
Vacation rentals with outdoor seating in Woodside
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Top-rated accommodations with outdoor seating in Woodside
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

Soak up the Serenity on the Patio of a Charming Cottage
Light the fire pit and dress for dinner in the vine-covered garden at a peaceful retreat with a soothing waterfall. Zen beachy decor and coastal paintings set the scene indoors, with abundant natural light enhancing easy open-plan living. Pets are welcome with a small cleaning fee of a $50 (one time fee) and additional pets $25 (one time fee). The main room is 12'x17'. Closet is 6 1/2' long. Bathroom 4'x5 1/2' + shower 3'3" x 3'3". kitchen 4 1/2' x 8". Simple breakfast served. Your own private entrance, plenty of parking on the street, nice neighborhood. We are available if you have any questions or need information on the area. 2 night minimum please. The cottage is tucked away off the street in a quiet, safe neighborhood where residents walk their dogs in pleasant weather. Nearby downtown Redwood City is home to shops and groceries and freeways and public transportation are within easy reach. There is a bus that runs at the corner of our block, it would take you to downtown Redwood City or travel down the El Camino Real. There is a train depot downtown as well. Pets - 2 small dogs in the main house, 2 outdoor cats.

Apartment w hot tub / forest & ocean view
Slow living on the farm. Welcome to Coop d’État Farm Retreat on Kings Mountain—set among old-growth redwoods with ocean views, a fire pit & a private hot tub. The apartment sits on our working glamping property, where chickens roam, goats graze, dogs stand guard, and our cats supervise from afar. We’re a 10-minute walk to the Purisima Open Space trail network. This cozy apartment occupies the lower floor of our home & includes a private entrance and parking, access to a shared picnic & BBQ area.

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.

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.

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!

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.

Custom Cabin Retreat in the Redwoods
This retreat offers guests a unique experience of living in a well designed, minimalist space while having all one really needs. From the nautically-inspired curved ceiling w/ skylights to the custom redwood trim, this cozy retreat will inspire. Relax on the private deck with the fire pit, walk to the river or enjoy the local trails thru the towering redwoods. Santa Cruz beaches are just 35 min away, 25 min to Big Basin and Henry Cowell, and 35 min to fine dining in Saratoga.

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.

Delightful Hideaway in San Carlos
Fully equipped executive studio in the heart of Silicon Valley. This studio is ideal for accommodating executives, visiting doctors and nurses and other professions that might require long term stays. Visitors will enjoy the warm family-friendly environment and delightful garden setting. It is also well-suited for those on vacation who delight in visiting the nearby cities, as well as those who have families close by and want to have their own private spot.

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.

Charming Studio Garden Cottage near Stanford
Come and relax in our light and airy studio cottage situated in a beautiful garden setting, the perfect get-away after a day of business meetings or visiting with family. We are close to major Silicon Valley destinations as well as Stanford Hospital, 45 minutes' drive from San Francisco, San Jose and the beach in Half Moon Bay — easy access to Highways 101 and 280. Our quiet neighborhood full of mature oak trees beckons you to take a walk.

Bicycle Shack @ La Honda Pottery
My place is close to miles of hiking and biking trails in county parks and openspace, great views, the beach and not far from the Peninsula, S.F. and Santa Cruz. You’ll love my place because of the location, the people, the ambiance, the outdoors space and that it is a self contained small cabin with a tiny deck.. My place is good for couples, solo adventurers, and furry friends (pets). Perfect for hikers and bikers.
Popular amenities for Woodside outdoor seating rentals
House rentals with outdoor seating

The French Door

10-Min SFO *A/C* Modern Comfort 2BR Family Retreat

Super Private Hidden Redwood City House and Garden

Immaculate 2 K Bed/2 Bath for business or travel

Remodeled Modern Home in Convenient Location

NEW! Woodside Retreat: Gorgeous Views & Hot Tub

Upscale Modern House Near Mountain View Downtown

Stairway to Heaven - 2 bedroom
Apartment rentals with outdoor seating

Beautiful private 1 bedroom apartment w/ Bay views

The Cozy Casita 2

Private & clean STUDIO 580/680 Tri-Valley

Desirable MV 2B/1B Palo Alto/Los Altos Border

Modern apt steps to beach, trails & downtown HMB

Newly Updated Guest Suite w/ Sweeping Ocean Views

Steps to Beach Ocean Retreat / Private Entrance 4

Studio Apartment with Kitchenette Alcove
Condo rentals with outdoor seating

Modern condo, Palo Alto, 1 Block to Stanford 2337

Twenty minutes to SF, one block to beach, fire pit

Private Modern Retreat - Patio, Fire Pit, Hot Tub+

Spacious top 1bd/1ba w/ pvt deck (no cleaning fee)

Pacific Heights Home Garden Near Fillmore & Union

Sunny 2b/1b with great Bay views!!!

Cozy condo in the heart of Alameda

Clean, Private and Safe San Francisco Apartment
When is the best time to visit Woodside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $304 CAD | $272 CAD | $306 CAD | $308 CAD | $356 CAD | $335 CAD | $342 CAD | $334 CAD | $299 CAD | $343 CAD | $330 CAD | $325 CAD |
| Avg. temp | 10 °C | 12 °C | 13 °C | 15 °C | 17 °C | 19 °C | 20 °C | 20 °C | 20 °C | 18 °C | 13 °C | 10 °C |
Quick stats about vacation rentals with outdoor seating in Woodside

Total vacation rentals
Explore 50 vacation rentals in Woodside

Nightly prices starting at
Woodside vacation rentals start at $123 CAD per night before taxes and fees

Verified guest reviews
Over 2,990 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
50 of Woodside vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Woodside rentals

4.9 Average rating
Woodside stays are highly rated by guests—averaging 4.9 out of 5!
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