
Family-friendly vacation rentals in Oakwood Village, York
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Top-rated family-friendly rentals in Oakwood Village, York
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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
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.

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)
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.

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

Lively 1+1 Lakeview Condo near CN Tower + Free Prk
Mehrdads condo was perfect for us. The view from the balcony, the proximity for bars and restaurants the CN tower and aquarium. Ten minute walk to union street train station. The condo was comfortable and well furnished and we felt very settled as soon as we moved in. Communication and entry on arrival was hassle free. Would totally recommend !

Beautiful suite in Downtown Toronto
Great space for folks attending public events in the downtown area.

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.

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
Perfect spot for a group trip. Quiet neighborhood, close to the TTC for easy access to downtown. Jay was awesome at handling our request to drop off our luggage prior to our scheduled check-in time. Would definitely stay again!

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.

Vibrant downtown place
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

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!
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 .

Modern Condo in the heart Downtown Toronto!
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!

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
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 vacation rentals that are family-friendly in Oakwood Village, York
Total rentals
100 properties
Nightly prices starting at
G$4,182 GYD 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
Wifi availability
90 properties include access to wifi
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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