Family-friendly vacation rentals in Oakwood Village, York

Find and book unique family-friendly homes on Airbnb

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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Guest favorite

An open concept living space features a comfortable blue sofa and a natural wood coffee table on a patterned rug. A large smart TV is positioned on a wooden TV stand. The dining area, with a table set for six, is visible in the background.

Guest suite in Vaughan

4.93 out of 5 average rating, 643 reviews

Luxury Modern Two Bedrooms Basement Apartment

No 3rd party booking! No parties! No visitors! Tons of upgrades and high end modern features! High ceiling above grade basement unit. Open concept living space include fireplace, smart TV, full kitchen, laundry and large wardrobe 1 parking Enjoy scenic trails in Woodbridge 10min to Vaughan Mills outlets & Canada's wonderland 15min to Pearson airport 24hr Exterior Surveillance. One camera over looking driveway. One camera above the front door and one outside the storm door to the Airbnb unit

Top guest favorite

A cozy living room features a vintage sofa adorned with decorative pillows, complemented by a plush armchair. A large window is framed by soft drapes, allowing natural light to brighten the space. An elegant coffee table holds a decorative tray, enhancing the inviting ambiance.

Home in Toronto

4.9 out of 5 average rating, 134 reviews

Charming Century Home Close to Vibrant Shops

A great for-families home. Stay close to city centre yet unwind in our quiet hood. The inviting space is steps from landmark city parks and the vibrant Junction- one of the most eclectic districts in North America. We just call it home. Hang-out in the airy living room, this spacious gem has comfy seating for all, convenient amenities and period details. Cook meals in the renovated chef kitchen and enjoy dining - both indoors and out. We provide yummies for self-serve breakfast, mostly organic.

Guest favorite

A spacious bedroom is highlighted by a comfortable bed dressed in a navy blue cover. A wooden dresser and side table provide functional accents. The room features a warm carpet, minimalistic wall decor including a world map, and natural light entering through a large mirror.

Apartment in Davisville Village

4.77 out of 5 average rating, 348 reviews

Spacious Midtown Suite, Clean, Bright, Near Subway

Renovated, spacious (1000 sqft), private basement suite in vibrant midtown, just a 5-min walk to Yonge-Eglinton Subway and 10 min ride to downtown. Clean, bright, and elegantly furnished, this suite features free parking, high-speed WiFi for remote work, and a comfortable Queen bed plus a sofa bed, ideal for 4 adults or 2 adults & 3 kids. Enjoy a sparkling, modern bathroom and easy access to top restaurants, theatres, and grocery stores. Perfect for families, couples, or business travelers.

Guest favorite

A modern living area features a sectional sofa and a coffee table on a colorful area rug. A fireplace adds warmth, positioned below a wall-mounted television. Accent chairs in yellow and green provide additional seating, while natural light spills in from a small window.

Guest suite in Toronto

4.92 out of 5 average rating, 109 reviews

Bright & Cheery Full Basement Suite walk to Subway

Our basement with private keypad entry in Toronto's tree-lined West End is ideal for tourists or folks coming to the city to work. It was completely renovated in early 2025 with a 1950s vintage travel vibe you'll love. Brand new bathroom, full separate bedroom with queen size bed (ENDY mattress), TV, desk, plus living area with fireplace & sofa bed. There is also a kitchenette/laundry. 3 min walk to Jane subway. Ceiling 6'5" with 1 lower beam. We live upstairs--the unit is noise insulated.

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 Toronto

4.89 out of 5 average rating, 235 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.

Top guest favorite

The open-space living area features a large leather sofa facing a flat-screen TV, with a dining table and chairs nearby. A modern kitchen with high-end appliances is visible in the background, complemented by bright, recessed lighting throughout the space.

