Holiday rentals in Hillsborough

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Top-rated holiday rentals in Hillsborough

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Top guest favourite
The bedroom features a spacious bed with white bedding, complemented by decorative pillows. A blue accent chair sits nearby, next to a decorative bedside table with a lamp. Natural light filters in through a window with white shutters, illuminating the light-colored walls and geometric rug.
Guest suite in Burlingame Hills
4.88 out of 5 average rating, 129 reviews

Gorgeous Suite close to SFO Airport, Self Check-In

Enjoy a peaceful stay at this newly appointed luxury suite. Burlingame is a suburb of San Francisco, known for it's tree-lined streets. Close to downtown San Mateo and Silicon Valley. This suite is part of a beautiful Spanish style house with a private entrance. Minutes from shops and restaurants Broadway Burlingame and Burlingame Avenue. Perfect for business travelers, couples or solo adventures! Features queen size bed, smart TV, refrigerator, microwave, Light and Bright! Wi-Fi, Parking.

Guest favourite
A cozy living area features a grey sofa adorned with colorful cushions. A sleek black coffee table sits in front of a modern television, with a decorative plant nearby. Bright yellow curtains covered in floral patterns frame the window, allowing natural light to illuminate the space.
Guest suite in Millbrae
4.78 out of 5 average rating, 780 reviews

Private 1 bedroom suite for quick SFO trip withA/C

1 bedroom 1 bathroom guest suite with private entrance. Good for a short SFO trip. But be aware it might not fit family vacation need! Newly remodeled kitchen, full bathroom, Wi-Fi, gas cooktop, coffee maker, toaster, microwave. Soft foam topper queen bed. Convenient for Bay Area commuter, 15 mins driving to SFO airport. Close to 101, 280 freeway. 30 mins driving to San Francisco or 50 mins to San Jose. 15 mins walk to grocery store, Starbucks and restaurants. Easy and free street parking.

Top guest favourite
The exterior of a cozy cottage is visible, surrounded by a lush garden filled with various plants and flowers. A stone path leads to the entrance, framed by vibrant greenery. Large windows allow glimpses of the inviting interior, enhanced by a seasonal wreath on the door.
Guest house in San Carlos
4.99 out of 5 average rating, 783 reviews

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 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). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

Top guest favourite
A spacious living area features a light grey couch adorned with patterned cushions, situated in front of a glass-topped table. A small succulent plant and coasters are placed on the table, with glimpses of a neat kitchen and a dedicated sleeping area visible in the background.
Guest house in Belmont
4.93 out of 5 average rating, 108 reviews

A private and quaint gateway on Belmont Hills

Welcome to our cozy Belmont studio! This charming retreat offers a comfortable stay with its stylish design, fully equipped kitchen, and a comfortable bed. Conveniently located in Belmont, CA, you'll be close to vibrant San Mateo downtown, the scenic coastline of Half Moon Bay, and the airport. This quaint studio is tucked away on a small hill, surrounded by greenery. As a delightful bonus, you'll find a lovely lemon tree in the driveway, providing complimentary lemons for your stay.

Top guest favourite
A sweeping landscape showcases vibrant orange poppies in the foreground, with rolling hills and the Pacific Ocean visible in the background. The scene captures a blend of natural beauty, framed by lush greenery and distant coastal views.
Guest suite in Linda Mar
4.98 out of 5 average rating, 196 reviews

Cozy, modern 1-bedroom with backyard ocean view!

Fall in love with this modern & sunny, 1 bedroom, 1 bath apartment with walk-in shower, refrigerator, TV, coffee/tea, & fast internet. First-floor unit (430 sq ft) with private entrance has views of nature & access to a peaceful backyard—steps from an awe-inspiring view of the Pacific Ocean. This one-of-a-kind, tranquil getaway offers the best of the Bay Area at your fingertips! Walk to hiking trails, drive 5-min. to the beach, & 20-min. to San Francisco or SFO airport.

Guest favourite
A small sitting area is presented, featuring two gray upholstered chairs with yellow accent pillows. A side table is positioned between the chairs. A microwave and mini refrigerator are located on a counter, with additional seating visible in the background.
Guest suite in San Bruno
4.87 out of 5 average rating, 1,009 reviews

Modern room & loft, private entrance

Modern room & loft with private entrance & private bathroom. Completely private space + free parking + self check-in + superfast Wi-Fi (up to 940 Mbps). Conveniently located in a quiet & safe residential neighborhood with Bayhill Shopping Center, Tanforan Mall, BART and Caltrain stations nearby. Easy access to highway 101 & 280, SFO airport (6-minute drive or 3 miles), San Francisco (16-25 minute drive to downtown), and San Francisco Baking Institute (11-minute drive).

