Family-friendly holiday 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, 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!

4.96 out of 5 average rating, 165 reviews

An A-Frame cabin is surrounded by lush greenery, positioned on elevated ground. A stone pathway leads to the entrance, flanked by wooden railings. The cabin features large glass panels on its façade, allowing natural light to flood the interior. A deck with seating overlooks the nature surroundings.

Cabin in Felton

Santa Cruz A-Frame

This unique A-Frame cabin, in a quiet mountain neighborhood with private creek access, was handbuilt in 1965 and remodeled in the summer of 2024. Now a little slice of heaven on the creek in the redwoods. *5-10 min to Henry Cowell Redwoods State Park, Roaring Camp Railroad, Loch Lomond Recreation Area, the Trout Farm Inn, Quail Hollow Ranch + Felton stores. *20 min to Santa Cruz, beach + Boardwalk. *1 min to Zayante Creek Market (EV charger) Find us on social: Insta @SantaCruzAFrame

4.92 out of 5 average rating, 108 reviews

Apartment in San Jose

2B2B Top Floor Apt | SJC airport | SAP Center 407

Welcome to your cozy retreat in the heart of Downtown San Jose! This stylish 2-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

4.94 out of 5 average rating, 527 reviews

An open living area features a glass dining table surrounded by modern chairs. Natural light pours in through expansive windows, illuminating the airy space. A staircase with wooden steps and metal railing leads to the upper floor, while decorative accents enhance the contemporary design.

Loft in San Jose

Santana Row Luxury Executive 2 Story Loft

Beautiful, luxury and clean 2 story open plan loft on the top floor at Margo building right on Santana Row. 2 bedroom 1,5 bath. Panoramic view of the mountains, downtown San Jose and the planes landing at SJC. Your favorite restaurants and shops downstairs. Valley Fair Mall is across the street. Brand new king size bed in the Master Bedroom, walk-in closet, kitchen, Nespresso coffee, teas. Underground parking with EV/Tesla hookup. Security on site 24/7. Ideal for business travelers and families.

4.99 out of 5 average rating, 254 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.

4.85 out of 5 average rating, 692 reviews

A cozy living area is characterized by a light-colored sectional sofa and a round coffee table with greenery. Natural light enters through multiple windows, illuminating the space. A lamp and decorative items are positioned next to a door leading outside.

Loft in San Jose

Rose Garden Cottage

A private free standing guest cottage on our property in San Jose's historic Rose Garden. 5 min to SJC airport, 1.5 miles to Diridon Station and VTA light rail. Walkable to restaurants, coffee shops, nightlife, parks and public transit. One mile to the SAP Center (Shark Tank) and Santa Clara University. 2 miles to Santana Row and Westfield Shopping Center. You’ll love our place because of it's tranquil setting. Kuerig coffee maker, Britta water filter small refrigerator and microwave.

Apartment in Downtown San Jose

4.94 out of 5 average rating, 262 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.

Home in Downtown San Jose

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, 443 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.

4.87 out of 5 average rating, 109 reviews

Cozy 2BR Bungalow | Garden Vibes in Downtown SJ

Welcome to our sunny 2BR California bungalow with a private backyard featuring fruit trees (kumquat, lime, pomegranate), string lights, and a dining table for six. Enjoy fast WiFi 6, in-unit washer/dryer, and dedicated parking. Centrally located in Silicon Valley with easy access to I-280, Hwy 87, and 101. Less than 10 minutes to SJC Airport, Caltrain, downtown San Jose, SAP Center, Levi’s Stadium & more. We’re here to ensure a smooth, comfortable stay—reach out anytime!

Home in Downtown San Jose

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, 330 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, 215 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.

Guesthouse in Downtown San Jose

A cozy bedroom is featured with a queen-sized bed dressed in a navy-blue coverlet. A ceiling fan provides airflow above the bed, which is complemented by a bedside lamp. Light colors dominate the walls, contributing to a bright atmosphere.

4.93 out of 5 average rating, 116 reviews

1-Bedroom Cottage in Downtown San Jose

Welcome to our private detached guest house located in the heart of downtown San Jose. Although small (about 250 sqft), it is well-equipped with queen-sized bed, full kitchen (oven, range, mini fridge, microwave, Keurig coffee maker), bathroom, washer/dryer and patio. This mini-home comes with basic wifi and a parking permit to park on the street (permit only). A beautiful, cozy, private place. Comfortable, Convenient!

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

Home in Downtown San Jose

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, 161 reviews

NewLuxHome!PoolTable!HotTub!Heart of Downtown SJ

Guest suite in Willow Glen

The image features a clear pool surrounded by a stone edge, with vibrant orange and purple flowers in bloom along the perimeter. Lush green palm trees and other landscaping elements provide a natural backdrop, creating a serene outdoor setting.

