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Family-friendly holiday rentals in Hillsborough

Find and book unique family-friendly homes on Airbnb

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 suite in Millbrae

4.78 out of 5 average rating, 1082 reviews

Charming Private Studio Near SFO

Private studio overlooks a beautiful garden is minutes away from the Bart Station and SFO Airport! Enjoy a bathroom, wi-fi, outdoor garden area, parking for a perfect little getaway/vacation. Queen bed and couch. Please note this listing only accommodates for two people and we do not accommodate additional guests. We hope you respect this rule as the neighborhood is quiet and would like to respect our neighbors. Infants and children are considered as guests. Note: No Kitchen, 3 night max stay

5–12 Sep

$159 SGD per night

Guest house in Half Moon Bay

4.82 out of 5 average rating, 425 reviews

Near harbor & Surfer’s beach, with outdoor Firepit

Guest cottage in village of El Granada w/ocean view from property. 5-minute walk to Surfer’s beach & 2-minute drive to harbor. Go biking or take a stroll on the paved coastal bluff trail. Hiking in the hills behind the cottage in Quarry Park. Full kitchen with attached covered deck. Cable TV & WIFI, Queen size memory foam bed. Sit around the outdoor firepit at night-see the stars & hear the ocean waves. Boat harbor nearby with seafood restaurants, brew pubs & live music. 5-min drive to Main St.

8–15 Jun

$227 SGD per night

Guest favourite

Cabin in Woodside

4.97 out of 5 average rating, 342 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!

3–10 Aug

$251 SGD per night

Guest favourite

Guest suite in Woodside

4.89 out of 5 average rating, 340 reviews

Stay Nestled in Ancient Redwoods in Silicon Valley

Welcome to our 6-acre home, High Ground, & have our kid and pet friendly carriage house to yourself! The large studio apt with separate entrance has stunning views of ancient redwood trees + the Bay/Mount Diablo. Immediate hiking trails, wildlife, minutes to: Alice's restaurant (5), Michelin-rated Village Pub (15) highway 280 (15) Palo Alto/Menlo Park/Half Moon Bay/Ocean (30), SFO (35) San Francisco (45). Perfect for a northern CA retreat, business in the Valley or sight-seeing in San Fran.

29 Jul – 5 Aug

$183 SGD per night

Guest favourite

Flat in Burlingame

4.97 out of 5 average rating, 403 reviews

Home away from home in wonderful Burlingame

We've been hosting for 11 years and love it. It's my honor to be your host and I will try to make your stay really great. I provide a list of summer events/festivals, farmer's markets, local "music in the park", and other suggestions but feel free to ask for advice! We donate 5% of all earnings to Airbnb.org to provide support in local, national and global housing emergencies. *** Please see House Rules at the end of the listing description to ensure our apartment will work for you.

31 Jul – 7 Aug

$264 SGD per night

Guest favourite

Guest house in San Francisco

4.94 out of 5 average rating, 949 reviews

Immaculate studio space with free parking

Immaculate, spacious lower level private studio space with private entrance and adjacent parking. Guests have completed contactless private entrance with no host interaction. Comfortable queen bed and attached spa like bath with tub/shower. Studio has a smart 40" TV, microwave and refrigerator, as well as seating area. Snacks, linens, toiletries are provided. Use of backyard, washer & dryer. All Airbnb COVID Cleaning protocols have been implemented to assure a clean environment.

30 Mar – 6 Apr

$124 SGD per night

Guest favourite

Guest suite in Lafayette

4.97 out of 5 average rating, 873 reviews

Mt. Diablo view 2 Bedroom/ King & Queen Suite

Our private 2 bedroom suite with amazing views of Mt. Diablo is located in a suburb of San Francisco and Berkeley called Lafayette in the East Bay. We neighbor Walnut Creek and are close to Hwys. 24/680. We are a 5-8 minute drive to the Lafayette BART station. San Francisco is a 25 minute train ride and when there is no traffic a quick 30 minute drive to downtown SF (with traffic add another 15-20 minutes). CAL or St. Mary's College bound? We are about 15-20 minutes away.

6–13 Oct

$161 SGD per night

Guest favourite

Home in Oakland

4.98 out of 5 average rating, 532 reviews

Private Casita with Stunning View

Relax in a private, fully equipped Casita with stunning views of East Oakland and the Bay. This newly constructed one-bedroom guest house in the quiet Eastmont Hills neighborhood has everything you need to work and play. Enjoy lounging in a hammock on the deck or on the couch streaming movies to a 32" television. Brand new stainless steel gas range and full-sized fridge make cooking a breeze, or you can partake in booming Oakland's restaurant scene.

5–12 Dec

$114 SGD per night

Guest favourite

Home in Redwood City

4.97 out of 5 average rating, 290 reviews

Private suite

Our home offers a private getaway perfect for business or a place to relax outside the city. Enjoy your private deck, complete with jacuzzi, and enter our large, sunny suite. Features Cal-King bed, on suite bath with heated tile flooring and bluetooth shower speaker. On site kitchenette includes mini bar, microwave, toaster oven, coffee maker & fridge/freezer. High speed WIFI connection and desk for workspace. Smart TV with blu ray, DVD, and cable.

22–29 Jun

$203 SGD per night

Home in Burlingame

4.86 out of 5 average rating, 155 reviews

Cozy, Spacious Villa with Private Pool & Bay View!

Set back from an already quite, wide residential street, the closed in the courtyard like creates an added layer of privacy that permeates the entire property. As a single level home with all four bedrooms, clustered together at one end of the house, and one junior suite, two living rooms, a kitchen, and a dining room clustered at the other, this home feels very comfortable on a daily basis, but also very capable for entertaining when needed.

