Hillsborough vacation rentals

We found 35 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Hillsborough to find one that's perfect for your trip. Whether you’re staying in a vacation home with your kids or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. Whatever you're looking for, you'll be able to choose a rental to meet everyone's needs, including accessible or non-smoking choices.
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Find out more about Hillsborough

Find out more about Hillsborough

Why visit Hillsborough

  1. Outdoor Adventures: Enjoy a variety of outdoor activities in Hillsborough's scenic parks and nearby beaches.
  2. Charming Neighborhoods: Explore the quaint streets of Hillsborough and nearby Chapel Hill, perfect for leisurely walks.
  3. Local Culture: Immerse yourself in the friendly, family-oriented atmosphere of the community.
  4. Diverse Accommodations: Choose from charming vacation homes, modern apartments, and cozy condos for a memorable stay.
  5. Scenic Views: Take in the picturesque landscapes and breathtaking views unique to the Hillsborough area.

Popular types of accommodation around Hillsborough

If you're planning a getaway to Hillsborough, you're in for a treat! Explore a variety of accommodation options, from charming houses to modern apartments and cozy condos. Whether you're searching for Hillsborough house rentals or rental properties in Hillsborough County, you'll find the perfect spot to make your stay memorable. Discover the ideal Hillsborough apartments to suit your needs and enjoy a seamless vacation experience.

  • Houses: The top choice for visitors in Hillsborough, offering spacious accommodations ideal for families or groups.
  • Apartments: A popular option for those seeking modern amenities and convenience, perfect for solo travellers or couples.
  • Condos: These stylish properties provide a blend of comfort and luxury, great for short stays.
  • Cottages: Charming and cozy, cottages are perfect for a quaint getaway amidst nature.
  • Villas: Elegant and expansive, villas offer a lavish retreat for those looking to indulge.**

Top attractions around Hillsborough

Hillsborough, California, is a delightful destination for outdoor enthusiasts and adventure seekers. This charming area offers a range of attractions, including beautiful beaches, vibrant urban parks, and historic colleges and universities. Visitors can immerse themselves in local culture while enjoying scenic views and city experiences. Whether you’re travelling solo, as a couple, or with family, Hillsborough has something for everyone to enjoy during their vacation.

  1. San Francisco Bay: A vibrant area located 12.9km from Hillsborough, offering stunning views and a bustling atmosphere. Enjoy waterfront dining and explore local shops while soaking in the city vibes.
  2. Golden Gate Park: Situated 22.5km away, this expansive park features beautiful gardens, playgrounds, and walking trails, making it perfect for family outings and outdoor adventures.
  3. San Mateo County Event Center: Just 8.0km from Hillsborough, this venue hosts various events and conferences, providing a professional atmosphere ideal for business activities.

Things to do recommended for couples

For a romantic getaway in Hillsborough, enjoy a concert at Bill Graham Civic Auditorium for lively entertainment, unwind at the Oceanic Foot Spa for ultimate relaxation, or embrace adventure together at the University of Surfing. Each experience offers a unique vibe to cherish as a couple.

Things to do recommended for families

Your family vacation in Hillsborough will be delightful! Enjoy the adventure vibes at GoKart Racer, only 3.2km away, and indulge in sweet treats at See's Candies, 8.0km away. For sports enthusiasts, Oracle Park, 22.5km away, offers an exciting atmosphere for all ages.

Things to do recommended for groups

Groups visiting Hillsborough can enjoy a round of golf at Crystal Springs Golf Course, shop at the Millbrae Square Shopping Center, and try their luck at Artichoke Joe's Casino for a fun-filled local experience. Each venue offers unique vibes perfect for group enjoyment.

What do I need to keep in mind when booking a vacation around Hillsborough

If you're planning a trip with a group, family, or pets, or if you're considering an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Hillsborough with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Hillsborough with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Hillsborough: For many, a family getaway wouldn't feel complete without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Hillsborough: If you're seeking vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search as well.

Where to stay around Hillsborough

Hillsborough, California, offers a delightful blend of outdoor adventures and scenic beauty, perfect for a vacation filled with exploration. Nearby, you'll find charming neighborhoods and vibrant city life that embody a friendly, family-oriented atmosphere. Don't miss the picturesque views of the Hillsborough area, and take time to explore the quaint streets of nearby Chapel Hill. Whether you're seeking tranquility or urban excitement, Hillsborough is an ideal base for your Californian getaway.

  • Burlingame Hills: Burlingame Hills is a serene neighborhood located a mere 966m from Hillsborough, perfect for those seeking outdoor adventures and stunning scenery. Visitors can enjoy picturesque views of the bay and explore the charming local town neighbourhoods. The area is ideal for leisurely walks and outdoor activities, making it a great spot for nature lovers and beach enthusiasts. The nearby tourist precinct offers a variety of recreational options, ensuring a fulfilling travel experience.
  • Easton Addition: Located 1.1km from Hillsborough, Easton Addition is a vibrant neighbourhood that beckons sports enthusiasts and adventure seekers. This area features access to a spacious recreational area where you can engage in various outdoor activities. Local landmarks include a stadium and a sports facility, making it an excellent destination for those wanting to catch a game or participate in athletic events. The proximity to a national state park further enhances its appeal, providing ample opportunities for exploration and outdoor fun.
  • Millbrae: Situated 3.2km from Hillsborough, Millbrae is a lively city that offers a delightful mix of family-friendly activities and urban experiences. The city boasts a bustling shopping mall centre and various educational institutions, making it suitable for families looking to explore. Visitors can enjoy shopping at local boutiques or dining at nearby restaurants while taking in the vibrant atmosphere. The proximity to a stadium and the scenic bay adds to Millbrae's charm, making it an attractive destination for a day of family fun and exploration.