Top guest favourite
A well-lit guestroom features a queen-size bed with floral bedding. A spacious loveseat sofa is positioned near a sliding glass door that opens to the backyard. A small coffee table rests in front of the sofa, and a portable air conditioner is visible in the corner.
Guest house in Park Pacifica
4.97 out of 5 average rating, 514 reviews

Elegant Guesthouse in Garden Close to SF/SFO/Beach

Built in 2020, our guesthouse is the perfect place for couples or solo travelers. It has a private entrance, smart lock, hotel-quality bedding, brand-new furniture, and the latest interior design selections. Staying in the sunbelt of beautiful Pacifica, there are a lot of fun activities nearby: spending your day on the beach, exploring the hiking trails, or road trip along Highway 1. Half Moon Bay, SF, and SFO are around 20 minutes away!

Superhost
A bright bedroom features a spacious bed with crisp white linens and an accent pillow. Natural light streams through large windows, and a modern desk with a lamp is positioned nearby. A mirrored closet reflects the room's stylish decor, enhancing the space's openness.
Guest suite in San Mateo
4.92 out of 5 average rating, 261 reviews

Luxury King Bed & Spa Bathroom

Our spacious guest suite has its own private entrance, comfortable pillow-top king size bed, work-friendly laptop desk, hi-speed wifi, spa bathroom with heated floor, mini fridge, and microwave. The guest suite is part of the main home, but there are no shared spaces and the areas are separated by a locked solid wood door & noise-dampening cushions. Our guest suite is ideal for couples visiting family in the neighborhood.

Superhost
Flat in Burlingame Terrace
4.78 out of 5 average rating, 210 reviews

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!

Top guest favourite
A private deck area is surrounded by lush greenery and colorful shrubs. A large umbrella provides shade over the wooden table and chairs, inviting relaxation outdoors. The deck is accessible from the yard, enhancing the tranquil outdoor experience.
Flat in Burlingame
4.97 out of 5 average rating, 456 reviews

Home away from home in wonderful Burlingame

It's my honor to be your host and I will try to make your stay really great. I provide suggestions of things to do but feel free to ask for advice! Our city requires their hosts obtain a 12% transient occupancy tax, therefore the price has been increased to reflect that tax. *** Please see House Rules and the complete description of the property to ensure our apartment will work for you.

Top guest favourite
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.
Guest house in Hillsborough
4.95 out of 5 average rating, 973 reviews

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. Since the coronavirus pandemic, we have been taking extra care to disinfect frequently touched surfaces between reservations. The cottage features a queen-sized bed, a fireplace,  private bathroom and kitchenette. Perfect for both leisure and Business travelers.

Top guest favourite
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.
Home in San Mateo
4.95 out of 5 average rating, 136 reviews

3BR haven w/ fire pit & fenced yard

Welcome to your cozy Bay Area retreat - a calm stay near SF w/ bright spaces perfect for relaxing or working remotely: - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium w/ custom mural - Private backyard w/ fire pit, outdoor dining & BBQ - Wood-burning fireplace - Workspace w/ fast Wi-Fi - Kitchen, in-unit laundry & free parking

Popular amenities for Hillsborough holiday rentals

When is the best time to visit Hillsborough?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$191 SGD$184 SGD$188 SGD$197 SGD$193 SGD$193 SGD$222 SGD$212 SGD$218 SGD$193 SGD$180 SGD$180 SGD
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Frequently Asked Questions

  • How much does it cost to stay in apartment rentals in Hillsborough?

    Experience the best of Hillsborough with our apartment rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Hillsborough have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Hillsborough. Enjoy a tailored experience with all the comforts you desire.

  • Are there Hillsborough vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Hillsborough, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Hillsborough have a kitchen?

    Absolutely! We offer over 50 house rentals with a kitchen in Hillsborough. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Hillsborough?

    Four-legged friends are welcome in Hillsborough. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Hillsborough?

    Yes! Work meets play with ease at over 90 vacation rentals in Hillsborough featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Hillsborough have free parking?

    Absolutely! We offer over 20 apartment rentals with free parking in Hillsborough. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Hillsborough have wifi?

    Absolutely! We offer over 60 house rentals with wifi in Hillsborough. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Hillsborough?

    Hillsborough has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Where should I stay in Hillsborough?

    Make yourself at home in Hillsborough by choosing from our most frequently booked neighborhoods. We have over 660 vacation rentals in Hillsborough Heights, over 660 vacation rentals in San Mateo Woods, and over 550 vacation rentals in Parrot Drive Area.

Quick stats about holiday rentals in Hillsborough

  • Total holiday rentals

    Explore 170 holiday rentals in Hillsborough

  • Verified guest reviews

    Over 7,330 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    160 of Hillsborough holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Hillsborough rentals

  • 4.8 Average rating

    Hillsborough stays are highly rated by guests – averaging 4.8 out of 5!