
Family-friendly holiday rentals in Oakwood Village, York
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Top-rated family-friendly rentals in Oakwood Village, York
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Oakwood Village, York family-friendly rentals
Family-friendly home rentals with a hot tub

Great Davenport Hillcrest House
I’m almost afraid to leave an accurate review because this place is such a hidden gem I don’t want to compete when we try to stay here again. This home is so beautiful, well stocked, cozy, incredible neighbourhood, and I could go on and on. Ottilie was a thoughtful host with excellent communication and she opened her home up to my family. I will never try to stay anywhere else in Toronto! Thank you, Ottilie!

Beautiful Condo + CN Tower View + Free Parking
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!

Downtown Markham Unionville
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!

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

Luxury heart of downtown by CN Tower/ MTCC/Union
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 !

Casa Di Mama | Beautiful 2BR Downtown-Free Parking
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!

Modern 1 Bdrm Suite Downtown District - Lake View
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.

Stunning Appt. in Richmond Hill- Parking included!
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

High Park Lux: Sauna •King Bed •Family Friendly
Beautiful home very spacious Appreciated the flowers and card Great neighborhood easy to get around Esther and her husband were lovely and easy to communicate with Highly recommend

Beautiful suite in Downtown Toronto
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!!!

Charming 3 Bedroom & 1.5 bath (Yonge&Eglinton)
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.

Studio Apt in Milton Dorset Park
Steve and Melissa's place was perfect. They were fantastic hosts. The place had everything you needed. Would definitely stay again and recommend it.

Entire Home - 3 Bedroom 1.5 Bath Richmond Hill
My hosts were really nice and accommodating. The place is very nice, bright, clean and roomy. I would definitely book again with them.

Garden Aptartment
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.

Luxury 5 beds, 6 Baths custom home
An amazing home meeting the needs of our multi-generational family spending a week together in the GTA to cheer on our daughter participating in a National sporting event. Listing is reflective of the gorgeous, clean home. We would definitely look to return should another opportunity present!

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

New condo w/ gorgeous lake views
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

2 BDRM + 2 BATH + Free Parking - MTCC, CN, Jays!
From booking through checkout, Krishna was friendly and responsive. The purpose for the visit was to see the Philadelphia Phillies play the Toronto Blue Jays and this urban apartment was perfect! Having a parking spot included for our stay was a bonus. Pedestrian-friendly access to entertainment and restaurants was also a bonus in the city.

Modern Condo in the heart Downtown Toronto!
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!

Milton Home- a Family Oasis
This place was absolutely amazing. It had everything you could possibly need and want. We enjoyed everything- the qames, pool table and darts. We wish we hadn't planned so much so we could make better use of everything. Thomas was very responsive and went out of his way to help when there was something we couldn't figure out. We loved being there and will definitely look to return if we return to Toronto

Chic, High-Rise Apartment with CN Tower Views
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.

Luxury 2 bedroom Condo With Pool Near Square One
Very nice stay at Bose and Esther's. Thanks again!

Explore the City Centre from Condo with Views
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!

King West Victorian Studio Gem
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.
Quick stats about holiday rentals that are family-friendly in Oakwood Village, York
Total rentals
100 properties
Nightly prices starting at
$31 AUD before taxes and fees
Total number of reviews
2.4K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wi-Fi availability
90 properties include access to Wi-Fi
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- Clifton Hill
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Exhibition Place
- The Danforth Music Hall
- Harbourfront Centre
- CF Toronto Eaton Centre
- Massey Hall
- BMO Field
- Trinity Bellwoods Park
- Niagara Falls State Park
- Casa Loma
- Legends on the Niagara Golf Course
- Royal Woodbine Golf Club
- Jackson-Triggs Niagara Estate
- Dufferin Grove Park