Family-friendly vacation rentals in Downtown San Jose

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, 577 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!

4.86 out of 5 average rating, 104 reviews

A spacious living area features a comfortable couch and an accent chair, arranged around a coffee table. The entertainment center holds a television. The adjacent kitchen area, stylishly equipped, is visible in the background along with a dining space, illuminated by soft lighting.

Apartment in San Jose

1B1B TopFloor Apt Peaceful Courtyard Facing 406 LC

Welcome to your cozy retreat in the heart of Downtown San Jose! This stylish 1-bedroom apartment is perfect for business travelers, traveling medical professionals, couples, solo adventurers, and interns! -> Very close to SJ Airport, SF Convention Center, SAP Center, SJ Downtown... -> Self-Check in with code -> Free private on-site parking spot in the gated garage -> Central A/C and heater -> In-unit washer and dryer -> High-Speed Wifi -> Comfortable King size bed -> Elevator in the building

4.96 out of 5 average rating, 104 reviews

The spacious sleeping area features a queen bed with a memory foam mattress, enhanced by light-colored bedding and a warm ambient lamp. A smart TV is mounted on the wall. The kitchenette includes modern appliances, and a well-lit private bathroom is visible with contemporary fixtures. The private entrance showcases a welcoming patio space.

Guest suite in San Jose

Private entry studio suite 1B1B walk to SantanaRow

✨✨WALKING TO VALLEY FAIR AND SANTANA ROW✨✨ Enjoy your own private studio with a private entrance and bathroom, perfectly situated in West San Jose. This cozy, modern space is ideal for solo travelers, couples, or business guests seeking comfort and convenience. ✨ Highlights: • Newly remodeled with modern finishes • Private bathroom and private entrance for full independence • Kitchenette for light cooking and snacks • Private AC & heating for year-round comfort • 1 driveway parking space

4.99 out of 5 average rating, 262 reviews

An open living area features a leather sofa paired with a small side table. A dining table is situated nearby, with a view of the modern kitchen that includes sleek cabinetry and ample lighting, creating a welcoming space for relaxation and dining.

Guest suite in San Jose

Modern luxury suite in Downtown San Jose

Welcome to your contactless stay in downtown San Jose! Self check-in + check-out with private gated entrance ensures your health and safety during your stay. There's a large living space, full kitchen, and luxurious bathroom with washer/dryer. A/C and heated floors provide comfort just like home. This guest suite is part of a Victorian home built in 1892 within San Jose's historic Lakehouse district. We created this space specifically to host family and guests and hope you enjoy your stay.

4.9 out of 5 average rating, 100 reviews

Bright, Stylish Suite in Central Silicon Valley

Newly remodeled guest suite, only steps away from SJSU. The main house hosts a boutique architect firm, adding creative energy by day while evenings stay quiet. This retreat offers modern comforts in a prime Silicon Valley location. With quick access to I-280, Hwy 87, and Hwy 101, you’re minutes from Caltrain, SJC Airport, the Convention Center, SAP Center, Levi’s Stadium, and downtown San Jose. Ideal for business or leisure, the suite blends style and convenience for a comfortable stay.

Condo in Downtown San Jose

4.94 out of 5 average rating, 268 reviews

Downtown San Jose Cozy Studio Free Parking

Our cozy studio is at heart of downtown San Jose and features gated parking, washer/dryer, and fully stocked kitchenette (NO STOVE) with a toaster oven, microwave, Keurig, electric kettle, mini fridge, strong WiFi. Enjoy the quality linens & cozy touches. Walk to Convention Center, 5 min drive to SAP Center, Diridon Station, SJC & Japantown. next to I-280/87. Wi-Fi TV, Youtube TV subscription only, login to your own Netflix, Hulu etc. Sorry, no portable hotplate can be brought in.

The exterior of a historical mansion is visible, showcasing traditional architectural features such as a gabled roof and decorative trim. A well-maintained white facade complements the large windows. Several parked cars are seen in front, contributing to the urban atmosphere of the downtown area.

4.83 out of 5 average rating, 450 reviews

#01 small 1 bedroom apartment downtown San Jose

Great location in San Jose's downtown commercial core. Our beautiful historical mansion is a non-residential commercial historical large guesthouse for stays less than 21 continuous nights in each unit. Walk to anywhere downtown. #1 is a small complete apartment used exclusively by the booked guest. #1 has a bedroom with a full size bed, a full bathroom and a kitchen/family room with a sofa/full size bed. #1 has no common areas, but #1 has full access to all common areas.

