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Family-friendly vacation 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
Apartment in Toronto
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 favorite
Condo in Downtown Toronto
4.97 out of 5 average rating, 322 reviews

Beautiful Condo + CN Tower View + Free Parking

JessicaRating, 5 stars2 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 favorite
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, 375 reviews

Modern Condo in the heart Downtown Toronto!

NicoleRating, 5 stars2 days 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 favorite
Condo in Downtown Toronto
4.89 out of 5 average rating, 839 reviews

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

JohannaRating, 5 stars1 month ago
Cal was an excellent host - always responsive and available to answer any questions. The location is great - close to union station and easy to access public transit with lots of restaurants within walking distance. I’ll definitely stay here again.
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, 104 reviews

Casa Di Mama | Beautiful 2BR Downtown-Free Parking

TheoRating, 5 stars3 weeks ago
Amazing stay! Julian’s place had neat decorations and art that made it feel like home. Great soundsystem and TV. Nice balcony. Very clean. Very happy with our stay. Would recommend!
Top guest favorite
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!

Family- and pet-friendly home rentals

Top guest favorite
Home in Roncesvalles
5 out of 5 average rating, 47 reviews

High Park Lux: Sauna •King Bed •Family Friendly

RobinRating, 5 stars2 weeks ago
A beautiful rental. Very well equipped kitchen. Location was perfect for us. Host was very accommodating when our other rental fell through at the last minute.
Guest favorite
Home in Toronto
4.88 out of 5 average rating, 25 reviews

Cozy Leslieville Retreat near the Beach & Downtown

KristineRating, 5 stars1 month ago
It was easy to work with Tracy to make our arrangements. Her place was neat and clean and just as pictured. Many amenities like coffee and toiletries. The bed was very comfortable. Perfect for our needs and we will look to stay again.
Top guest favorite
Condo in Downtown Toronto
4.93 out of 5 average rating, 158 reviews

Beautiful suite in Downtown Toronto

ChloeRating, 5 stars2 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
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 favorite
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 favorite
Home in Toronto
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 favorite
Tiny home in Schomberg
4.99 out of 5 average rating, 210 reviews

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

JustinRating, 5 stars1 week ago
A great weekend getaway! We enjoyed the cozy, rustic atmosphere and the wonderful waterfront views from our cabin.
Guest favorite
Guest suite in Toronto
4.89 out of 5 average rating, 236 reviews

Midtown Luxury Yonge/Lawrence Close to Downtown

KathrynRating, 5 stars3 days ago
Great location. Easy to access transportation to all over Toronto. Lots of shops and restaurants locally. Lovely and friendly hosts who were very welcoming. Would highly recommend them and their apartment. Thoroughly enjoyed the stay. Has everything in the apartment you could wish for. Very clean.

Family-friendly home rentals with a pool

Guest favorite
Condo in Downtown Toronto
4.93 out of 5 average rating, 218 reviews

College Park :2Bd+2bth + Free parking

FrancesRating, 5 stars3 weeks ago
My family had a great stay at Arjun’s place during our visit to Toronto. The condo is very well located with easy walkable access to many stores and restaurants, while feeling safe and secure in a large city. The place was clean and the beds were comfortable. Great communication with the host.
Superhost
Condo in Downtown Toronto
4.7 out of 5 average rating, 313 reviews

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

JenniferRating, 5 stars1 week 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
Guesthouse in Bronte West
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 favorite
Condo in Downtown Toronto
4.97 out of 5 average rating, 242 reviews

Chic, High-Rise Apartment with CN Tower Views

MarisaRating, 5 stars1 month ago
The apartment was fabulous: lovely decor, quiet, and well-equipped. It is close to Union Station, so it was straightforward to travel to the airport. The apartment is very central and it was easy to walk to many places. I would definitely stay here again.
Townhouse in Niagara
4.75 out of 5 average rating, 166 reviews

King West Triplex Main FLR PVT APT 1 BDRM Parking

YanaRating, 5 stars3 weeks ago
Amazing location! Just a 10-minute walk to both King Street and Queen Street, and about 30 minutes to the CN Tower. The neighborhood is quiet and safe, with plenty of cafes, restaurants, and grocery stores nearby. The apartment itself was clean, cozy, and had everything we needed for a comfortable stay. The host was responsive and made check-in super easy. Since the building is older, we could occasionally hear footsteps from the unit above, but it didn’t really affect our overall experience.
Guest favorite
Condo in Mississauga
4.85 out of 5 average rating, 59 reviews

2 Bedroom Condo Near Square One with Massage Chair

maudeRating, 5 stars1 month ago
Very nice stay at Bose and Esther's. Thanks again!
Guest favorite
Home in Niagara
4.91 out of 5 average rating, 303 reviews

King West Victorian Studio Gem

JessieRating, 5 stars3 weeks 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 favorite
Condo in Downtown Toronto
4.76 out of 5 average rating, 359 reviews

Airbnb Friendly- Sleeps 6 With FreeParking!

MattRating, 5 stars2 weeks ago
We had a great time here! The location couldn't have been better, the views from the balcony were incredible and it is just minutes away from Ripley's Aquarium, the CN Tower, and the Roger's Centre. Tiyana was amazing, super responsive and helpful with anything we needed. Her place is comfortable and well thought out. We would stay again!

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

  • Total rentals

    610 properties

  • Nightly prices starting at

    G$2,098 GYD 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

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