
Holiday houses in Hillsborough
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Top-rated holiday rentals in Hillsborough
Guests agree: these stays are highly rated for location, cleanliness and more.

10-Min SFO *A/C* Modern Comfort 2BR Family Retreat
Welcome to our beautifully remodeled 2-bedroom home, just minutes from Downtown San Mateo! Whether you’re a couple, a family, or a business traveler, this is the perfect spot for you. Enjoy a fully equipped kitchen, comfortable living space, and kids-friendly amenities. Explore San Mateo's vibrant neighborhoods or take a short drive to San Francisco. We've thought of everything to make your stay comfortable, including fast WiFi and plush bedding. Book now and experience the best of the Bay Area!

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.

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.

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.

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.

Modern room & loft, private entrance
Modern room & loft with private entrance & private bathroom. Completely private space + free parking + self check-in + superfast Wi-Fi (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).

Luxury King Bed & Spa Bathroom
Our spacious guest suite has its own private entrance, comfortable pillow-top king size bed, work-friendly laptop desk, hi-speed wifi, spa bathroom with heated floor, mini fridge, and microwave. The guest suite is part of the main home, but there are no shared spaces and the areas are separated by a locked solid wood door & noise-dampening cushions. Our guest suite is ideal for couples visiting family in the neighborhood.

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!

New, modern quiet private studio
New modern private studio attached to the main house with a private staircase entrance. Easy free parking in front of the entrance. Located in heart of the Bay Area: 15 minutes to SFO airport, 19 minutes to Half Moon Bay, 17 minutes to Stanford. Enjoy nice views with morning coffee. Ideal for 1-2 guests. Working desk, wifi, tv, comfortable linens, small fridge, microwave and Phillips coffee machine.

Home away from home in wonderful Burlingame
It's my honor to be your host and I will try to make your stay really great. I provide suggestions of things to do but feel free to ask for advice! Our city requires their hosts obtain a 12% transient occupancy tax, therefore the price has been increased to reflect that tax. *** Please see House Rules and the complete description of the property to ensure our apartment will work for you.

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.

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.
Popular amenities for Hillsborough holiday rentals
Other great holiday rentals in Hillsborough

Near SF Airport 1-bedroom home

Kasa the Niche Redwood City | Micro-pod Full Bed

Private garden bedroom near SFO, BART & CalTrans

Private bedroom with double bed.

Sunny Sillicon Valley Getaway/Crashpad/Workspace

Cozy Retreat in a High-End, Walkable Neighborhood

Private Room near SFO

Chic Art House- 3 Bedroom-near SFO
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $227 AUD | $218 AUD | $223 AUD | $234 AUD | $229 AUD | $229 AUD | $264 AUD | $252 AUD | $259 AUD | $229 AUD | $214 AUD | $214 AUD |
| 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
How much does it cost to stay in guesthouse rentals in Hillsborough?
Experience the best of Hillsborough with our guesthouse rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Hillsborough have air conditioning?
Absolutely! We offer over 10 apartment 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 660 vacation rentals in Hillsborough Heights, and over 550 vacation rentals in Parrot Drive Area.
Quick stats about holiday rentals in Hillsborough

Total holiday rentals
Explore 170 holiday rentals in Hillsborough

Verified guest reviews
Over 7,330 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
160 of Hillsborough holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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