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Family-friendly holiday rentals in Pickering

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Pickering family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Flat in Mimico-Queensway
4.9 out of 5 average rating, 59 reviews

New condo w/ gorgeous lake views

ConorRating, 5 stars3 months ago
Really amazing view and building in a great location with easy access to GO trains and TTC. Building facilities are great! Check out is 10am
Guest favourite
Apartment in Entertainment District
4.97 out of 5 average rating, 322 reviews

Beautiful Condo + CN Tower View + Free Parking

JessicaRating, 5 stars3 weeks ago
Amazing location for downtown. Right across the street from the Rogers Centre. Amenities were amazing. Our second time staying in this building and we love it. Katherine was a great host. Highly recommend!
Guest favourite
Apartment in Unionville
4.91 out of 5 average rating, 114 reviews

Downtown Markham Unionville

AndreaRating, 5 stars3 months ago
We had a great stay at Thomas' place. He met us at check in, showed us the building, parking and any details we needed to know. He was very responsive, provided early check in, and coordinated parking spots for both our vehicles. The place was very clean and quiet. We would definitely stay again!
Superhost
Apartment in Entertainment District
4.67 out of 5 average rating, 377 reviews

Modern Condo in the heart Downtown Toronto!

NicoleRating, 5 stars1 week ago
Myself and 2 friends enjoyed our 3 night stay to the fullest! Location was amazing! Jonathan was extremely responsive. Bed was very comfortable. Pull out bed not so comfy but was to be expected. Lots of feminine products under the sink for guests to use in including salon style hairspray. Roof top pool was amazing and not too busy! Would highly recommend Jonathan's place!
Guest favourite
Apartment in Entertainment District
4.89 out of 5 average rating, 840 reviews

1 Bedroom Suite - DT Core (Office/Bidet/Balcony)

KeyannaRating, 5 stars4 days ago
Cal was an amazing host! Very responsive! The location of the AirBnb was perfect. We had tickets to see Kendrick Lamar at Rogers Centre and it was literally across the street from the Apartment Building. Great walking distance from EVERYWHERE. No complaints!
Superhost
Apartment in Entertainment District
4.87 out of 5 average rating, 326 reviews

Luxury heart of downtown by CN Tower/ MTCC/Union

JuliaRating, 5 stars3 months ago
Lovely place , felt right at home . Crystal was very helpful and responsive, given it was a very last minute booking. The street was very quiet and so was the building itself . Very cozy getaway in the heart of downtown Toronto for an incredibly good price . Thank you so much for making our short stay nothing short of AMAZING !
Superhost
Apartment in Entertainment District
4.87 out of 5 average rating, 106 reviews

Casa Di Mama | Beautiful 2BR Downtown-Free Parking

AnaïsRating, 5 stars4 days ago
We had a great weekend in Toronto. The location is perfect, 10 min walk from the Rodger center. The condo is great, easy check in!
Guest favourite
Apartment in Richmond Hill
4.77 out of 5 average rating, 53 reviews

Stunning Appt. in Richmond Hill- Parking included!

PartoRating, 5 stars1 week ago
Nice stay in this one-bedroom unit in Richmond Hill. The location is great in Richmond Hill, with easy access to stores just a few minutes’ walk away. It was a comfortable and convenient stay, and I would recommend it to others visiting the area.

Family- and pet-friendly home rentals

Top guest favourite
Apartment in Entertainment District
4.93 out of 5 average rating, 158 reviews

Beautiful suite in Downtown Toronto

ChloeRating, 5 stars3 weeks ago
10/10 perfect Air BnB, will most definitely book again next time we go down (especially for a concert), it was literally right across the street from the Roger’s Center which is where our Post Malone concert was. Oron is super descriptive on the process to check in/out and how to find parking, which as someone with OCD this was a blessing. Anything I needed or had questions about he literally answered within 5min! Also you literally get a view of the beautiful CN tower… jaw dropping! Bonus: that bed is hella comfy!!!
Superhost
Home in Yonge-Eglinton
4.67 out of 5 average rating, 139 reviews

Charming 3 Bedroom & 1.5 bath (Yonge&Eglinton)

AmandaRating, 5 stars4 days ago
We had a great stay at Julie’s place & would stay again. Beautiful vintage home tucked into a quiet neighbourhood. Accurately described and she was always responsive and friendly. Great if you don’t want to be in the city centre - easy to get downtown & come back to some peace and quiet. Beds were comfortable and the house was well equipped.
Superhost
Townhouse in Richmond Hill
4.75 out of 5 average rating, 4 reviews

Entire Home - 3 Bedroom 1.5 Bath Richmond Hill

AndrewRating, 5 stars1 month ago
The best Airbnb in richmond hill , bright , so much space , well equipped , great host . 10/10 recommended
Top guest favourite
Home in Ajax
4.97 out of 5 average rating, 29 reviews

3 bedroom bungalow in South Ajax

SamoriaRating, 5 stars2 months ago
my stay at Mrinals place was amazing! it looks exactly like the photos and was so clean. my family stayed here before moving out of the country and it was literally stocked with anything you’d need! anything we needed in the kitchen they had as well as laundry detergent and cleaning supplies. there was so many extra towels, sheets, and bedding. the check in was super easy and everything was exactly like the photos. The driveway has good space as well, me and my family were able to fit 2 SUV’s. Mrinal was an amazing host and very responsive and kind. I highly recommend!
Top guest favourite
Home in High Park North
4.9 out of 5 average rating, 134 reviews

