Family-friendly holiday rentals in San Jose

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!

Kitchen · Indoor spaces · Check-in

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

Indoor spaces · Family · Accuracy

New! Stylish Condo on Santana Row

Enjoy an indulgent experience at this stylish and centrally-located condo in the heart of Santana Row. "The Row" is a premium blend of residential, retail, and dining spaces in the center of Silicon Valley. Revel in gourmet restaurants, upscale shops, cinemas and a lively atmosphere with outdoor concerts and seasonal festivals. Take a short stroll to Westfield Valley Fair to continue your journey in fine dining, entertainment and shopping venues Located right off of highways 17, 280, and 880.

Kitchen · Family · Amenities

Private Queen Suite-Pool & Hot Tub, private entry

This is your Getaway spot! Enjoy your private suite, bathroom and large smart TV, pool and hot tub outside your door. Located within 3 miles of downtown Los Gatos and Campbell with great food options. Levi's Stadium/49ers 9.5 miles, Mountain Winery Concerts 7.5 miles, San Jose International Airport 6.5 miles, SFO 35 miles, SAP Center/NCAA/Sharks 4.6 miles. We have professional cleaning. Check-out like a hotel, no starting laundry! Hot tub and Pool are a perfect way to relax and end the evening.

Kitchen · Family · Grill

Santana Row Loft | Luxe Stay in Silicon Valley

Amazing Loft with the View at Santana Row The Space 1,090 sq ft open-concept loft on the top floor with soaring ceilings, minimalist décor, and stunning views of Santana Row. 2 bed / 1.5 bath- perfect for couples, families, or business travelers. INCLUDED ∙King-size bed with premium Ghost mattress + full-size bed ∙NEST thermostat ∙Small library for light reading ∙New fridge and TV Access & Parking: Keyless entry +1 designated underground parking spot. Accessible via garage or lobby with key fob.

Family · Indoor spaces · Parks

Airstream With Gorgeous Views of Silicon Valley

Stay in a Vintage Airstream with Scenic Views Near San Jose, CA Escape to our beautifully restored vintage Airstream, perfectly located in the peaceful San Jose foothills. Just minutes from the heart of Silicon Valley, our hillside retreat offers stunning panoramic views, cozy charm, and easy access to top Bay Area attractions. Only 12 minutes from Highway 680, you're ideally situated to explore San Francisco, Santa Cruz, Napa Valley, and beyond — all while enjoying a quiet, nature-filled stay.

Indoor spaces · Kitchen · Solo travel

Airy Open Concept Modern Home: 3br/2bath + Office

Newly renovated home with a 1 Master Bedroom Suite, 2 Bedrooms and an Office (1,500 SF). The house features an open concept Kitchen/Dining/Living room with a sliding door to a large deck. The house has been completely decluttered to give you an airy and a peaceful stay. Located just 15 minutes from SJC airport and a short drive to most key destinations in the South Bay Area. Ideal for families or business travelers looking for a home away from home with all the amenities and complete privacy.

Kitchen · Family · Wifi

Paradise Treehouse & Heavenly Cabin

A soulful and energetic paradise. Beautiful, private, peaceful & wild surroundings complimented with modern luxuries and comfort. A stunning, unique, & unrivaled experience sure to impact you deeply. Soak in the outdoor tub while you plan your next adventure. Just minutes from the beach, amazing hiking, views and biking. Outfitted with organic latex mattresses, down comforters, top of the line appliances, smoking fast internet and a spectacular wifi sound system with world class acoustics.

Family · Kitchen · Amenities

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.

Indoor spaces · Kitchen · Bathroom

Cozy BUS on Farm Animal Rescue with CITY VIEW

Stay on a farm animal rescue in a 38’ yellow school bus conversion. If you are interested we also host an Airbnb Experience called Life With Farm Animals At Rancho Roben Rescues where you get a 90-120 minute up close encounter with all of the animals - taking time to learn about each of the unique creatures that lives here and the opportunity to interact with them directly. Pet a chicken, groom a pony, feed a goat, take a walk patrolling the fields with our livestock guardian dogs.

Family · Indoor spaces · Walkability

Warm and Cozy Two-Story Loft Overlooking Santana Row

Welcome! We have worked hard to create a beautiful, relaxing atmosphere for the business traveler who has been traveling/working all day or for families who are visiting and want a comfortable “home base”. Our beautiful, clean and comfortable 2 story loft overlooks the main “Row” with popular restaurants and shops or you can take an easy walk across the street to Valleyfair Mall. Our 2 bedroom 1.5 bathroom is equipped with everything you need for a comfortable stay!

Kitchen · Family · Cleanliness

Views for Miles | Hot Tub | Gated Hilltop Home

Retreat above the city in this one-of-a-kind home and gaze at the sweeping view of Silicon Valley. Rancho Ruby is a revived 1950s ranch designed with a modern California style. Every amenity and detail has been thoughtfully considered for the tech-savvy travelers. The home is open, peaceful, and cool. It sits on a hilltop, situated on a secluded & gated third acre lot to allow tranquility for guests but is only a 15 minutes drive to the city center.

Kitchen · Family · Hospitality