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, 141 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.

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, 136 reviews

Private, stylish, clean detached studio

Our charming SOFA District Victorian (on 2nd St.) is 5 - 10 minutes walking distance to San Jose McEnery convention center, center for performing arts, SJSU, restaurants, Tech Museum, rock climbing, Ritz & bars. SAP (Sharks & concerts) is a 15 minute walk. (We are in the real downtown perimeter.) This reservation is for our fully-loaded, newly remodeled detached unit bedroom studio in the back of the home. To add guests beyond 2, requires approval.

Apartment in Downtown San Jose

The living room features a comfortable teal sofa adorned with a cozy white throw. A modern glass coffee table sits on a textured area rug. Large bay windows allow ample natural light, and a custom-made work desk is visible, complemented by elegant artwork on the walls.

4.95 out of 5 average rating, 119 reviews

New Modern Craftsman Guest House with Bay Windows

Close to all the action downtown San Jose has to offer, our renovated suite was designed with beauty and comfort in mind. You'll have a private entrance and a front porch all to yourself. This modern/luxurious home features a large living room/dining/kitchen/work area combo, dramatic bay windows, a textured stone wall fireplace, modern amenities, a cozy bedroom, specially commissioned artwork, laundry, and spa-like bathroom - a home away from home.

The living area features a blue sofa and a wooden coffee table positioned on a dark rug. A flat-screen television is mounted above a white brick fireplace. Natural light enters through large windows, framed with light green blinds, and a decorative plant is situated in the corner.

4.81 out of 5 average rating, 343 reviews

Charming Craftsman in Downtown SJ

Amazing 2 Bedroom home in the middle of everything great in downtown San Jose. New AC! Custom details throughout including pergola, barn door, redwood shelving and remodeled kitchen. Walking distance to SAP center, downtown San Jose, San Pedro square, Diridon Caltrain station, restaurants on the Alameda, and the wonderful Whole Foods and attached brewery (Floodcraft). Right next to the beautiful Guadalupe trail for great bike rides and walks.

Guesthouse in Downtown San Jose

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, 231 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 Downtown San Jose family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.8 out of 5 average rating, 290 reviews

A California bungalow style home is presented with a welcoming yellow exterior. A well-maintained front yard features manicured grass and shrubs. A concrete driveway extends to the gated entrance. Two inviting seating areas are positioned near the front porch, enhancing the property's curb appeal.

Bungalow in San Jose

Cozy 2BR Bungalow with Hot Tub near Santana Row

Guesthouse in Willow Glen

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, 644 reviews

Cabana with Warm Watsu Pool

Guest suite in Willow Glen

4.95 out of 5 average rating, 204 reviews

Private Queen Suite-Pool & Hot Tub, private entry

4.94 out of 5 average rating, 157 reviews

A modern living area features a comfortable blue leather sofa and a light, textured armchair. A wooden coffee table with decorative items is centered on a patterned rug. Large sliding glass doors provide a view of the sunset and access to the outdoor space.

Home in East San Jose

Views for Miles | Hot Tub | Gated Hilltop Home

4.95 out of 5 average rating, 181 reviews

Home in Willow Glen

Charming Willow Glen Home with Spacious Yard

4.99 out of 5 average rating, 618 reviews

The spacious interior features rustic wooden walls and exposed beams. A cozy bed with plush bedding is highlighted by warm lighting. A comfortable seating area is nearby, along with a large round mirror and a modern flat-screen TV on the wall.

Guesthouse in Los Gatos

Sanctuary in Sierra Azul Open Space Preserve

4.92 out of 5 average rating, 107 reviews

Cabin in Boulder Creek

Either Way Hideaway

A spacious living room features two red tufted sofas set against a light grey wall. A patterned blue area rug anchors the seating arrangement, complemented by a coffee table with a decorative centerpiece. Natural light filters through a window, highlighting the room's modern artwork and greenery.

4.95 out of 5 average rating, 169 reviews

NewLuxHome!PoolTable!HotTub!Heart of Downtown SJ

Family- and pet-friendly home rentals

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, 229 reviews

TheStudio in Willow Glen (San Jose) CA-95125

A cozy living area features a light blue sofa and a stylish lounge chair, complemented by a decorative area rug. Wall art is displayed above a low table, while houseplants adorn the space. Warm, orange accent walls provide a welcoming touch.

