Holiday rentals with outdoor seating 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.

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).

Fabulous Beach Get Away - Brand New Beach House

Amazing Newly Built Beach House. Wake-up in this beautiful beach house in a tranquil neighborhood just a short stroll to the beach, walking trails, and restaurants. This beautifully decorated, two story home is perfect for your next beach get away! This house is fully equipped with TV, fireplace, new cozy beds, outdoor fire pit and BBQ, and much more. Enjoy this town which features horseback riding, fishing, boating, surfing, quaint downtown with shops, wine tasting, restaurants and much more.

40 Acre Redwood Forest With Private Trails

We are the descendants of an old San Mateo County pioneer family. We have been passed down and live on a 40 acre redwood forest, backed by 1000 acres of parkland. We would like to share our forest with you. Take a walk and learn of the history behind La Honda's Woodwardia Lodge built in 1913. Walk on private 150 year old logging trails at this historic getaway. Enjoy the natural beauty of the surrounding Redwood forest. Cozy up in a 40' New 2024 RV. All proceeds go to restoring WJS Log Cabin.

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.

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.

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.

SFO 10 Min • Family 2BR + Patio Games • Baby-Ready

Two queen bedrooms, a private patio with lawn games, an in-unit washer/dryer, and a baby-and-toddler setup that covers everything from crib to high chair — this is the Bay Area family home you've been searching for. Ten minutes from SFO, a block from groceries and restaurants, and a short walk to Seal Point Park's waterfront trails, it's the kind of place where you actually unpack and settle in, not just sleep between activities

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.

Edge of the Redwoods, cozy cabin retreat

Come enjoy the redwoods at this cozy, cabin retreat on a flower farm in La Honda! We are located 30 minutes from 280. 5 minutes from the famous Alice’s Restaurant - great food, great music, great company. 6 minutes from the neighborhood bar, Apple Jack’s - bbq and live music! 15 minutes from world class surfing, beaches, and hiking. Come relax and unwind at The Edge of the Redwoods!