
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.

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.

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.

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.

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.

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!

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.

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.

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

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).

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
Other great holiday rentals in Hillsborough

Business-Friendly 2/1. Walk to Caltrain/Downtown.

Modern 3BR/3.5BA House with Parking & Laundry

Ocean-View Moss Beach Coastal Retreat

Spectacular California Ocean Front Home!

Charming 3BR Executive Home Minutes from SFO & SF

Brand New Modern Luxury Unit | Walk to Downtown

Renovated 3b1.5b San Mateo hill near SFO/Stanford

SanMateo Comfortable 2BR Home/WiFI & Free Parking
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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. temp | 11°C | 12°C | 13°C | 14°C | 16°C | 17°C | 18°C | 18°C | 19°C | 17°C | 14°C | 11°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!
Destinations to explore
- Northern California Holiday rentals
- San Francisco Bay Area Holiday rentals
- San Francisco Holiday rentals
- Gold Country Holiday rentals
- Central California Holiday rentals
- San Francisco Peninsula Holiday rentals
- San Jose Holiday rentals
- Silicon Valley Holiday rentals
- North Coast Holiday rentals
- Santa Barbara Holiday rentals
- Wine Country Holiday rentals
- Oakland Holiday rentals
- Rentals with a patio Hillsborough
- Rentals with outdoor seating Hillsborough
- Apartment rentals Hillsborough
- House rentals Hillsborough
- Rentals with a washing machine and dryer Hillsborough
- Rentals with a fire pit Hillsborough
- Rentals with a hot tub Hillsborough
- Family-friendly rentals Hillsborough
- Fitness-friendly rentals Hillsborough
- Rentals with a fireplace Hillsborough
- Pet-friendly rentals Hillsborough
- Rentals with pools Hillsborough
- Moscone Center
- Stanford University
- Golden Gate Park
- Santa Cruz Beach
- Oracle Park
- Muir Woods National Monument
- Capitola Beach
- Golden Gate Bridge
- Rio Del Mar Beach
- SAP Center
- Santa Cruz Beach Boardwalk
- Mission Dolores Park
- Pier 39
- Seacliff State Beach
- Henry Cowell Redwoods State Park
- Twin Peaks
- University of California-Berkeley
- Six Flags Discovery Kingdom
- Palace of Fine Arts
- Rodeo Beach
- Montara Beach
- Levi's Stadium
- Winchester Mystery House
- Bolinas Beach




