Vacation rentals in Hillsborough

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Top-rated vacation rentals in Hillsborough

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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 favorite
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, 779 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 favorite
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.
Guesthouse in San Carlos
4.99 out of 5 average rating, 780 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 favorite
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.
Home in San Mateo
4.92 out of 5 average rating, 180 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.

Top guest favorite
A cozy outdoor seating area features two rattan chairs positioned on a deck. A small table rests between them, with a scenic ocean view visible in the background. Sunrise colors illuminate the sky, and a vibrant pink flamingo adds a playful touch to the greenery.
Guest suite in Half Moon Bay
4.95 out of 5 average rating, 349 reviews

Oceanview Penthouse, Stylish, Walking to Beach

A perfect romantic getaways to this stylish indoor/outdoor Penthouse! We are 10 mins walk to beaches and 15 mins walk to award winning restaurants. There are a lot of fun activities: spending your days on the beach, exploring the hiking, biking, golfing, surfing, kayaking, paddle boarding or just simply kick back relax in this quiet and picturesque property with a panoramic ocean view, enjoying the sunset and the beautiful garden. We are 30 mins to SF or 60 mins to Santa Cruz.

Top guest favorite
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, 192 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.

Top guest favorite
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, 1,008 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).

Superhost
Apartment in Burlingame Terrace
4.78 out of 5 average rating, 209 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 favorite
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, 135 reviews

Stylish 3BR home w/ private backyard

Welcome to your Bay Area retreat - a mid-century haven where comfort meets creative charm near San Francisco & SFO! - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium w/ custom mural - Private backyard w/ fire pit, BBQ & outdoor dining - Wood-burning fireplace & open living area - Dedicated office w/ fast Wi-Fi - Full kitchen & in-unit washer/dryer - Peaceful Highlands neighborhood location

Top guest favorite
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.
Guesthouse in Hillsborough
4.95 out of 5 average rating, 968 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. Due to the coronavirus, we are 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 favorite
A coastal cabin is situated on rugged cliffs overlooking the ocean. The structure features large windows, allowing for expansive views of the water. Lush greenery surrounds the home, highlighting its natural setting against a cloudy sky.
Home in Montara
5 out of 5 average rating, 113 reviews

Sea Wolf Bungalow

If you're looking for the most spectacular views on the San Mateo Coast, come to Sea Wolf Bungalow. Located just 20 minutes southwest of San Francisco and 7 miles north of Half Moon Bay, this historic cabin sits on its on own point with sweeping views of the Pacific. Enjoy whale watching, the beach, surfing, fishing, golf, hiking and the fabulous dining of the coastal area.

Superhost
A modern living space features a light-colored sectional sofa and a sleek coffee table. A dining table with four chairs occupies one corner, while large windows allow natural light to fill the room. The warm wood flooring complements the neutral wall tones.
Apartment in Burlingame
4.77 out of 5 average rating, 110 reviews

Dreamy Downtown Flat

Welcome to your cozy getaway while staying in the Bay! This downtown flat is in the perfect location, just a 5 minute drive from SFO and a short walk to restaurants and shopping on beautiful Burlingame Avenue. With 1 bedroom and 1 sofa bed, this place can house up to 3 guests comfortably. The kitchen is stocked with all the essentials to cook at home.

Popular amenities for Hillsborough vacation rentals

When is the best time to visit Hillsborough?

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Avg. priceﺩ.ﺇ547ﺩ.ﺇ525ﺩ.ﺇ536ﺩ.ﺇ562ﺩ.ﺇ551ﺩ.ﺇ551ﺩ.ﺇ635ﺩ.ﺇ606ﺩ.ﺇ624ﺩ.ﺇ551ﺩ.ﺇ514ﺩ.ﺇ514
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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 house rentals in Hillsborough have air conditioning?

    Absolutely! We offer over 10 house 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 apartment rentals in Hillsborough have a kitchen?

    Absolutely! We offer over 50 apartment 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 guesthouse rentals in Hillsborough have free parking?

    Absolutely! We offer over 10 guesthouse 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 San Mateo Woods, over 550 vacation rentals in Parrot Drive Area, and over 660 vacation rentals in Hillsborough Heights.

Quick stats about vacation rentals in Hillsborough

  • Total vacation rentals

    Explore 170 vacation rentals in Hillsborough

  • Verified guest reviews

    Over 7,330 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    160 of Hillsborough vacation rentals include wi-fi 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!