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!

2B2B Apt Near Airport | SAP | Apple | Zoom 314 LC

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

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.

Charming Home nearby Airport/San Jose Downtown/SAP

Centrally located to explore the heart of Silicon Valley. This beautiful home has all the conveniences and is a ideal location to experience all of activities. About 7 to 15 minutes drive from most attractions: SJC airport,SAP center,SJ downtown,Hi-tech companies, Santana Row,Valley Fair Mall, Levi’s stadium,Avaya stadiums,Rose Garden, Great mall outlets,Museums and Restaurants..Santa Cruz 35 minutes. Stanford 25 minutes. San Francisco 45 minutes. Close to major freeways I-280, I- 880, US-101.

Sunnyvale2B/1B/Family/Free EV Charging/AC/WiFi/PKG

~Close to many tech companies ~Yard with kids play structure/Gazebo ~Pack'n Play for baby ~Free parking and EV Charging ~Hi-speed WiFi ~New kitchen and appliances ~Sofa bed for 1 extra person ~Central AC and Heater with Nest ~Smart 55''TV with Netflix. ~Walking distance to downtown/shops/parks ~Quick access to 101 fwy and Central Expy ~Kitchen equipped with utensil essentials ~Best value Airbnb The big lot is separated into 2 units. This Unit B is a 2B/1B ADU with full privacy, the RED area

Comfortable Whole Home on two house lot

This home has lots of light, new appliances and furniture. You are renting the entire home in the rear of the property. This is in an older, diverse neighborhood, with friendly Hispanic, Portuguese, Viet, Black and White neighbors, and a low crime rate. The pets in the listing are actually in the front house. The back house is pet friendly, but cleaned after each visit. There are neighborhood cats outside. Easy access to bus lines, and two major highways (101 and 280).

Zen Retreat‧1777sqft‧4B2.5B‧AC‧Fruitful Backyard

Time is of the essence! Our discount, starting at 30% off May 2026 - July 2026, is filling up. If you're interested, consider adding our house to your wishlist and securing your reservation. Experience the ultimate peace and safety in San Jose. Our sanctuary has welcomed countless group travelers, workers, families. 20+ restaurants, Westfield Oakridge, 2 Costcos nearby, Cheesecake Factory, movies, Ranch 99, and the Apple Store are all within 5-8 minutes of driving.

Walk to Santana Row + Valley Fair | 6min drive SJC

Private guest suite with it's own front door, bedroom and bathroom. There is no kitchen but we provide a mini fridge, microwave and kettle. It is a short walk to Santana row and Valley Fair Mall and a 5 minute drive to SJC Airport. This suite is 1 of 2 Airbnbs on the property. 1 Parking spot on the driveway, directly in front of the Airbnb. Fujitsu split system for cooling and heating 0.3 mi to Santana Row 0.3 mi to Westfield/Valley Fair 3.1 mi to SJC Airport

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!

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.

Lively Santana Row Loft for Business or Leisure

A Silicon Valley hot spot. Right on the main Santana Row strip by Tesla Show Room, Straits Restaurant, and Yard House. It's central for business in Silicon Valley or for the traveler visiting for leisure. 12 min* from SJC 13 min* to Apple HQ 16 min* to G00GLE HQ 14 min* to Cisco HQ 15 min* to LinkedIn HQ 10 min* to Adobe HQ 13 min* to Levi's Stadium 15 min* to Great America Theme Park Walking distance to many amazing restaurants and shops.

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.