
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.

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.

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.

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

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.

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.

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.

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.

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’.

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.

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.

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.

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
Family-friendly home rentals with a hot tub

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

Lux Waterfront Condo by Rogers -IndoorPool-Parking

The Fort York Flat

Luxury Stay w/phenomenal view!

Luxur condo in downtown Mississauga

Stylish Downtown Toronto Condo with Free Parking

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

Large & Bright 2BR+Den in Midtown w/ Free Parking
Family- and pet-friendly home rentals

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Comfy Oasis In Historic Downtown Neighborhood

Mid-town T.O. getaway - conveniently located

2BR+2Bath! 2queen beds! Luxury Private Quiet Clean

Trendy & Cozy 1BD Condo in the Heart of Toronto

Private 1-br Apartment: Your Secluded Getaway!

Large Artsy Loft w 30ft Ceilings and Natural Light

Spacious & Vibrant upstairs apartment
Family-friendly home rentals with a pool

The Snug Oasis - Burrow (Near Airport)

Private 1 bed/1.5 bath in-law suite in a house!

Condo in Heart of Mississauga

Hidden gem in Humber bay shores Toronto w/ parking

Guest suite 10 min to subwy w kitchen FREE parking

Chic, High-Rise Apartment with CN Tower Views

Luxury Condo w. Pool @ Yorkdale, Free Parking!

Luxury City Vacation Getaway
When is the best time to visit Oakwood Village?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 89 | € 95 | € 100 | € 107 | € 117 | € 126 | € 126 | € 129 | € 121 | € 120 | € 120 | € 116 |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
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!
Destinations to explore
- Rentals with a fireplace Oakwood Village
- Pet-friendly rentals Oakwood Village
- Rentals with a patio Oakwood Village
- Apartment rentals Oakwood Village
- Rentals with a fire pit Oakwood Village
- Rentals with outdoor seating Oakwood Village
- Private suite rentals Oakwood Village
- Rentals with a washer and dryer Oakwood Village
- Fitness-friendly rentals Oakwood Village
- House rentals Oakwood Village
- Family-friendly rentals Toronto
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Budweiser Stage
- Distillery District
- Metro Toronto Convention Centre
- Port Credit
- Clifton Hill
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- Toronto Zoo
- Financial District
- CF Toronto Eaton Centre
- Trinity Bellwoods Park
- BMO Field
- Niagara Falls State Park
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Legends on the Niagara Golf Course
- Rouge National Urban Park
- Casino Niagara