Vacation rentals in Hillsborough

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.

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.

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

SFO recharge. Hilltop guest house nested in nature

Stay at this newly built retreat for an extended stay or SFO flight layover. Surround by nature, redwood trees, up on the hill overlooking the Bay. It is a guest house on the lower level of a main house, 10 mins Uber from SFO. Reliable Wifi for all your calls. This is your retreat. Spacious layout w separate secluded entrance. In-unit washer, and dryer for sanitizing, make any long term stay, business travel, or relaxing trip extremely convenient. Desk and Office chair set up already.

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.

SFO Panoramic Views 4BR/3BA near SF-Silicon Valley

Located in the SF Bay Area Peninsula with 180-degree panoramic views of the Bay Area, 3,012 square feet, 4 bedrooms and 3 full bathrooms. Located on the upper level is the kitchen, dining room, TV room, and spacious living room. Lower level has four bedrooms. Must be able to climb stairs. Refinished hardwood floors and carpet in the bedrooms. Backyard extends into multiple decks, including BBQ grill and hot tub. Located between San Francisco and Silicon Valley. Very close to SFO.

Oceanfront Home in Pacifica, CA

Experience the ultimate coastal living with the Pacific Ocean as your backyard on Pedro Point—recently featured on the television series Staycation NorCal: A Golden Baycation. Boasting breathtaking, unobstructed ocean views, this stunning 3 BR 2-bath home offers a serene retreat. Walk to the surf and beach just steps from home. Enjoy sunsets from the deck, cozy nights by the gas fire pit, and catch the Golden Gate Bridge on a clear horizon.

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!

3BR Eichler home w/ backyard & BBQ grill

Welcome to a classic Eichler home in San Mateo - thoughtfully renovated, full of character, and perfectly placed for Bay Area access. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium w/ custom mural & red maple tree - Private backyard w/ fire pit, BBQ & 8-person dining area - Dedicated office w/ door & fast Wi-Fi - ideal for remote work - 20 mins to SF | 15 mins to SFO | near Caltrain

Clean&Cozy Cottage near downtown Burlingame & SFO

Our sunny backyard cottage, with outdoor private entry, is centrally located in Burlingame between Burlingame Avenue and Broadway and is a great spot suited to a business traveler in search of a home away from home while also being ideal for vacationers looking to live like a local, only miles from SF. Enjoy and unwind!

Little Cottage on the Hill

Enjoy a peaceful stay at this charming, secluded detached garden cottage great for a stay-cation or as a work-from-home alternative. The cottage features a queen-sized bed, a fireplace,  private bathroom and kitchenette. Perfect for both leisure and Business travelers.