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.

Guest favorite

Home in San Mateo

4.93 out of 5 average rating, 105 reviews

Lovely Mid-Century home near SF, SFO, & Peninsula

Walk through the enclosed atrium sporting a custom mural and stunning red maple in this home dating back to 1956. The spacious house boasts mid-century furniture and art with a wall of glass overlooking the deck with a backdrop of fruit trees. Spacious 2 bedrooms & den with TV converts to a sofa bed. You also have a private office if you're working from home, right off the atrium. Enjoy a lovely dinner in back garden on a cool summer night. Though we love children, our home is not childproof, and we prefer not to host children under 12 years of age, thank you for understanding. This home was built in 1956 by Joseph Eichler and completely remodeled in 2017 with the goal of staying true to its original Mid-Century design while updating the house for modern living. It features a collection of beautiful Mid-Century furniture and art made by the owner and friends. Guests enter through an enclosed atrium that sports a custom mural and stunning red maple. The back yard features a large dining area with a backdrop of fruit tree and a spacious deck overlooking thousands of acres of open space and the Coastal Range. This home has two bedrooms with queen size beds and one bedroom with a full size sofa-bed. The master bedroom has an en suite bathroom with walk-in shower, the other two rooms share a bathroom with a deep tub. There is a spacious, well lit office for your use. One of the best features of this home is it's great room with a wood-burning fireplace, dining room, and kitchen--perfect for entertaining a small group. The backyard features an 8 person outdoor dining table and 6 burner BBQ for your use, as well a large outdoor sofa surrounding a fire pit. The front atrium is another well lit modern get away where you can to sit back and enjoy nature and art. Guests will have access to the entire property including the house and gardens. There is a washer and drier for guest use in the garage. I have a co-host who will be there for you 24/7. The house is in the Highlands neighborhood, which was developed by Joseph Eichler in the mid-1950s. The community center across the street from the property features a great playground for children. San Francisco Airport is 15 minutes away. - Caltrain (Goes up and down to San Francisco and San Jose) - BART (Goes to Downtown San Francisco and East Bay) - Lyft (Use referral code JEN573431) - Uber (Use referral code jcc271ue) Parking in the drive way only (no garage use for cars). TV in one of the bedrooms, not the living room. No parties or events allowed. No curtains in two of the bedrooms, but no one can see into these room as a building wall hides them. 20 minutes to downtown San Francisco We take cleaning in this climate very seriously, we are in full compliance with the cleaning guidelines approved by WHO (Worldwide Health Organization) CDC (Center for Disease Control) and the EPA (Environmental Protection Agency)

May 10 – 17

ﺩ.ﺇ1,729 per night
Guest favorite

Apartment in San Mateo

4.94 out of 5 average rating, 182 reviews

Fabulous apartment in downtown San Mateo

Relax away from the hustle of the city in your apartment in downtown San Mateo. Located only two blocks from the San Mateo Caltrain, you can get to or from SF or SJ in 30 minutes. Our home has a separate entrance for the guest apartment on the second floor. Tuck yourself away in the California King sized bed, or explore downtown on foot. With over 100 restaurants in walking distance, you will not have a shortage of delicious dining. Eat out or enjoy a meal in the comfort of your home. Welcome!

Apr 1 – 6

ﺩ.ﺇ450 per night
Guest favorite

Guest suite in San Mateo

4.92 out of 5 average rating, 295 reviews

San Mateo Getaway Private 2 Bedroom

Bright & spacious 2 bedroom apartment with beautiful backyard in San Mateo. In-law apartment with private entrance dedicated to hosting guests. Located in quiet residential neighborhood, but close to activities for families and singles. Amenities include wet bar area with toaster oven, coffee maker, mini fridge and microwave! Laundry available upon request. Easy access to San Francisco/San Jose via 280 & 101. Close to SFO, Cal train/BART and Downtown San Mateo. Lots of street parking.

Apr 18 – 25

ﺩ.ﺇ528 per night

Popular amenities for Hillsborough vacation rentals

Stay near Hillsborough's top sights

Limon Rotisserie Burlingame8 locals recommend
Crepevine14 locals recommend
RASA11 locals recommend
Copenhagen Bakery & Cafe24 locals recommend
Mingalaba Restaurant28 locals recommend
Sawyer Camp Trail54 locals recommend

Other great vacation rentals in Hillsborough

Guest favorite

Guesthouse in San Carlos

4.99 out of 5 average rating, 579 reviews

Private Garden Cottage

Jun 12 – 19

ﺩ.ﺇ563 per night
Guest favorite

Guesthouse in Belmont

4.97 out of 5 average rating, 361 reviews

A Comfortable & Private Guest House

Feb 16 – 23

ﺩ.ﺇ414 per night
Guest favorite

Guesthouse in Pacifica

4.98 out of 5 average rating, 367 reviews

NEW Private Studio! Close to SF/SFO/Beach Sanitize

Sep 1 – 8

ﺩ.ﺇ468 per night
Superhost

Home in San Mateo

4.83 out of 5 average rating, 260 reviews

❤️ Delightful 1B/1B modern with a leisure garden

ﺩ.ﺇ441 per night
Superhost

Apartment in Pacifica

4.79 out of 5 average rating, 670 reviews

Luxury Beach View Apartment

Mar 13 – 20

ﺩ.ﺇ591 per night
Guest favorite

Guesthouse in Redwood City

4.98 out of 5 average rating, 374 reviews

Quiet , Private Studio / Cottage

Jan 14 – 21

ﺩ.ﺇ415 per night
Superhost

Home in Burlingame

4.86 out of 5 average rating, 155 reviews

Cozy, Spacious Villa with Private Pool & Bay View!

Apr 22 – 29

ﺩ.ﺇ3,372 per night
Guest favorite

Guest suite in Emerald Hills

4.92 out of 5 average rating, 145 reviews

Elegant retreat in Redwood City

Mar 1 – 8

ﺩ.ﺇ453 per night
Guest favorite

Guesthouse in Belmont

4.84 out of 5 average rating, 199 reviews

Charming Cottage Studio

Jul 11 – 18

ﺩ.ﺇ357 per night
Guest favorite

Condo in Hillsborough

5.0 out of 5 average rating, 7 reviews

Breathtaking View Modern 1b1b on Top of the World

Jan 19 – 26

ﺩ.ﺇ613 per night
Guest favorite

Home in Hillsborough

4.92 out of 5 average rating, 13 reviews

Modern San Francisco Bay Area home, 4bed/2bath

Jan 25 – Feb 1

ﺩ.ﺇ2,813 per night
Guest favorite

Guest suite in Burlingame

4.85 out of 5 average rating, 84 reviews

Gorgeous Suite close to SFO Airport, Self Check-In

Jun 7 – 14

ﺩ.ﺇ572 per night

Quick stats about vacation rentals in Hillsborough

Total rentals

220 properties

Rentals with dedicated workspaces

100 properties have a dedicated workspace

Rentals with a pool

30 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

70 properties are a good fit for families

Total number of reviews

7.6K reviews

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 $90 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 20 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 30 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 50 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 100 vacation rentals in Hillsborough featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Hillsborough have free parking?

    Absolutely! We offer over 40 apartment rentals with free parking 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.

  • 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.

  • Where should I stay in Hillsborough?

    Make yourself at home in Hillsborough by choosing from our most frequently booked neighborhoods. We have over 600 vacation rentals in Parrot Drive Area, over 900 vacation rentals in Lakeview, and over 730 vacation rentals in Hillsborough Heights.

Destinations to explore