Family-friendly holiday rentals in Downtown San Jose

The exterior of the Craftsman home is shown at twilight, illuminated by soft lighting around the porch and nearby greenery. A well-kept lawn is visible, enhancing the welcoming presence of the home. The neighboring houses are softly lit, contributing to the peaceful ambiance.

4.87 out of 5 average rating, 312 reviews

San Jose, Downtown, Cozy Craftsman Duplex

You will enjoy your own private living space. Duplex. Our place is a beautifully restored Craftsman home, spacious, clean, and wonderfully appointed for a very comfortable stay. I’m available on the premises next door if you need anything. Near the end of a leafy, quiet street close to downtown San Jose. We are close to San Jose Airport, Convection Center, Train/Bus station, highways 280, 101, and 87. NOTE: We are compliant with COVID-19 cleaning guidelines to keep our quest and ourselves safe.

4.96 out of 5 average rating, 103 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

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

This is a newly renovated 2b2b guest house on the first floor of a single family home. The kitchen is fully stocked with everything you'd need to cook at home. We have a Keurig and we supply k-cups for coffee and tea. Lounge in the living room with TV and really fast wifi. Each room has its own working spaces.Two designated free parking spaces at driveway. Only a 5 minute drive to the heart of San Jose's downtown area, SJSU, San Jose Convention center, SAP center and other Hi-tech companies.

4.99 out of 5 average rating, 258 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.

4.87 out of 5 average rating, 127 reviews

Apartment in San Jose

2B2B Top Floor Apt | SAP Center | SJC airport 415

Welcome to spacious 2BR/2BA apt with court yard view in Downtown San Jose! This 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

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, 446 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, 116 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!

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.

4.92 out of 5 average rating, 132 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, 113 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.

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, 336 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

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, 247 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.

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, 163 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

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.

4.95 out of 5 average rating, 178 reviews

Charming Willow Glen Home with Spacious Yard

4.96 out of 5 average rating, 127 reviews

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.

Guesthouse in San Jose

Garden Cottage w/ Hot Tub • World Cup home base

4.97 out of 5 average rating, 1,023 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, 441 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, 122 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, 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

A modern kitchen features white cabinetry and stainless steel appliances. Natural light filters through the window, illuminating the spacious countertops. Essential utensils are neatly arranged, while a green plant adds a touch of color to the corner, enhancing the overall bright atmosphere.

4.88 out of 5 average rating, 106 reviews

M&J@Morden 3B2B SFH*AC*Heart of Willow Glen|487

4.93 out of 5 average rating, 210 reviews

A modern living area features a blue sofa adorned with white pillows. A glass coffee table sits on a patterned rug, with decorative items placed thoughtfully atop. An accent chair with a cozy cushion offers additional seating, while framed artwork decorates the walls.

Home in Santa Clara

Executive Class Stay in Tech Hub 3b2B Near SJC

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

4.94 out of 5 average rating, 165 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, 203 reviews

Cozy Suite, Private Entrance + Bath (Pets Welcome)

4.96 out of 5 average rating, 247 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, 455 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

A spacious backyard is enclosed by white fencing, featuring a small shed and manicured plants. A table with two chairs is positioned on a paved patio, allowing for outdoor seating. Sunlight highlights the area, creating a serene environment for relaxation.

4.82 out of 5 average rating, 123 reviews

Cozy house 2BR/2BA Sleep 6 AC+Parking+Wifi+Pet

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, 461 reviews

Quiet Poolside Cottage for Solitude

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.

4.8 out of 5 average rating, 233 reviews

Beautiful Large 4BR Home with POOL

Place to stay in Los Gatos

An aerial view displays the serene property nestled among towering redwoods. A sparkling pool is surrounded by lush greenery, with a patio and seating area visible in the background. The landscape features diverse plants, enhancing the tranquil atmosphere of this private retreat.

4.81 out of 5 average rating, 98 reviews

Stay Alpha Home • Modern Redwood Retreat with Pool

4.88 out of 5 average rating, 192 reviews

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

Little Poolside House near Downtown Mountain View!

Apartment in Downtown San Jose

A landscaped pool area features a clear blue pool surrounded by lounge chairs. Palm trees and greenery enhance the serene environment. Adjacent buildings are visible, providing a modern backdrop to the outdoor space.

5 out of 5 average rating, 24 reviews

Luxe Apartment Downtown San Jose w/ Gym, Pool

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, 292 reviews

Apartment above Levi Stadium.

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