
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

“Lakeside Dreams”: All season HotTub w/lake views

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! 👍

Luxury Villa! Swim Spa! 6 Bedroom 3 Family Rooms
Family- and pet-friendly home rentals

Retreat 82

Modern Nest - Pickering 5 beds, 2.5 baths, 3 park

Spacious Guest Room close to 401

Cozy private backyard garden studio

Cosy 3-Bedroom Home in Quiet Cul-de-Sac.

Mackenzie Cottage

Aqua Dream: Modern Private Apt 2B/1B, 5G, Kitchen

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

Beautiful Cottage in Ajax

The Hilton BnB Adult Luxury Suite

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

Toronto Vacation Pool/Park/Zoo/Casino

Modern Custom Home w/ Pool, Games & Parking
Quick stats about holiday rentals that are family-friendly in Pickering
Total rentals
600 properties
Nightly prices starting at
£7 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
- Apartment rentals Pickering
- Rentals with a patio Pickering
- Cottage rentals Pickering
- Rentals with a hot tub Pickering
- Rentals with a firepit Pickering
- Rentals with breakfast Pickering
- Flat rentals Pickering
- Rentals with a fireplace Pickering
- House rentals Pickering
- Private suite rentals Pickering
- Rentals with a washing machine and dryer Pickering
- Rentals with an EV charger Pickering
- Guest house rentals Pickering
- Pet-friendly rentals Pickering
- Rentals with lake access Pickering
- Rentals with outdoor seating Pickering
- Rentals with beach access Pickering
- Waterfront rentals Pickering
- Fitness-friendly rentals Pickering
- Rentals with pools Pickering
- Smoking-friendly rentals Pickering
- Beachfront rentals Pickering
- Townhouse rentals 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
- Financial District
- Exhibition Place
- The Danforth Music Hall
- Toronto Zoo
- Harbourfront Centre
- CF Toronto Eaton Centre
- Trinity Bellwoods Park
- Massey Hall
- BMO Field
- Casa Loma
- Dufferin Grove Park
- Royal Ontario Museum
- Jackson-Triggs Niagara Estate
- Rouge National Urban Park
- Cedar Park Resort
- Royal Woodbine Golf Club