Family-friendly holiday rentals in Pickering

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Pickering

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

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Guest favourite

Guest suite in Pickering

4.94 out of 5 average rating, 125 reviews

Separate 2 Bedroom & 2 Washroom up to 4 people.

Hotel-style apartment in a home annex. Not a basement. The apartment has 2 bedrooms with attached washrooms, Living area, kitchen, dining. Our property accommodates up to 4 people. Children are welcome to stay. Conveniently located just off Highway 401. Close to downtown Pickering, Go Station, mall, restaurants. We are a good stopover point if you are traveling to downtown Toronto which is only a 40 min drive. Note: Show us your ID when "Checking In" and it has to match with your booking name.

19–26 Jul

$164 SGD per night

Guest favourite

Guest suite in Vaughan

4.92 out of 5 average rating, 542 reviews

Luxury Modern Two Bedrooms Basement Apartment

No 3rd party booking! No parties! No visitors! ARRIVING W/ EXTRA GUEST WILL GET CHARGED DOUBLE 24hr Exterior Surveillance Tons of upgrades and high end modern features! High ceiling above grade basement unit. Open concept living space include fireplace, smart TV(no cable, please use your streaming login), full kitchen, laundry and large wardrobe One parking on our driveway Free Wifi Enjoy scenic trails in Woodbridge 10min to Vaughan Mills outlets & Canada's wonderland 15min to Pearson airport

21–28 Jul

$141 SGD per night

Guest favourite

Flat in Richmond Hill

4.87 out of 5 average rating, 275 reviews

Spacious private apartment includes coffee/tea bar

Cozy-Contemporary Spacious Private Apt. in the Historical Downtown Core of Richmond Hill. 15 MINUTES FROM YYZ. Fully functional complete kitchen, NEWLY RENOVATED bathroom, heated floor, spacious shower, private entrance, parking COVID-Super-CLEAN Very quite, beautiful Mature trees and gardens. The Old Mill Pond area is known for it's canopy of trees, ponds and walking trails. Close to Yonge Street, GO transit, and 15 MINUTES FROM AIRPORT Walking distance to Major Mackenzie Health Hospital.

10–17 May

$116 SGD per night

Guest favourite

Flat in Whitby

4.95 out of 5 average rating, 156 reviews

Serenity Suite w/Sauna-Your Entire Apt Awaits You

LONG-TERM stays welcome. A short drive to Thermea Spa Village. This is a beautiful, newly renovated, spacious basement apartment, perfect for two. Located in Whitby Shores (w/ hot tub) just a few minutes’ walk to Lake Ontario, a park, & trails, the house is situated in a quiet and friendly neighbourhood. It is close to all amenities - shopping, movie theatre, and other entertainment options, restaurants, GO Train station, Hwy 401, and easy access to Hwy 407. We look forward to meeting you!

1–8 Nov

$115 SGD per night

Guest favourite

Guest suite in Toronto

4.87 out of 5 average rating, 135 reviews

Modern 2 Bedroom Apartment

Escape to this modern and spacious basement apartment, perfect for families, couples, and business travelers. With 9ft ceilings and plenty of natural light, this fully-furnished unit boasts: - 2 private entrances - 2 bedrooms - 2 bathrooms - Living room with a fireplace - Fully-equipped kitchen - Smart TV with cable - Highspeed Wi-Fi - Heated marble floors throughout the space - Convenient parking space Stay with us and enjoy the privacy, comfort, and warmth this apartment has to offer!

6–13 May

$157 SGD per night

Guest favourite

Flat in Oshawa

4.95 out of 5 average rating, 621 reviews

Just like home

This is an fully furnished basement apartment Quiet neighborhood close to bus stop, shopping and restaurants. Ten minute drive to Oshawa Center and downtown Oshawa. Reserve parking in driveway on left side. Breakfast ingredients are included; Eggs, Bacon, Cereal ,Toast, Coffee , Tea and etc. Our guests can rest assured that the bedding is washed and changed with each and every new guest, and for those who stay for a week or more , bedding is changed every five days or upon request.

21–28 Sep

$73 SGD per night

Guest favourite

Guest suite in Pickering

4.83 out of 5 average rating, 196 reviews

Spacious suite Sleeps 4 & free Parking

The suite is close to public transport, parks and Toronto Zoo. You’ll love this place because of its serene location, and the ambiance of the entire suite. Rouge national park and Altona forests are on few minutes drive. Living here is like almost living in Toronto, because the house is literally on the border of Toronto and Pickering. You will be on a quaint, serene Crescent that is great for couples, families, solo adventurers, and business travellers.

9–16 Mar

$94 SGD per night

Guest favourite

Apartment in Toronto

4.89 out of 5 average rating, 187 reviews

Cozy space in one of Toronto's best neighbourhoods

My place is a clean and quiet spot in the heart of Toronto's entertainment district. Location, location, location! Access the CN Tower, Ripley's Aquarium, The Royal Ontario Museum, The Art Gallery of Ontario and many more within a short walk or commute. The neighbourhood contains many restaurants and bars showcasing Toronto's cuisine and culture. My place is in the King West neighbourhood of downtown Toronto and is very convenient to access.

24–29 Jun

$199 SGD per night

Guest favourite

Guest house in Schomberg

4.93 out of 5 average rating, 344 reviews

Country Cabin for Long and Short Stays Queen bed

Our Country Cabin get-away is perfect for those looking to get out of the city and back to nature for a short or extended stay! Enjoy a little winter getaway and share our paradise in the countryside and be part of it all. You’ll love our location, full kitchen, access to camp fire pit, propane bbq, wifi internet, 40" Smart TV, three piece bathroom, laundry facilities and more.

15–22 May

$148 SGD per night

Guest favourite

Guest house in Oakville

4.93 out of 5 average rating, 175 reviews

Self Contained Luxury Studio Coach House

Immaculate studio apartment, completely separate from the main house with your own private entrance. Centrally located between all highways, in a quiet suburban neighbourhood, this studio apartment is beautifully furnished. Cozy in winter and cool in summer, everything you need is onsite. All of our past guests have said that the coach house is a special experience.

28 Nov – 5 Dec

$123 SGD per night

Guest favourite

Guest suite in Whitby

4.9 out of 5 average rating, 462 reviews

Canadiana Suite private entry, walk to Thermëa Spa

We welcome travellers "from away" to our Canadiana themed guest suite. Here you will see Canadian artwork and sculptures and hopefully learn something new about Canada! In addition, we have refinished much of the furniture in the space ourselves. Each piece has its own story. We are located 2 km away from the Thermëa Spa, which attracts many of our Airbnb guests.

20–27 Jun

$96 SGD per night

Guest favourite

Guest suite in Whitby

4.91 out of 5 average rating, 186 reviews

Ocean Pearl Luxury Suite

The basement suite features 900 sq ft space with 1 bedroom, 1 bathroom, open concept living & dining room and full kitchen, near lake. Wifi, cable, air condition etc. We provide the feeling of home away from home. Less than 5 mins to HWY 401, OC mall, various restaurants and 10 mins. drive to the lake.

1–8 May

$132 SGD per night