Holiday rentals in San Francisco Bay Area

Step back in time on this beautiful classic yacht

Good Luck is a hundred-year-old classic yacht, lovingly restored and ready to transport you to another time while luxuriously spoiling you on your bay area adventure. This dockside charter gives you complete privacy and an amazing nautical experience. Alameda is a beautiful island community in the heart of the Bay, filled with beautiful homes, adorable shops, and many great restaurants. The San Francisco ferry is close by to whisk you to the big city, so why would you want to stay anywhere else?

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.

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.

Newly Remodeled Coastal Retreat

Cute mid-century home that is newly remodeled with a modern and minimalist vibe. Featuring high-speed internet, a working space, vinyl record player, a small library, 4k tv with streaming options, a nice outdoor deck to enjoy with a propane grill, outdoor shower and three person sauna as well. Experience stunning nature views and serenity from a private fenced in property. Lookout or listen for the cute quail residents. Explore the nearby beaches, nature hikes and a tiny but vibrant downtown.

Private suite on 1918 heritage property

Originally settled in 1918 this heritage property, situated in Concord’s most coveted neighborhood boasts warm, old-world charm and timeless finishes while incorporating the modern amenities. Fully furnished & welcoming studio features a well-appointed kitchen, laundry and spa inspired bathroom. The adjoining patio is the perfect venue for enjoying morning coffee or evening cocktails. The incredible 1 acre lot, intersected by the spring-fed Galindo Creek has plentiful on-site parking!

Immaculate Vintage Airstream in Mill Valley

Capture the spirit of 1960s American wanderlust in a gleaming 1969 Airstream trailer. Painstakingly restored with period décor. We added our "aluminum guest house" to our back yard with a 100 foot crane! Quiet, green and private backyard. Plenty of headroom, modern amenities and new plumbing with delightful 1969 Vintage décor. 1000 thread count sheets on a queen size bed. Great WIFI and onsite tech support. Well equipped kitchen. Additional guests welcome no charge! Parking in front.

Sonoma Mountain Artist's Retreat

Enjoy the perched feeling of Sonoma Mountain's setting with sweeping views and nature. The slightly tamed wilderness with an olive orchard and gardens sets the tone as you chill on the redwood deck. This is a studio cottage with expansive views to the western valley and Marin. Mount Tam appears through the windows from your super comfy bed. This is a beautiful and unique space adjacent to a mellow artist's studio. NOTE: Well behaved and Pre-Approved dogs available for a nightly fee.

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.

Moonside: inspiring spaces for wild creatives

Moonside retreat is purpose-built to connect you with pristine nature amidst lush amenities & modern workspaces. The secluded geodome will be your home base within 60 acres of extraordinary redwood forest, ocean views, surreal rock landscapes, streams, caves, waterfalls, and winding trails dating back to logging days. When focused pursuits call, dedicated work pods offer state-of-the art offices at your disposal, ensuring your most inspired & productive days of work, ever.