Family-friendly holiday rentals in Los Altos Hills

Cozy straw bale haven

The Straw Bale Haven welcomes you! This in-law studio has the amenities that you need for a home base, whether you are visiting for work or play. Come and go as you please with a private entrance. Although the studio is compact, it is also cozy and private. We want you to feel at home. All are welcome here! Update: 04/2026 - The house next door is being renovated and noise may bother some. Please read the entire listing, including house rules, to make this stay pleasant with no surprises.

3 BR Home on Vineyard nr Palo Alto & Stanford

Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

Luxurious Guest House in Los Altos Hills/Stanford

Enjoy secluded luxury in Los Altos Hills! This private GuestHouse located at the end of a cul-de-sac, has two spacious bedrooms, private bath, in unit laundry, central air and a functional fully-equipped kitchen. With 15-foot ceilings, beautiful natural light, hardwood floors, marble & granite finishes, and high-end fixtures & appliances, enjoy an elegant and peaceful stay in the heart of Silicon Valley. Wake up with birds chirping and fresh air. Spend the quiet night at patios or hammock.

Peaceful & Safe Garden Guesthouse in Midtown PA

Recently painted, our quiet, safe, very clean and quaint Mediterranean style guesthouse, is located in a landscaped yard underneath a Redwood tree, and is suitable for only 1 guest. You can conveniently walk to Midtown neighborhood cafés, great eateries and markets. Quickly access the Stanford campus, Silicon Valley companies, San Antonio Shopping areas, and California Ave Caltrain Station by car. You're welcome to enjoy our backyard, nap in the hammock or work on the patio with WiFi access.

Your Room: Calm and Quiet-Private Entry/Restroom

Affluent heart of Silicon Valley-centrally located near major tech companies and El Camino/Kaiser hospitals. Quiet and calm quaint suite with a comfy new full-size bed, a new AC, a working desk with fast WiFi, and an elegant restroom. Near downtown Mountain View . . We are sure you will rest well here. Famous Castro Street for food and Safeway/Ranch 99 grocery stores just blocks away. Google's beautiful Shoreline nature preserve & wetlands nearby. Windows' hillside. Apple nearby. Stanford.

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.

SkyHigh Redwoods Retreat with Bay Views

Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.

Palo Alto-Stanford Sanctuary | 2BR

Great two bedroom apartment with central air conditioning / heating at the center of Silicon Valley on a single-family home property in a unique rural neighborhood setting just a few minutes from Stanford University, Stanford Medical Center, downtown Palo Alto (Houzz, Palantir) , Stanford Research Park (VMWare, HP, Tesla, PARC, Sk ype, WSGR, VA Medical Center, Nest, etc.). Also, within 15-20 min drive to Face book, Go ogle, LinkedIn, Intel, Apple, and more.

Woodsy Silicon Valley Cottage

Discover a laid-back side of Silicon Valley in a cozy, cedar-shake guesthouse surrounded by mature trees. Walking distance from a great network of destination hiking and biking trails. 15-30 minutes from Stanford, Sand Hill Road, and major tech companies. This 400 square foot space is on top of our garage and next to our home. There is no public transportation nearby and ride share services are available but not always reliable so you'll need a car.

Sherwood Cottage @ Royal-T Ranch

Relax at this unique getaway. Stay in the original farmhouse built in 1900. 1 bedroom 1 bath with full kitchen.This is not just a place to stay. It is a fully hands on animal experience that you will not forget. Great for the whole family. The grounds are beautiful and park like. Enjoy meals on the patio with umbrellas, tables and bbq or picnic on the grass. Stay includes 2 hr animal experience. Check in anytime after three. Check out 10 AM.

Caboose in the redwoods just outside of Cupertino

This rustic caboose is just 10 minutes from Cupertino and downtown Saratoga, perfect for both business travelers, outdoor adventurers, and everything in between. There are lots of nearby hiking and biking trails, as well as other exciting outdoor activities. Being so close to Silicon Valley, yet feeling so far from it all is a truly unique experience unlike anywhere else. Pets generally ok. Check with hosts. Pets must not be left alone.

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.