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
A secluded outdoor area features a hot tub surrounded by lush greenery. A shaded patio sits nearby with white lounge chairs, while a portion of the building is visible in the background, incorporating large windows and a deck area adorned with outdoor furnishings.
Farm stay in Woodside
4.96 out of 5 average rating, 136 reviews

Apartment w hot tub / forest & ocean view

Slow living on the farm. Welcome to Coop d’État Farm Retreat on Kings Mountain—set among old-growth redwoods with ocean views, a fire pit & a private hot tub. The apartment sits on our working glamping property, where chickens roam, goats graze, dogs stand guard, and our cats supervise from afar. We’re a 10-minute walk to the Purisima Open Space trail network. This cozy apartment occupies the lower floor of our home & includes a private entrance and parking, access to a shared picnic & BBQ area.

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, 796 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
A bright living room is visible, featuring a comfortable sofa with striped accents, a coffee table made of natural wood, and an inviting fireplace below a flatscreen TV. Large windows provide natural light and views of the outside, complemented by tasteful wall art and decorative elements.
Home in Half Moon Bay
4.96 out of 5 average rating, 168 reviews

Stairway to Heaven - 2 bedroom

PLEASE NOTE, we live in a 3 story home and this unit is on the lower level of our home. Also available in a 1 bedroom, this suite features a spacious living room with a fire place, flatscreen TV & a kitchenette with most everything you will need to feel at home. A nice large bedroom with a quality queen bed & linens, a large bathroom with a double sink, tub and shower. The private entrance leads to a patio with stunning views and quiet space. There is a second sunning patio do dine and rest.

Top guest favorite
A spacious living area is shown, featuring a modern desk and a unique chair. Natural light fills the room through large windows, which are complemented by dark curtains. Decorative elements include a wall clock and a circular mirror, enhancing the overall inviting feel.
Apartment in Half Moon Bay
4.99 out of 5 average rating, 169 reviews

Modern Oceanview 2-Bed Apartment Home

Located in just 5mins walk from the beach, this freshly renovated apartment home has a style of its own. Yet, it is the Pacific Ocean views and all of its marine life, that captures your attention from the moment you open the front door. Beautiful, fully equipped modern kitchen, with large aisle, from where you could enjoy a cup of morning coffee while gazing at the ocean waves. Spend your evenings on the large outdoor patio with electric BBQ grill while enjoying timeless Pacific sunsets.

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
4.92 out of 5 average rating, 186 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, 216 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

Guest favorite
A serene beach scene at sunset is captured, featuring gentle waves reflecting the hues of orange and blue in the sky. Silhouettes of people can be seen walking along the shoreline, while lights from the distant marina twinkle against the darkening landscape.
Guesthouse in El Granada
4.97 out of 5 average rating, 115 reviews

Coastal Cottage Guest House

Guest house is attached to our primary residence but has a separate exterior entrance. The interior is separated by double doors that lock from both sides, similar to adjoining hotel rooms. The backyard is shared by us, the owners. There’s a very real chance you’ll be greeted by our friendly Australian Shepherd, Gracie, during your stay! You may see us in the yard during your stay. Feel free to say hi! Otherwise, we like to give our guests privacy.

Top guest favorite
A welcoming living area features a red sofa adorned with patterned pillows, accompanied by a brown armchair. A dark coffee table sits in front of the seating, while a small desk is positioned nearby. Light fills the space through large windows covered with white blinds.
Apartment in San Carlos
4.98 out of 5 average rating, 133 reviews

Beauty in San Carlos! 1 large bedroom apartment

Newly beautifully remodeled large corner unit with quaint views, this one bedroom apartment is in an Excellent location, walking distance to downtown San Carlos, to fine restaurants, parks, library, coffee, shopping, 30 minutes from San Francisco and San Jose and just minutes from Palo Alto Stanford and Menlo Park, Redwood City and San Mateo Assigned gated parking space, laundry room in the building: http://www.tourfactory.com/idxr1906024

Guest favorite
Apartment in Burlingame
4.78 out of 5 average rating, 215 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 sleek Airstream is positioned on a wooden deck overlooking the beach and ocean, surrounded by lush hills. Cozy seating is provided with Adirondack chairs near a fire pit, creating a tranquil outdoor area for relaxation while enjoying the captivating coastal views.
Camper/RV in Half Moon Bay
4.98 out of 5 average rating, 183 reviews

Airstream Beach View (Dream) - New Listing

On 9 private acres overlooking the stunning Beach and Ocean from a breathtaking cliff top view. Stunning sunsets. Surf views with large windows. Fully loaded with all the amenities to make your glamping experience perfect. Fire pit, outside BBQ, outside griddle, Heat, A/C and fully stocked kitchen. Full bathroom with shower. If this one is booked, there are three other equally similar Airstreams on the property.

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, 140 reviews

Relaxing retreat w/ fire place & atrium

Welcome to your mid-century Bay Area retreat - a peaceful stay designed for comfort, work, and relaxation: - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium w/ mural & serene indoor-outdoor feel - Private backyard w/ BBQ, fire pit & outdoor dining - Dedicated workspace + WiFi for remote work - Full kitchen, dining area & indoor fireplace - Free parking, self check-in & single-level layout

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.ﺇ657ﺩ.ﺇ657ﺩ.ﺇ727
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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!