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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

Guest favourite
Condo in Downtown Toronto
4.97 out of 5 average rating, 324 reviews

Beautiful Condo + CN Tower View + Free Parking

JosieRating, 5 stars4 days ago
A few days in Toronto watching some baseball. Perfect location, 5 minute walk, view of the CN Tower from the balcony. Very spacious for 4 adults and two grown teenagers. Everything we required in the accommodation. Very easy check in and parking. Excellent, prompt communication from Katherine. Will definitely stay here again.
Guest favourite
Condo 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
Condo in Downtown Toronto
4.67 out of 5 average rating, 379 reviews

Modern Condo in the heart Downtown Toronto!

FelipeRating, 5 stars4 days ago
I had a wonderful stay at Jonathan’s apartment in Toronto. From the moment I arrived, he was incredibly attentive and made sure everything was perfect. The apartment is in an excellent location — right in the heart of the city, with a stunning view facing the CN Tower. Waking up to that view every morning was truly unforgettable. I highly recommend this place to anyone traveling to Toronto. It’s the perfect spot for a comfortable and memorable stay!
Guest favourite
Condo in Downtown Toronto
4.89 out of 5 average rating, 842 reviews

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

Glen & TraceyRating, 5 stars6 days ago
Wow and thank you. To find such a perfect location was so fortunate. Cal sent a warm and welcoming message that just set the experience off to a great start. The condo was clean and modern and just felt so comfortable. There is something energizing about being right in the centre of thing’s, especially when you have such a wonderful space to come “home” to. Thanks to Cal for providing such a terrific space.
Superhost
Condo in Downtown Toronto
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
Condo in Downtown Toronto
4.87 out of 5 average rating, 107 reviews

Casa Di Mama | Beautiful 2BR Downtown-Free Parking

AnaïsRating, 5 stars1 week 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
Condo in Downtown Toronto
4.86 out of 5 average rating, 151 reviews

Modern 1 Bdrm Suite Downtown District - Lake View

ClintonRating, 5 stars1 month ago
Beautiful apartment within walking distance to everything you need. Host was accommodating and responded quickly to inquiries. Apartment was spotless. Was easy to find and check-in was easy. Would stay here again.
Guest favourite
Condo in Richmond Hill
4.77 out of 5 average rating, 53 reviews

Stunning Appt. in Richmond Hill- Parking included!

PartoRating, 5 stars2 weeks 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
Condo in Downtown Toronto
4.93 out of 5 average rating, 159 reviews

Beautiful suite in Downtown Toronto

LesleyRating, 5 stars1 week ago
Great space for folks attending public events in the downtown area.
Guest favourite
Townhouse in Richmond Hill
4.8 out of 5 average rating, 5 reviews

Entire Home - 3 Bedroom 1.5 Bath Richmond Hill

LeonardoRating, 5 stars1 week ago
My hosts were really nice and accommodating. The place is very nice, bright, clean and roomy. I would definitely book again with them.
Top Guest favourite
Home in Ajax
4.93 out of 5 average rating, 30 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 Toronto
4.9 out of 5 average rating, 136 reviews

Charming Century Home Close to Vibrant Shops

RigoRating, 5 stars2 weeks ago
Beyond the house itself, the hosts were truly outstanding. They were not only extremely courteous but also incredibly responsive to any questions we had, making us feel welcomed and well-cared for throughout our entire stay. Their genuine hospitality added significantly to the positive experience. If you're looking for a unique and memorable stay in Toronto, especially if you appreciate the charm of a well-preserved historic home combined with the warmth of exceptional hosts, look no further. We highly recommend this house.
Superhost
Guest suite in Riverdale
4.64 out of 5 average rating, 121 reviews

Garden Aptartment

JeannetteRating, 5 stars1 week 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 stars6 days 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.
Guest favourite
Guest suite in Toronto
4.89 out of 5 average rating, 240 reviews

Midtown Luxury Yonge/Lawrence Close to Downtown

RachelRating, 5 stars1 week ago
I stayed here with my family for two nights while visiting the city! The space was super nice and welcoming. Spotless, updated, and comfortable. About a 10min walk to transit but straight forward and the neighbourhood felt very safe.
Guest favourite
Condo in Downtown Toronto
4.92 out of 5 average rating, 240 reviews

Vibrant downtown place

LeandroRating, 5 stars3 weeks ago
The apartment is very nice and clean, located in a great area with plenty of shops and restaurants nearby. It's also equipped with everything you need for a short or long stay. Alexandru is very friendly and made sure everything was impeccable.

Family-friendly home rentals with a pool

Guest favourite
Condo in Downtown Toronto
4.93 out of 5 average rating, 220 reviews

College Park :2Bd+2bth + Free parking

JeanneRating, 5 stars1 week 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 Toronto
4.9 out of 5 average rating, 59 reviews

New condo w/ gorgeous lake views

ConorRating, 5 stars4 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
Superhost
Condo in Downtown Toronto
4.7 out of 5 average rating, 315 reviews

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

TaraRating, 5 stars4 days ago
Krishna is the ideal host. Frequent and regular communication from check in right up to check out and everything in between. Apartment was exactly as described and location is right in the heart of some of the big must see attractions Toronto has to offer. Also loved the facilities in the complex - pool gym etc. 100% worth, would stay again no questions asked .
Superhost
Guesthouse in Bronte West
4.6 out of 5 average rating, 10 reviews

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

JulieRating, 5 stars5 months ago
A truly intimate and comfortable internet spot perfect for a vacation
Top Guest favourite
Condo in Downtown Toronto
4.97 out of 5 average rating, 245 reviews

Chic, High-Rise Apartment with CN Tower Views

KevinRating, 5 stars2 weeks ago
We were in town to attend a couple Jays games and see DT Toronto. This location was great for both. Also easy access to Union station. Condo was just right for us.
Guest favourite
Condo 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
Condo in Downtown Toronto
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 Niagara
4.91 out of 5 average rating, 305 reviews

King West Victorian Studio Gem

TamerRating, 5 stars1 week ago
It was great to stay at Kathleen's. The place is very spacious and perfect for a one person or a couple. The location is very close to a lot of nice restaurants, coffee shops, bars, and a lot more. I like the neighborhood a lot. In the summer, you can also enjoy the park right across the street. The place was very clean, and Kathleen was a great communicator - on top of everything. It really felt like home. I stayed there for one month as I was in between places and honestly I wish I could have stayed more.

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

  • Total rentals

    610 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

    400 properties have a dedicated workspace

Destinations to explore