Family-friendly holiday rentals in Hillsborough

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.

Family · Kitchen · EV charging

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.

Kitchen · Indoor spaces · Hiking

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.

Kitchen · Indoor spaces · Hiking

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.

Indoor spaces · Kitchen · Backyard

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.

Kitchen · Indoor spaces · Check-in

Serene Modern Home with Yard & Parking

This spacious, tastefully decorated and full of natural light large house is a perfect combination of comfort and style. The house is recently renovated and has got everything to accommodate all your needs for a perfect stay. Convenient strategic location and easy commute to SF, Silicon Valley, BART and Airport, full amenities, parking, safe and quiet neighborhood, professionally managed, immaculately clean and more. Book now before someone else does!

Family · Kitchen · Getting around

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

Indoor spaces · Kitchen · Access

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.

Kitchen · Indoor spaces · Shared spaces

Seaside Home Modern Retreat with Breathtaking

Discover coastal serenity in this modern 4BR, 3 bath retreat in Half Moon Bay's Miramar district. With clean interior, wood accents & an amazing 2nd-floor balcony, this home offers a serene escape. Enjoy the landscaped backyard, fully stocked kitchen & proximity to popular beaches and the Coastal Trail. Experience seaside charm in this unforgettable home

Family · Indoor spaces · Getting around

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!

Kitchen · Family · Long stay

Private Garden Cottage Belmont Hills*Pool*HotTub*

Charming, fully equipped cottage in a quiet Bay Area retreat. Enjoy a newly renovated backyard with blooming gardens, fruit trees, hot tub, and pool. Frequent deer visits and soft evening lighting create a magical forest-like escape. Multiple patios for relaxing, plus a fun treehouse for kids.

Family · Kitchen · View

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.

Indoor spaces · Family · Wi-Fi