Apartment in Davisville Village

4.94 out of 5 average rating, 138 reviews

Midtown modern 1 bedroom suite

Located in the heart of Midtown, Davisville Village. Very close to public transit, grocery stores and trendy restaurants. New property, modern look, high-end new appliances (incl. washer & dryer), modern comfortable furniture. Highest standards of cleaning, including proper disinfection of all high-touch areas. All kitchen, bathroom and bedroom supplies for comfortable stay provided. On-site parking is available for a separate fee. High-speed Wi-Fi access, Netflix, cable TV.

Guest favorite

A modern dining area features a glass table surrounded by vibrant blue chairs. A colorful artwork depicting a forest scene adorns the wall, while a gallery of city prints is displayed nearby. Natural light enhances the bright and airy atmosphere of the space.

Home in York

4.89 out of 5 average rating, 194 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 well-appointed bedroom features a spacious bed adorned with neatly arranged white towels. A decorative throw enhances the bedding, while bedside lamps provide soft illumination. An exercise bike is positioned near the bed, and a tree-like light fixture adds a unique touch to the ambiance.

Home in Roncesvalles Village

4.92 out of 5 average rating, 157 reviews

Cozy one bedroom apartment in Roncesvales village

Clean, convenient, cozy and spacious one bedroom apartment located right in the heart of unique and lovely Roncesvales village and High park area. The apartment is minutes away from award-winning restaurants, bars, pubs, coffee shops, grocery store, bakeries, delis, retail shop, 24 hours gyms and movie theatre. Great for all kinds of travelers. We hope to make your stay comfortable, enjoyable and unforgettable.

Guest favorite

A bright living area features a comfortable grey sofa paired with a patterned armchair. A large mirror reflects the light, enhancing the open feel. Decorative art pieces and indoor plants add a touch of warmth, while large windows allow natural light to fill the space.

Home in Midtown

4.8 out of 5 average rating, 171 reviews

Contemporary cozy home in the Annex

This 2 bed/2bath home is located in the more northern part of the downtown core called West Annex/Seaton Village and is on a cul de sac. Steps from TTC, Yorkville, art galleries, restos & more. The small urban-chic, clean and bright home boasts two balconies off either bed & a spacious backyard off kitchen. Permit No: STR-2010-GZSXPH Application Reference No: 3383-645

Top guest favorite

A modern two-story home is featured with a sleek gray exterior and large front windows. Lush greenery surrounds the entrance, highlighted by blooming flowers and a stone pathway leading to the door. The structure is positioned between neighboring homes, conveying a sense of community.

Guest suite in Toronto

4.96 out of 5 average rating, 131 reviews

Large new 1-bdrm/1 bath - king bed & parking

Bright newly-renovated one-bedroom basement unit with king bed, full kitchen, and living room, and free dedicated parking spot. This backs onto Bickford park, is a 5 minute walk from Christie subway station, Korea town, and bustling Bloor street. A total of 700 square feet of space (65 sq meters), in-floor heating throughout. We welcome guests from all places.

Guest favorite

A living room features a comfortable light-colored sofa positioned near a large flat screen TV. Red walls create a bold atmosphere, and a decorative rug lays on the tiled floor. Wall art and mirrors enhance the vibrant decor, while a clock is mounted above.

Guest suite in Central Etobicoke

4.91 out of 5 average rating, 861 reviews

Cozy and Hip Space for Rental

This beautiful space is the perfect blend of cozy and hip. It has lots of light and comes with most amenities necessary for your stay. The space in our home is run by myself and my wife, Ariana. It is the perfect environment for any family. It has a living room, bedroom (with a queen size bed) and a 3 piece bathroom.

Top guest favorite

The open-concept living area features warm orange walls complemented by framed artwork. A cozy sitting area includes a gas fireplace and inviting seating. A dining table is positioned nearby, and large sliding doors provide access to the outdoor garden patio.

Guest suite in Little Portugal

4.95 out of 5 average rating, 332 reviews

Private Suite - Walk to Everything!

It’s a cozy, fully private suite in our downtown, modern and fully-renovated Toronto Victorian townhouse. We're the perfect base for a Toronto visit, located on the downtown west side, one minute to buses and streetcars and an easy walk to restaurants, nightlife, attractions and neighbourhood amenities.