
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.

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.

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.

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.

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.

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.

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.

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

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.

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

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!

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.

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
Other great vacation rentals in Hillsborough

San Mateo Sanctuary | Central • Near SFO • Quiet

Miramar Penthouse Coastal Elegance in the Heart of

Modern 3BR/3.5BA House with Parking & Laundry

Great Studio San Mateo near SFO

Private Modern Studio & Patio with stunning views

Charming Burlingame Beauty!

Brand new modern 2 Bed/2 bath Guesthouse

A Private Retreat in Nature - Bluebird Day Cottage
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ547 | ﺩ.ﺇ525 | ﺩ.ﺇ536 | ﺩ.ﺇ562 | ﺩ.ﺇ551 | ﺩ.ﺇ551 | ﺩ.ﺇ635 | ﺩ.ﺇ606 | ﺩ.ﺇ624 | ﺩ.ﺇ657 | ﺩ.ﺇ657 | ﺩ.ﺇ727 |
| Avg. temp | 11°C | 12°C | 13°C | 14°C | 16°C | 17°C | 18°C | 18°C | 19°C | 17°C | 14°C | 11°C |
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!
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- Moscone Center
- Stanford University
- Santa Cruz Beach
- Golden Gate Park
- Oracle Park
- Capitola Beach
- Muir Woods National Monument
- Golden Gate Bridge
- Rio Del Mar Beach
- SAP Center
- Santa Cruz Beach Boardwalk
- Mission Dolores Park
- Seacliff State Beach
- Pier 39
- Twin Peaks
- Henry Cowell Redwoods State Park
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- University of California-Berkeley
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- California’S Great America




