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Family-friendly vacation 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 favorite
A cozy living area features a comfortable sofa paired with two black chairs, set against built-in bookshelves filled with books and art. A decorative chandelier hangs above, while a fireplace serves as a focal point, surrounded by a tasteful arrangement of art on the walls.
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 favorite
The bedroom features a spacious bed dressed in a mix of striped and patterned linens, complemented by matching nightstands on either side. A floral artwork adorns the wall above, and modern bedside lamps provide soft lighting, enhancing the calm ambience.
Condo in Downtown Toronto
4.97 out of 5 average rating, 324 reviews

Beautiful Condo + CN Tower View + Free Parking

JosieRating, 5 stars5 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 favorite
The modern condo building features a multi-story design with balconies and large windows. Soft greenery lines the ground level, enhancing the urban landscape. A clear blue sky provides a bright backdrop, while the street is lined with manicured trees, creating an inviting atmosphere for residents and visitors.
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 favorite
A modern workspace is presented with a sleek black desk and stylish chair. Floating orange shelves display decorative items, while a globe adds a touch of elegance. The kitchen area is visible in the background, featuring dark cabinetry and contemporary appliances.
Condo in Downtown Toronto
4.89 out of 5 average rating, 842 reviews

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

Glen & TraceyRating, 5 stars1 week 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
A modern kitchen features a central island with a wooden countertop, surrounded by white bar stools. Stainless steel appliances, including a refrigerator and oven, are visible. Natural light floods the space through large windows, highlighting the sleek cabinetry and minimalist design.
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
A colorful abstract artwork hangs above a wooden bed, featuring flowing lines in shades of blue, pink, and beige. Two exposed bulb lights are mounted on the walls beside the bed, enhancing the space's artistic expression.
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 favorite
A modern living space features a large sectional sofa adorned with striped cushions. A vibrant rug covers the floor, and a bright piece of art hangs above a sleek red media console. Floor-to-ceiling windows offer natural light and views of the city beyond.
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 favorite
A serene bedroom features a spacious bed adorned with decorative pillows. Natural light flows through large windows, framed by soft curtains. A round mirror enhances the room's aesthetic, while a piece of artwork adds a touch of color to the neutral walls.
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 favorite
A small balcony features a bistro table and two wooden chairs, overlooking a serene view of Lake Ontario. A potted plant sits in the center of the table, with the shimmering water and distant shore visible in the background.
Condo in Downtown Toronto
4.97 out of 5 average rating, 299 reviews

Lively 1+1 Lakeview Condo near CN Tower + Free Prk

MalcolmRating, 5 stars5 days ago
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 !
Top guest favorite
A cozy living area features a light-filled space with a large, neutral-colored sofa adorned with patterned cushions. Two accent chairs with geometric patterns complement a white coffee table, while a dining table is visible in the background near a modern kitchen area.
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.
Superhost
Home in Yonge-Eglinton
4.67 out of 5 average rating, 140 reviews

Charming 3 Bedroom & 1.5 bath (Yonge&Eglinton)

AmandaRating, 5 stars1 week 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 favorite
An open-concept living space features a leather couch and an armchair, with a coffee table positioned nearby. A light wood kitchen island provides seating with two yellow stools. Natural light enters through two windows, illuminating the modern decor and warm wood flooring.
Apartment in Milton
4.72 out of 5 average rating, 162 reviews

Studio Apt in Milton Dorset Park

CharleneRating, 5 stars1 month 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
A spacious wooden deck is featured, with a large umbrella providing shade over a rectangular dining table and several chairs. A barbecue grill is positioned nearby, and lush greenery surrounds the area, enhancing the outdoor setting.
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.
Guest favorite
A modern living area is presented with soft white seating arranged around a central coffee table. Shelves hold decorative items, while a large window allows natural light to fill the space, offering views of greenery outside. A mounted television complements the inviting atmosphere.
Home in Richmond Hill
4.89 out of 5 average rating, 157 reviews

Luxury 5 beds, 6 Baths custom home

StephenRating, 5 stars3 days ago
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!
Top guest favorite
The interior of the cabin features warm wooden walls and a cozy woodstove. Two blue lounge chairs are positioned near a rustic table. Natural light floods through a large window, illuminating the space, while a striped rug adds comfort underfoot.
Tiny home in Schomberg
4.99 out of 5 average rating, 212 reviews

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

JoelRating, 5 stars1 week 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 favorite
A modern kitchen area is equipped with stainless steel appliances, including a large refrigerator and oven. A glass-topped breakfast bar is accompanied by two neutral-colored stools. Decorative wall art and a small plant add visual interest, while natural light enhances the bright ambiance.
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

Superhost
A light-filled living space features a neutral sofa adorned with patterned cushions. A wooden coffee table is centered on a textured rug. In the background, an open-concept kitchen is visible, showcasing modern cabinetry and fixtures, with large windows framing views of the surrounding area.
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, 316 reviews

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

TaraRating, 5 stars5 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
The rooftop pool area features a swimming pool surrounded by lounge chairs and shaded cabanas. Barbecue grills are positioned along the edge, with a hot tub nearby. The expansive urban skyline is visible in the background under clear blue skies.
Condo in Downtown Toronto
4.67 out of 5 average rating, 379 reviews

Modern Condo in the heart Downtown Toronto!

FelipeRating, 5 stars5 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 favorite
A clear view of a private heated pool is presented, surrounded by a green patio. A striped chair and glass table are visible in the foreground, with a blue waterslide and shaded seating area observed in the background.
Bungalow in Milton
4.91 out of 5 average rating, 35 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
Top guest favorite
A spacious living area is highlighted by a plush couch adorned with throw pillows and a soft blanket. A modern coffee table has a wooden tray atop it. Art is displayed on the walls, and a leafy plant is positioned beside a light source.
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 favorite
An indoor swimming pool is set within a sleek environment, featuring a clear water surface reflecting the light from overhead fixtures. The pool area includes decorative mosaic accents on the edges and two stainless steel ladders for entry.
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 favorite
A corner of the living area features a plant in a black pot beside a bookshelf filled with various books. A wall with dark stone adds texture, while a sleek television is mounted above a modern fireplace. A door leads to an outdoor space.
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 favorite
An open-concept living area features hardwood floors and exposed brick walls. A spacious bed is complemented by elegant chandeliers, while a white futon is situated nearby. Decorative artwork adorns the walls, and a light-filled kitchen area is visible in the background.
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 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

Destinations to explore

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