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
Condo in Toronto
4.81 out of 5 average rating, 302 reviewsSpacious Downtown (midtown) 2bed 2 bath free parki
5–12 May
Apartment in Toronto
4.91 out of 5 average rating, 257 reviewsHoney House in the Beach
2–9 Jan
Condo in Toronto
4.84 out of 5 average rating, 121 reviewsModern 1 Bdrm Suite Downtown District - Lake View
11–18 May
Condo in Toronto
4.89 out of 5 average rating, 273 reviewsCENTRAL DOWNTOWN LUXURY APT STEPS TO CN TOWER/LAKE
29 Sep – 6 Oct
Condo in Toronto, Canada
4.93 out of 5 average rating, 189 reviewsCollege Park :2Bd+2bth + Free parking
3–10 Nov
Condo in Toronto, Canada
4.97 out of 5 average rating, 291 reviewsBeautiful Condo + CN Tower View + Free Parking
22–29 Oct
Condo in Toronto
4.87 out of 5 average rating, 291 reviewsLuxury heart of downtown by CN Tower/ MTCC/Union
9–16 Mar
Condo in Mississauga
4.83 out of 5 average rating, 46 reviewsLuxurious Condo by Celebration Square & Square One
25 Feb – 4 Mar
Family- and pet-friendly home rentals
Cottage in Wilson, New York, US
4.98 out of 5 average rating, 186 reviewsBeautiful Lakeside Cottage
18–25 Mar
Tiny home in Schomberg, Canada
4.99 out of 5 average rating, 190 reviewsSNAKE CABIN(rustic, 'off-the-grid')
11–18 Nov
Guest suite in King City
4.98 out of 5 average rating, 177 reviewsSpacious guest apartment on beautiful greenspace
24 Feb – 3 Mar
Apartment in Milton
4.71 out of 5 average rating, 143 reviewsStudio Apt in Milton Dorset Park
15–22 Mar
Condo in Toronto
4.96 out of 5 average rating, 247 reviewsLively 1+1 Lakeview Condo near CN Tower + Free Prk
1–8 Nov
Home in Richmond Hill
4.87 out of 5 average rating, 127 reviewsLuxury 5 beds, 6 Baths custom home
30 Jan – 6 Feb
Home in Toronto
4.93 out of 5 average rating, 178 reviewsClassic 1 Bedroom Suite
16–23 Dec
Condo in Toronto
4.93 out of 5 average rating, 218 reviewsVibrant downtown place
30 Sep – 7 Oct
Family-friendly home rentals with a pool
Townhouse in Toronto
4.74 out of 5 average rating, 152 reviewsKing West Triplex Main FLR PVT APT 1 BDRM Parking
17–24 Oct
Guest suite in Mississauga
4.92 out of 5 average rating, 132 reviewsFull apt on Upper floor near HWY - S Mississauga
29 Oct – 5 Nov
Guest suite in Oakville
4.85 out of 5 average rating, 176 reviewsLL*1 BR Suite*Wi-fi*Parking*Near Lake
27 Sep – 4 Oct
Home in Toronto
4.91 out of 5 average rating, 264 reviewsKing West Victorian Studio Gem
16–23 Jul
Condo in Toronto
4.86 out of 5 average rating, 178 reviewsBest View in Downtown 5 Star Luxury 1+1 w/office
14–19 May
Condo in Toronto
4.97 out of 5 average rating, 217 reviewsChic, High-Rise Apartment with CN Tower Views
8–15 May
Apartment in Toronto
4.79 out of 5 average rating, 141 reviewsStunning Condo @ the Heart of Toronto (w/ Parking)
7–14 May
Farm stay in Kawartha Lakes
4.87 out of 5 average rating, 111 reviewsSky Haven Retreat & Equine Experience
23–30 Dec
Quick stats about holiday rentals that are family-friendly in Pickering
Total rentals
550 properties
Rentals with dedicated workspaces
370 properties have a dedicated workspace
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
140 properties allow pets
Total number of reviews
11K reviews
Nightly prices starting at
$17 NZD before taxes and fees
Destinations to explore
- Niagara Falls Holiday rentals
- Brampton Holiday rentals
- Niagara-on-the-Lake Holiday rentals
- Muskoka Lakes Holiday rentals
- Niagara Falls Holiday rentals
- Kitchener Holiday rentals
- Waterloo Holiday rentals
- Buffalo Holiday rentals
- Deep Creek Lake Holiday rentals
- London Holiday rentals
- Mississauga Holiday rentals
- Montreal Holiday rentals
- Family-friendly rentals Toronto
- Family-friendly rentals Canada
- Family-friendly rentals Ontario
- Family-friendly rentals Downtown Toronto
- Family-friendly rentals Mississauga
- Smoking-friendly rentals Pickering
- Rentals with an EV charger Pickering
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- Rentals with beach access Pickering
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- Monthly Rentals Pickering
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- Kid-friendly rentals Pickering
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- Pet-friendly rentals Pickering
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- Rentals with a hot tub Pickering
- Family-friendly rentals Regional Municipality of Durham
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