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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 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

★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!

LocationFamilySleep quality

4.94 out of 5 average rating, 358 reviews
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

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.

LocationFamilyAmenities

4.96 out of 5 average rating, 195 reviews
Top guest favorite
A welcoming living room features high ceilings and large windows allowing natural light to fill the space. A comfortable sofa with blue and yellow pillows faces a wooden coffee table, while decorative armchairs and a flat-screen TV complete the inviting atmosphere.
Home in Half Moon Bay

Half Moon Bay Coastal Home Walk Beach & Harbor SPA

Coastal Vacation House is a short 10 minute walk to Surfers Beach, Pillar Point Harbor & Sam's Chowder House! 15 miles/ 30 mins to San Francisco! Just a few blocks from the best restaurants, shops & Marina! Near ocean bluffs ( Mavericks) & Coastal Trail perfect for hiking, walking, bike riding. Short drive to downtown Half Moon Bay shops! Ideal for holidays & entertaining family on vacation! Fun for everyone including kids! The 2,100 sq ft home is cozy & roomy for a relaxing weekend in HMB!

ValueLocationBeach

4.99 out of 5 average rating, 413 reviews
Top guest favorite
Home in San Mateo

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.

FamilyValueParking

4.93 out of 5 average rating, 203 reviews
Guest favorite
A dining area features a round table surrounded by four light-colored chairs, positioned near large windows offering panoramic ocean views. Natural light floods the space, highlighting the minimalist decor and the neutral color palette.
Home in Pacifica

Coastal Retreat w/ Ocean Views

Welcome to your dream coastal retreat! This stunning 4bd, 3ba modern home boasts breathtaking ocean views. Just minutes from the beach and a short drive to San Francisco, it's perfect for surfing, hiking, and relaxing. Unwind in the backyard hot tub after a day of exploring! Whether you're here to catch waves, explore trails, or simply relax with loved ones, our clean and stylish home offers the ideal setting for lasting memories. Book your stay and experience the ultimate luxury getaway!

ValueFamilyLayout

4.95 out of 5 average rating, 229 reviews
Guest favorite
The living area features a leather sofa paired with a patterned rug and a glass coffee table. A dining area is visible in the background, illuminated by natural light from large windows. Soft decorative elements, including a fluffy pouf and indoor plants, enhance the welcoming ambiance.
Home in Belmont

Sunlit 2B1B house w/ Deck & Garden on Belmont hill

Escape to this peaceful retreat with new furniture, beautiful garden and nice views over Belmont hill! Luxury like your own home: - Leather sofa & Smart TV - Complete cookware and dining essentials - Big deck with a dining set - Large Private Backyard for relaxation Convenience: - Surrounded by various attractions - San Francisco and San Jose are both half-an-hour away - Easy access to Caltrain, US 101, I-280, and SR 92 - 15-minute drive from San Francisco International Airport

FamilyLocationGetting around

4.94 out of 5 average rating, 105 reviews
Top guest favorite
A spacious outdoor dining area features a large wooden table surrounded by comfortable chairs, offering a front-row view of a vibrant sunset over the ocean. The warm colors of the sky reflect on the water, creating a serene atmosphere.
Home in Moss Beach

New- Stunning Oceanfront "Pelican Bluffs"

Perched on a dramatic oceanfront bluff, Pelican Bluffs fuses modern comfort with coastal charm. Gaze at pelicans gliding over crashing waves, create masterpieces in the the gourmet kitchen, enjoy playful havens for family time, and find workspaces where inspiration abounds. End your day, gathered around the gorgeous fire pit as the fiery sunset turns into a canopy of stars and unforgettable memories see additional photos section for prior reviews from an earlier host

FamilyLocationBathroom

4.98 out of 5 average rating, 106 reviews
Top guest favorite
An open-concept living area is highlighted by a wood-burning fireplace with a textured white surround. Mid-century furniture, including a leather sofa and colorful chairs, is arranged around a plush area rug, while large windows provide natural light and views of the outdoor space.
Home in San Mateo

Spacious Home w/ Fire Pit & BBQ Grill

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 & dining area - Enclosed atrium w/ custom mural & red maple tree - Dedicated office w/ door & Wi-Fi - Wood-burning fireplace, full kitchen & in-unit washer/dryer - 20 mins to SF | 15 mins to SFO | near Caltrain

FamilyValueSleep quality

4.95 out of 5 average rating, 154 reviews
Superhost
An outdoor seating area features a spacious table surrounded by ten chairs, complemented by a cozy texture of orange cushions on a wicker sofa. A fire pit occupies the center, with a sunshade above to provide comfort during warm days.
Home in San Mateo

Relaxing Backyard Retreat -Spacious + Bright Home

Escape, relax, and recharge at our beautiful 3-bedroom, 2-bath retreat in San Mateo, perfectly designed for families, friends, and remote workers seeking comfort and convenience. Featuring a modern open-concept layout, this spacious home is ideal for gathering, entertaining, or unwinding in style. Step outside to your private backyard oasis with lush greenery, a cozy patio, and glowing string lights,the perfect spot to enjoy peaceful Bay Area evenings.

