
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

Modern Downtown Condo Free Parking/ Walk to Lake

The Penty: Luxurious Penthouse with Pool, Hot Tub

Heated Pool-tub Open 365 Days

The Fort York Flat

Luxury Stay w/phenomenal view!

Family Friendly | HOT TUB | Near Toronto & UOIT
Family- and pet-friendly home rentals

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

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

Mercedes Palace

Spacious Guest Room close to 401

Cozy private backyard garden studio

Mackenzie Cottage

Orchard cottage, experience the farm in the city

NEWLY RENOVATED, 3 Bdrm Modern Oasis W/ Parking!!!
Family-friendly home rentals with a pool

The Hilton BnB Adult Luxury Suite

Treehouse on private, isolated forest (300 acres)

Beautiful Penthouse with Breathtaking View

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Beautiful Condo Across CN Tower and MTCC

Ravine Paradise ! heated pool and hot tub!

Hidden gem in Humber bay shores Toronto w/ parking

King West Triplex Main FLR PVT APT 1 BDRM Parking
Quick stats about holiday rentals that are family-friendly in Pickering
Total rentals
600 properties
Nightly prices starting at
$17 NZD 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
- Niagara Falls Holiday rentals
- Capital District, New York Holiday rentals
- Pittsburgh Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Northeast Ohio Holiday rentals
- Rentals with breakfast Pickering
- Rentals with lake access Pickering
- Waterfront rentals Pickering
- Townhouse rentals Pickering
- Condo rentals Pickering
- Smoking-friendly rentals Pickering
- Apartment rentals Pickering
- Rentals with a fireplace Pickering
- Cottage rentals Pickering
- Rentals with a hot tub Pickering
- Pet-friendly rentals Pickering
- Rentals with a patio Pickering
- Rentals with pools Pickering
- Guesthouse rentals Pickering
- Fitness-friendly rentals Pickering
- Rentals with an EV charger Pickering
- House rentals Pickering
- Rentals with outdoor seating Pickering
- Rentals with a washing machine and dryer Pickering
- Rentals with a fire pit Pickering
- Private suite rentals Pickering
- Rentals with beach access Pickering
- Beachfront rentals Pickering
- Family-friendly rentals Durham Region
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Budweiser Stage
- Exhibition Place
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Toronto Zoo
- Harbourfront Centre
- Financial District
- CF Toronto Eaton Centre
- BMO Field
- Trinity Bellwoods Park
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Rouge National Urban Park
- Royal Ontario Museum
- Toronto City Hall
- Christie Pits Park
- Jackson-Triggs Niagara Estate