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 2,490 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 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

    60 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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Top guest favorite
Home in Half Moon Bay
4.91 out of 5 average rating, 406 reviews

Poplar Beach Getaway: Family-Friendly, Near Beach!

Family-friendly, relaxed home in a quiet residential neighborhood - 1/2 block from the blufftops, a 10-minute stroll to lovely Poplar Beach, and 1/2 mile from scenic Main Street restaurants, shops, and cafes. 3 bedrooms with queen beds, two baths, a living area, a well-equipped kitchen, a spacious kid-friendly den, and a backyard with a new deck ensure you all have room to spread out and relax after a fun day at the beach or exploring the area. Short drive to San Francisco, Santa Cruz, San Jose.

Top guest favorite
A light-filled living room features a comfortable sofa, an inviting fireplace, and a wall-mounted flatscreen TV. A mix of seating options, including an armchair and a recliner, are arranged around a coffee table. Large windows provide views and natural light.
Home in Half Moon Bay
4.99 out of 5 average rating, 347 reviews

Stairway to Heaven - 1 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 2 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
An expansive patio features comfortable seating, overlooking lush greenery and the scenic Pacific Ocean in the distance. Soft lighting from hanging bulbs creates a welcoming environment for relaxation. Potted plants add a touch of nature, enhancing the tranquil outdoor space.
Home in Pacifica
4.96 out of 5 average rating, 224 reviews

Incredible Ocean Views from Tuscan Villa Suite

Enjoy this clean, quiet, & comfortable suite in a Tuscan Villa with incredible Pacific Ocean views. Surrounded by nature, you'll wake up to birds singing and watch the sunset in the company of bunnies, red tail hawks, and the occasional deer. Beautiful hikes are right outside the door here in the Golden Gate National Recreation Area. Just 15 minutes from SFO or downtown San Francisco, you are close to everything, but far from the hustle and bustle. You can even walk to the beach if you like!

Guest favorite
Home in Redwood City
4.95 out of 5 average rating, 116 reviews

Cozy & Fully Equipped Studio

Welcome to your perfect retreat! Our studio is fully equipped, modern, and super comfortable, offering all the amenities for an unforgettable stay. Whether you’re traveling for business or leisure, this space provides the ideal balance between comfort and convenience. 🛋 Cozy living area: Beautifully decorated with a comfortable sofa, TV 🍽 Fully equipped kitchen 🌿 Private patio: A perfect outdoor space to relax and enjoy fresh air. 🚗 Private parking with independent entrance self check in

Top guest favorite
Home in San Mateo
4.92 out of 5 average rating, 195 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, 184 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.

Top guest favorite
A private backyard scene features a wooden deck with a circular table and an outdoor sofa amid lush greenery. Tall grasses sway gently in the breeze, while nearby trees provide a natural backdrop under a clear blue sky.
Home in San Mateo
4.95 out of 5 average rating, 148 reviews

Mid-century retreat - fire pit and backyard

Welcome to a beautifully renovated 1956 Eichler home in the San Mateo Highlands - a distinctive mid-century space with soaring ceilings, natural light, and a private backyard made for gathering. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & outdoor dining - Enclosed atrium w/ custom mural & red maple tree - Dedicated private office w/ door - Wood-burning fireplace & full kitchen w/ gas stove - 20 mins to SF | 15 mins to SFO | Near Caltrain

Top guest favorite
A sunlit dining area is framed by large windows that provide a clear view of the ocean and sunset. A small round table is set with two black chairs, and a woven basket sits at the center, while a soft rug covers the floor.
Home in Moss Beach
4.95 out of 5 average rating, 144 reviews

Oceanfront Oasis, Sunsets & Crashing Waves

The Bluffs Oceanfront Oasis awaits you. Our beautifully appointed home sits right on the cliff boasting crashing waves and endless sunsets. Start your day in the zen room for a bit of yoga and meditation or take a leisurely walk on the beach trail right out the back gate. After dining out or in, end your evening with something special while seated at the firepit over looking the Pacific. Come for a romantic getaway, a weekend of golf or a family fun filled vacation.

Guest favorite
Home in Foster City
4.93 out of 5 average rating, 312 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, 143 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 favorite
A bright living area features a comfortable dark sofa and two light-colored armchairs beside a round coffee table. A flat-screen television is mounted above a traditional fireplace. Open French doors lead to a bright adjoining room, while a patterned rug adds texture to the wooden floor.
Home in Burlingame
4.98 out of 5 average rating, 99 reviews

Charming Burlingame Beauty!

Charming, newly remodeled air conditioned home in peaceful and centrally-located neighborhood in Burlingame. Minutes from the San Francisco Airport, downtown San Francisco and numerous restaurants and shopping in downtown Burlingame. Full kitchen, full house reverse osmosis water filtration system, and a private office makes this home perfect for work or play.

Popular amenities for Hillsborough house rentals

When is the best time to visit Hillsborough?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$54,615 GYDG$62,567 GYDG$59,219 GYDG$42,060 GYDG$53,360 GYDG$53,360 GYDG$52,313 GYDG$42,060 GYDG$41,641 GYDG$52,104 GYDG$52,104 GYDG$52,313 GYD
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