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Family-friendly vacation rentals in Hillsborough

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Hillsborough

  • Total vacation rentals

    Explore 70 vacation rentals in Hillsborough

  • Nightly prices starting at

    Hillsborough vacation rentals start at G$14,634 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,450 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 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!

Top-rated family-friendly rentals in Hillsborough

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
A bright interior space features large windows allowing natural light to fill the area. Colorful cushions in various shades are arranged on the floor, complemented by wooden accents and an open ceiling design that highlights the natural surroundings.
Treehouse in Half Moon Bay

Paradise Treehouse & Heavenly Cabin

A soulful and energetic paradise. Beautiful, private, peaceful & wild surroundings complimented with modern luxuries and comfort. A stunning, unique, & unrivaled experience sure to impact you deeply. Soak in the outdoor tub while you plan your next adventure. Just minutes from the beach, amazing hiking, views and biking. Outfitted with organic latex mattresses, down comforters, top of the line appliances, smoking fast internet and a spectacular wifi sound system with world class acoustics.

KitchenIndoor spacesSleep quality

4.99 out of 5 average rating, 159 reviews
Top guest favorite
Home in San Mateo

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.

KitchenFamilyAir conditioning

4.93 out of 5 average rating, 204 reviews
Guest favorite
Guest suite in Burlingame

Cozy Modern Craftsman Retreat

Private studio with a large outdoor patio. Just a short walk to the dinning and shopping on Burlingame Avenue and also on historic Broadway. Caltrain and Bart are minutes away to get take you to wherever you need to go. Fast wifi and espresso maker provided. Enjoy fresh fruit from our orange tree, and a rosemary bush for those that enjoy cooking. Relax with our large queen bed, recessed dimmable lighting and a large flat panel 4K smart TV w/apps for Netflix, Amazon Video, etc.

Indoor spacesFamilyValue

4.92 out of 5 average rating, 200 reviews
Guest favorite
A cozy living area features a sectional sofa and coffee table, complemented by a 55" smart TV mounted on the wall. A standing desk with dual monitors and a small kitchenette, including a microwave and refrigerator, provide convenience. Three nature-themed artworks adorn the walls.
Guesthouse in San Mateo

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

Indoor spacesFamilyParking

4.98 out of 5 average rating, 254 reviews
Top guest favorite
The exterior of the home is presented with distinct mid-century architecture, featuring large glass windows framed by dark walls. Lush landscaping, including tall grasses and shrubs, surround a smooth stone pathway leading to the entrance.
Home in San Mateo

Mid-Century Retreat w/ BBQ & Fire Pit

Welcome to this 1956 Eichler-designed home in San Mateo's Highlands - a thoughtfully renovated mid-century retreat with a private backyard, fire pit & dedicated workspace. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & 8-person outdoor dining - Dedicated home office w/ door & fast Wi-Fi - Wood-burning fireplace & open-concept living - Enclosed atrium w/ custom mural & red maple tree - 20 mins to SF | 15 mins to SFO | Caltrain nearby

KitchenFamilyComfort

4.95 out of 5 average rating, 155 reviews
Top guest favorite
A spacious living room features large windows allowing for ample natural light. Comfortable seating is arranged with a gray sofa and dark armchairs. A glass coffee table sits atop a plush area rug, while artwork adorns the walls, adding a touch of color to the neutral palette.
Home in San Mateo

Serene Modern Home with Yard & Parking

This spacious, tastefully decorated and full of natural light large house is a perfect combination of comfort and style. The house is recently renovated and has got everything to accommodate all your needs for a perfect stay. Convenient strategic location and easy commute to SF, Silicon Valley, BART and Airport, full amenities, parking, safe and quiet neighborhood, professionally managed, immaculately clean and more. Book now before someone else does!

FamilyIndoor spacesBreakfast

4.92 out of 5 average rating, 318 reviews
Top guest favorite
Home in San Mateo

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

KitchenIndoor spacesParking

4.9 out of 5 average rating, 154 reviews
Superhost
Apartment in Burlingame

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!

