Holiday rentals with outdoor seating in Santa Clara County

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!

Executive Class Stay in Tech Hub 3b2B Near SJC

Unwind in style in Silicon Valley's heart. Our backyard offers a peaceful retreat, complete with fruit-bearing trees and ambient lighting. Modern comforts await indoors, from brand-new furnishings, high speed internet, an executive office and a large dining. Your culinary adventures are supported by a well-stocked kitchen and our complimentary treats. With ADT protection and generous parking, convenience is a given. All set in a serene neighborhood, minutes away from tech hubs and entertainment.

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.

Eclectic Escape

The perfect stay for adventure seekers and relaxation enthusiasts. (Permit 251052) Unwind with yard games and bbq, soak up the sun from the deck or relax in a hammock under redwood shade. Cozy up on a comfy couch, enjoy forest views through skylights, or watch movies on the big screen. Explore hiking trails just steps away, vast mountain biking trails (10 min), or hit the beach and surf (13 min). Indulge in wine tasting at a local mountain vineyard nestled amongst the redwood giants (5 mins).

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.

Luxury Silicon Valley Wellness and Work Oasis

Ideal for guests attending matches at Levi’s Stadium, business travelers, couples, and nature lovers, while staying in a quiet residential setting. Peaceful upscale exclusive use 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Fast fiber Wi-Fi, workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, saline pool. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

Redwood Cottage & Hot Tub

Enjoy this peaceful redwood retreat tucked away in the Santa Cruz Mountains. This small private cottage comes with a private hot tub, outdoor shower, propane fire pit and hammock. You'll be 10 minutes to downtown Felton and 25 minutes to Santa Cruz. The cottage is on a shared property and next door to the main house. Please note there is no indoor shower (outdoor only). Although 4 wheel is needed, THE ROAD IS RURAL, NARROW AND STEEP. Ideal for confident drivers. Permit #211304

Dreamy Redwoods A-Frame+fireplace+tub for 2+dogs

Featured in Condé Nast’s “30 Cozy A-Frame Cabins for Cold-Weather Getaways,” Whiskey Hollow is the quintessential romantic retreat! Wake to majestic Redwood views from the loft bed, soak by candlelight in the oversized tub, cozy up by the wood fireplace, or cook a meal in the fully appointed kitchen. Nestled in the Redwoods yet just 2 miles to downtown Felton, 1.5 miles to Henry Cowell State Park, 15 minutes to downtown Santa Cruz, and 20 minutes to the beach (Permit #191282).

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!