Guesthouse holiday rentals in San Jose

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!

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, 222 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!

4.99 out of 5 average rating, 308 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.

A cozy bedroom features a full-size bed with soft bedding against a vibrant green leaf-patterned wall. A nightstand with a lamp is positioned beside the bed, and a spacious closet is visible in the background, showcasing additional wall decor.

4.91 out of 5 average rating, 203 reviews

1 Bed Cottage w/Kitchenette + yard

Enjoy this cozy 450sqft cottage centrally located between Campbell & Downtown San Jose, close to Santa Row & Valley Fair Mall. This studio will meet your needs for an enjoyable stay in a great area. Kitchenette fully equipped with refrigerator, toaster-oven, electric cook-top, coffee maker & dish essentials. Bedroom w/ spacious closet. Comfortable Full size bed, sofa bed for additional sleeping, an a flat screen tv. Netflix and other streaming networks availablel-log in w/your credentials.

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

Welcome to Cory Cottage, your private oasis in the heart of San Jose! Located less than a mile from Santana Row and Santa Clara University, this modern and stylish cottage is the perfect getaway for anyone looking to escape the hustle and bustle of everyday life. With a gated private entry and fully equipped kitchen, you can unwind and relax in complete privacy. Whether you're traveling for business or pleasure, Cory Cottage has everything you need to make your stay comfortable and cozy.

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.

4.95 out of 5 average rating, 129 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 yard and private drive-way parking included!

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, 218 reviews

Stylish standalone guesthouse near Santana Row

Enjoy a stylish experience at this centrally-located guest house in West SJ. Modern finishes and well maintained backyard with gas fireplace for your enjoyment. Queen day bed with pull out twin trundle underneath to sleep up to 3 people. About a 10 minute walk to Santana Row and Valley Fair Mall. Enjoy the booming night life at Santana Row and come back to sleep in a quiet neighborhood. Minutes from SJ Airport, downtown SJ and Campbell, high tech companies and world class eateries.

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, 1,019 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!

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

Our detached guesthouse near Japantown & DTSJ is designed for comfort and relaxation. Enjoy a king-sized ultra-comfy bed, A/C in both the bedroom and living room/kitchen, a fully equipped kitchen, in-unit washer and dryer, and a dedicated workstation with an ergonomic sit-stand desk. The private outdoor pergola space features a 65” Smart TV, ambient lighting, ceiling fan, propane fire pit, and dining/lounge area. Free and ample street parking included.

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

Stay at Flora's: Our Abodu guesthouse is the perfect spot for a solo traveler or a couple to stay in downtown San Jose. The Abodu has everything you need to feel at home. Enjoy our backyard or the great indoors at the end of your day. We offer really fast Wi-Fi, an easy to use coffee machine, and high quality linens for our guests' comfort. Our full kitchen includes high end appliances and everything you need to prepare your own meals.

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, 214 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.

The open living space features a contemporary kitchen equipped with stainless steel appliances, including a refrigerator and oven. A dining table for four is positioned centrally, surrounded by sleek chairs. Light wood flooring enhances the bright atmosphere of the area, complemented by white cabinetry and a decorative sliding barn door.

4.98 out of 5 average rating, 626 reviews

Private Cottage nearby Airport/SAP/SJ Downtown/SCU

The cottage is located in the central of Silicon Valley. Convenient access to most attractions and places. About 7 to 15 minutes drive from most attractions: San Jose Airport, SAP Center, Avaya Stadium, SAn Jose Downtown, Caltrain/Diridon Station, Levi Stadium, SJ state university, Santa Clara university, Malls. Santa Cruz 35 minutes, San Francisco airport- 45 minutes. Close to major freeways I-280, I-880, US-101.

Popular amenities for San Jose guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

4.96 out of 5 average rating, 266 reviews

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.

Guesthouse in Oakland

Charming Cozy Cottage in Eco-Garden Oasis

4.99 out of 5 average rating, 364 reviews

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.

Guesthouse in Woodside

Rustic Cabin in the Redwoods

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

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, 168 reviews

Orchard Cottage in convenient countryside location

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

4.95 out of 5 average rating, 130 reviews

Large Private Oasis with Yard, Minutes to Downtown

4.9 out of 5 average rating, 256 reviews

Guesthouse in Campbell

Private Entry Studio with parking

4.93 out of 5 average rating, 123 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

Guesthouses with a patio

5 out of 5 average rating, 109 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

Superhost

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.

Guesthouse in West Oakland

4.94 out of 5 average rating, 125 reviews

Charming Victorian Retreat | Minutes to SF

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, 113 reviews

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

4.92 out of 5 average rating, 402 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.

Guesthouse in Oakland

Guesthouse Garden Retreat

4.99 out of 5 average rating, 143 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

Guesthouse in Redwood City

A private outdoor area is enclosed by wooden fencing, featuring a wooden gate and a trellis overhead. Lush greenery and flowering plants are visible throughout the space, with decorative seating positioned near a small water feature, enhancing the natural setting.

4.93 out of 5 average rating, 101 reviews

Sunny Cottage in Redwood City

4.92 out of 5 average rating, 133 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.

Guesthouse in Alameda

Detached Cozy Studio w/ private patio garden & BBQ

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

Guest house rentals with a washing machine and dryer

4.99 out of 5 average rating, 238 reviews

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.

Guesthouse in Oakland

Redwood Heights Cottage with Stunning Bay Views

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

4.89 out of 5 average rating, 130 reviews

Guesthouse in Palo Alto

Guesthouse in Serene Neighborhood

4.99 out of 5 average rating, 170 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

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, 232 reviews

Greenwood Guest House, a Peaceful Oasis

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

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, 103 reviews

Five Star Smart Home Living Experience

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.