KitchenIndoor spacesPets

4.78 out of 5 average rating, 229 reviews
Top guest favorite
A private deck area is surrounded by lush greenery and colorful shrubs. A large umbrella provides shade over the wooden table and chairs, inviting relaxation outdoors. The deck is accessible from the yard, enhancing the tranquil outdoor experience.
Apartment in Burlingame

Home away from home in beautiful Burlingame!

It's my honor to be your host and I will try to make your stay really great. Please let me know if you have any questions ahead of time as I want to make sure you have the best visit. Our city requires their hosts obtain a 12% transient occupancy tax, therefore the price reflects that tax. *** Please see House Rules and the complete description of the property to ensure our apartment will work for you.

FamilyIndoor spacesHospitality

4.97 out of 5 average rating, 472 reviews
Guest favorite
A cozy sleeping space features a queen bed with white linens and colorful decorative pillows. A light fixture stands beside the bed, and a wall art piece composed of natural materials adds interest. A closet with sliding doors is visible in the background.
Guesthouse in Burlingame

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!

Indoor spacesFamilyHospitality

4.97 out of 5 average rating, 364 reviews
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

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. The cottage features a queen-sized bed, a fireplace,  private bathroom and kitchenette. Perfect for both leisure and Business travelers.

Indoor spacesKitchenBackyard

4.95 out of 5 average rating, 1035 reviews
Top guest favorite
A spacious bedroom features a comfortable bed with dark gray bedding, flanked by matching bedside tables and lamps. Two large windows allow natural light to fill the room, highlighting the textured wallpaper and organized bookshelf in the corner.
Guesthouse in Belmont

A Comfortable, Clean, & Private Guest House

Beautiful, Secluded, Safe, Fully Stocked, Comfortable, Newly Renovated, & Close to Public Transportation. In the heart of Silicon Valley with its own private entrance. It's 30 mins. N of San Jose, and 30 mins. of San Francisco.

KitchenFamilyParking

4.98 out of 5 average rating, 501 reviews

Popular amenities for Hillsborough family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
Guesthouse in Belmont

Private Garden Cottage Belmont Hills*Pool*HotTub*

FamilyIndoor spacesParking

4.87 out of 5 average rating, 295 reviews
Guest favorite
A wooden hot tub is positioned on a deck facing the ocean, with waves gently lapping at the shore. The sunset casts warm hues over the water, while wooden posts and ropes define the perimeter of the deck.
Home in Moss Beach

Walk to the Beach from this Ocean Front Home

KitchenIndoor spacesAir conditioning

4.92 out of 5 average rating, 298 reviews
Guest favorite
A spacious grassy yard is surrounded by lush gardens, showcasing colorful flowers and greenery. A seating area with wooden chairs is situated near a fountain, providing a tranquil spot to enjoy the views. The sky displays varying shades of blue, contributing to the serene atmosphere.
Home in Half Moon Bay

Oceanfront w/ Direct Beach Access + New Hot Tub

KitchenFamilyCheck-in

4.86 out of 5 average rating, 340 reviews
Guest favorite
A well-maintained pathway leads to a transparent entrance framed in red, surrounded by lush greenery. Flowering plants, including vibrant lavender and colorful blooms, enhance the inviting atmosphere. Sunlight filters through the glass walls, illuminating the area and connecting the indoors to nature.
Home in Half Moon Bay

2 bedroom house with hot tub

FamilyKitchenAccuracy

4.93 out of 5 average rating, 169 reviews
Superhost
Home in Moss Beach

Oceanfront Home Retreat w Breathtaking Views of

FamilyKitchenSleep quality

4.82 out of 5 average rating, 140 reviews
Top guest favorite
A spacious deck is depicted with comfortable wicker seating arranged around a light-colored table. Lush greenery is observed in planters, enhancing the natural ambiance. Sliding glass doors provide a view into the indoor living area, inviting the outdoors inside.
Guesthouse in Woodside

