House holiday rentals in Hillsborough

4.96 out of 5 average rating, 204 reviews

The sunroom features expansive glass windows that offer a panoramic view of the city and hills at sunset. A cozy seating area with a light blanket and soft cushions is present, providing a relaxing space to enjoy the scenic landscape.

Home in Daly City

SF Amazing View & SUNroom: Spacious Private 1 bdrm

👋 Welcome to our spacious, clean, private getaway studio on Southern Hill in Daly City. Escape the hustle and bustle of the city. Enjoy a stunning view of day/night in clear days ☀️ - Easy street parking - Great Summit Loop Trail at San Bruno Mountain (6-min🚘) - Cow Palace Arena (8-min🚘) - H Mart grocery mall (10-min🚘) - 9.2 miles to SFO (17-min🚘) - 6.7 miles to Civic Center（>30-min🚘 w/ traffic or 20-min🚘 w/o traffic) - 11 miles to Fisherman's Wharf(>35-min🚘 w/ traffic or 23-min🚘 w/o traffic)

A light-filled living room features a comfortable white sofa and a stylish armchair, positioned around a wooden coffee table. A modern television is mounted above a decorative stone fireplace. Soft curtains frame the window, enhancing the open feel of the space.

4.87 out of 5 average rating, 113 reviews

10-Min SFO *A/C* Modern Comfort 2BR Family Retreat

Welcome to our beautifully remodeled 2-bedroom home, just minutes from Downtown San Mateo! Whether you’re a couple, a family, or a business traveler, this is the perfect spot for you. Enjoy a fully equipped kitchen, comfortable living space, and kids-friendly amenities. Explore San Mateo's vibrant neighborhoods or take a short drive to San Francisco. We've thought of everything to make your stay comfortable, including fast WiFi and plush bedding. Book now and experience the best of the Bay Area!

4.99 out of 5 average rating, 340 reviews

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

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.

A stylish living room features a modern red chair alongside a patterned gray-and-white armchair. A wooden coffee table sits on a plush area rug, with a television mounted above a classic fireplace. Decorative elements are arranged on the mantel, adding a touch of sophistication.

4.92 out of 5 average rating, 178 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, 152 reviews

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

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.

4.93 out of 5 average rating, 377 reviews

A large window showcases a view of lush trees and a serene outdoor area. Natural light floods the space, enhancing the warm tones of the elegant decor, which includes a small decorative bicycle and a floral arrangement on a nearby table.

Home in Belmont

Hidden French Gem for Fam/Biz~near Caltrain,SFO

Highly welcome respectful travelers to step through the 750ft super quiet European-style private studio with secluded bay view. Curl up in front of the 4K TV for movie nights at this stylish, soundproofed nest with a luxury mattress, washer and dryer! — welcome infant & kids. — Read everything to avoid surprises. — 5 min walks to park, Caltrain/restaurants; 10~13 min drive to SFO/Stanford; 20-25 min SF. — No pets, no smoking/vaping, no party! — book for 3 if need single bed

4.96 out of 5 average rating, 282 reviews

The guest house is presented with a charming Tudor-style exterior, featuring a pitched roof and decorative wooden beams. Large glass doors provide a view into the interior space, framed by a covered porch supported by sturdy beams. Lush landscaping and a vibrant red entry gate enhance the inviting ambiance.

Home in San Carlos

The Perfectly Appointed Modern English Guest House

Relax and unwind in this newly constructed guest house. Completed in 2019 it offers all the amenities of a 5-star hotel suite with the privacy and ambiance of a quaint English Tudor home. Located just 2 blocks from charming downtown San Carlos in the “City of Good Living”. We are 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain).

An open-concept living area features a combination of mid-century furniture and modern design. A cozy sofa and colorful chairs surround a low table, while a dining area with a bright yellow table sits adjacent. Light filters in through large windows, highlighting the space's contemporary aesthetic.

4.95 out of 5 average rating, 134 reviews

Stylish 3BR home w/ BBQ & outdoor dining

Welcome to your mid-century Bay Area retreat - perfect for families, professionals & design lovers alike! Enjoy stylish comfort, peaceful surroundings & easy access to SF & SFO: - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & dining area - Wood-burning fireplace & enclosed atrium - Full kitchen & private office w/ fast Wi-Fi - Washer/dryer, free parking & streaming TV apps - Single-level home in tranquil Highlands neighborhood

4.98 out of 5 average rating, 369 reviews

The studio apartment features an open layout, showcasing a full kitchen with wooden cabinetry and a dining area. A comfortable window seat offers serene views, while light wood flooring adds warmth to the space. Modern lighting fixtures complement the overall aesthetic.

Home in Montara

A private beachy pad in Montara

Welcome to Chez Sage! Your own private apartment get-away, with a private deck and ocean views, is just 30 minutes south of San Francisco. The entrance to your private apartment leads you up the stairs to a deck with an ocean peek. Enter your home away from home and relax in the window seat to gaze at Montara Mountain or eat breakfast on the island with peeks of the ocean. Once you're settled, it's just a short stroll to watch the sunset from the beach.

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, 284 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!

A living area is highlighted by a light-toned laminate floor and neutral-colored walls. Two soft armchairs with yellow cushions face a modern white sofa. A round coffee table is placed atop a patterned area rug. A tall plant stand holds greenery, complementing the inviting space.

4.9 out of 5 average rating, 367 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.

4.93 out of 5 average rating, 286 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.

Popular amenities for house rentals in Hillsborough

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 218 reviews

A private outdoor area features a modern hot tub alongside a comfortable seating arrangement. Bright turquoise chairs offer a pop of color, while tall trees provide natural shade. The concrete patio is spacious, ensuring ample room for relaxation and enjoyment.

