Holiday rentals with outdoor seating in San Mateo County

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.

Creekside Oasis - Getaway Near the Four Seasons

Our home is tucked away behind a tall redwood fence, which surrounds the property. When you step through the gate, you will know why we consider it our oasis (& only 1.3 mile walk to downtown Palo Alto!) We are across the street from a wild creek bed, and surrounded by beautiful trees. Though we are under the same roof as our guests, you will have a separate entrance, your own kitchen, bathroom with tub and shower and very comfy queen size bed PLUS pull out full bed. We are onsite if needed.

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.

Silicon Valley Work Retreat | Wellness Oasis

Upscale Los Altos Hills. Peaceful and spacious 1,500 sq. ft. retreat. Ideal for business travelers, couples, nature lovers. Adjacent to 3,988-acre Rancho San Antonio Preserve with direct trail access, wildlife, serenity. Inside: workspace with fiber-optic Wi-Fi, fireplace, sauna, pool table, fully equipped kitchen and plush queen bed with guest praised mattress. Outside: exclusive access to saline heated pool and hot tub, patio with BBQ. Minutes from Stanford, Palo Alto, and top tech campuses.

Huge Suite w/ own bathroom, patio, dining, office

Forget your worries in this spacious & serene space. Large Private Suite w/ office zone, dining table, private patio w/ furniture, indoor & outdoor showers & dining, large walk-in closet. Super fast & reliable wifi. Vaulted ceilings, skylights, ceiling fans, & beautiful artwork. The suite located at back of a spacious home shared w/ 2 other suites. Walkable distance to large shopping center. Centrally located close to Stanford U & Hospital, Tech Companies & Freeways to entire Bay Area

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.

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.

Cozy Room with "Private" Entrance, quiet neighbhd

Our charming private guest room (suite) is located on the first floor of a townhouse if you want a private, comfortable, and centrally-located place. The room has a queen-sized bed, a huge closet, and a stocked bathroom. Our self-check-in system allows for flexible check-in times anytime after 3 pm. Ideal for Stanford or downtown Palo Alto visitors, nearby grocery and convenience stores. An excellent choice for a comfortable and private stay in Palo Alto.

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.

Cozy retreat w/ fire pit & atrium

Welcome to your mid-century Bay Area retreat – perfect for families, remote work & relaxed getaways! Enjoy timeless comfort, open spaces & cozy evenings by the fire: - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & outdoor dining - Enclosed atrium w/ seating & custom mural - Wood-burning indoor fireplace & 42" TV - Full kitchen & dining area - Dedicated workspace & fast wifi - Free parking & self check-in

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.