
Vacation rentals in Hillsborough
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Hillsborough
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

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.

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!

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

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

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!

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.

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.

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

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
Other great vacation rentals in Hillsborough

Business-Friendly 2/1. Walk to Caltrain/Downtown.

Super Private Hidden Redwood City House and Garden

Ocean-View Moss Beach Coastal Retreat

Charming 3BR Executive Home Minutes from SFO & SF

Brand New Modern Luxury Unit | Walk to Downtown

Jane's Home (MI) | Relaxing Retreat w/ Deck & View

Renovated 3b1.5b San Mateo hill near SFO/Stanford

The Nest: A Luxury Loft Retreat
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,184 GYD | G$29,928 GYD | G$30,556 GYD | G$32,021 GYD | G$31,393 GYD | G$31,393 GYD | G$36,207 GYD | G$34,533 GYD | G$35,579 GYD | G$37,463 GYD | G$37,463 GYD | G$41,439 GYD |
| 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!
Destinations to explore
- Northern California Vacation rentals
- San Francisco Bay Area Vacation rentals
- San Francisco Vacation rentals
- Gold Country Vacation rentals
- Central California Vacation rentals
- San Francisco Peninsula Vacation rentals
- San Jose Vacation rentals
- Silicon Valley Vacation rentals
- North Coast Vacation rentals
- Santa Barbara Vacation rentals
- Wine Country Vacation rentals
- Oakland Vacation rentals
- Apartment rentals Hillsborough
- Rentals with outdoor seating Hillsborough
- Rentals with a fire pit Hillsborough
- Rentals with a hot tub Hillsborough
- Rentals with a patio Hillsborough
- Pet-friendly rentals Hillsborough
- Family-friendly rentals Hillsborough
- Rentals with a fireplace Hillsborough
- Rentals with a washer and dryer Hillsborough
- House rentals Hillsborough
- Rentals with pools Hillsborough
- Fitness-friendly rentals Hillsborough
- 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
- Pier 39
- Seacliff State Beach
- Henry Cowell Redwoods State Park
- Twin Peaks
- University of California-Berkeley
- Six Flags Discovery Kingdom
- Palace of Fine Arts
- Montara Beach
- Levi's Stadium
- Winchester Mystery House
- Bolinas Beach
- California’S Great America




