Cabin holiday rentals in San Mateo

The Coach House

The Coach House is located on our mountain top horse and lavender farm. We offer youth summer camps so are set up for fun outdoor adventures and activities. Have fun with our horses, goats, and chickens! You can take a 10 min walk over to Nonno's Restaurant for wine/pizza/BBQ and bacchi ball, or take an 8 min drive into Los Gatos, or 15 min to Santa Cruz for the beach and some of the best restaurants and spas around!. Good for couples, solo adventurers, business travelers, kids, & behaved dogs!

Wit's End, Stinson Beach

The best rental in all Stinson Beach! Read the reviews! 5 houses to the beach down the lane, 25 yards from a surfboard rental shop and 300 yards from "downtown" Stinson Beach. Central air and heat. Huge outdoor area with firepit. Walk to everything: the market, restaurants, beach, etc. Hot tub. Dog friendly. No better place! Ask about our rock and roll history, you’ll be Grateful… If you submit a reservation request, please do be sure to include the total number of people in your party.

The Biggest, Little, Surf Cabin

The Biggest, Little, Surf Cabin is a perfect vacation getaway, in the highly desirable coastal community of Bolinas. This bright sunny spot has a fenced off yard, private entrance and all the modern amenities for a relaxing stay. A charming one bedroom cottage, with an extra loft area, perfect for kids, along with a cozy pull out sofa . The rental is perfect for a couple or small family. With a shaded hammock right outside your door, and plenty of peace and quiet, you will never want to leave.

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.

Surfer’s Perch, rustic cabin overlooking the ocean

A unique and tranquil getaway on the Bolinas mesa overlooking the Pacific ocean. Our 1940's small hand-built cabin is located one house in from the end of a dirt road, and the builder's family still calls it home. A rustic and cozy place with everything you need, a launchpad for you to connect with nature & a gorgeous view to Stinson Beach. Enjoy watching the wildlife: deer, raccoons, quail & many birds that enjoy the yard right outside the window and follow the rhythm of the rising sun & moon.

King Suite Cabin | Santa Cruz Mountains

Experience the majesty of the Santa Cruz Mountains. Starting with a relaxing king bed suite and clawfoot tub, this unique and tranquil mountain retreat is nestled among the redwoods only a short drive from Santa Cruz. Find yourself cozy by a fireplace, relaxing under a gazebo, or doing yoga overlooking the redwoods. Location is a hikers paradise as it backs up to lower Castle Rock and Big Basin National Park and many of the best hiking trails in the Santa Cruz Mountains. Kid and pet friendly.

Cabin in the Woods

Step away from the rush of city life at our remote cabin retreat. This hidden gem offers the perfect setting to unwind, reflect, and reconnect. Located beside a county park, the cabin offers privacy, stillness, and true escape, yet it’s just a short drive from parks, wineries, restaurants, and beaches. Whether you're a small family in need of quality time, friends seeking a meaningful getaway, or a team looking for an inspiring off-site, this cabin offers a space to create lasting memories.

Luxe Glamping Cabin Near Big Basin State Park

Nestled among madrones and redwoods near Big Basin State Park, this unique glamping cabin is the only one of its kind in the United States. Imported from the UK, the Fuselage offers a quiet, private retreat amongst the trees, comfortably accommodating two adults, and perfect for a couple's escape. A wraparound deck connects the cabin to a second Fuselage featuring a full private bathroom and shower. The deck has seating with a private gas fire pit, BBQ, and an outdoor redwood picnic table.

Either Way Hideaway

Relax and enjoy riverside views in our tranquil Santa Cruz Mountains guesthouse. Cozy by our fire pits, take a dip in a private hot tub and enjoy the sounds of the river flow by. Hike Big Basin, Castle Rock and Henry Cowell State Parks. Close to historic downtown Boulder Creek and the Santa Cruz boardwalk, it’s the perfect base for exploring Santa Cruz county. Immerse yourself in of nature while staying connected and comfortable. Either way, you’ll enjoy your stay! SCC Permit #251382

Guesthouse in woodside -

This private guest house is located on one of the most prestigious properties in Woodside with it's own private entrance & setting on a 1.5 acre lot. Includes living room, 1 queen bedroom, sofa bed, kitchen and private patio - * There are 15 stairs from where the car is parked to the guest house. Access to basketball court and play structure. No access to the pool/hot tub/fire pit. Close to restaurants, 2 mins from 280 HW, 3 mins to downtown Woodside, 10 mins to Stanford University.

Hike-in Bay Views Cabin w HotTub

Hike up to a well designed, small-but-mighty modern cabin with fast WiFi, your own hot tub and a panoramic view spanning across the bay from the Golden Gate to the San Mateo bridge. 108 stairs lead up to the Aerie, so if you don’t want to get your steps in, this is probably not the space for you! 15 min from OAK and city life, but a world away. Sunsets are glorious here. The Aerie is a special spot just for 1 or 2, so leave the posse behind. Registered guests only.

Charming cabin in the Redwoods

Kick back and relax in this peaceful, stylish space, surrounded by soaring redwoods. With generous shared spaces, and many places to lounge or nap. You could take a moment to stop doing anything, and just breath in the silence, take a walk up the dirt road to the top of the hill, or enjoy a meal with family. Santa Cruz, and three state parks are within 1/2 hour. End of the road privacy on over an acre.