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.

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Top guest favorite
The bedroom features a spacious bed with white bedding, complemented by decorative pillows. A blue accent chair sits nearby, next to a decorative bedside table with a lamp. Natural light filters in through a window with white shutters, illuminating the light-colored walls and geometric rug.
Guest suite in Burlingame Hills
4.88 out of 5 average rating, 129 reviews

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.

Guest favorite
A cozy living area features a grey sofa adorned with colorful cushions. A sleek black coffee table sits in front of a modern television, with a decorative plant nearby. Bright yellow curtains covered in floral patterns frame the window, allowing natural light to illuminate the space.
Guest suite in Millbrae
4.78 out of 5 average rating, 781 reviews

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.

Top guest favorite
The exterior of a cozy cottage is visible, surrounded by a lush garden filled with various plants and flowers. A stone path leads to the entrance, framed by vibrant greenery. Large windows allow glimpses of the inviting interior, enhanced by a seasonal wreath on the door.
Guesthouse in San Carlos
4.99 out of 5 average rating, 783 reviews

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.

Top guest favorite
A cozy living area features a gas fireplace, providing warmth. A television is mounted above, and natural light enters through two windows. A round red rug is positioned on the hardwood floor, with a light-colored sofa and a dark chair visible, creating an inviting space.
Cottage in Woodside
4.98 out of 5 average rating, 442 reviews

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!

Top guest favorite
A spacious living area features a light grey couch adorned with patterned cushions, situated in front of a glass-topped table. A small succulent plant and coasters are placed on the table, with glimpses of a neat kitchen and a dedicated sleeping area visible in the background.
Guesthouse in Belmont
4.92 out of 5 average rating, 111 reviews

A private and quaint gateway on Belmont Hills

Welcome to our cozy Belmont studio! This charming retreat offers a comfortable stay with its stylish design, fully equipped kitchen, and a comfortable bed. Conveniently located in Belmont, CA, you'll be close to vibrant San Mateo downtown, the scenic coastline of Half Moon Bay, and the airport. This quaint studio is tucked away on a small hill, surrounded by greenery. As a delightful bonus, you'll find a lovely lemon tree in the driveway, providing complimentary lemons for your stay.

Top guest favorite
The studio apartment features an open layout, showcasing a full kitchen with wooden cabinetry and a dining area. A comfortable window seat offers serene views, while light wood flooring adds warmth to the space. Modern lighting fixtures complement the overall aesthetic.
Home in Montara
4.98 out of 5 average rating, 374 reviews

A private beachy pad in Montara

Welcome to Chez Sage! Your own private apartment get-away, with a private deck and ocean views, is just 30 minutes south of San Francisco. The entrance to your private apartment leads you up the stairs to a deck with an ocean peek. Enter your home away from home and relax in the window seat to gaze at Montara Mountain or eat breakfast on the island with peeks of the ocean. Once you're settled, it's just a short stroll to watch the sunset from the beach.

Top guest favorite
A well-lit guestroom features a queen-size bed with floral bedding. A spacious loveseat sofa is positioned near a sliding glass door that opens to the backyard. A small coffee table rests in front of the sofa, and a portable air conditioner is visible in the corner.
Guesthouse in Park Pacifica
4.97 out of 5 average rating, 516 reviews

Elegant Guesthouse in Garden Close to SF/SFO/Beach

Built in 2020, our guesthouse is the perfect place for couples or solo travelers. It has a private entrance, smart lock, hotel-quality bedding, brand-new furniture, and the latest interior design selections. Staying in the sunbelt of beautiful Pacifica, there are a lot of fun activities nearby: spending your day on the beach, exploring the hiking trails, or road trip along Highway 1. Half Moon Bay, SF, and SFO are around 20 minutes away!

Guest favorite
Apartment in Burlingame Terrace
4.78 out of 5 average rating, 210 reviews

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!

Guest favorite
A modern studio bedroom features a spacious queen-size bed, dressed in a light blue quilt. Two large windows allow natural light to fill the room, complemented by a small working desk and chair. Neutral tones create a calming environment.
Guest suite in Belmont
4.95 out of 5 average rating, 117 reviews

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.

Top guest favorite
The entrance to the studio features double glass doors framed by potted plants and flowers in various sizes. A welcome mat is positioned at the threshold, and small wall-mounted lights provide illumination. Natural light can be seen streaming through the doors.
Guesthouse in San Mateo
4.93 out of 5 average rating, 238 reviews

Charming Private Quiet Backyard Studio

This charming, sunny, secluded backyard studio is located in the heart of San Mateo, near public transportation, freeways, restaurants, shopping, and 15 minutes to SFO. Private entrance, quiet backyard setting, plenty of street parking. Less than a 5-min walk to Safeway, CVS, Starbucks and restaurants. * To my regular guests, the rate increase is due to SM County increasing the tax rate. *

Top guest favorite
A spacious room features vaulted ceilings with wooden beams. A queen-sized bed, draped in a geometric patterned blanket, sits next to a sleek fireplace. A dining table and chairs are visible, along with a large TV and two closets that provide storage options.
Guesthouse in Hillsborough
4.95 out of 5 average rating, 975 reviews

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.

Top guest favorite
A coastal cabin is situated on rugged cliffs overlooking the ocean. The structure features large windows, allowing for expansive views of the water. Lush greenery surrounds the home, highlighting its natural setting against a cloudy sky.
Home in Montara
4.99 out of 5 average rating, 118 reviews

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 vacation rentals

When is the best time to visit Hillsborough?

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Frequently Asked Questions

  • How much does it cost to stay in apartment rentals in Hillsborough?

    Experience the best of Hillsborough with our apartment rentals, starting at about $10 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 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.

  • Do guesthouse rentals in Hillsborough have wifi?

    Absolutely! We offer over 10 guesthouse 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 540 vacation rentals in Parrot Drive Area, over 660 vacation rentals in San Mateo Woods, and over 660 vacation rentals in Hillsborough Heights.

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!