Vacation rentals in Hillsborough

4.93 out of 5 average rating, 204 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 suite in Burlingame

Cozy Modern Craftsman Retreat

Private studio with a large outdoor patio. Just a short walk to the dinning and shopping on Burlingame Avenue and also on historic Broadway. Caltrain and Bart are minutes away to get take you to wherever you need to go. Fast wifi and espresso maker provided. Enjoy fresh fruit from our orange tree, and a rosemary bush for those that enjoy cooking. Relax with our large queen bed, recessed dimmable lighting and a large flat panel 4K smart TV w/apps for Netflix, Amazon Video, etc.

4.92 out of 5 average rating, 200 reviews

4.98 out of 5 average rating, 254 reviews

A cozy living area features a sectional sofa and coffee table, complemented by a 55" smart TV mounted on the wall. A standing desk with dual monitors and a small kitchenette, including a microwave and refrigerator, provide convenience. Three nature-themed artworks adorn the walls.

Guesthouse in San Mateo

Modern guest house in great location

Private 1 bedroom + 1 bathroom with your own entrance. Highlights: • self-checkin with code on digital lock • free parking + additional free street parking • professional cleaning and sanitizing • king size bed with premium mattress and linens • located at end of cul-de-sac in a safe and quiet neighborhood • standing desk with monitor and docking station • high speed WiFi • 55” smart TV • Rainfall shower, bidet toilet with heated seat, heated towel rack, makeup mirror

The exterior of the home is presented with distinct mid-century architecture, featuring large glass windows framed by dark walls. Lush landscaping, including tall grasses and shrubs, surround a smooth stone pathway leading to the entrance.

4.95 out of 5 average rating, 155 reviews

Mid-Century Retreat w/ BBQ & Fire Pit

Welcome to this 1956 Eichler-designed home in San Mateo's Highlands - a thoughtfully renovated mid-century retreat with a private backyard, fire pit & dedicated workspace. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & 8-person outdoor dining - Dedicated home office w/ door & fast Wi-Fi - Wood-burning fireplace & open-concept living - Enclosed atrium w/ custom mural & red maple tree - 20 mins to SF | 15 mins to SFO | Caltrain nearby

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, 318 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!

4.9 out of 5 average rating, 154 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

Superhost

Apartment in Burlingame

LuxoStays l! ! Lovely 2BR #SFO #Train #Laundry

*Entire Home-No sharing* Conveniently located! This spacious apartment is only 5min to SFO, 1-2 blocks from Starbucks, Walgreens, and other stores that you'll need! Many restaurants are right around the corner to eat at. Free Shuttles, Caltrain, Samtrans, and freeways are just blocks away. Longer inquiries are very welcome. Inquire even if the calendar is blocked off Send us a message now to secure your booking!

4.78 out of 5 average rating, 229 reviews

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

This bright and beautiful Spanish-style home is located in the charming city of Burlingame, on the San Francisco Peninsula, conveniently located between the city of San Francisco and Silicon Valley. The property comfortably sleeps 6 guests, with 2 bedrooms (1 king and 1 queen) and a queen sofa bed in the living room, and has 1 full bathroom with shower and bathtub, and 1 half bath.

4.95 out of 5 average rating, 124 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 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

4.97 out of 5 average rating, 364 reviews

A cozy sleeping space features a queen bed with white linens and colorful decorative pillows. A light fixture stands beside the bed, and a wall art piece composed of natural materials adds interest. A closet with sliding doors is visible in the background.

Guesthouse in Burlingame

Clean&Cozy Cottage near downtown Burlingame & SFO

Our sunny backyard cottage, with outdoor private entry, is centrally located in Burlingame between Burlingame Avenue and Broadway and is a great spot suited to a business traveler in search of a home away from home while also being ideal for vacationers looking to live like a local, only miles from SF. Enjoy and unwind!

Guesthouse in Hillsborough

A spacious room features vaulted ceilings with wooden beams. A queen-sized bed, draped in a geometric patterned blanket, sits next to a sleek fireplace. A dining table and chairs are visible, along with a large TV and two closets that provide storage options.

Little Cottage on the Hill

Enjoy a peaceful stay at this charming, secluded detached garden cottage great for a stay-cation or as a work-from-home alternative. The cottage features a queen-sized bed, a fireplace, private bathroom and kitchenette. Perfect for both leisure and Business travelers.

4.95 out of 5 average rating, 1035 reviews

4.98 out of 5 average rating, 501 reviews

A spacious bedroom features a comfortable bed with dark gray bedding, flanked by matching bedside tables and lamps. Two large windows allow natural light to fill the room, highlighting the textured wallpaper and organized bookshelf in the corner.

Guesthouse in Belmont

A Comfortable, Clean, & Private Guest House

Beautiful, Secluded, Safe, Fully Stocked, Comfortable, Newly Renovated, & Close to Public Transportation. In the heart of Silicon Valley with its own private entrance. It's 30 mins. N of San Jose, and 30 mins. of San Francisco.

Popular amenities for Hillsborough vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Hillsborough

4.96 out of 5 average rating, 28 reviews

A contemporary living room is shown with a comfortable sectional sofa and two patterned armchairs. A round coffee table is centered on a light area rug. A massage chair is positioned alongside a piano, while a television mounted on the wall displays a sleek design.

Townhouse in Burlingame

Modern Chic | Near Starbucks, Safeway, CVS & Shops

4.8 out of 5 average rating, 44 reviews

Home in Burlingame

Cozy Retreat in a High-End, Walkable Neighborhood

4.91 out of 5 average rating, 65 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

Superhost

Guesthouse in Burlingame

Guesthouse by Mills Canyon

4.83 out of 5 average rating, 6 reviews

Guest suite in Burlingame

A compact suite is visible, featuring a spacious bed dressed in white linens, accompanied by two pillows. A dining table with two chairs sits nearby, while a purple armchair adds color. Natural light enters through windows, illuminating the serene sunset image on the wall.

Burlingame Downtown Sophisticated Suite Spot

4.95 out of 5 average rating, 82 reviews

4.94 out of 5 average rating, 16 reviews

Guesthouse in Burlingame

Charming Executive Home - Near SFO Burlingame & SF

5.0 out of 5 average rating, 75 reviews

A spacious living area features modern furnishings, with large windows offering natural light. A full-size pool table and foosball table are visible in separate areas. An outdoor basketball hoop and Tesla charging station are also present, enhancing the recreational offerings of the home.

Villa in San Mateo

Tesla EV Charger Basketball Pool Table Hot Tub Spa

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.