4.95 out of 5 average rating, 192 reviews

Private Queen Suite-Pool & Hot Tub, private entry

4.95 out of 5 average rating, 176 reviews

A welcoming entrance is framed by mature trees, with a pathway of pavers leading to the front door. Lush green foliage and colorful flowers provide a vibrant touch, complementing the classic white exterior of the home and the dark shutters enhancing the overall charm.

Home in Willow Glen

Charming Willow Glen Home with Spacious Yard

4.97 out of 5 average rating, 1,020 reviews

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.

Guesthouse in Los Gatos

Cabana in Sierra Azul Open Space Preserve

4.94 out of 5 average rating, 440 reviews

An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.

Home in Los Altos

Luxury Silicon Valley Wellness and Work Oasis

4.98 out of 5 average rating, 120 reviews

A private yard is surrounded by tall trees, featuring a hot tub with bubbles rising to the surface. A hammock is visible to the side of the yard, alongside two Adirondack chairs. The cabin's entrance is shown, with a window allowing natural light to enter.

Cabin in Boulder Creek

Forest Cabin & Hot Tub

4.95 out of 5 average rating, 1,040 reviews

A cozy living area features a comfortable gray sofa adorned with patterned cushions. Natural light enters through multiple windows, highlighting a black wood stove. A rocking chair and a small side table add to the inviting setup, complemented by neutral carpeting.

Cottage in Ben Lomond

Sunny redwood forest cottage

4.95 out of 5 average rating, 121 reviews

A scenic pool area is framed by tall pine trees, with a vibrant sunset reflecting in the calm water. The landscape features gentle hills in the background, enhancing the serene environment.

Home in Ben Lomond

The Hacienda- Santa Cruz Mountain Ridgetop Retreat

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 434 reviews

The cabin is nestled among lush greenery, featuring a wooden exterior and a gently sloping roof. A wraparound deck is visible, surrounded by vibrant trees. Windows offer a glimpse into the interior, blending the structure harmoniously with its natural surroundings.

Cabin in Los Gatos

The Lavender House

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, 449 reviews

Comfortable Whole Home on two house lot

4.93 out of 5 average rating, 207 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

4.94 out of 5 average rating, 164 reviews

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

Guest suite in East San Jose

The guest suite features a spacious layout with a large bed and a futon sofa bed. A television is positioned against the wall, and a mini refrigerator is accessible. Light-colored walls and natural wood flooring enhance the inviting atmosphere. A doorway leads to the adjacent private bathroom.

4.87 out of 5 average rating, 200 reviews

Cozy Suite, Private Entrance + Bath (Pets Welcome)

4.96 out of 5 average rating, 246 reviews

A queen-size bed is centered between two light, airy curtains and adorned with a colorful patterned throw blanket. Framed wall art in earthy tones flanks the headboard, while bedside tables house decorative items. Natural light filters in through the window, creating a serene atmosphere.

Bungalow in Milpitas

Casa Blanca - Mediterranean inspired Serene and Minimal Abode

4.93 out of 5 average rating, 452 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

Superhost

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, 106 reviews

Modern&Homely 2B2B Guesthouse in Heart of San Jose

Family-friendly home rentals with a pool

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

Superhost

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

4.8 out of 5 average rating, 233 reviews

Beautiful Large 4BR Home with POOL

4.95 out of 5 average rating, 171 reviews

A resort-style pool surrounded by lounge chairs is visible, with modern apartment buildings framing the scene. The area is bright and airy, showcasing a leisure space ideal for relaxation, with neatly landscaped greenery along the pool's edge.

Apartment in Menlo Park

Charming 2BR Apartment near tech Giants & Stanford

Superhost

A spacious living area is equipped with a flat-screen TV mounted on the wall and an ornate cabinet. A comfortable grey chair and a glass coffee table are positioned on a soft carpet. Natural light is welcomed through a nearby window, enhancing the cozy atmosphere.

Home in Mountain View

4.88 out of 5 average rating, 192 reviews

Little Poolside House near Downtown Mountain View!

4.88 out of 5 average rating, 125 reviews

A light blue exterior of the cottage is complemented by white double doors and a large window. Floral arrangements in red planters and a white bench enhance the inviting entrance. A comfortable chair adds to the cozy outdoor seating area.

Guesthouse in Sunnyvale

Private & Quiet Garden Cottage

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, 288 reviews

Apartment above Levi Stadium.

4.94 out of 5 average rating, 153 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