House holiday rentals in Hillsborough

Find and book unique houses on Airbnb

Top-rated house rentals in Hillsborough

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

%{current} / %{total}1 / 1
Top Guest favourite
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, 167 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.

Guest favourite
A well-lit living room features a comfortable sofa adorned with decorative cushions, positioned near a large window with blinds. A coffee table sits on a geometric-patterned rug, complemented by a side table with a floral arrangement. A dog relaxes on the floor beside the fireplace.
Home in Westlake
4.95 out of 5 average rating, 199 reviews

Pet Friendly, Gem of a House 5 mins to beach & SF

Dog-friendly, beautifully refurbished Doelger architectural oasis minutes from SF, the beach, Bart, several golf courses and SFO. Quiet, safe neighborhood with lots of parking and character. Large shopping center within three blocks with Trader Joes, 24 Hour Walgreens, Safeway, Starbucks, a Gym which offers day passes, Yoga studio and lots of dining choices. Cook in fully appointed chef’s kitchen, gather around the fire pit in the backyard, or melt your stress away in the deep-soaking tub.

Top Guest favourite
The exterior of the property features a small, well-maintained front garden with smooth pebbles and three ornamental plants. A garage door is visible, and a colorful bougainvillea bush adds vibrancy to the scene, complementing the blue house façade.
Home in Pacifica
4.98 out of 5 average rating, 115 reviews

Cute beach house with skylights and open spaces

Located in Pacifica, CA a block away from the ocean shoreline(3 mins stroll to the shoreline). You can hear the gentle sounds of the ocean on our quiet street. With xeriscaping characterized by local plants and bougainvillea, our little blue beach house has a large front porch with lots of sunlight to relax in and a small backyard deck to enjoy the warm weather. Inside, the living room has 14' ceilings with skylights. The guest room is fully furnished as are the kitchen and master bedroom.

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
4.92 out of 5 average rating, 184 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.

Superhost
A living room is featured with a beige sofa and dark blue armchair. A large mirror is positioned against the wall, reflecting natural light. A decorative pouf and a small coffee table are placed on a textured area rug, creating an inviting space.
Home in Park Pacifica
4.85 out of 5 average rating, 325 reviews

Hot Tub Home in Pacifica Free Parking /Beach/SFO

🏡 Your Perfect Getaway Near San Francisco & SFO – Quiet, Convenient, and Comfortable! If you like to stay close to the city yet have a feel of being on a gateway, this is your place. Located in the quiet Park Pacifica, our home is 18miles from downtown San Francisco & 11miles from SFO. 6 mins drive to beaches, shops, and the iconic Highway 1 road trip route. Whether you're here to explore or relax, this is the ideal spot to unwind. Free parking is available right in front of the house.

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, 178 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 favourite
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, 153 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.

Top Guest favourite
A vibrant yellow dining table set for eight is positioned in a spacious open-plan area, surrounded by natural light from large glass doors. A soft, textured light fixture hangs overhead, complementing the modern aesthetic. The backdrop features a landscaped outdoor space visible through the glass.
Home in San Mateo
4.95 out of 5 average rating, 140 reviews

Bright retreat w/ fire place & atrium

Welcome to your Bay Area retreat - a thoughtfully renovated 1956 Joseph Eichler home offering mid-century charm and comfortable spaces for relaxing or working remotely. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium w/ custom mural & red maple tree - Private backyard - BBQ grill, fire pit & outdoor dining - Wood-burning indoor fireplace & open-concept living - Dedicated workspace & Wifi - Kitchen, air conditioning, washer/dryer & free parking

Top Guest favourite
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, 294 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 favourite
Home in San Mateo
4.9 out of 5 average rating, 375 reviews

Cozy San Mateo home / Near SFO Airport

Looking for the perfect short-term rental in the Bay Area? This fully furnished 3-bed, 2-bath home in San Mateo is ideal for families, business travelers, and vacationers. Located just six blocks from vibrant downtown, you’ll be steps from ethnic restaurants, boutique shopping, and local charm. Just 10 minutes from SFO airport. Easy access to San Francisco and San Jose. This inviting home is your ideal base for experiencing the best of the Peninsula.

Guest favourite
Home in San Mateo
4.87 out of 5 average rating, 127 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

Top Guest favourite
An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.
Home in Los Altos
4.94 out of 5 average rating, 421 reviews

Luxury Silicon Valley Wellness and Work Oasis

Peaceful upscale 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Ideal for business travelers, couples, and nature lovers. Fast fiber Wi-Fi, dedicated workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, heated saline pool May–Oct. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

Popular amenities for Hillsborough house rentals

When is the best time to visit Hillsborough?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$282 AUD$315 AUD$315 AUD$284 AUD$360 AUD$360 AUD$353 AUD$284 AUD$281 AUD$352 AUD$352 AUD$353 AUD
Avg. temp11°C12°C13°C14°C16°C17°C18°C18°C19°C17°C14°C11°C

Quick stats about house rentals in Hillsborough

  • Total holiday rentals

    Explore 60 holiday rentals in Hillsborough

  • Verified guest reviews

    Over 3,180 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Hillsborough holiday 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!