Best time to go to Hillsborough

If you're planning a trip to Hillsborough, it's a good idea to check both the weather and property rates. The warmest month is September. Peak season runs from March to May, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January51.4°F (10.8°C)Light RainMostly SunnyAverageSlightly Low
February52.2°F (11.2°C)Light RainMostly SunnyAverageSlightly Low
March53.4°F (11.9°C)Light RainMostly SunnyHighSlightly Low
April55.8°F (13.2°C)No Rain (Dry)Mostly SunnyHighAverage
May58.1°F (14.5°C)No Rain (Dry)SunnyHighAverage
June62.1°F (16.7°C)No Rain (Dry)SunnyAverageSlightly High
July63.1°F (17.3°C)No Rain (Dry)SunnyAverageSlightly High
August64.2°F (17.9°C)No Rain (Dry)SunnyAverageSlightly High
September64.9°F (18.3°C)No Rain (Dry)SunnyAverageAverage
October62.6°F (17.0°C)No Rain (Dry)SunnyLowAverage
November56.1°F (13.4°C)No Rain (Dry)Mostly SunnyLowAverage
December51.3°F (10.7°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, use our filters to refine your search by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, refine your travel arrangements, or manage your existing bookings. The properties you’ve saved or reserved are thoughtfully categorized into Potential, Upcoming, or Current Trips, making it easier to stay organized. To check out Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Hillsborough?
According to our research, houses are the most sought-after vacation rental type in Hillsborough. But naturally, everyone’s idea of the perfect trip isn’t the same. Vrbo has vacation rentals in a variety of sizes and shapes, and we’ll help you find the best fit for your needs.
How much does it cost to rent a vacation rental in Hillsborough?
The average price for a vacation rental in Hillsborough can vary depending on factors including length of stay, season and property type. Whether you’re in search of a sprawling villa with lots of bedrooms or a cozy condo ideal for just you and the kids, just add your dates of travel to find stays with unbeatable value.
How much does it cost to rent a beach house in Hillsborough?
Prices for beach houses in Hillsborough will vary depending on the type and size of the property and time of year you’re traveling. All you have to do is enter your travel dates into Vrbo and the number of guests to view vacation rental options and prices. From there you can use our filter tool to narrow your search by amenities, ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Hillsborough?
Pack a suitcase for the pup in your life because Hillsborough has three vacation homes that open their doors to pets. Let your four-legged buddy enjoy fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates and destination, then check the “Pets allowed” filter box.
What are popular rental amenities in Hillsborough?
A fireplace, a barbecue grill and a garden rank as the most popular rental amenities in Hillsborough. Whether you’re heading away as a party of one, with your spouse or a group of friends, Vrbo can help you find a vacation home that suits your style with a load of extras you’ll love.
Are there large group vacation rentals in Hillsborough?
Yes, you’ll find two vacation properties in Hillsborough that can host five or more people. From family reunions to a special event, these stays have enough room to kick back with your favorite people.
Are there vacation rentals in Hillsborough that welcome kids?
Hillsborough has three family-friendly vacation homes to pick from. And booking a stay that welcomes youngsters is easy with Vrbo’s “Properties good for families” filter. As well as having the entire place to yourselves, you can also look forward to conveniences and perks like dining rooms, full kitchens and yards.
What are the top attractions for families in Hillsborough?
Keeping the kids occupied during your vacation in Hillsborough is a snap with these leading family-friendly attractions:

  • GoKart Racer
  • Crystal Springs Golf Course
  • Burlingame Golf Center

Are there vacation rentals with WiFi in Hillsborough?
Hillsborough has three vacation rentals with WiFi, so you’ll be able to stay connected while you’re away. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming movie blockbusters to checking emails, these Vrbo homes make it a cinch to get online.
How can I find vacation rentals with air conditioning in Hillsborough?
Choose from two Vrbo vacation homes with air conditioning in Hillsborough providing that cooling breeze and extra element of comfort. Just enter your desired travel dates and then make use of our filters to help you find stays with air conditioning.
How old do you have to be to rent a vacation rental in Hillsborough?
You’ll have to check with the Hillsborough vacation property you’re considering on Vrbo as the minimum age differs. However, it’s typically 16, 18 or 21.
How long can I rent a vacation rental in Hillsborough for?
The amount of time you can book a Hillsborough vacation home for is up to each property. Simply tap in your preferred travel dates to view options that offer long-term stays. They feature everything you need to make your extended break more convenient and enjoyable, such as kitchens and backyards. Some Vrbo vacation rentals may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

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