Home in Concord

Pool, Hot tub, Napa, SFO Clean

4.91 out of 5 average rating, 102 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 w/Pool

4.88 out of 5 average rating, 183 reviews

A spacious living area is equipped with a flat-screen TV mounted on the wall and an ornate cabinet. A comfortable grey chair and a glass coffee table are positioned on a soft carpet. Natural light is welcomed through a nearby window, enhancing the cozy atmosphere.

Home in Mountain View

Little Poolside House near Downtown Mountain View!

4.99 out of 5 average rating, 110 reviews

A single-level home displays a clean architectural design, surrounded by well-maintained green grass and landscaped areas. The entrance features two outdoor chairs positioned on a concrete patio, with large windows inviting natural light into the interior.

Home in Mill Valley

Chic & Fun Mid-Century Modern sleeps 8 (pool)

4.86 out of 5 average rating, 125 reviews

An inviting outdoor space features a covered patio with wooden beams and soft lighting. A circular stone fire pit occupies the center, surrounded by cushioned seating. A BBQ grill is positioned nearby, with a private heated pool glimmering in the background.

Home in San Jose

Beautiful 3BD Home w/ Heated Pool and Fire Pit

4.94 out of 5 average rating, 402 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

Silicon Valley Work Retreat | Wellness Oasis

4.92 out of 5 average rating, 543 reviews

The image captures a calm pool area surrounded by palm trees under a clear blue sky. The reflection of the trees and deck is visible in the water, creating a serene outdoor setting. A well-maintained landscape can be seen beyond the pool.

Home in San Rafael

MCM Waterfront Pool/Hot Tub between SF and Napa

4.93 out of 5 average rating, 172 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

Weekly house rentals

4.81 out of 5 average rating, 131 reviews

A spacious deck is showcased, featuring a vibrant red umbrella providing shade over a circular table. A hammock with colorful stripes is visible, gently swaying in the sunlight. Surrounding greenery creates a serene backdrop, enhancing the outdoor relaxation spaces.

Home in San Carlos

Canyon Oak House: Private, tranquil with trees

A bright living area features a round table with a floral centerpiece and two cushioned chairs. The backdrop displays an open kitchen with cabinetry, leading to a warmly painted bedroom door. A small plant and modern decor enhance the welcoming atmosphere, illuminated by natural light.

4.83 out of 5 average rating, 281 reviews

❤️ Delightful 1B/1B modern with a leisure garden

Superhost

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, 206 reviews

12-Min From SFO, Tastefully Designed, Work Station

4.98 out of 5 average rating, 260 reviews

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

4.93 out of 5 average rating, 164 reviews

The modern exterior of the house features a combination of wood and light-colored siding. A covered porch is highlighted by vertical lighting, while large windows provide views of the surrounding landscape. A manicured lawn and driveway contribute to the welcoming entryway.

Home in Mountain View

Upscale Modern House Near Mountain View Downtown

4.86 out of 5 average rating, 148 reviews

A mid-century modern entrance welcomes guests with rich wooden walls and a vibrant yellow front door. A stylish console table is positioned against the wall, beside decorative plants. Bar stools line a counter, contributing to the open and airy ambiance of the space.

Home in Oakmore

Architectural Gem Mid Century Modern in the Trees

4.92 out of 5 average rating, 183 reviews

A spacious living area is featured, showcasing a cozy gray sofa with a textured throw blanket. A decorative fireplace sits against a light-colored wall, complemented by built-in bookshelves adorned with plants and books. Glass-paned doors lead to a bright dining space.

Home in Alameda

Cozy 2-BR Garden Bungalow w/ Parking and King Bed

4.91 out of 5 average rating, 537 reviews

A spacious bedroom is featured with a large bed covered in a colorful patterned blanket. Two lamps are positioned on each side of the bed, and artwork depicting the Golden Gate Bridge adorns the walls. Natural light streams in through a window dressed with white curtains.

Home in Portola

Spacious & Clean Apartment on Traditional SF Hill

Private house rentals

4.98 out of 5 average rating, 43 reviews

A spacious living area features a white sectional sofa adorned with decorative teal pillows. Light streams through large windows framed by sheer curtains, illuminating the wooden floors and highlighting the rich textures of the room. A simple coffee table is positioned in front of the sofa.

Home in Edgewood Park

Super Private Hidden Redwood City House and Garden

4.95 out of 5 average rating, 88 reviews

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 Miramar

Seaside Home Modern Retreat with Breathtaking

4.93 out of 5 average rating, 30 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

5 out of 5 average rating, 71 reviews

A modern kitchen is presented, featuring a spacious island with seating for four. Sleek stainless steel appliances are complemented by white cabinetry and a stone backsplash. Natural light floods through a skylight, enhancing the vibrant blue accent wall and warm wood flooring.

Home in Foster City

Lavish Modern Home 4BR near SFO/Palo Alto/Stanford

5 out of 5 average rating, 22 reviews

An aerial view illustrates the oceanfront property surrounded by lush greenery. A hot tub is positioned near the rocky shore, offering views of the vibrant blue ocean and crashing waves. The coastline and distant hills create a scenic backdrop to this serene location.

Home in Montara

Spectacular California Ocean Front Home!

4.95 out of 5 average rating, 60 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

4.99 out of 5 average rating, 78 reviews

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

Charming Burlingame Beauty!

A spacious living area features elegant hardwood floors and a charming fireplace, providing a focal point for the room. A plush leather sofa is arranged thoughtfully, with natural light illuminating the space from large windows. A dining area is visible in the background.