Family-friendly vacation rentals in Oakwood Village

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Oakwood Village

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
The entrance hall features a gas fireplace with a large mantle, hardwood floors, and historic quarter-sawn oak paneling. A round table is centrally placed, complemented by a stylish chandelier overhead. Stairs lead to the upper level, while a chair and decorative elements enhance the inviting ambiance.
Home in Wychwood
5 out of 5 average rating, 126 reviews

Grand & Luxurious Historic Home | Central Toronto

Welcome to Baraset House. CONDE NAST: Toronto's best Airbnbs TRIP 101: #1 Luxury Toronto Airbnb BELLAMY LOFT: #1 Toronto Airbnb SLICE: A Toronto Airbnb fit for Royalty In the heart of Toronto, this meticulously restored Historical Home provides the perfect setting for grand family gatherings, wedding groups & corporate retreats. Relax in 3300 sq' of stately principle rooms, Chef's Kitchen & six hotel-inspired bedrooms. Gorgeous outdoor spaces & private parking. An unforgettable destination.

Guest favorite
A Mid-Century Modern themed bedroom features a queen bed with crisp white linens and decorative pillows in warm tones. Floral artwork adorns the walls above the bed. A nightstand holds a lamp and a small vase with flowers, adding a touch of color to the space.
Guest suite in Earlscourt
4.95 out of 5 average rating, 146 reviews

Midtown Mid-Mod

Bright, clean and spacious lower-level guest suite located in Mid-Town’s trendy St. Clair West neighbourhood. Our suite is best suited for adults who want to explore the city and take in the sites, business travelers who want privacy and a comfortable workspace or families visiting relatives. We offer the amenities you’d need and some you wouldn’t expect. Mid-mod inspired bedroom with Queen bed makes for a great place to rest your head after a visiting one of our many trendy local restaurants.

Guest favorite
A well-lit living area features a large window allowing natural light to flow in. Seating is provided by a dark sofa and a dining table with two white chairs. Decorative curtains add a touch of warmth, complemented by a mounted television on the wall.
Home in Oakwood Village
4.82 out of 5 average rating, 100 reviews

CHARMING 3 BEDROOM HOME IN THE CITY W FREE PARKING

Welcome to our clean, cozy 3 bedroom country style bungalow situated in the middle of the city. Close to anywhere you wish to go, but just far enough from all the hustle and bustle. Designed to host visiting families or multiple couples. 3 bedrooms (1 King and 2 Queen size beds). Free parking. 2 televisions, Wifi, Netflix all included for your entertainment. Kitchen, 2 washrooms, enclosed private patio and a backyard. Laundry washer available on site. High speed internet and working space

Guest favorite
A neatly made bed is presented, featuring a neutral-toned quilt and three pillows arranged in shades of gray. The bed frame is metal with a simple design, contributing to the room's aesthetic. Light is visible from a nearby window, illuminating the laminate flooring.
Apartment in Junction Area
4.72 out of 5 average rating, 145 reviews

Clean Private Basement Apt.

One bedroom apartment located in the heart of vibrant Junction/High Park area, near trendy restaurants and bars. Suitable for a couple or single person. Strictly only 2 guests. First day breakfast items provided, full kitchen, shared laundry. Separate walk down entrance with keypad entry. Bike rental/hiking trail steps away. Walk or short bus ride to the subway. Unfortunately only street parking available, also the train passes at any time of day of night. Outside smoking allowed.

Guest favorite
A living room features a gray sofa accented with decorative cushions, paired with two mid-century modern chairs. A large window allows natural light to illuminate the space. A mounted flat-screen TV and an electric fireplace are visible, enhancing the cozy atmosphere.
Guest suite in Bedford Park
4.89 out of 5 average rating, 253 reviews

Midtown Luxury Yonge/Lawrence Close to Downtown

Located in the upscale Yonge & Lawrence Village in Midtown Toronto. Steps to Yonge St. bus, 5 min walk to the Subway. The heart of the city is within minutes. There are several restaurants, coffee shops, pubs & bars within a 1-5 min walk. Public tennis courts, parks. The suite is completely self-contained. We live on the main floor above, we are usually available help. There is a 75"Samsung TV, 2 Extra large washers and 2 Extra large Gas dryers for all of your laundry needs.

Superhost
An inviting sleeping area is highlighted by a spacious bed with neatly arranged pillows. A stylish lamp provides warm lighting, while a full-length mirror is positioned beside the wall. A cozy throw blanket is draped over the bed, and a magazine rests on the bedside table.
Home in York
4.82 out of 5 average rating, 199 reviews

Cozy and Chic Gem in the City

Entire lower level unit. Very clean and cozy unit in a great friendly neighborhood. The unit is bright and airy. The bathroom and kitchen is yours to use. Separate entrance through the side door of the house. Closet space to store your luggage and clothes. Coffee machine with pods and kettle are at your disposable. Extra blankets and pillows are available upon request. While the unit offers a private setup, the main house may also be accessed or shared as per your needs.