A beautiful Tree house -your own retreat

KitchenIndoor spacesLayout

4.94 out of 5 average rating, 221 reviews
Top guest favorite
A welcoming living room features high ceilings and large windows allowing natural light to fill the space. A comfortable sofa with blue and yellow pillows faces a wooden coffee table, while decorative armchairs and a flat-screen TV complete the inviting atmosphere.
Home in Half Moon Bay

Half Moon Bay Coastal Home Walk Beach & Harbor SPA

FamilyIndoor spacesGrill

4.99 out of 5 average rating, 414 reviews
Top guest favorite
An expansive living room features a leather sectional sofa, a circular coffee table, and a stone fireplace. Large glass windows provide views of the surrounding greenery, while wooden beams and a rustic stone wall create a natural ambiance. A television is positioned near the sofa.
Home in Mill Valley

Two Creeks Treehouse

Indoor spacesKitchenAmenities

4.99 out of 5 average rating, 139 reviews

Family- and pet-friendly home rentals

Top guest favorite
The cozy sleeping area features a large bed adorned with a geometric pattern comforter. Natural light filters through sheer curtains, illuminating the room. A wall mirror reflects the space, and a laundry basket is positioned near the window, providing functional convenience.
Guesthouse in Burlingame

Cozy private studio near SFO & Downtown Burlingame

Indoor spacesFamilyWalkability

4.96 out of 5 average rating, 212 reviews
Guest favorite
Guesthouse in Belmont

Treehouse w/ Canyon Views · King · Workspace · SFO

KitchenFamilyBathroom

4.83 out of 5 average rating, 210 reviews
Top guest favorite
A bright living room is visible, featuring a comfortable sofa with striped accents, a coffee table made of natural wood, and an inviting fireplace below a flatscreen TV. Large windows provide natural light and views of the outside, complemented by tasteful wall art and decorative elements.
Home in Half Moon Bay

Stairway to Heaven - 2 bedroom

Indoor spacesKitchenLocation

4.96 out of 5 average rating, 201 reviews
Guest favorite
The living area features a leather sofa paired with a patterned rug and a glass coffee table. A dining area is visible in the background, illuminated by natural light from large windows. Soft decorative elements, including a fluffy pouf and indoor plants, enhance the welcoming ambiance.
Home in Belmont

Sunlit 2B1B house w/ Deck & Garden on Belmont hill

Indoor spacesFamilyTV

4.94 out of 5 average rating, 109 reviews
Top guest favorite
The two-story house showcases a well-maintained exterior, featuring large windows framed with green accents. A charming porch is visible, along with a neatly landscaped yard. The driveway provides access to a two-car garage, and the peaceful neighborhood setting is enhanced by surrounding trees.
Home in Pacifica

Scenic Retreat w/ AC Hidden Gem Near SFO/SF/Beach

KitchenFamilyLocation

4.98 out of 5 average rating, 132 reviews
Superhost
Home in Half Moon Bay

Seaside Art Gallery Loft Inspire Your Creativity

FamilyIndoor spacesLayout

4.79 out of 5 average rating, 116 reviews
Top guest favorite
A cozy outdoor seating area features two rattan chairs positioned on a deck. A small table rests between them, with a scenic ocean view visible in the background. Sunrise colors illuminate the sky, and a vibrant pink flamingo adds a playful touch to the greenery.
Guest suite in Half Moon Bay

Oceanview Penthouse, Stylish, Walking to Beach

KitchenIndoor spacesParking

4.96 out of 5 average rating, 423 reviews
Guest favorite
The dining area features a large, rectangular table surrounded by four upholstered chairs, providing a comfortable setting. Natural light floods in through large windows, showcasing a view of the landscape. A decorative wall clock and a framed artwork add character to the space.
Home in South San Francisco

