Family-friendly holiday rentals in San Jose

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.

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.

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.

Apartment above Levi Stadium.

18 miles from Levi Stadium! Your Superbowl HQ Take tram to stadium and avoid traffic JAM and parking nightmare! This 2 bedroom apartment. With with spectacular view of Silicon Valley and Levi Stadium). There are two bedrooms, one bathroom and a combined full kitchen/living room. Living room has couch, TV, and Roku streaming. Apartment has good WiFi. Sit on the private deck and you may see wild turkeys, deer, and even a cow! The Rental fee includes the Santa Clara Short Term Rental Tax!

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.

Gorgeous 3-bedroom home, quiet, close to shopping!

Enjoy the Bay Area in your own private, quaint, and comfortable cozy home! Gaze out of your master bedroom window or living room to green grass and Bamboo tree lined backyard with fruit trees and 6' fences. The home is in a safe, quiet, neighborhood, within 2-3 minute drive to Oakridge mall. Conveniently located w/all shopping imaginable within 5 minutes drive. Our inviting full kitchen contains pots, pans, dishes, a Keurig coffee maker, rice cooker, Ninja Air fryer and much more.

Urban 4BR Oasis: Your Home Away

Escape to our unique 4BR oasis! A fusion of modern design and family comfort awaits. Unwind in spacious living areas – a cozy family room for bonding, a chic living room for relaxation. Serene bedrooms and well-appointed bathrooms cater to groups. Our tranquil backyard, a private haven for all. A fully-equipped kitchen for culinary adventures, Wi-Fi for work/play, and a workspace for convenience. Nestled in a peaceful neighborhood, close to attractions, it's the best of both worlds.

Family Favorite: Mickey Dream Loft & TREE house

Welcome to your next unforgettable stay — where comfort meets adventure in a space designed for fun-loving families and couples. 🌟 🧗‍♂️ Sleeping lofts accessed by indoor ladders — best suited for physically agile, adventurous guests 🌳 Relax in a magical backyard featuring a real treehouse, firepit & BBQ 🛁 Unwind in a spa-style bathroom with luxe touches 👨‍🍳 Cook like home in a fully stocked kitchen 🎮 Enjoy games, 65” TVs, and flexible workspaces 🌟 Discover More Below!

Family friendly 5BR house w/backyard +playground

✔No check-out chores ✔High-speed WiFi ✔ Two dedicated workstations ✔ Great amenities for families with children+ Backyard playground ✔ Wood burning fire place Premium furnished single-story home with spacious backyard overlooking Martial Cottle Park with views of Lick Observatory & surrounding hills with nothing to block views. Huge extended family room. Fully furnished large backyard with table, sofas, chairs, kid's play zone & fruit trees. Wifi throughout the house.

Spacious 3BR/2BA | Near SJC & Convention Ctr

Welcome to our charming 3BR classic bungalow with a private backyard, covered patio, outdoor sofa, and dining for four. Enjoy blazing-fast WiFi 6, in-unit washer/dryer, and dedicated parking. Centrally located in Silicon Valley with quick 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. Whether for work or play, we’re here to make your stay smooth and comfortable—reach out anytime!

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.

Newly Built, Luxury Living

Located just four blocks from the famous “San Jose’s local treasure” downtown Willow Glen, you are surrounded by historic homes, unique architecture, tree-lined streets, and a thriving community. We want you to have a stress-free experience, so there is no check-out to-do list. Just enjoy your stay and leave 👍 You are in the front main home. No parking on the driveway, but there’s plenty of free street parking right in front of the house.