Holiday rentals in Mount Madonna

Airstream With Gorgeous Views of Silicon Valley

Stay in a Vintage Airstream with Scenic Views Near San Jose, CA Escape to our beautifully restored vintage Airstream, perfectly located in the peaceful San Jose foothills. Just minutes from the heart of Silicon Valley, our hillside retreat offers stunning panoramic views, cozy charm, and easy access to top Bay Area attractions. Only 12 minutes from Highway 680, you're ideally situated to explore San Francisco, Santa Cruz, Napa Valley, and beyond — all while enjoying a quiet, nature-filled stay.

Peaceful Treehouse with Ocean View

Featured by Sunset Magazine as a “chic escape.” Inside, mid-century furniture and architectural details are made of natural materials like wood and stone setting a calming, sanctuary tone throughout. Curl up with a good read by the light streaming through floor to ceiling windows and under soaring wooden beams or tuck in for the evening by closing the sliding doors inspired by Japanese screens. Please note that during the winter months, our 1960s artistically unique treehouse may get chilly. H

An oasis on a private retreat

A beautifully secluded area (40+ acres) surrounded by natural beauty with lovely views of Elkhorn Slough and the Pacific Ocean, away from the maddening crowd. Yet, accessible to Carmel / Pebble Beach / Santa Cruz. A variety of outdoor activities, including hiking, bicycling, kayaking, golfing and whale watching. A full breakfast is served daily. It should also be noted it is a gated property and the home is accessed through a dirt / gravel private country lane which is 0.75 mile from the gate.

Redwood Retreat - 191203

Rustic Redwood Cabin - Tranquil Getaway Escape to our remote, rustic cabin surrounded by Redwoods. Relax on the spacious deck or by the indoor woodstove ($50 fee/2-nite). Perfect for guests seeking peace and quiet. Cell service available. Please Note: Respect neighbors and follow house rules/no trespassing. Limited cell service & satellite Wi-Fi. Seasonal, self-service wood-burning heated cedar hot tub: $250 fee/2 nite, advance notice required, starting 7/1. Book soon to unwind in nature!

Enjoy Private Redwoods from Your Bed or the Deck

Come and visit our own private slice of the REDWOOD FOREST with over 40 trees and large deck to enjoy. Hosted Rental Permit 241236 Wake up to fresh mountain air, a view of nature and coffee. After a day of WINE tasting, HIKING, BEACHES, exploration, bring a bottle back & sprawl in comfort reflecting, chatting, or sipping. The perfect little getaway spot. Treat yourself to some nature. A winter fireplace, easy walking and parking makes this scene. 1.5 miles to downtown Boulder Creek and fun!

Entire Guest Suite Private Entrance Kitchen & Bath

Whether you’re here for a business trip, traveling for pleasure, visiting your friends/relatives, or looking for a short term rental, our fully furnished unit can offer everything you need! What you’ll get from staying at our converted garage: * Separate entrance with self check-in (keyless entry) * Workspace with high-speed wifi * TV with Netflix * Fully stocked & equipped kitchen * Private bedroom with queen bed, wall closet, high ceiling * Private bathroom * Free parking on premise

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!

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.

Airstream Beach View (Dream) - New Listing

On 9 private acres overlooking the stunning Beach and Ocean from a breathtaking cliff top view. Stunning sunsets. Surf views with large windows. Fully loaded with all the amenities to make your glamping experience perfect. Fire pit, outside BBQ, outside griddle, Heat, A/C and fully stocked kitchen. Full bathroom with shower. If this one is booked, there are three other equally similar Airstreams on the property.