★EV+★Hillside SFO View★Home Theater★Pool Table

Indoor spacesKitchenCheckout

4.94 out of 5 average rating, 363 reviews

Family-friendly home rentals with a pool

Top guest favorite
A rustic cabin is situated among tall redwood trees. A wooden deck extends towards a tranquil pool, which is surrounded by greenery and flower beds. The warm tones of the cabin's exterior complement the natural surroundings, enhancing the serene atmosphere.
Guesthouse in Woodside

Rustic Cabin in the Redwoods

KitchenIndoor spacesNearby

4.99 out of 5 average rating, 380 reviews
Superhost
An aerial view captures the expansive outdoor area of the Anton Menlo Apartments. A resort-style pool is centrally located, surrounded by lounge chairs and shaded seating areas. Lush landscaping and modern architecture define the space, with additional amenities visible, including a community lounge.
Apartment in Menlo Park

Beautiful Spacious Living w/Resort Like Feel

KitchenFamilyHot tub

4.93 out of 5 average rating, 179 reviews
Guest favorite
A spacious living area features a cozy sectional sofa adorned with decorative pillows. A wooden coffee table sits atop a soft area rug. Natural light pours in through large windows, illuminating the vibrant artwork of a beach scene. The kitchen, equipped with modern appliances, is visible in the background.
Guest suite in Alameda

Coastal Zen Den

FamilyIndoor spacesGetting around

4.83 out of 5 average rating, 111 reviews
Guest favorite
A serene outdoor space features a swimming pool surrounded by lush vegetation and a gently sloping waterfall. Steps lead from the house to the pool area, with a slide positioned nearby. A vineyard is visible in the background, enhancing the tranquil setting.
Home in Portola Valley

3 BR Home on Vineyard nr Palo Alto & Stanford

KitchenFamilyAir conditioning

4.93 out of 5 average rating, 182 reviews
Guest favorite
The interior of the converted school bus features rustic wooden cabinetry and appliances. A spacious teak countertop extends over the cooking area, complemented by a red refrigerator. Sunlight illuminates the living area, showcasing a cozy seating arrangement and large windows with views of the surrounding nature.
Bus in East San Jose

Cozy BUS on Farm Animal Rescue with CITY VIEW

Indoor spacesKitchenAir conditioning

4.94 out of 5 average rating, 160 reviews
Top guest favorite
A large saltwater pool glistens under a clear blue sky, surrounded by lush greenery. The view overlooks the hills and twinkling lights of San Rafael, providing a serene backdrop for relaxation.
Guesthouse in San Rafael

Hillside Wellness Retreat | Pool, Gym & A/C

KitchenIndoor spacesBackyard

4.98 out of 5 average rating, 253 reviews
Top guest favorite
A spacious bed with an intricate patterned cover is positioned in a well-lit room. Towels are neatly arranged on the bed. A colorful piece of wall art adds a touch of character, while natural light filters through a nearby window.
Guest suite in Woodside

Separate entry room near Stanford

FamilyKitchenLocation

4.88 out of 5 average rating, 490 reviews
Guest favorite
A wooden deck is framed by palm trees, featuring a round table and an adjacent chair. The view captures a sparkling pool, surrounded by lush greenery, inviting relaxation in a serene outdoor setting.
Guesthouse in Walnut Creek

Tropical Garden Cottage +HOT TUB &POOL by Downtown

FamilyKitchenBackyard

4.91 out of 5 average rating, 662 reviews

When is the best time to visit Hillsborough?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$70,662 GYDG$62,509 GYDG$71,707 GYDG$53,519 GYDG$59,373 GYDG$72,961 GYDG$64,808 GYDG$63,972 GYDG$61,463 GYDG$57,909 GYDG$60,000 GYDG$58,118 GYD
Avg. temp11°C12°C13°C14°C16°C17°C18°C18°C19°C17°C14°C11°C

Destinations to explore