LocationFamilyAccuracy

4.83 out of 5 average rating, 121 reviews
Guest favorite
Home in Foster City

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.

ValueFamilyParks

4.93 out of 5 average rating, 323 reviews
Top guest favorite
Home in San Mateo

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

FamilyValueBackyard

4.89 out of 5 average rating, 151 reviews
Guest favorite
The living room features a light-filled space with large windows on either side, framed by minimalist decor. A modern fireplace serves as a focal point, complemented by a surfboard mounted above. Comfortable seating is arranged around a neutral-toned coffee table on a textured area rug.
Home in Half Moon Bay

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

LocationFamilyOutdoor spaces

4.95 out of 5 average rating, 121 reviews

Popular amenities for Hillsborough house rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
A serene outdoor space features a swimming pool surrounded by lush vegetation and a gently sloping waterfall. Steps lead from the house to the pool area, with a slide positioned nearby. A vineyard is visible in the background, enhancing the tranquil setting.
Home in Portola Valley

3 BR Home on Vineyard nr Palo Alto & Stanford

ValueFamilyCleanliness

4.93 out of 5 average rating, 179 reviews
Top guest favorite
The salt-water pool offers a serene atmosphere, featuring a natural stone waterfall that cascades into the shimmering water. Surrounding oak trees create a calming environment, while the clear, inviting pool reflects dappled sunlight.
Home in Lafayette

Lafayette Treehouse - Relax and Rejuvenate

LocationValueAir conditioning

4.98 out of 5 average rating, 412 reviews
Top guest favorite
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

Luxury Silicon Valley Wellness and Work Oasis

FamilyLocationOutdoor spaces

4.94 out of 5 average rating, 452 reviews
Top guest favorite
The solar-heated pool is illuminated at night, showcasing a serene blue hue. Three water features flow gracefully into the pool, highlighting the tranquil setting. The surrounding area is dimly lit, enhancing the peaceful ambiance of the outdoor space.
Home in Campbell

Luxury 4-Suite Carbon-Neutral Home With Pool

LocationFamilyCondition

4.96 out of 5 average rating, 103 reviews
Guest favorite
A two-story home is surrounded by well-maintained grass and trees. The front features a welcoming porch with two green chairs, a brick chimney, and large windows showcasing the indoor space. A pathway leads to the entrance, framed by manicured landscaping.
Home in Palo Alto

Large Home in Palo Alto, 5 bedrooms, Pool

LocationFamilyDecor

4.92 out of 5 average rating, 123 reviews
Top guest favorite
A spacious living area is designed with a large L-shaped sectional sofa adorned with colorful throw pillows. A dark coffee table is centrally placed on a vibrant area rug, while natural light filters through large windows, enhancing the overall brightness of the room.
Home in Santa Clara

Silicon Valley Executive home in Santa Clara

ValueFamilyCheckout

4.92 out of 5 average rating, 100 reviews
Guest favorite
A clear blue pool is surrounded by a stone deck, featuring two wooden lounge chairs positioned for relaxation. Lush greenery and palm trees frame the area, providing a natural and serene setting in the private backyard.
Home in San Rafael

Private cul-de-sac home in Marin with pool

FamilyLocationLong stay

4.96 out of 5 average rating, 112 reviews
Top guest favorite
The spacious living room features light wooden flooring and white ceiling beams. Comfortable gray sofas surround a white coffee table on a patterned rug. Large windows allow natural light to fill the room, illuminating the fireplace and inviting atmosphere.
Home in Mountain View

Modern 4bd/3ba w/ pool In Downtown MV

ValueFamilyCleanliness

4.85 out of 5 average rating, 147 reviews

Weekly house rentals

Top guest favorite
A welcoming living area showcases a leather sofa paired with an armchair and a round coffee table. A fireplace sits beneath a wall-mounted TV, and warm hardwood floors enhance the cozy ambiance. Natural light streams through nearby windows, offering a bright and airy feel.
Home in San Mateo

Modern House w A/C No Pet in San Mateo

ValueFamilyLaundry

4.88 out of 5 average rating, 260 reviews
Top guest favorite
A well-maintained pathway leads to a transparent entrance framed in red, surrounded by lush greenery. Flowering plants, including vibrant lavender and colorful blooms, enhance the inviting atmosphere. Sunlight filters through the glass walls, illuminating the area and connecting the indoors to nature.
Home in Half Moon Bay

2 bedroom house with hot tub

LocationFamilyHeating

4.94 out of 5 average rating, 167 reviews
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

Oceanfront Oasis, Sunsets & Crashing Waves

ValueFamilyHeating

4.95 out of 5 average rating, 151 reviews
Guest favorite
A dining area features a light wood table surrounded by four upholstered chairs. A decorative bench sits along one side of the table. Two abstract art pieces adorn the wall, and a potted plant adds a touch of greenery in the corner. Natural light enters through a large window.
Home in San Mateo

