Pet-friendly holiday rentals in Woodside

Beach Airstream (Bliss) - New Listing

On 9 private acres overlooking the stunning Beach and Ocean from a breathtaking cliff top view. Stunning sunsets. Famous 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. Within 10 mins of Half Moon Bay shopping. Beach access short walk or drive. If this one is booked, there are three other equally similar Airstreams on the property.

Night & Day Cabin, a National Park like experience

Night and Day Cabin is located within a gated conservation community in the Coastal Redwood Forest of Pescadero, California. Originally deemed “Little Yosemite” this one-of-a-kind neighborhood inspired us to create a sanctuary to escape and create, to immerse ourselves with nature and connect with each other. Enjoy a private studio with full amenities: kitchen, bathroom, sleeper sofa, queen bed, and outdoor porch with fire pit. Everything you need to relax or adventure. Perfect for two adults.

Apartment w hot tub / forest & ocean view

Slow living at this farm (Coop d'état Farm) retreat on Kings Mountain. Set in old-growth forest with ocean views, a fire pit and a hot tub, the apartment sits on a working campsite (Kings Mountain Fancy Camp) with chickens, goats, dogs, and cats. A 10-minute walk from the Purisima Open Space trail network. It has a bedroom a living room, a bathroom and an office space. It occupies the lower floor of our home and has a private entrance and parking. With access to a shared picnic area / bbq.

Sunny 🌞 guesthouse near Stanford 🌲 w/private patio

Enjoy a stylish experience at this brand new, centrally-located 1 bed/1 bath guesthouse. Private driveway for off street parking with free EV charger. Sunny patio and lawn area for outdoor dining/ outdoor living space. Dedicated desk and free fiber internet/WiFi to work from home. Quiet, centrally located neighborhood walking distance to grocery, restaurants including Michelin star Selby’s & KL Wine store. 10 mins drive to Stanford 5 mins drive to Menlo Park DT 5 mins drive to RWC

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.

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.

A beautiful Tree house -your own retreat

This charming 2 bedrooms is nestled among the trees in beautiful Woodside, California. This town is 30 minutes from San Francisco and right behind Stanford University. Our tree house is a private, peaceful, modern and very comfortable detached guest house. The house has a fully equip kitchen, BBQ and very peaceful settings where you can enjoy nature hikes and be surrounded by peaceful trees and yet just minutes away from town.

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.