Family-friendly holiday rentals in Hillsborough

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

Welcome to our beautifully remodeled 2-bedroom home, just minutes from Downtown San Mateo! Whether you’re a couple, a family, or a business traveler, this is the perfect spot for you. Enjoy a fully equipped kitchen, comfortable living space, and kids-friendly amenities. Explore San Mateo's vibrant neighborhoods or take a short drive to San Francisco. We've thought of everything to make your stay comfortable, including fast WiFi and plush bedding. Book now and experience the best of the Bay Area!

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!

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.

Cozy Modern Craftsman Retreat

Private studio with a large outdoor patio. Just a short walk to the dinning and shopping on Burlingame Avenue and also on historic Broadway. Caltrain and Bart are minutes away to get take you to wherever you need to go. Fast wifi and espresso maker provided. Enjoy fresh fruit from our orange tree, and a rosemary bush for those that enjoy cooking. Relax with our large queen bed, recessed dimmable lighting and a large flat panel 4K smart TV w/apps for Netflix, Amazon Video, etc.

Beautiful Spacious Living w/Resort Like Feel

Welcome to our lovely spacious studio apartment located in Menlo Park! Our unit is situated in the luxurious Anton Menlo Apartments, which boasts a range of amenities for our guests to enjoy during their stay. Our unit features a fully furnished living area, queen comfortable bed, and a large modern bathroom, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals. Bedroom does not have a door, as this is a studio.

Mid-Peninsula Gem | Peloton + Hot Tub Escape

Welcome to San Carlos, the City of Good Living! Relax in a clean, comfortable home located in a peaceful, safe neighborhood. The space offers fast WiFi, four bedding options, and workspaces. It is just a 7-minute walk to the train and bus stations, with restaurants, coffee shops, and sports bars nearby. I provide complimentary bikes, coffee, and tea. The living room and backyard are set up for guests to enjoy, including access to the hot tub for relaxation.

New modern 1 bedroom unit

New modern 1 bedroom/studio unit in beautiful residential neighborhood near the water. Separate entrance that is fully furnished with top of the line appliances and high ceilings. Full size bed. Close access to highway 101, 92 and 280. Plenty of shopping nearby, Bridgepointe Shopping Center and Hillsdale Mall. Need to relax, stroll down to Gull Park to enjoy the water. Kayak and Stand-up Paddle Board available to borrow

Home away from home in beautiful Burlingame!

It's my honor to be your host and I will try to make your stay really great. Please let me know if you have any questions ahead of time as I want to make sure you have the best visit. Our city requires their hosts obtain a 12% transient occupancy tax, therefore the price reflects that tax. *** Please see House Rules and the complete description of the property to ensure our apartment will work for you.

Charming Private Quiet Backyard Studio

This charming, sunny, secluded backyard studio is located in the heart of San Mateo, near public transportation, freeways, restaurants, shopping, and 15 minutes to SFO. Private entrance, quiet backyard setting, plenty of street parking. Less than a 5-min walk to Safeway, CVS, Starbucks and restaurants. * To my regular guests, the rate increase is due to SM County increasing the tax rate. *

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. Since the coronavirus pandemic, we have been taking extra care to disinfect frequently touched surfaces between reservations. The cottage features a queen-sized bed, a fireplace,  private bathroom and kitchenette. Perfect for both leisure and Business travelers.

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!