
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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pickering family-friendly rentals
Family-friendly home rentals with a hot tub

Vacation Retreat•4BR 4BA•Hot Tub•BBQ•Near Toronto

Downtown Markham Unionville

The Penty: Luxurious Penthouse with Pool, Hot Tub

Heated Pool-tub Open 365 Days

Family Friendly | Cozy | HOT TUB | Near UOIT

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

Artsy and Comfy Home with a View

Papa Bear Cabin @ Newcastle Cabin Oasis B&B
Family- and pet-friendly home rentals

GTA Suite | Lakeridge Ski Resort | Pickering GO

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Spacious 2BD 3-6 ppl homestyle BSMT mansion with window basement 130sqm

Spacious Guest Room close to 401

*BRAND NEW*Perfect 4 BR Townhouse Markham *Sleep 8

Mackenzie Cottage

2 Plush Queen Beds + 1 Sofa-bed - Sleeps 6 - Apt

Orchard cottage, experience the farm in the city
Family-friendly home rentals with a pool

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

The Hilton BnB Adult Luxury Suite

Home away from home with a hot tub and pool

Treehouse on private, isolated forest (300 acres)

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Four season glamping dome under the stars

Hidden gem in Humber bay shores Toronto w/ parking

Guest suite 10 min to subwy w kitchen FREE parking
Quick stats about holiday rentals that are family-friendly in Pickering
Total rentals
600 properties
Nightly prices starting at
$15 AUD before taxes and fees
Total number of reviews
15K reviews
Pet-friendly rentals
160 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
390 properties have a dedicated workspace
Destinations to explore
- Montreal Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Mount Pocono Holiday rentals
- Capital District, New York Holiday rentals
- Niagara Falls Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Pittsburgh Holiday rentals
- Island of Montreal Holiday rentals
- Condo rentals Pickering
- Townhouse rentals Pickering
- Guesthouse rentals Pickering
- Fitness-friendly rentals Pickering
- Rentals with a hot tub Pickering
- Rentals with pools Pickering
- Rentals with an EV charger Pickering
- Rentals with breakfast Pickering
- Waterfront rentals Pickering
- Rentals with outdoor seating Pickering
- Rentals with a patio Pickering
- Pet-friendly rentals Pickering
- Rentals with lake access Pickering
- Private suite rentals Pickering
- Rentals with a washing machine and dryer Pickering
- Rentals with beach access Pickering
- House rentals Pickering
- Smoking-friendly rentals Pickering
- Cottage rentals Pickering
- Apartment rentals Pickering
- Rentals with a fireplace Pickering
- Beachfront rentals Pickering
- Rentals with a fire pit Pickering
- Family-friendly rentals Durham Region
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Financial District
- Exhibition Place
- Toronto Zoo
- Harbourfront Centre
- CF Toronto Eaton Centre
- BMO Field
- Trinity Bellwoods Park
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Rouge National Urban Park
- Royal Ontario Museum
- Jackson-Triggs Niagara Estate
- Toronto City Hall
- Royal Woodbine Golf Club