5–12 Oct

$1,322 SGD per night

Guest favourite

Flat in El Granada

4.87 out of 5 average rating, 402 reviews

Studio near Harbor/Half Moon Bay

Studio with a comfy queen sized bed , kitchen and bathroom. Queen air mattress also available (additional charge for more than two guests- please book with the correct number). Second bed is a choice between an air mattress and pull out couch. Blocks from the beach/Princeton harbor and coastside trail. Quaint Half Moon Bay is a couple of miles south, San Francisco is 20 miles north.

13–20 Apr

$219 SGD per night

Guest favourite

Guest house in Hillsborough

4.95 out of 5 average rating, 810 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. Due to the coronavirus, we are 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.

1–8 Dec

$194 SGD per night

Holiday rentals for every style

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Popular amenities for Hillsborough family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Guest house in Kensington

4.94 out of 5 average rating, 605 reviews

Secluded luxury cottage & hot tub

10–17 Feb

$214 SGD per night

Guest suite in Los Altos Hills

4.8 out of 5 average rating, 148 reviews

A private hillside suite nestled among oaks

23–30 May

$222 SGD per night

Guest favourite

Guest house in San Leandro

4.94 out of 5 average rating, 216 reviews

Garden getaway near SF

7–14 Sep

$158 SGD per night

Guest favourite

Home in Burlingame

4.98 out of 5 average rating, 144 reviews

SFO Luxury House 4BR/3BA near SF & Silicon Valley

12–19 Jul

$960 SGD per night

Guest favourite

Guest house in Walnut Creek

4.91 out of 5 average rating, 502 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown

7–14 Mar

$179 SGD per night

Guest favourite

Cabin in Oakland

4.97 out of 5 average rating, 185 reviews

Spa style cottage! Jacuzzi, Sauna, Pool, Views!

15–22 Sep

$363 SGD per night

Guest favourite

Cabin in Oakland

4.92 out of 5 average rating, 172 reviews

Hike-in Bay Views Cabin w HotTub

27 Jul – 3 Aug

$309 SGD per night

Guest favourite

Home in Half Moon Bay

4.98 out of 5 average rating, 313 reviews

Half Moon Bay Coastal Home Walk Beach & Harbor SPA

3–10 Apr

$764 SGD per night

Family- and pet-friendly home rentals

Guest favourite

Cabin in Los Gatos

4.9 out of 5 average rating, 398 reviews

The Coach House

24–31 Aug

$144 SGD per night

Guest favourite

Guest suite in Oakland

4.96 out of 5 average rating, 124 reviews

Montclair Creekside Retreat

30 May – 6 Jun

$130 SGD per night

Guest favourite

Flat in Mill Valley

4.87 out of 5 average rating, 664 reviews

Mill Valley Retreat

25 Apr – 2 May

$177 SGD per night

Guest favourite

Guest suite in Berkeley

4.93 out of 5 average rating, 549 reviews

Garden Apt. with Gourmet Vittles

16–23 Oct

$158 SGD per night

Flat in Oakland

4.87 out of 5 average rating, 269 reviews

Montclair Retreat-quiet, elevator, in unit laundry

5–12 Jul

$166 SGD per night

Guest suite in San Jose

4.88 out of 5 average rating, 644 reviews

Hillside Retreat Private 2-Room Guest Unit & Pool

15–22 Jul

$180 SGD per night

Guest favourite

Train in Cupertino

4.92 out of 5 average rating, 346 reviews

Caboose in the redwoods just outside of Cupertino

29 Oct – 5 Nov

$303 SGD per night

Guest favourite

Home in Stinson Beach

4.93 out of 5 average rating, 257 reviews

Luxury and Design- 200 ft or 1 min walk to beach

11–18 Oct

$1,021 SGD per night

Family-friendly home rentals with a pool

Guest favourite

Guest house in San Rafael

4.9 out of 5 average rating, 380 reviews

Romantic Mtn Studio - Pool, Sauna, Views!

3–10 Mar

$342 SGD per night

Guest favourite

Guest suite in San Jose

4.92 out of 5 average rating, 116 reviews

Quiet and Comfortable Studio

22–29 May

$94 SGD per night

Guest favourite

Guest house in Monte Sereno

4.9 out of 5 average rating, 186 reviews

Greenwood Guest House, a Peaceful Oasis

17–24 Feb

$257 SGD per night

Guest favourite

Home in Portola Valley

4.92 out of 5 average rating, 137 reviews

3 BR Home on Vineyard nr Palo Alto & Stanford

1–6 Jun

$792 SGD per night

Guest favourite

Apartment in Mountain View

4.95 out of 5 average rating, 122 reviews

Spacious Top Floor Condo Retreat

8–15 Jun

$381 SGD per night

Home in Menlo Park

4.85 out of 5 average rating, 155 reviews

Modern French Country Style Home

15–22 Feb

$1,593 SGD per night

Guest favourite

Home in San Jose

4.92 out of 5 average rating, 154 reviews

Splash Pad

22–29 Jan

$1,515 SGD per night

Guest favourite

Guest suite in San Rafael

4.87 out of 5 average rating, 433 reviews

STUNN SF BAY/ MT TAM VIEW, LRG APT. SLEEPS 6, POOL

25 Mar – 1 Apr

$306 SGD per night

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

Total rentals
60 properties
Popular amenities
Kitchen, Wifi and Pool
Wifi availability
60 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
2K reviews

Destinations to explore