Vacation rentals with outdoor seating in Woodside

3 BR Home on Vineyard nr Palo Alto & Stanford

Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

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.

Airstream Coastal Hideaway (Sunset)

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.

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those who are inclined to have an active lifestyle, We are close to Purisima Creek, Huddart Park, and El Corte De Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space) 20 minutes away from Half Moon Bay with beautiful beaches and 30 min. from Stanford, Palo Alto. We are adjacent to The Mountain House Restaurant. Res recommended. Short drive to local breakfast place. NO PETS!

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.

Mid-century retreat w/ firepit & patio

Welcome to your Bay Area retreat in San Mateo’s tranquil Highlands neighborhood. Relax by the wood-burning fireplace, gather around the fire pit under the stars, and enjoy easy access to both nature and the city. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium w/ mural & red maple tree - Pvt backyard w/ fire pit, BBQ & 8-person dining - Fully equipped kitchen w/ stainless appliances - 42” TV w/ streaming & wood-burning fireplace - 15 min to SFO, 20 min to San Francisco

Elegant retreat in Redwood City

NOW with new AC & Heating! Gorgeous one bedroom apartment with en-suite bathroom, a spacious walk-in closet, ample light, and stunning views. Private fully equipped kitchen and sitting area allow for very comfortable living. Bedroom and sitting area/kitchen are separated by a door to allow for 2 separate work spaces. Washer/dryer and many other amenities available. This is part of a ~4000 sq ft luxury single family home with a completely separate and private entrance.

Mt Carmel Cottage Charmer-Bright, Stylish & Clean

Beautiful cottage constructed with its own entry, offering beauty, comfort and privacy for your travel needs. Great location for couples, solo & business travelers alike. Cottage well appointed with many travel needs. Expertly maintained and cleaned. Walking distance to Caltrain (.9 mile), bustling downtown Redwood City (.6 mi), boutiques, coffee, restaurants, parks, movies (1.1 mi) & 5 miles to Palo Alto. Easy access to San Francisco, San Jose and the Silicon Valley.

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.