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.

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Top Guest favourite
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
4.88 out of 5 average rating, 133 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.

Top Guest favourite
Home in San Mateo
4.92 out of 5 average rating, 193 reviews

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.

Top Guest favourite
A patio area is surrounded by tall redwood trees, featuring a grill and outdoor seating arrangement. Colorful plants and flowers enhance the natural setting, while a fenced yard creates a sense of privacy. The cabin’s exterior is visible, with a decorative wall accent.
Guesthouse in Woodside
4.98 out of 5 average rating, 471 reviews

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those inclined toward an active lifestyle, we are close to Purisima Creek, Huddart Park, and the El Corte de Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space)Note 20 minutes from Half Moon Bay with beautiful beaches and 30 min from Stanford in Palo Alto. We are adjacent to The Mountain House Restaurant. (note) The bed is a Murphy bed in the living area. NO PETS!

Guest favourite
The exterior of a three-level house is shown, featuring large windows that provide ample natural light and showcase views. Landscaping includes shrubs and trees, enhancing the home's presence. The entrance is highlighted by decorative lighting, uplifting the inviting appeal of the structure.
Home in Burlingame
4.96 out of 5 average rating, 182 reviews

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.

Top Guest favourite
A spacious living area features mid-century furniture, including a sofa with colorful cushions and wooden armchairs. A wood-burning fireplace is positioned within a textured white wall. Large glass doors provide natural light and an inviting view of the outdoors, enhancing the open layout.
Home in San Mateo
4.95 out of 5 average rating, 144 reviews

Private retreat - atrium, BBQ & fire pit

Step into a beautifully restored 1956 Eichler home in San Mateo - mid-century architecture with modern comforts, a private backyard, and easy Bay Area access. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & 8-person outdoor dining - Enclosed atrium w/ custom mural & red maple tree - Dedicated workspace (private room w/ door) & fast Wi-Fi - Wood-burning fireplace, full kitchen & in-unit washer/dryer - 20 mins to SF | 15 mins to SFO | Near Caltrain

Top Guest favourite
Guesthouse in San Mateo
4.99 out of 5 average rating, 233 reviews

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

Top Guest favourite
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, 404 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 favourite
Home in San Mateo
4.88 out of 5 average rating, 138 reviews

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

Guest favourite
Apartment in Burlingame
4.78 out of 5 average rating, 220 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 favourite
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
4.94 out of 5 average rating, 124 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 favourite
Home in Half Moon Bay
4.96 out of 5 average rating, 108 reviews

Seaside Home Modern Retreat with Breathtaking

Discover coastal serenity in this modern 4BR, 3 bath retreat in Half Moon Bay's Miramar district. With clean interior, wood accents & an amazing 2nd-floor balcony, this home offers a serene escape. Enjoy the landscaped backyard, fully stocked kitchen & proximity to popular beaches and the Coastal Trail. Experience seaside charm in this unforgettable home

Top Guest favourite
Guesthouse in Burlingame
4.98 out of 5 average rating, 351 reviews

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 holiday rentals

When is the best time to visit Hillsborough?

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Avg. price$334 NZD$337 NZD$329 NZD$262 NZD$257 NZD$257 NZD$296 NZD$282 NZD$291 NZD$306 NZD$306 NZD$339 NZD
Avg. temp11°C12°C13°C14°C16°C17°C18°C18°C19°C17°C14°C11°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 private suite rentals in Hillsborough?

    Experience the best of Hillsborough with our private suite rentals, starting at about $130 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 10 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 550 vacation rentals in Parrot Drive Area, and over 670 vacation rentals in Hillsborough Heights.

  • 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.

  • Do guesthouse rentals in Hillsborough have a kitchen?

    Absolutely! We offer over 10 guesthouse rentals with a kitchen 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.

  • 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.

Quick stats about holiday rentals in Hillsborough

  • Total holiday rentals

    Explore 170 holiday rentals in Hillsborough

  • Verified guest reviews

    Over 6,980 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    170 of Hillsborough holiday 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!