Holiday houses in Hillsborough

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Hillsborough

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top Guest favourite
The bedroom features a spacious bed with white bedding, complemented by decorative pillows. A blue accent chair sits nearby, next to a decorative bedside table with a lamp. Natural light filters in through a window with white shutters, illuminating the light-colored walls and geometric rug.
Guest suite in Burlingame Hills
4.88 out of 5 average rating, 131 reviews

Gorgeous Suite close to SFO Airport, Self Check-In

Enjoy a peaceful stay at this newly appointed luxury suite. Burlingame is a suburb of San Francisco, known for it's tree-lined streets. Close to downtown San Mateo and Silicon Valley. This suite is part of a beautiful Spanish style house with a private entrance. Minutes from shops and restaurants Broadway Burlingame and Burlingame Avenue. Perfect for business travelers, couples or solo adventures! Features queen size bed, smart TV, refrigerator, microwave, Light and Bright! Wi-Fi, Parking.

Top Guest favourite
A quaint cottage is displayed with a yellow exterior and charming architectural details. Lush green grass and two rose bushes frame the pathway leading to the front door, while sunlight illuminates the inviting entryway. Trees provide a natural canopy, enhancing the peaceful curb appeal.
Home in San Mateo
4.93 out of 5 average rating, 188 reviews

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.

Guest favourite
The exterior of a multi-level home features a blend of large windows and a distinctive round window. The light-colored facade is complemented by lush greenery and flowering plants in the foreground. A spacious front deck is visible, enhancing the inviting appearance of the property.
Home in Burlingame
4.96 out of 5 average rating, 179 reviews

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.

Top Guest favourite
The studio apartment features an open layout, showcasing a full kitchen with wooden cabinetry and a dining area. A comfortable window seat offers serene views, while light wood flooring adds warmth to the space. Modern lighting fixtures complement the overall aesthetic.
Home in Montara
4.98 out of 5 average rating, 395 reviews

A private beachy pad in Montara

Welcome to Chez Sage! Your own private apartment get-away, with a private deck and ocean views, is just 30 minutes south of San Francisco. The entrance to your private apartment leads you up the stairs to a deck with an ocean peek. Enter your home away from home and relax in the window seat to gaze at Montara Mountain or eat breakfast on the island with peeks of the ocean. Once you're settled, it's just a short stroll to watch the sunset from the beach.

Guest favourite
A serene beach scene at sunset is captured, featuring gentle waves reflecting the hues of orange and blue in the sky. Silhouettes of people can be seen walking along the shoreline, while lights from the distant marina twinkle against the darkening landscape.
Guesthouse in El Granada
4.97 out of 5 average rating, 117 reviews

Coastal Cottage Guest House

Guest house is attached to our primary residence but has a separate exterior entrance. The interior is separated by double doors that lock from both sides, similar to adjoining hotel rooms. The backyard is shared by us, the owners. There’s a very real chance you’ll be greeted by our friendly Australian Shepherd, Gracie, during your stay! You may see us in the yard during your stay. Feel free to say hi! Otherwise, we like to give our guests privacy.

Top Guest favourite
Home in San Mateo
4.88 out of 5 average rating, 130 reviews

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

Guest favourite
Apartment in Burlingame
4.78 out of 5 average rating, 217 reviews

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!

Top Guest favourite
A spacious room features vaulted ceilings with wooden beams. A queen-sized bed, draped in a geometric patterned blanket, sits next to a sleek fireplace. A dining table and chairs are visible, along with a large TV and two closets that provide storage options.
Guesthouse in Hillsborough
4.95 out of 5 average rating, 1,003 reviews

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.

Top Guest favourite
A coastal cabin is situated on rugged cliffs overlooking the ocean. The structure features large windows, allowing for expansive views of the water. Lush greenery surrounds the home, highlighting its natural setting against a cloudy sky.
Home in Montara
4.99 out of 5 average rating, 124 reviews

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.

Top Guest favourite
Home in San Mateo
4.95 out of 5 average rating, 142 reviews

Mid-century home w/ fire pit & BBQ

Welcome to your mid-century Bay Area retreat - perfect for families & relaxing stays near San Francisco! - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ BBQ, fire pit & outdoor dining - Enclosed atrium w/ custom mural - Dedicated workspace + fast Wifi - Indoor fireplace & open living space - Fully equipped kitchen & family-friendly layout

Guest favourite
A bright kitchen space is highlighted by two windows that provide natural light. A circular table with two chairs is positioned near the windows. Cream-colored cabinetry and dark countertops complement the stainless steel appliances, creating a functional and inviting area.
Guest suite in Burlingame
4.95 out of 5 average rating, 221 reviews

2 Bedroom Home Away from Home

Apartment above garage (up one flight of stairs) with a separate entrance. Recently renovated and fully furnished with queen-size beds in both bedrooms. Easy access to Highway 101 for easy access to San Francisco and South Bay as well as SFO Airport (7 min). Very walkable to Broadway (2 blocks) and Burlingame Ave (about 15 min).

Top Guest favourite
A cozy sleeping space features a queen bed with white linens and colorful decorative pillows. A light fixture stands beside the bed, and a wall art piece composed of natural materials adds interest. A closet with sliding doors is visible in the background.
Guesthouse in Burlingame
4.98 out of 5 average rating, 345 reviews

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!

Popular amenities for Hillsborough holiday rentals

When is the best time to visit Hillsborough?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$255 NZD$245 NZD$250 NZD$262 NZD$257 NZD$257 NZD$296 NZD$283 NZD$291 NZD$307 NZD$307 NZD$339 NZD
Avg. temp11°C12°C13°C14°C16°C17°C18°C18°C19°C17°C14°C11°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Hillsborough?

    Hillsborough has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Hillsborough?

    Experience the best of Hillsborough with our apartment rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Hillsborough?

    Four-legged friends are welcome in Hillsborough. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Hillsborough?

    Yes! Work meets play with ease at over 80 vacation rentals in Hillsborough featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Hillsborough vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Hillsborough, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Hillsborough?

    Make yourself at home in Hillsborough by choosing from our most frequently booked neighborhoods. We have over 660 vacation rentals in San Mateo Woods, over 550 vacation rentals in Parrot Drive Area, and over 670 vacation rentals in Hillsborough Heights.

  • Do house rentals in Hillsborough have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Hillsborough. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Hillsborough have a kitchen?

    Absolutely! We offer over 50 apartment rentals with a kitchen in Hillsborough. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Hillsborough have wifi?

    Absolutely! We offer over 60 house rentals with wifi in Hillsborough. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Hillsborough have free parking?

    Absolutely! We offer over 50 house rentals with free parking in Hillsborough. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Hillsborough

  • Total holiday rentals

    Explore 170 holiday rentals in Hillsborough

  • Verified guest reviews

    Over 7,430 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    160 of Hillsborough holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Hillsborough rentals

  • 4.8 Average rating

    Hillsborough stays are highly rated by guests—averaging 4.8 out of 5!