Charming Century Home Close to Vibrant Shops

CourtneyRating, 5 stars2 months ago
The home was beautiful! We loved the decor and all of the characteristics of this historical house. The neighborhood was very safe, a 12 minute walk to the station of a 8 minute walk to the bus stop near aisle 3. The hosts were so friendly! They even had snacks and food waiting for us at the air bnb upon arrival. If you’re looking to get close to downtown without the hassle of driving this area is in a very good spot! We will definitely be returning, thanks again!
Top guest favourite
Cottage in Wilson
4.98 out of 5 average rating, 211 reviews

Beautiful Lakeside Cottage

LainaRating, 5 stars1 month ago
We loved our little stay here. It's great for a relaxing long weekend. Lots of great places to eat and drink within driving distance. The views were amazing! Gorgeous water and was fun to see Toronto in the distance. We definitely underestimated the presence of the bugs. Krista does warn that they come out in the summer, but they were everywhere by the water. Definitely hampered our time spent outside but if you can ignore the bugs you'll be fine. Krista was a wonderful communicator and the place was spotless.
Superhost
Guest suite in Riverdale
4.64 out of 5 average rating, 121 reviews

Garden Aptartment

JeannetteRating, 5 stars3 days ago
I very much enjoyed my stay. The place is filled with wonderful character and a sense of history. It is peaceful and restful. The garden and deck wrap around the place making it feel like it is out in the country, rather than in the heart of the city. The location is excellent with easy access for walking, driving and TTC. Many fabulous restaurants in the area too. It was the perfect place for my stay in Toronto.
Top guest favourite
Tiny home in Schomberg
4.99 out of 5 average rating, 212 reviews

SNAKE CABIN(rustic, 'off-the-grid')

JoelRating, 5 stars1 day ago
Peaceful, rustic, and completely off the grid. Just what we needed to slow down and breathe. We spent our time on the porch, watching the sunset paint the sky while listening to the soothing sounds of nature—geese calling in the distance, frogs croaking nearby, birds chirping in every direction. No city noise, no rush—just pure, simple quiet. The perfect place to disconnect and truly recharge.

Family-friendly home rentals with a pool

Guest favourite
Apartment in Discovery District
4.93 out of 5 average rating, 219 reviews

College Park :2Bd+2bth + Free parking

JeanneRating, 5 stars3 days ago
This condo was a great location, especially for guests visiting U of T or wanting to be in the heart of Toronto with easy access to adjoining neighborhoods. The apartment had great views of the area, was comfortable, clean with excellent amenities including a superb pool and exercise area on the 2nd floor of the building. Arjun is a most friendly and reliable host. I look forward to staying at his condo for an upcoming visit to Toronto.
Superhost
Apartment in Entertainment District
4.7 out of 5 average rating, 313 reviews

2 BDRM + 2 BATH + Free Parking - MTCC, CN, Jays!

JenniferRating, 5 stars3 weeks ago
I would 100% stay here again. Not only was the location convenient and beautiful, it was well kept and had everything we needed for our stay. The host was polite and communication was ongoing and prompt. Had a wonderful 2 night stay!
Superhost
Guest house in Bronte
4.6 out of 5 average rating, 10 reviews

*Cozy&Chic LL 2Bed 2Bath-Kitchenette l *Near LAKE*

JulieRating, 5 stars4 months ago
A truly intimate and comfortable internet spot perfect for a vacation
Guest favourite
Apartment in Entertainment District
4.97 out of 5 average rating, 244 reviews

Chic, High-Rise Apartment with CN Tower Views

NickRating, 5 stars3 weeks ago
Always a pleasure staying at Virginia's place!
Guest favourite
Apartment in Mississauga
4.85 out of 5 average rating, 59 reviews

Luxury 2 bedroom Condo With Pool Near Square One

maudeRating, 5 stars1 month ago
Very nice stay at Bose and Esther's. Thanks again!
Top guest favourite
Apartment in Entertainment District
4.93 out of 5 average rating, 92 reviews

Explore the City Centre from Condo with Views

KaitlynRating, 5 stars3 months ago
Robert's place is in a great location, right next to the CN tower, aquarium, and Rogers center. He provides a binder of local recommendations which is really helpful. I would definitely stay again!
Guest favourite
Home in West Queen West
4.91 out of 5 average rating, 303 reviews

King West Victorian Studio Gem

JessieRating, 5 stars1 month ago
What an absolute gem of a house! I felt right at home and so relaxed with the cherry tree blooming in the back yard. Kathleen added thoughtful details and helpful instructions. The house was within walking distance of amazing restaurants, cafes and shops.
Guest favourite
Apartment in Entertainment District
4.76 out of 5 average rating, 362 reviews

Airbnb Friendly- Sleeps 6 With FreeParking!

ThRating, 5 stars2 weeks ago
Great location, great host super nice would recommend to anyone

Quick stats about holiday rentals that are family-friendly in Pickering

  • Total rentals

    610 properties

  • Nightly prices starting at

    ₹868 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

    400 properties have a dedicated workspace

Destinations to explore