
Holiday houses in Hillsborough
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Hillsborough

Total holiday rentals
Explore 170 holiday rentals in Hillsborough

Verified guest reviews
Over 7,210 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
170 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!
Top-rated holiday rentals in Hillsborough
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Eichler Home w/ Fire Pit & Private Backyard
Step into a rare 1956 Eichler home in San Mateo - mid-century architecture, a private backyard, and everything you need to work, unwind, or explore the Bay Area. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private fenced backyard w/ fire pit, BBQ & 8-person dining area - Enclosed atrium w/ custom mural & red maple tree - Dedicated office w/ door & fast Wi-Fi throughout - Wood-burning fireplace, full kitchen & in-unit washer/dryer - 20 mins to SF | 15 mins to SFO | near Caltrain

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.

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!

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

Luxury King Bed & Spa Bathroom
Our spacious guest suite has its own private entrance, comfortable pillow-top king size bed, work-friendly laptop desk, hi-speed wifi, spa bathroom with heated floor, mini fridge, and microwave. The guest suite is part of the main home, but there are no shared spaces and the areas are separated by a locked solid wood door & noise-dampening cushions. Our guest suite is ideal for couples visiting family in the neighborhood.

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!

Entire Private Coastal Retreat - Spectacular Ocean
Guest will enjoy the privacy of being the only residence on the premises - Your own private coastal retreat with spectacular ocean front views. A fully stocked gourmet kitchen with chef’s appliances, ample cookware, basic spices and condiments, luxurious linens and bedding, beach towels, blankets, board games, Apple TV and Netflix, and toiletries for your stay.

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

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.
Popular amenities for Hillsborough holiday rentals
Other great holiday rentals in Hillsborough

Modern guest house in great location

Cozy Retreat in a High-End, Walkable Neighborhood

Bright Spanish-style home in Burlingame

Modern Chic | Near Starbucks, Safeway, CVS & Shops

Burlingame Downtown Sophisticated Suite Spot

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

Modern 3BR/3.5BA House with Parking & Laundry

Bright and sunny Central San Mateo 3/2.5 Craftsman
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $328 NZD | $331 NZD | $323 NZD | $296 NZD | $299 NZD | $299 NZD | $291 NZD | $277 NZD | $286 NZD | $301 NZD | $301 NZD | $333 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 guesthouse rentals in Hillsborough?
Experience the best of Hillsborough with our guesthouse rentals, starting at about $90 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 30 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 10 vacation homes with pools in Hillsborough, available on Airbnb. Make a splash and soak up the sun in style!
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 house rentals in Hillsborough have a kitchen?
Absolutely! We offer over 40 house rentals with a kitchen in Hillsborough. Enjoy a tailored experience with all the comforts you desire.
Do private suite rentals in Hillsborough have wifi?
Absolutely! We offer over 10 private suite 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 40 house rentals with free parking in Hillsborough. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Guesthouse Rentals in Hillsborough?
Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- San Francisco Holiday rentals
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- Reno Holiday rentals
- Monterey Holiday rentals
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- Stanford University
- Santa Cruz Beach
- Santa Cruz Beach Boardwalk
- Golden Gate Park
- Muir Woods National Monument
- Capitola Beach
- Golden Gate Bridge
- Moscone Center
- Oracle Park
- University of California-Berkeley
- SAP Center
- Levi's Stadium
- Henry Cowell Redwoods State Park
- Rio Del Mar Beach
- Mission Dolores Park
- Pier 39
- University of California San Francisco
- Six Flags Discovery Kingdom
- California’S Great America
- Oakland Arena
- Bernal Heights
- Palace of Fine Arts
- Rodeo Beach
- Seacliff State Beach