12-Min From SFO, Tastefully Designed, Work Station

ValueLocationQuiet

4.88 out of 5 average rating, 246 reviews
Guest favorite
A spacious grassy yard is surrounded by lush gardens, showcasing colorful flowers and greenery. A seating area with wooden chairs is situated near a fountain, providing a tranquil spot to enjoy the views. The sky displays varying shades of blue, contributing to the serene atmosphere.
Home in Half Moon Bay

Oceanfront w/ Direct Beach Access + New Hot Tub

LocationValueAir conditioning

4.86 out of 5 average rating, 339 reviews
Guest favorite
A wooden hot tub is positioned on a deck facing the ocean, with waves gently lapping at the shore. The sunset casts warm hues over the water, while wooden posts and ropes define the perimeter of the deck.
Home in Moss Beach

Walk to the Beach from this Ocean Front Home

FamilyLocationGrill

4.93 out of 5 average rating, 296 reviews
Guest favorite
The modern two-story home is designed with a striking wooden exterior and large glass windows. A spacious patio area is visible at the ground level, featuring a stone-paved surface. Lush trees surround the property, contributing to the coastal ambiance.
Home in Half Moon Bay

Spectacular Coastal Half Moon Bay Home

FamilyLocationHeating

4.79 out of 5 average rating, 182 reviews
Top guest favorite
The private balcony features two stylish chairs facing the ocean, providing an inviting space to relax. The deck is made of durable composite material, and the view includes the distant shoreline and coastal community, enhancing the serene atmosphere.
Home in Pacifica

Oceanview Retreat, Steps to Beach|Pier|Golf Course

LocationFamilyTV

4.98 out of 5 average rating, 306 reviews

Private house rentals

Top guest favorite
Home in Half Moon Bay

Poplar Beach Getaway: Family-Friendly, Near Beach!

ValueFamilyPets

4.91 out of 5 average rating, 417 reviews
Superhost
The game room features a basketball arcade game, a colorful air hockey table, and cornhole boards for recreational activities. A large television screen is mounted on the wall, showcasing vibrant game graphics while bright lighting enhances the playful environment.
Home in South San Francisco

NEW Modern Home w/ FUN Game Room & Amazing views!

ValueLocationKitchen

4.81 out of 5 average rating, 131 reviews
Guest favorite
The enchanting exterior of a Spanish style home is highlighted by a textured yellow facade and red tiled roof. Arched doorways lead into the entrance, surrounded by vibrant greenery and blooming plants. A pathway made of patterned tiles guides towards the front door.
Home in San Carlos

Charming 1930 Spanish Haven close to everything

ValueLocationParks

4.82 out of 5 average rating, 202 reviews
Guest favorite
A modern kitchen features a spacious island with four high stools. White cabinetry surrounds a stylish backsplash of geometric tiles, complementing stainless steel appliances and ample countertop space, enhancing a well-lit and functional cooking area.
Home in South San Francisco

Modern Central 4BD/2.5Bath Home Near SF, SFO!

ValueLocationGetting around

4.96 out of 5 average rating, 121 reviews
Guest favorite
An expansive living room features a leather sectional sofa, a circular coffee table, and a stone fireplace. Large glass windows provide views of the surrounding greenery, while wooden beams and a rustic stone wall create a natural ambiance. A television is positioned near the sofa.
Home in Mill Valley

Two Creeks Treehouse

LocationFamilyCheckout

4.99 out of 5 average rating, 137 reviews
Top guest favorite
A spacious living room features a large sectional sofa adorned with accent pillows. A coffee table sits at the center, complemented by a patterned area rug. Natural light floods in through the large windows, highlighting the wooden beams on the ceiling and the stone fireplace.
Home in Half Moon Bay

5 min walk to Beach, Sleeps 11, perfect for family

LocationFamilyIndoor spaces

4.94 out of 5 average rating, 226 reviews
Top guest favorite
A spacious living area features a light-colored sofa adorned with throw pillows, a coffee table made of wicker, and a cozy area rug. A chandelier hangs from the ceiling, while natural light streams through large windows, illuminating the room. A wood-burning fireplace with stacked logs adds warmth to the ambiance.
Home in Half Moon Bay

Beautiful Beach House steps from the Beach

FamilyLocationComfort

4.99 out of 5 average rating, 101 reviews
Top guest favorite
A modern living area features a sectional sofa complemented by a glass coffee table. Large sliding doors provide natural light and a view of the outdoor space. A sleek fireplace adds warmth to the room, with a stylish area rug enhancing the comfortable setting.
Home in Half Moon Bay

Fabulous Beach Get Away - Brand New Beach House

LocationValueGrill

5.0 out of 5 average rating, 156 reviews

When is the best time to visit Hillsborough?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$54,602 GYDG$62,552 GYDG$59,205 GYDG$51,464 GYDG$55,439 GYDG$66,736 GYDG$52,301 GYDG$42,050 GYDG$41,632 GYDG$52,092 GYDG$52,092 GYDG$52,301 GYD
Avg. temp11°C12°C13°C14°C16°C17°C18°C18°C19°C17°C14°C11°C

Destinations to explore