Holiday rentals in Hillsborough

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

Our Black & White designer home is curated by an artist. It offers a respite for your family & friends, and is a launching pad for work or local adventures. Light-filled, tranquil and spacious, the house is hugged by the garden and outdoor living spaces. Located 10 minutes from SFO and 20-minutes from San Francisco by car. Or, connect via mass transit; 5 blocks away. Equipped with full kitchen. Fluffy linens adorn the beds. Spa-like bathrooms. Plush sofas embrace you; welcoming you home.

4.93 out of 5 average rating, 205 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.

4.96 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

Welcome to SunlightStays! Enjoy total comfort with brand-new beds, a fully equipped kitchen, massage chair, piano, dedicated workspace, and a garden-view patio. Unbeatable Location: - 7-min drive to SFO Airport - 3-min walk to Safeway, Starbucks, CVS & dining - 15-min walk to Burlingame Ave & Caltrain for easy trips to SF, Palo Alto, and San Jose The Best Part? Zero check-out chores—just pack up, lock up and go! Our professional cleaning crew takes care of everything after you depart.

An inviting living room features a large sectional sofa and a light rug centered under a TV stand. Natural light illuminates the space through multiple windows, and hardwood floors enhance the clean, modern design. Decor elements include a framed artwork and indoor plants.

4.85 out of 5 average rating, 100 reviews

SanMateo Comfortable 2BR Home/WiFI & Free Parking

Welcome to this entire newly remolded 2-bedroom home , located in a desirable neighborhood. The home offers a spacious living space with a very clean and fresh interior design. You’ll be close to downtown San Mateo’s restaurants and shops, the beautiful Japanese Garden at Central Park, Hillsdale Shopping Center, and major routes including Highway 101 and Highway 92. SFO is just a short drive away, making this a convenient home base for both business and leisure travel. SFO 5miles

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

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!

4.8 out of 5 average rating, 44 reviews

Home in Burlingame

Cozy Retreat in a High-End, Walkable Neighborhood

Escape to our luxurious one-bedroom rental nestled in a safe and upscale neighborhood, surrounded by multi-million-dollar homes. With ample space to accommodate 2-4 guests, our cozy haven promises a memorable stay just 10 minutes away from SFO. An easy 5-10 minute walk gets you to the premier downtown Burlingame with plenty of shopping, dining, and relaxing opportunities. Plus, enjoy the convenience of free driveway parking during your stay.

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

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, 163 reviews

An outdoor seating area features a circular gas fire pit surrounded by a smooth stone ledge. A coastal view of the Pacific Ocean is visible, with the horizon meeting the sky in soft hues at sunset. The patio is enclosed by modern railing.

Home in Pacifica

Oceanfront Home in Pacifica, CA

Experience coastal living on Pedro Point, featured on Staycation NorCal: A Golden Baycation. This 3-bedroom, 2-bath home offers unobstructed ocean views and is available exclusively for 30+ day stays. Walk to the beach, enjoy sunsets from the deck, relax by the gas fire pit, and on clear days, take in views of the Golden Gate Bridge.

Guest house in Burlingame

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.

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!

4.97 out of 5 average rating, 365 reviews

Guest house 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

Popular amenities for Hillsborough holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Hillsborough

Superhost

Guest house 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, 83 reviews

Guest house in Burlingame

Charming Executive Home - Near SFO Burlingame & SF

4.94 out of 5 average rating, 16 reviews

5.0 out of 5 average rating, 76 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.

4.98 out of 5 average rating, 51 reviews

Renovated 3b1.5b San Mateo hill near SFO/Stanford

4.94 out of 5 average rating, 53 reviews

The living room features two cozy sofas arranged for relaxation, with a coffee table positioned in the center. A smart TV is mounted on the wall, while a glass door opens to a balcony. Natural light fills the space, enhancing the modern decor.

Flat in San Mateo

1725 - Modern & Cozy 2B2B at Heart of San Mateo

4.91 out of 5 average rating, 22 reviews

Guest suite in San Mateo

Remodeled-Private Guest Suite-1 mile from downtown