House vacation rentals in Hillsborough

Home in South San Francisco

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.

4.94 out of 5 average rating, 358 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!

ValueFamilyAir conditioning

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.

4.96 out of 5 average rating, 195 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.

LocationValueComfort

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.

4.99 out of 5 average rating, 413 reviews

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!

ValueFamilyHiking

4.93 out of 5 average rating, 202 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.

ValueLocationSleep quality

4.95 out of 5 average rating, 228 reviews

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!

ValueLocationIndoor spaces

4.94 out of 5 average rating, 105 reviews

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

FamilyLocationOutdoor spaces

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.

4.95 out of 5 average rating, 154 reviews

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

ValueFamilyBathroom

4.98 out of 5 average rating, 105 reviews

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

LocationFamilyView

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.

4.83 out of 5 average rating, 121 reviews

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.

FamilyLocationCondition

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.

4.92 out of 5 average rating, 316 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!

ValueFamilyBackyard

4.93 out of 5 average rating, 321 reviews

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.

ValueLocationCondition

4.89 out of 5 average rating, 151 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

FamilyValueCheck-in

Popular amenities for Hillsborough house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 179 reviews

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

FamilyValueQuiet

4.94 out of 5 average rating, 452 reviews

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

ValueFamilyCleanliness

4.96 out of 5 average rating, 103 reviews

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

FamilyValueCheck-in

4.95 out of 5 average rating, 111 reviews

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

FamilyLocationCondition

4.92 out of 5 average rating, 122 reviews

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

ValueFamilyAmenities

4.92 out of 5 average rating, 100 reviews

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

FamilyLocationWalkability

4.85 out of 5 average rating, 147 reviews

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

LocationValueLayout

4.99 out of 5 average rating, 240 reviews

A serene outdoor area features a pool surrounded by lush greenery and tropical plants. Poolside, colorful lounge chairs are arranged for relaxation, with playful floaties brightening the water. Umbrellas provide shade, and a seating area is visible in the background, enhancing the inviting ambiance.

Home in El Sobrante

Zen Meets Pool Retreat!

ValueFamilyHospitality

Weekly house rentals

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.

4.88 out of 5 average rating, 260 reviews

Modern House w A/C No Pet in San Mateo

ValueFamilyGetting around

4.93 out of 5 average rating, 296 reviews

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

ValueLocationBeach

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.

4.88 out of 5 average rating, 245 reviews

12-Min From SFO, Tastefully Designed, Work Station

LocationFamilyCheck-in

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.

4.86 out of 5 average rating, 338 reviews

Oceanfront w/ Direct Beach Access + New Hot Tub

ValueFamilyCheck-in

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.

4.79 out of 5 average rating, 182 reviews

Spectacular Coastal Half Moon Bay Home

FamilyLocationCheckout

4.99 out of 5 average rating, 133 reviews

A coastal cabin is situated on rugged cliffs overlooking the ocean. The structure features large windows, allowing for expansive views of the water. Lush greenery surrounds the home, highlighting its natural setting against a cloudy sky.

Home in Montara

Sea Wolf Bungalow

ValueLocationAccuracy

4.95 out of 5 average rating, 151 reviews

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

ValueLocationTV

Superhost

4.79 out of 5 average rating, 115 reviews

Seaside Art Gallery Loft Inspire Your Creativity

LocationValueLaundry

Private house rentals

Superhost

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

4.9 out of 5 average rating, 213 reviews

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

LocationValueCheck-in

4.99 out of 5 average rating, 142 reviews

A vibrant sunset sky displays shades of purple and orange, casting a warm glow over the ocean waves below. Silhouetted trees frame the view, adding depth to the picturesque coastal landscape with distant mountains visible under the evening light.

Home in Montara

Extraordinary Ocean Views from Modern Abode

FamilyValueAccess

4.95 out of 5 average rating, 166 reviews

A cozy living room displays two red armchairs facing a blue sofa adorned with decorative pillows. Natural light filters through the large windows, highlighting the hardwood floor. A television is mounted on a wooden stand beside a bookshelf, with artwork depicting trees hanging on the wall.

Home in San Carlos

New!! Silicon Valley Charming 3B2B House Fast wifi

ValueFamilyHospitality

4.79 out of 5 average rating, 43 reviews

Home in Burlingame

Cozy Retreat in a High-End, Walkable Neighborhood

FamilyValueHeating

4.96 out of 5 average rating, 72 reviews

A spacious entryway features warm wood flooring and neutral wall colors. An elegant light fixture hangs from the ceiling, and a console table is adorned with greenery and a lamp. An archway leads into a bright living area with large windows.

Home in Burlingame

Bright Spanish-style home in Burlingame

LocationFamilyDecor

4.91 out of 5 average rating, 64 reviews

A modern living area is presented with a large round mirror and two stylish lamps flanking a sleek console table. Soft, muted colors are complemented by artistic lighting fixtures and distinctive ceiling beams. The adjacent open space hints at a contemporary kitchen and dining area.

Home in Burlingame

Chic Art House- 3 Bedroom-near SFO

ValueFamilyNearby

4.96 out of 5 average rating, 48 reviews

A modern kitchen is highlighted by a large island with seating for four. Natural light floods in through the windows, which open to a balcony. Sleek cabinetry and stainless steel appliances are present, accompanied by a decorative plant near the entrance.

Home in Millbrae

Modern 3BR/3.5BA House with Parking & Laundry

ValueFamilyWalkability

A bright living room features light-colored sofas with yellow accent pillows, arranged around a wooden coffee table. A decorative blanket is draped over a chair. A fireplace is set within a white brick structure, flanked by built-in shelves displaying decor and plants.