Holiday rentals in San Mateo County

Rustic Cabin in the Redwoods

Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

Forest Cabin & Hot Tub

Take it easy in this cozy cabin retreat in the Santa Cruz Mountains. 30 minutes from downtown Santa Cruz and beaches. This charming 400 sq. ft. studio is the perfect setting to disconnect from city life and immerse yourself in the redwoods. The cabin features a queen bed, full bathroom, kitchen & BBQ. The private yard includes a hot tub, propane firepit and hammock to fully relax and unwind. Please note the cabin is on a one way, windy road. There is WiFi but no TV or A/C. SCC Permit# 241449

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

Paradise Treehouse & Heavenly Cabin

A soulful and energetic paradise. Beautiful, private, peaceful & wild surroundings complimented with modern luxuries and comfort. A stunning, unique, & unrivaled experience sure to impact you deeply. Soak in the outdoor tub while you plan your next adventure. Just minutes from the beach, amazing hiking, views and biking. Outfitted with organic latex mattresses, down comforters, top of the line appliances, smoking fast internet and a spectacular wifi sound system with world class acoustics.

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

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those inclined toward an active lifestyle, we are close to Purisima Creek, Huddart Park, and the El Corte de Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space)Note 20 minutes from Half Moon Bay with beautiful beaches and 30 min from Stanford in Palo Alto. We are adjacent to The Mountain House Restaurant. (note) The bed is a Murphy bed in the living area. NO PETS!

Oceanview Penthouse, Stylish, Walking to Beach

A perfect romantic getaways to this stylish indoor/outdoor Penthouse! We are 10 mins walk to beaches and 15 mins walk to award winning restaurants. There are a lot of fun activities: spending your days on the beach, exploring the hiking, biking, golfing, surfing, kayaking, paddle boarding or just simply kick back relax in this quiet and picturesque property with a panoramic ocean view, enjoying the sunset and the beautiful garden. We are 30 mins to SF or 60 mins to Santa Cruz.

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.

Woodsy Silicon Valley Cottage

Discover a laid-back side of Silicon Valley in a cozy, cedar-shake guesthouse surrounded by mature trees. Walking distance from a great network of destination hiking and biking trails. 15-30 minutes from Stanford, Sand Hill Road, and major tech companies. This 400 square foot space is on top of our garage and next to our home. There is no public transportation nearby and ride share services are available but not always reliable so you'll need a car.

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.

Beachfront California Coast Airstream_Luxury (NEW)

This spectacular location comes fully equipped with the 'top of the line' 28 foot' Airstream, (Big Sur & Tommy Bahama class limited edition) with horizontal flip rear tail door for seamless indoor/outdoor living. Overlooking a stunning beach, perched high on a cliff this one of a kind experience boasts breathtaking views of the California coastline and Pacific Ocean to create an unforgettable magical experience of a lifetime.

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.