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, 533 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.

4.96 out of 5 average rating, 103 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.

Guesthouse 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.

4.94 out of 5 average rating, 108 reviews

Santa Clara Guest House w/King Bed and Parking

Newly updated guest house centrally located in the Silicon Valley. Easy access to everything! Close to San Jose Int. Airport, Downtown San Jose, Santa Row, Valley Fair Shopping Center, and more! This stylish guest house will meet all your needs. Fully equipped kitchen with refrigerator, oven/stove, Keurig coffee pot, and dish essentials. Large bedroom with comfortable King bed, en-suite bathroom, laundry, and lots of closet space. Beautiful private yard and private drive-way parking included!

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, 447 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.

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, 212 reviews

TheStudio in Willow Glen (San Jose) CA-95125

Vacationers, Extended Family, Work Travelers with Fast Internet! ALL the Comforts & Gourmet Kitchen!! Optional 2nd Full Size bed set-up fee - separate bill for 3rd person. 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!

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.

4.9 out of 5 average rating, 124 reviews

Los Gatos Cozy 2BD 2BA Private Guesthouse

Enjoy a nice quiet stay in this newly constructed guesthouse located in Los Gatos. A safe, peaceful, high-end neighborhood. Private side yard, designated parking, private entrance. Guesthouse is designed with an open living space, oversized bedrooms, and functioning kitchen. Security camera/systems outside of the property. 20 min to SJ Airport, 6 min to Netflix, 6 min to Downtown Los Gatos, less than 5 min to Vasona Park, 3 min to Good Samaritan Hospital, 25 min to Stanford Hospital

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, 186 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!

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, 1,002 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 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, 213 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.

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, 222 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, 149 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 local private hiking trails 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!

Guesthouse in Downtown San Jose

A modern living area is depicted, featuring large windows that allow natural light to fill the space. An inviting sofa and a coffee table are positioned in front of a wall-mounted television. The open kitchen showcases sleek cabinetry and a dining table with white chairs.

4.99 out of 5 average rating, 148 reviews

Quiet guesthouse near SJ airport with EV charger

Kick back and relax in this calm, stylish space. Brand new guesthouse build and landscape completed in 2023. Our guesthouse offers a full kitchen, WiFi, self check-in, FREE parking and washer and dryer. Tesla Universal EV charger Level 2 60 amp avilable for guest use. Centrally located in Downtown San Jose. A quick drive to the SJ airport, SAP Center, San Pedro Square, Levi’s Stadium, San Jose State University and Santa Clara University.

Popular amenities for Los Gatos guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

4.93 out of 5 average rating, 349 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

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, 400 reviews

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

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.

4.9 out of 5 average rating, 115 reviews

Private, stylish, clean detached studio

Guesthouse in Downtown San Jose

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, 521 reviews

Beautiful private guest house in downtown San Jose

4.96 out of 5 average rating, 450 reviews

The entrance to the studio cottage is framed by lush greenery, with steps leading up to an open door. Natural light spills into the interior, showcasing wooden accents and inviting outdoor space. Paved stones create a pathway, bordered by a wooden fence.

Guesthouse in Sunnyvale

Private cottage in a garden

4.93 out of 5 average rating, 107 reviews

A spacious yard features a children's play structure with a slide and swings, accompanied by a patio seating area under a shade umbrella. Lush green grass enhances the outdoor setting, surrounded by wooden fencing for privacy.

Guesthouse in Sunnyvale

Sunnyvale2B/1B/Family/Free EV Charging/AC/WiFi/PKG

Guesthouse in Mountain View

The studio space features a cozy double bed with striped bedding, complemented by wood cabinetry. A round dining table is positioned near the kitchenette, which includes an undercounter refrigerator and sink. Natural light enters through windows covered by beige shades.

4.96 out of 5 average rating, 314 reviews

Private studio in downtown

Guesthouse in Santa Clara

A cozy guestroom features a spacious bed covered with a vibrant teal bedspread. A white kitchenette is visible, equipped with essential appliances, while a small dining area is present nearby. Natural light filters through sheer curtains, illuminating the modern decor.

4.93 out of 5 average rating, 165 reviews

Entire guesthouse Santa Clara smart lock entrance.

Guesthouses with a patio

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.

4.98 out of 5 average rating, 89 reviews

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

4.95 out of 5 average rating, 118 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

4.99 out of 5 average rating, 120 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

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, 117 reviews

Garden Cottage w/ Hot Tub • 3 mi. to SJC

4.89 out of 5 average rating, 145 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, 232 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

A bright living area features a light grey sofa with decorative pillows, paired with a round black coffee table. A teal armchair is positioned nearby. Large windows with striped shades allow natural light to fill the space, complemented by a tall indoor plant.

4.94 out of 5 average rating, 101 reviews

Adorable 2 bed guesthouse walk to Willow Glen DWTN

A serene bedroom features a spacious bed adorned with a patterned quilt and decorative pillows. Two framed art pieces hang above the bed, complemented by natural light filtering through sheer curtains. A comfortable bench sits at the foot of the bed, alongside wooden nightstands and a bedside lamp.

4.86 out of 5 average rating, 71 reviews

Cozy Retreat Home

Guest house rentals with a washing machine and dryer

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.

4.82 out of 5 average rating, 140 reviews

1 bedroom attached guesthouse

5 out of 5 average rating, 222 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.

Guesthouse in Atherton

Charming Studio Garden Cottage near Stanford

Guesthouse in Monte Sereno

A charming outdoor patio area features a round table surrounded by four decorative chairs. Lush greenery decorates the space, including potted plants and foliage. Two turquoise doors are complemented by wall-mounted lanterns and classical sculptures, creating a peaceful setting for relaxation.

4.84 out of 5 average rating, 166 reviews

Private Cozy Suite Los Gatos - Saratoga

4.98 out of 5 average rating, 233 reviews

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.

Guesthouse in Hensley

Private Abodu Guesthouse in Downtown San Jose

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, 184 reviews

Modern 2Bed/1Bath suite in San Jose

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.

4.98 out of 5 average rating, 379 reviews

Private unit close to Santa Clara University

An exterior view of the cottage showcases a spacious patio area, featuring a dining set with an umbrella. The home is painted in a light color, complemented by a well-manicured garden. A stone fountain stands to the side, adding to the tranquil outdoor setting.

4.97 out of 5 average rating, 212 reviews

Lemon Tree Cottage, central silicon valley

An outdoor patio features a round dining table surrounded by black mesh chairs. A large red umbrella provides shade over the seating area. Colorful cushions adorn two lounge chairs, while potted plants add greenery to the space. A nearby door leads into the guest house.