House vacation rentals in Hillsborough

Find and book unique houses on Airbnb

Quick stats about house rentals in Hillsborough

  • Total vacation rentals

    Explore 60 vacation rentals in Hillsborough

  • Verified guest reviews

    Over 2,530 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Hillsborough vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Hillsborough rentals

  • 4.9 Average rating

    Hillsborough stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated house rentals in Hillsborough

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

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Guest favorite
The sunroom features expansive glass windows that offer a panoramic view of the city and hills at sunset. A cozy seating area with a light blanket and soft cushions is present, providing a relaxing space to enjoy the scenic landscape.
Home in Daly City
4.96 out of 5 average rating, 269 reviews

SF Amazing View & SUNroom: Spacious Private 1 bdrm

👋 Welcome to our spacious, clean, private getaway studio on Southern Hill in Daly City. Escape the hustle and bustle of the city. Enjoy a stunning view of day/night in clear days ☀️ - Easy street parking - Great Summit Loop Trail at San Bruno Mountain (6-min🚘) - Cow Palace Arena (8-min🚘) - H Mart grocery mall (10-min🚘) - 9.2 miles to SFO (17-min🚘) - 6.7 miles to Civic Center(>30-min🚘 w/ traffic or 20-min🚘 w/o traffic) - 11 miles to Fisherman's Wharf(>35-min🚘 w/ traffic or 23-min🚘 w/o traffic)

Guest favorite
The dining area features a large, rectangular table surrounded by four upholstered chairs, providing a comfortable setting. Natural light floods in through large windows, showcasing a view of the landscape. A decorative wall clock and a framed artwork add character to the space.
Home in South San Francisco
4.94 out of 5 average rating, 351 reviews

★EV+★Hillside SFO View★Home Theater★Pool Table

Instant Booking Confirmation! Ample parking: Over-sized 2-car driveway! EV charging (12kW, level II, pay by kWh for EV charging, Tesla users: Please bring your own adapter) A charming, detached and private 3-bedroom, 2 bathroom house with a view to SFO on the Bay, Home Theater, Pool Table, Fully-Fenced Terrace Garden, Piano. WFH friendly: multiple desks, High Speed WiFi (100Mbps). Digital keypad entry for self check-in. You’ll have the entire house, backyard, front yard completely to yourself!

Guest favorite
A private fenced backyard features comfortable seating, including a sectional sofa and coffee table. Soft lighting from cafe lights enhances the outdoor environment. Lush greenery surrounds the space, providing a natural backdrop, with a welcoming mat positioned at the entry.
Home in Pacifica
4.93 out of 5 average rating, 203 reviews

Cozy 2 Bedroom Home, Dog Friendly, w/Private Yard

Home is dog friendly! Cozy 2 bedroom [Queen Beds] home, one bath, centrally located, private entry, lots of natural light, private fenced backyard, cafe lights, space for kids, pets to run around. Beach access trail on Mori Point 1/2 block away, 1/2 mile walk down the trail to Sharp Park Beach, you may see whales from the shore! Sharp Park Golf Course is one block walking distance. 15 min to SFO | 20 min to downtown San Francisco, private driveway and lots of free street parking available!

Top guest favorite
A bright living room is visible, featuring a comfortable sofa with striped accents, a coffee table made of natural wood, and an inviting fireplace below a flatscreen TV. Large windows provide natural light and views of the outside, complemented by tasteful wall art and decorative elements.
Home in Half Moon Bay
4.96 out of 5 average rating, 188 reviews

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.

Top guest favorite
Home in San Mateo
4.95 out of 5 average rating, 149 reviews

Fire pit & backyard - 15 mins to SFO

Welcome to this 1956 Eichler home in San Mateo's Highlands - a mid-century gem with warm design, a pvt backyard, and easy access to San Francisco, SFO & Silicon Valley. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & 8-person outdoor dining - Wood-burning indoor fireplace & open-concept living - Dedicated private office w/ door - ideal for remote work - In-unit washer & dryer, full kitchen & 42" TV w/ streaming - 20 mins to SF | 15 mins to SFO | near Caltrain

Top guest favorite
Home in San Mateo
4.92 out of 5 average rating, 196 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 favorite
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, 186 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.

Guest favorite
The exterior of the property is showcased, highlighting its unique architectural design with wooden paneling and large windows. A staircase leads to the entrance, and lush greenery is visible in the background, enhancing the coastal setting.
Home in Half Moon Bay
4.95 out of 5 average rating, 159 reviews

Luxury Ocean Front & Harbor View Home

Nestled in the quaint fishing village of Princeton by the Sea, just a mile north of Half Moon Bay, this stunning property is the perfect destination for your next coastal retreat. The two-bedroom, three-bathroom beautiful space sleeps up to 6 people and features spectacular views of Pillar Point Harbor and Half Moon Bay throughout the common areas and bedrooms. This is the ultimate in coastal luxury, featuring modern appliances and an open floor plan through all the common areas.

Guest favorite
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
4.97 out of 5 average rating, 413 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.

Top guest favorite
A spacious living room features large windows allowing for ample natural light. Comfortable seating is arranged with a gray sofa and dark armchairs. A glass coffee table sits atop a plush area rug, while artwork adorns the walls, adding a touch of color to the neutral palette.
Home in San Mateo
4.92 out of 5 average rating, 310 reviews

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!

Guest favorite
Home in Foster City
4.93 out of 5 average rating, 313 reviews

Lagoonfront Retreat: 3BR House Near SFO

Our stunning Airbnb listing offers both convenience and relaxation. 5min to multiple supermarkets and 15mins to SFO. Enjoy breathtaking views of the lagoon, modern decor, a fully-equipped kitchen, two comfortable living areas, and three cozy bedrooms with high-quality linens. We provide high-speed Wi-Fi, working desks, and heating for your comfort. We look forward to hosting you and helping you make the most of your stay in this beautiful area.

Top guest favorite
Home in San Mateo
4.89 out of 5 average rating, 145 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

Popular amenities for Hillsborough house rentals

When is the best time to visit Hillsborough?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$54,635 GYDG$62,590 GYDG$59,240 GYDG$42,075 GYDG$53,379 GYDG$53,379 GYDG$52,333 GYDG$42,075 GYDG$41,657 GYDG$52,123 GYDG$52,123 GYDG$52,333 GYD
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