House holiday 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, 357 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!

4.96 out of 5 average rating, 195 reviews

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.

4.99 out of 5 average rating, 413 reviews

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!

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.

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!

4.94 out of 5 average rating, 104 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

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

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

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.

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!

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.