Holiday rentals with outdoor seating in Hillsborough

Santa Cruz A-Frame

This unique A-Frame cabin, in a quiet mountain neighborhood with private creek access, was handbuilt in 1965 and remodeled in the summer of 2024. Now a little slice of heaven on the creek in the redwoods. *5-10 min to Henry Cowell Redwoods State Park, Roaring Camp Railroad, Loch Lomond Recreation Area, the Trout Farm Inn, Quail Hollow Ranch + Felton stores. *20 min to Santa Cruz, beach + Boardwalk. *1 min to Zayante Creek Market (EV charger) Find us on social: Insta @SantaCruzAFrame

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.

Stairway to Heaven - 2 bedroom

PLEASE NOTE, we live in a 3 story home and this unit is on the lower level of our home. Also available in a 1 bedroom, this suite features a spacious living room with a fire place, flatscreen TV & a kitchenette with most everything you will need to feel at home. A nice large bedroom with a quality queen bed & linens, a large bathroom with a double sink, tub and shower. The private entrance leads to a patio with stunning views and quiet space. There is a second sunning patio do dine and rest.

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!

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.

Andulore Cottage - Walk to Burlingame Dining/Shops

​​​​Welcome to Andulore Cottage! Remodeled home in great location in quiet neighborhood. Walk to Burlingame Avenue shops, restaurants and Caltrain Station! This 1944 WWII era cottage has been lovingly restored, updated and renovated while preserving historic detail and charm throughout. Interior decor of this home is styled mid-century transitional. There are three bedrooms, living room, dining room, kitchen, and spacious backyard with beautiful patio with brick BBQ and fireplace.

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.

Private Garden Cottage in Belmont Hills

A fully accessorized cottage in a private and quiet setting at the heart of the San Francisco Bay Area. Newly renovated backyard with always blooming flowers, fruit trees, hot tub, and pool. Regular visits from deer, and professional night illumination make this place feel like a magical forest getaway, quiet and secluded from the surrounding city. Enjoy the multitude of patios for reading and relaxation. We even have a tree house for the kids.

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

LuxoStays l! ! Lovely 2BR #SFO #Train #Laundry

*Entire Home-No sharing* Conveniently located! This spacious apartment is only 5min to SFO, 1-2 blocks from Starbucks, Walgreens, and other stores that you'll need! Many restaurants are right around the corner to eat at. Free Shuttles, Caltrain, Samtrans, and freeways are just blocks away. Longer inquiries are very welcome. Inquire even if the calendar is blocked off Send us a message now to secure your booking!

Sea Wolf Bungalow

If you're looking for the most spectacular views on the San Mateo Coast, come to Sea Wolf Bungalow. Located just 20 minutes southwest of San Francisco and 7 miles north of Half Moon Bay, this historic cabin sits on its on own point with sweeping views of the Pacific. Enjoy whale watching, the beach, surfing, fishing, golf, hiking and the fabulous dining of the coastal area.

Cozy retreat w/ fireplace & BBQ grill

Welcome to your cozy Bay Area retreat - a peaceful San Mateo stay perfect for relaxing evenings & easy gatherings. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Wood-burning fireplace & backyard fire pit - Private backyard - fully fenced w/ BBQ grill - Enclosed atrium w/ custom mural - Dedicated workspace w/ door & Wifi - Free parking on premises + self check-in