Guest favorite
A living area features a sleek black futon and a modern television on a low-profile media console. A glass coffee table is placed in front of the seating, while a small dining table with black chairs is positioned against the blue wall. Decorative wall art adds subtle interest.
Home in Mississauga
4.89 out of 5 average rating, 117 reviews

Mississauga Bsmt Apartment off of Bloor St!

Basement apartment with seperate entrance and complete privacy, located in Mississauga bordering Toronto. A minute walk to Bloor Street which goes directly to downtown Toronto. For people taking public transportation there is a great connection on Bloor St to the Kipling Subway station and to Square One Mall. If looking to visit downtown Toronto by public transportation, it will take about 50 minutes. Parks and lots of attractions near by. New Baby and Toddler in house.

Guest favorite
An open-concept living area showcases a comfortable sofa and modern furnishings on a patterned area rug. Natural light streams through large windows, illuminating the space. A wooden floating staircase leads to the upper floor, while a stylish dining space and kitchen are visible in the background.
Home in Oakwood Village
4.9 out of 5 average rating, 209 reviews

Family Home Near St Clair W and Public Transport

Steps away from vibrant St Clair West with great dining, access to public transport and shopping. A real family home with space and amenities for everyone. Free parking for 2 cars. Open-concept living & dining, well-equipped kitchen. Sunny back deck. 3 comfortable bedrooms. Spa bathroom with heated floor. Perfect for families who are in town for reunions, weddings, birthday parties and visiting. Quiet hours after 10pm - not suitable for groups in town ‘to party’.

Guest favorite
A modern living area features a comfortable gray couch positioned near a low white coffee table. A decorative shelving unit displays various sculptures and vases, while light streams in through two small windows above. A neat sleeping area is visible in the background, separated by the shelving.
Guest suite in Eglinton West
4.85 out of 5 average rating, 211 reviews

BRIGHT MODERN STUDIO WITH TERRACE

Bright, airy, modern and new unit with private entrance in midtown Toronto. One minute to transportation, supermarket, bakeries, pharmacies, and all other conveniences. Thirty minutes to downtown and 25 minutes to Yonge and Eglinton by public transport. The space is recently renovated with a small terrace for outdoor space. The unit is self contained with a private kitchen, bathroom and laundry. Sorry, there is no smoking on the property.

Guest favorite
A bright entryway showcases a spacious seating area with a light-colored couch. Decorative plants are placed strategically, beside a standing mirror and a flat-screen TV mounted on the wall. Soft lighting illuminates the modern design, leading to a glimpse of the bedroom area in the background.
Apartment in Stockyards District
4.98 out of 5 average rating, 349 reviews

Modern Retreat in Trendy JUNCTION Neighbourhood

A newly renovated, hotel-inspired lower level suite nestled in Toronto’s buzzing Junction neighbourhood. This vibrant, bright basement, brought to life by its charming and colourful accents, is a quick stroll from a variety of restaurants, breweries, parks, and shops. With public transportation steps away, it's the perfect base for exploring the neighbourhood and the city beyond. And, of course, for unwinding afterward.

Guest favorite
A cozy bedroom is presented, featuring a queen size bed with a light-colored blanket draped across. An art piece adorns the wall above the bed. A small side table stands next to the bed, and a fireplace with a decorative brick surround is visible.
Home in North York
4.91 out of 5 average rating, 102 reviews

Private Midtown Suite 5 min walk to Subway Station

This cozy basement guest suite is located in a safe, family-oriented neighborhood and a 5 minute walk to Glencairn Subway Station connecting you to the hustle and bustle of downtown Toronto in 15-20 min. For drivers, it’s a quick connection to highway 401 with free parking in the driveway. You will appreciate the comfortable queen size bed after a day of exploring. I live upstairs if you should need anything.

Top guest favorite
A spacious room is displayed with a comfortable queen bed positioned against the wall, accompanied by two bedside lamps. A soft sofa and a green accent chair create a cozy sitting area, while framed artworks and a large window provide a bright, airy ambiance.
Guest suite in York
5 out of 5 average rating, 141 reviews

Private, Spacious,Separate Entrance, Bath, Parking

My Airbnb is located in a green and safe valley between one of the biggest Toronto parks and Bloor West Village/Junction just steps away from trendy cafes and shops. Our Airbnb has a separate entrance. Stunning biking trails are 2 min walk at Etienne Brule gate and lead to Lake Ontario passing Old Mill or north, James' Gardens. You can see salmon traveling upstream of the Humber River in the Fall.

Popular amenities for Oakwood Village family-friendly rentals

When is the best time to visit Oakwood Village?

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Quick stats about vacation rentals that are family-friendly in Oakwood Village

  • Total vacation rentals

    Explore 90 vacation rentals in Oakwood Village

  • Nightly prices starting at

    Oakwood Village vacation rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 2,550 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Oakwood Village vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oakwood Village rentals

  • 4.8 Average rating

    Oakwood Village stays are highly rated by guests—averaging 4.8 out of 5!

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