Guesthouse vacation rentals in Los Gatos

Guesthouse in Santa Clara

4.94 out of 5 average rating, 100 reviews

Guest House w/King Bed and Parking in Santa Clara

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!

4.83 out of 5 average rating, 581 reviews

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.

Guesthouse in Los Gatos

Rustic Cottage, Redwoods, Beaches.

Tiny, quaint Cottage sequestered in a Redwood forest. Outdoor Clawfoot Bathtub with Shower under the Stars overlooking a Spring fed creek ! Mature Pond & Marina with sitting areas with Koi and Turtles ! Solar powered lights come on at night! Lighting at the Cottage is Electric, Solar and Battery powered. Lanterns are provided ! There is a Cell Phone & device Charging Station available. No Kitchen or cooking facilities. Summit Market, four miles away, open 7 days a week, hours are 7am to 7pm.

Guesthouse in Almaden Valley

5 out of 5 average rating, 110 reviews

Newly Built | Modern 1BR/1BA Private Cottage

Welcome to this private newly built modern Guesthouse in Silicon Valley, nestled in San Jose, with a view of Santa Cruz Mountains. Close to all major highways in the South Bay, San Jose Downtown (9 miles), San Jose Airport (12 miles), SAP Center (9 miles), Levi's Stadium (16 miles), Santa Cruz Beach (32 miles), Great America Parkway (16 miles), Santana Row (12 miles), Apple (16 miles), Netflix (8 miles) and major tech companies in Sunnyvale, Santa Clara, Mountain View, Cupertino and Palo Alto.

4.99 out of 5 average rating, 775 reviews

The exterior of a cozy cottage is visible, surrounded by a lush garden filled with various plants and flowers. A stone path leads to the entrance, framed by vibrant greenery. Large windows allow glimpses of the inviting interior, enhanced by a seasonal wreath on the door.

Guesthouse in San Carlos

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

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, 446 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, 211 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!

4.96 out of 5 average rating, 311 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

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.

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, 179 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, 1,001 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, 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.

5 out of 5 average rating, 146 reviews

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.

Guesthouse in Los Gatos

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!

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, 614 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 guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in La Selva Beach

A rustic wooden sign marked 'Sand Dollar Farms' directs left towards a gravel road. Surrounding grasses gently sway in a natural landscape, with a soft gradient of browns and greens visible in the background.

4.91 out of 5 average rating, 665 reviews

cute cottage walking distance to beach

Superhost

A broad street is depicted, featuring well-maintained sidewalks lined with palm trees. A trash bin is positioned on the curb, and a variety of parked vehicles can be seen. Residential buildings and greenery are visible in the background, under a clear blue sky.

4.86 out of 5 average rating, 121 reviews

Entire Private Studio Apt + Kitchen & Backyard

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, 113 reviews

Private, stylish, clean detached studio

A private entrance is visible, featuring a white door with decorative glass. A small window is positioned to the right, allowing natural light. A potted plant provides a touch of greenery, and a wooden fence creates a sense of privacy.

4.85 out of 5 average rating, 110 reviews

Adorable cottage in Burbank area of San Jose

A spacious backyard area features lush green grass and charming flowers, illuminated by string lights overhead. A gazebo with outdoor seating is visible, surrounded by a neatly maintained garden. The detached cottage appears inviting in the background, evoking a serene setting during twilight.

4.9 out of 5 average rating, 172 reviews

*1 Bed Cottage w/Kitchenette + yard

4.9 out of 5 average rating, 599 reviews

A charming path is framed by lush greenery and colorful flowering bushes, leading to welcoming garage doors nestled between whimsical Victorian-style houses. Sunlight filters through the overhead canopy, creating a warm and inviting space.

Guesthouse in Santa Cruz

Timeless Coastal Carriage House

A private entrance is framed by a decorative awning and features double glass doors. Potted plants are arranged on either side, complementing a small stool and artistic planter. A lush patch of grass is visible in front of the entrance, enhancing the inviting ambiance.

4.95 out of 5 average rating, 169 reviews

Lena’s 1BR apartment (in-law unit) near downtown

The well-lit studio guesthouse features a spacious layout with a queen bed and a cozy seating area. A large window allows natural light in, while a ceiling fan offers comfort. Wall art and framed photos add character, complementing the stylish decor.

4.95 out of 5 average rating, 284 reviews

Private Studio Guesthouse with A/C in Willow Glen

Guest house rentals with a patio

4.98 out of 5 average rating, 87 reviews

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.

Guesthouse in Los Gatos

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

4.96 out of 5 average rating, 113 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, 117 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, 116 reviews

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

4.89 out of 5 average rating, 142 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

4.93 out of 5 average rating, 227 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, 100 reviews

Adorable 2 bed guesthouse walk to Willow Glen DWTN

4.99 out of 5 average rating, 157 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 washer and dryer

4.93 out of 5 average rating, 344 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 The Willows

The entrance of the two-story cottage is framed by neatly maintained greenery. A solid blue front door is centered between two windows, allowing natural light to enter. A brick path leads from the garden, guiding guests to the doorway.

4.99 out of 5 average rating, 147 reviews

Quaint Cottage Near Downtown Palo Alto

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, 210 reviews

Woodsy Silicon Valley Cottage

Superhost

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.

Guesthouse in Downtown San Jose

4.78 out of 5 average rating, 518 reviews

Beautiful private guest house in downtown San Jose

5 out of 5 average rating, 219 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 Cottage near Stanford in Lovely Garden

Superhost

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.

Guesthouse in Monte Sereno

4.84 out of 5 average rating, 166 reviews

Private Cozy suite Los Gatos -Saratoga

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, 371 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.