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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Superhost
The guest suite features a spacious bed with neutral bedding, accompanied by two light pillows. A modern desk and chair sit beside a large window, which allows natural light to fill the room. A ceiling fan and wall-mounted television enhance the contemporary design.
Guest suite in Millbrae
4.88 out of 5 average rating, 262 reviews

Boutique Hotel Feel - Private Luxury Master Suite

Private luxury guest suite in newly built architectural gem in Mills Estate. Boutique hotel feel, spacious guest room and bathroom suite. This two room suite has a private entry and smart lock for self check-in. The suite is attached to the main house, but closed off from the rest of the house. No amenities are shared. Super fast internet, 1000 mbps. Prime location, located in a quiet residential neighborhood, just 15 mins from SFO, 10 mins from Bart/Caltrain station, 20 mins to San Francisco.

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, 131 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.

Top guest favorite
A cozy living area features a gas fireplace, providing warmth. A television is mounted above, and natural light enters through two windows. A round red rug is positioned on the hardwood floor, with a light-colored sofa and a dark chair visible, creating an inviting space.
Guesthouse in Woodside
4.98 out of 5 average rating, 459 reviews

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those who are inclined to have an active lifestyle, We are close to Purisima Creek, Huddart Park, and El Corte De Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space) 20 minutes away from Half Moon Bay with beautiful beaches and 30 min. from Stanford, Palo Alto. We are adjacent to The Mountain House Restaurant. Res recommended. Short drive to local breakfast place. NO PETS!

Top guest favorite
A quaint cottage is displayed with a yellow exterior and charming architectural details. Lush green grass and two rose bushes frame the pathway leading to the front door, while sunlight illuminates the inviting entryway. Trees provide a natural canopy, enhancing the peaceful curb appeal.
Home in San Mateo
4.93 out of 5 average rating, 187 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 favorite
The exterior of a multi-level home features a blend of large windows and a distinctive round window. The light-colored facade is complemented by lush greenery and flowering plants in the foreground. A spacious front deck is visible, enhancing the inviting appearance of the property.
Home in Burlingame
4.96 out of 5 average rating, 178 reviews

SFO Panoramic Views 4BR/3BA near SF-Silicon Valley

Located in the SF Bay Area Peninsula with 180-degree panoramic views of the Bay Area, 3,012 square feet, 4 bedrooms and 3 full bathrooms. Located on the upper level is the kitchen, dining room, TV room, and spacious living room. Lower level has four bedrooms. Must be able to climb stairs. Refinished hardwood floors and carpet in the bedrooms. Backyard extends into multiple decks, including BBQ grill and hot tub. Located between San Francisco and Silicon Valley. Very close to SFO.

Top guest favorite
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 Hillsdale
4.99 out of 5 average rating, 218 reviews

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

Top guest favorite
Home in San Mateo
4.88 out of 5 average rating, 128 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
4.78 out of 5 average rating, 216 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
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, 1,001 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 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
4.99 out of 5 average rating, 123 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.

Top guest favorite
Home in San Mateo
4.95 out of 5 average rating, 141 reviews

Cozy retreat w/ fireplace & BBQ grill

Welcome to your cozy Bay Area retreat - a peaceful San Mateo stay perfect for relaxing evenings & easy gatherings. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Wood-burning fireplace & backyard fire pit - Private backyard - fully fenced w/ BBQ grill - Enclosed atrium w/ custom mural - Dedicated workspace w/ door & Wifi - Free parking on premises + self check-in

Top guest favorite
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
4.98 out of 5 average rating, 345 reviews

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!

Popular amenities for Hillsborough vacation rentals

When is the best time to visit Hillsborough?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,184 GYDG$29,928 GYDG$30,556 GYDG$32,021 GYDG$31,393 GYDG$31,393 GYDG$36,207 GYDG$34,533 GYDG$35,579 GYDG$37,463 GYDG$37,463 GYDG$41,439 GYD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Hillsborough?

    Hillsborough has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Hillsborough with our guesthouse rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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 80 vacation rentals in Hillsborough featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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!

  • 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 540 vacation rentals in Parrot Drive Area, and over 660 vacation rentals in Hillsborough Heights.

  • 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.

  • 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.

  • Do private suite rentals in Hillsborough have wifi?

    Absolutely! We offer over 10 private suite rentals with wifi in Hillsborough. Enjoy a tailored experience with all the comforts you desire.

  • 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.

Quick stats about vacation rentals in Hillsborough

  • Total vacation rentals

    Explore 170 vacation rentals in Hillsborough

  • Verified guest reviews

    Over 7,430 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 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

    80 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!