
Family-friendly holiday 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.

Guest Suite in Trendy Bloordale Village
Welcome to fabulous Bloordale Village! My home is conveniently located next to everything you need for your stay in Toronto. It is a stone's throw away from Bloor Street West, home to some of the best restaurants, cafes, bars, breweries, vintage shops and galleries Toronto has to offer. There are also many grocery stores nearby, should you wish to take advantage of your private kitchen. The house is walking distance to the subway and a train station bringing you directly to and from the airport.

Cozy 1-bdm suite filled with amenities & parking
A whimsically decorated basement apartment with a separate entrance that welcomes all. The exposed brick gives it a unique character and the location means you're not too far from downtown, close to public transportation and away from congestion. Enjoy amenities such as a kitchenette with all the fixings for a continental breakfast, plentiful snacks and refreshments. The kitchen offers an induction cooktop & toaster oven instead of a stove. Guests can enjoy Netflix, Wifi, and free parking.

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.

Brand new lower-level studio in Toronto
Welcome to our totally renovated -modern clean- Lower Level studio apartment with everything you need for your stay. Our place is a 10 mins drive from the Pearson airport, 10 min to the subway and 30 mins - off peak - into downtown. The place is a walking distance from a grocery plaza ( Metro, Shoppers Drug Mart, LCBO ). We are located in the quiet green area, two parks are close by. We will be happy to help and to answer any questions! Short and Long stays are welcome.

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.

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.

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.

Cozy private space in mid-town Toronto
Welcome to our recently renovated unit that is part our home but completely separate from it. We are located in a Hillcrest Village a great neighbourhood that includes a mix of international restaurants, pubs and independent shops. We are very close to the St. Clair streetcar (tram) which takes you downtown in less than 20 minutes.

Annex Garden Coach House
Welcome to the Annex Garden Coach House! Well suited for solo and family travellers alike, seeking a centrally located, quiet little house, surrounded by backyard trees, in the leafy Annex neighbourhood. You're able to park for free at your private front door, and it's a quick walk to your choice of three nearby subway stations.
Popular amenities for Oakwood Village family-friendly rentals
Family-friendly home rentals with a hot tub

Beautiful Penthouse with Breathtaking View

Year-Round Heated Pool & Hot Tub Family Oasis

The Penty: Luxurious Penthouse with Pool, Hot Tub

The Fort York Flat

Luxury Stay w/phenomenal view!

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

Large & Bright 2BR+Den in Midtown w/ Free Parking

Charming Condo w Parking, CN Tower View & Pool
Family- and pet-friendly home rentals

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

A spectacular and authentic loft!

Comfy Oasis In Historic Downtown Neighborhood

Stunning Yorkville Townhome Backing onto Park

Mid-town T.O. getaway - conveniently located

Stylish Apartment in Toronto - Long term available

Private 1-br Apartment: Your Secluded Getaway!

5 Km to Toronto Pearson Airport , Sleeps 4-6
Family-friendly home rentals with a pool

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

Bright Sun Filled Condo + Pool + Gym, CN Tower

The Snug Oasis - Burrow (Near Airport)

Lux Waterfront Condo Pool Hot Tub Free Parking

Humber Bay Family Friendly condo w Terrace&Parking

Condo in Heart of Mississauga

Hidden gem in Humber bay shores Toronto w/ parking

Studio by Lake -Close to Central Airport & Station
When is the best time to visit Oakwood Village?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 88 | € 94 | € 99 | € 105 | € 116 | € 124 | € 130 | € 132 | € 128 | € 118 | € 119 | € 115 |
| 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 holiday rentals that are family-friendly in Oakwood Village

Total holiday rentals
Explore 90 holiday rentals in Oakwood Village

Nightly prices starting at
Oakwood Village holiday rentals start at € 25 per night before taxes and fees

Verified guest reviews
Over 2,550 verified reviews to help you choose

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
90 of Oakwood Village holiday rentals include wifi 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
- Private suite rentals Oakwood Village
- Rentals with a washing machine and dryer Oakwood Village
- Pet-friendly rentals Oakwood Village
- Rentals with a patio Oakwood Village
- Fitness-friendly rentals Oakwood Village
- House rentals Oakwood Village
- Rentals with outdoor seating Oakwood Village
- Rentals with a fireplace Oakwood Village
- Rentals with a firepit Oakwood Village
- Flat rentals Oakwood Village
- Family-friendly rentals Toronto
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- Clifton Hill
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- BMO Field
- Toronto Zoo
- Toronto Eaton Centre
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Niagara Falls State Park
- Casa Loma
- Dufferin Grove Park
- Legends on the Niagara Golf Course
- Toronto City Hall
- Casino Niagara
- Rouge National Urban Park




