Holiday rentals with outdoor seating in Santa Clara County

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

Peaceful Treehouse with Ocean View

Permit 171035 Featured by Sunset Magazine as a “chic escape,” this Peaceful Treehouse-style retreat blends mid-century design with natural materials like wood and stone for a calming, sanctuary feel. Light pours through floor-to-ceiling windows beneath soaring wooden beams, and Japanese-inspired doors add to the architectural charm. Set high in the trees with ocean views, the home offers three elevated decks including one with a hammock. Perfect for relaxing and enjoying the surrounding canopy.

Private Guest-House in the Redwoods

Our custom built guesthouse was completed in 2016. It is situated on 5 redwood-covered acres, 10 minutes south of Los Gatos and 20 minutes from Santa Cruz. We have easy access to hiking and biking trails, world-class wine-tasting, microbreweries, shops, amazing dining, and more! There is something for everyone in our area! We are surrounded by a 35 acre tree farm, so it's very private, yet close to the silicon valley! Our property has a standby generator so we are not affected by power outages.

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.

Cozy Coastal Redwood Cabin

Rest and connect in this warm, cozy, and private cabin that is nestled in the redwoods. Only minutes away from Henry Cowell State Park, where you can enjoy world class mountain biking trails, hiking, or swimming in the river. Or, enjoy the beach 15 minutes away. This is a perfect place to refresh in the magic of the Coastal Redwoods. Music fills most nights either from the Felton Music Hall or from the chorus of frogs. And wake up in the mornings to the mist in the trees when the fog rolls in.

Kinderwood Farm Stay • Animal & Culinary Adventure

*UPDATE Baby goats & piglets born March 2026* Nestled in an enchanting forest of redwood trees & ferns, lies a treasured, sustainability-focused homestead, waiting for you to enjoy its bounty. This is a one of a kind, immersive culinary & farm adventure with cozy accommodations & unique experiences. Subject to availability, Add-On Activities may include goat milking & feeding baby goats, cheesemaking, sourdough, and soapmaking. Join us for a visit you will remember for a lifetime.

Peaceful Coastal Mountain Cabin

Redwood Skye, our classic A-frame home, is nestled among the towering trees in the Santa Cruz mountains. Escape, unwind, and enjoy nearby hiking, biking, beaches, parks and more — all of which got us featured on the Emmy award-winning TV series, “Staycation.” Conveniently located: 5 mins to Henry Cowell State Park, Roaring Camp Railroad & Felton Music Hall; 15 mins to Santa Cruz with its famous boardwalk and spectacular beaches; 45 mins to San Jose; ~1 hr to SFO.

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!

Mount Hermon Creekside Cottage

Have fun with the whole family at this adorable cottage nestled in the redwoods. (Permit Number 231151) Views of the creek and only steps to the conference center at Mount Hermon, less than 1/2 mile to the famous redwood forest of Henry Cowell; this home is perfect to stay in and relax or to go explore and use as a homebase. Newly remodeled kitchen, with everything you would need to host a dinner party, kids games, books, TV and so much more.

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.

Mountain Top Yurt in the Redwoods

Peaceful, clean, spacious, beautifully decorated and quiet 24' Yurt completely surrounded by Redwoods on top of the Santa Cruz Mountains. Spend a couple days meditating, reading or writing the next chapter of your memoir. Walking distance to Mount Madonna Retreat Center (open now through reservation only). County Park hiking and horseback riding trails located within 3 miles. Ideal place for photography and mountain/road biking.