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Family-friendly holiday rentals in Oakwood Village, York

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Oakwood Village, York family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Midtown
4.96 out of 5 average rating, 48 reviews

Great Davenport Hillcrest House

LindsayRating, 5 stars1 month ago
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!
Guest favourite
Condo in Downtown Toronto
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
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!
Guest favourite
Condo in Downtown Toronto
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
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, 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
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 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
Home in Roncesvalles
5 out of 5 average rating, 48 reviews

High Park Lux: Sauna •King Bed •Family Friendly

LindaRating, 5 stars2 weeks ago
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
Top Guest favourite
Condo in Downtown Toronto
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 stars5 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.
Guest favourite
Apartment in Milton
4.72 out of 5 average rating, 162 reviews

Studio Apt in Milton Dorset Park

CharleneRating, 5 stars3 weeks ago
Steve and Melissa's place was perfect. They were fantastic hosts. The place had everything you needed. Would definitely stay again and recommend it.
Superhost
Townhouse in Richmond Hill
4.8 out of 5 average rating, 5 reviews

Entire Home - 3 Bedroom 1.5 Bath Richmond Hill

LeonardoRating, 5 stars2 days ago
My hosts were really nice and accommodating. The place is very nice, bright, clean and roomy. I would definitely book again with them.
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.
Guest favourite
Home in Richmond Hill
4.89 out of 5 average rating, 156 reviews

Luxury 5 beds, 6 Baths custom home

PaulineRating, 5 stars1 month ago
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!
Top Guest favourite
Tiny home in Schomberg
4.99 out of 5 average rating, 212 reviews

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

JoelRating, 5 stars2 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.

Family-friendly home rentals with a pool

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
Superhost
Condo in Downtown Toronto
4.7 out of 5 average rating, 313 reviews

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

MaureenRating, 5 stars2 weeks ago
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.
Superhost
Condo in Downtown Toronto
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
Bungalow in Milton
4.91 out of 5 average rating, 34 reviews

Milton Home- a Family Oasis

SherryRating, 5 stars9 months ago
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
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, 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.

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

Destinations to explore

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  2. Canada
  3. Ontario
  4. Toronto
  5. Oakwood Village
  6. Family-friendly rentals