4.93 out of 5 average rating, 292 reviews

Convenient 1BR Home Near SJ Airport & Santa Clara

4.94 out of 5 average rating, 168 reviews

Private Spanish Casita near SJSU-2B/1B & Backyard

An open-concept kitchen and dining area is displayed, featuring dark cabinetry and new stainless steel appliances. A dining table with wooden chairs sits adjacent to a spacious island. Soft lighting from pendant fixtures complements the natural light flowing through large windows.

4.93 out of 5 average rating, 454 reviews

Comfortable Whole Home on two house lot

The exterior of the guest house features a welcoming front porch and a manicured lawn. The interior showcases a modern kitchen equipped with stainless steel appliances and a neutral color palette, accentuated by wooden details and a decorative 'HOME' sign on the counter.

4.83 out of 5 average rating, 110 reviews

Modern&Homely 2B2B Guesthouse in Heart of San Jose

4.93 out of 5 average rating, 459 reviews

A rustic caboose, painted in bright red, is nestled among lush green trees. Vintage machinery, featuring large wheels and a copper detail, is positioned nearby, surrounded by a gravel area. The ambiance is quietly rural, under the canopies of towering redwood trees.

Train in Cupertino

Caboose in the redwoods just outside of Cupertino

4.93 out of 5 average rating, 216 reviews

The spacious kitchen features an expansive island with four bar stools, allowing for casual dining. Light wood flooring complements the bright cabinetry and stainless-steel appliances. A view of the open living area is visible in the background, promoting a welcoming atmosphere.

Home in Santa Clara

4B/2.5B / Office Space / Open Plan / Huge Backyard

4.97 out of 5 average rating, 103 reviews

An outdoor patio area features two rattan chairs with plush cushions, positioned around a small table. String lights are draped overhead, providing a warm glow. A barbecue grill is located to the side, with greenery lining the perimeter, creating an intimate atmosphere.

Home in Berryessa

Modern Tech-Hub Home · Chef's Kitchen · EV · Patio

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 255 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•Pool

4.94 out of 5 average rating, 156 reviews

The interior of the converted school bus features rustic wooden cabinetry and appliances. A spacious teak countertop extends over the cooking area, complemented by a red refrigerator. Sunlight illuminates the living area, showcasing a cozy seating arrangement and large windows with views of the surrounding nature.

Bus in East San Jose

Cozy BUS on Farm Animal Rescue with CITY VIEW

Apartment in East San Jose

A refreshing pool glistens under the sun, surrounded by well-manicured green lawns. A white picket fence encloses the area, enhancing the garden's appeal. The charming two-story structure features a sloped roof and multiple balconies, providing a welcoming atmosphere in a serene outdoor setting.

4.98 out of 5 average rating, 296 reviews

Apartment above Levi Stadium.

4.96 out of 5 average rating, 103 reviews

The solar-heated pool is illuminated at night, showcasing a serene blue hue. Three water features flow gracefully into the pool, highlighting the tranquil setting. The surrounding area is dimly lit, enhancing the peaceful ambiance of the outdoor space.

Home in Campbell

Luxury 4-Suite Carbon-Neutral Home With Pool

A welcoming exterior view of the family house is showcased, surrounded by a spacious front yard. A large pine tree offers shade while a decorative pot with greenery adds a touch of nature. The driveway leads to a double garage with a clean facade.

4.77 out of 5 average rating, 128 reviews

Modern Rustic Home With Private Pool

A bright living area features a spacious sectional sofa adorned with neutral cushions. A modern coffee table sits in the center, complemented by a decorative bowl. Natural light streams through multiple windows, illuminating the light wooden floor and the cozy fireplace with a stone surround.

4.92 out of 5 average rating, 150 reviews

Private Oasis with Pool and Fire Pit

4.8 out of 5 average rating, 236 reviews

A spacious living area features a striking stone wall, complemented by a large flat-screen TV mounted above an elegant dark cabinet. Plush seating options, including a brown leather sofa and chairs, invite relaxation, while a decorative chandelier adds a refined touch to the room.

Home in Willow Glen

Beautiful Large 4BR Home with POOL