 359 reviews

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

SkyHigh Redwoods Retreat with Bay Views

Large glass doors open to reveal a bright, open kitchen and living area. A modern design includes white cabinetry, stainless steel appliances, and a comfortable seating area with a light sofa. Natural light floods the space from a skylight above.

4.99 out of 5 average rating, 215 reviews

Quiet guesthouse near SJ airport with EV charger

The entrance of the cottage features a welcoming white door with a clear window, flanked by decorative plants in a variety of pots. A wooden bench sits beneath the windows, adding a functional touch to the inviting exterior.

4.97 out of 5 average rating, 420 reviews

Private unit close to Santa Clara University

4.99 out of 5 average rating, 251 reviews

A dining area features a round table surrounded by four white chairs, illuminated by a decorative chandelier. Natural light enters through large windows adorned with sheer curtains, complementing the light green walls and adding a bright, open feel to the space.

Guesthouse in Sunnyvale

Lush Luxury Villa • Sunny Deck & Private Escape

A spacious backyard is showcased, featuring lounge chairs arranged on manicured grass. A modern guesthouse with large windows and a bar area is set against lush greenery. Pathways of stone slabs lead to various outdoor seating areas beneath umbrellas, enhancing the space's inviting quality.

5 out of 5 average rating, 219 reviews

Stylish standalone guesthouse near Santana Row

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, 276 reviews

An Adventurer's Private Cottage Paradise

Guesthouses with a patio

5 out of 5 average rating, 110 reviews

A glimpse into the living space is provided, showcasing a bright area with wooden floors and a dining table surrounded by chairs. A shower stall can be seen through an open door, adding to the cottage's functionality. A mirror hangs near the entrance, enhancing the welcoming feel.

Guesthouse in Livermore

Quiet wine country cottage sleeps 4 - Pet Friendly

Guesthouse in Moss Landing

The entrance to a rustic studio features a covered porch with white wicker chairs and a hanging chair. Light-colored flooring leads into the interior where a cozy sleeping area can be seen, enhancing the warm welcome of this private space.

4.89 out of 5 average rating, 150 reviews

Artsy&Private UNIT C

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.

4.95 out of 5 average rating, 124 reviews

Cozy Private 1B1B Cottage near Japantown

4.99 out of 5 average rating, 144 reviews

An inviting deck area features two white lounge chairs adorned with pillows, positioned near a door leading into the studio. A light-colored rug lies in front of the entrance, while a wooden railing offers a view of the surrounding greenery.

Guesthouse in San Carlos

Delightful Hideaway in San Carlos

4.99 out of 5 average rating, 102 reviews

The exterior of the guest house features a welcoming entrance with wooden steps leading to double doors. Lush greenery, including palm trees, surrounds the area, while the blue sky and distant hills form a scenic backdrop.

Guesthouse in Hayward

Bungalow Guest House

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.

4.96 out of 5 average rating, 126 reviews

Garden Cottage w/ Hot Tub • World Cup home base

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, 137 reviews

Near Japantown & SJC ARPT, King Bed, Fast Internet

4.97 out of 5 average rating, 127 reviews

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.

Guesthouse in El Granada

Coastal Cottage Guest House

Guest house rentals with a washing machine and dryer

4.99 out of 5 average rating, 171 reviews

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.

Guesthouse in Menlo Park

Quaint Cottage Near Downtown Palo Alto

A modern living area is showcased with a light-colored sofa adorned with blue decorative pillows and a patterned armchair. A round coffee table sits in front, surrounded by hardwood flooring. Natural light enters through large windows with sheer white curtains, illuminating the space.

5 out of 5 average rating, 123 reviews

Newly Built | Modern 1BR/1BA Private Cottage

Guesthouse 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, 222 reviews

Woodsy Silicon Valley Cottage

Guesthouse in Scotts Valley

A spacious living area features a large sectional sofa adorned with pillows, positioned near windows allowing natural light. A round dining table with chairs complements the open design, while abstract wall art adds a modern touch to the environment.

4.97 out of 5 average rating, 126 reviews

Treescape, a perfect modern, rustic, SV getaway.

4.98 out of 5 average rating, 293 reviews

Private cottage in the heart of Silicon Valley

A light-filled living area features a fold-out sofa bed and a wooden dining table surrounded by four chairs. A wall-mounted TV is visible, along with a small coffee station on a dark table. A doorway leads to the bathroom, and a window provides natural light.

4.78 out of 5 average rating, 553 reviews

Beautiful private 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, 246 reviews

Private Abodu Guesthouse in Downtown San Jose