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.

%{current} / %{total}1 / 1
Superhost
A comfortable living area features a gray couch with teal accent pillows, positioned on a soft area rug. A wooden coffee table sits at the center, complemented by a potted plant. Framed art adorns the wall, enhancing the space’s modern aesthetic.
Guest suite in Dufferin Grove
4.85 out of 5 average rating, 119 reviews

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.

Top guest favourite
A compact bedroom is furnished with a spacious bed dressed in striped linens. Artwork is displayed on the walls, and a mirrored closet adds depth to the space. Natural light enters through partially covered windows, while soft bedside lamps provide illumination.
Flat in Oakwood Village
4.96 out of 5 average rating, 139 reviews

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.

Top guest favourite
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, 148 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 favourite
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, 101 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 favourite
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.
Flat in Junction Area
4.72 out of 5 average rating, 150 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.

Top guest favourite
A clean and modern studio space features a queen-size bed with soft pink bedding and a white headboard. A light-colored sofa is positioned beside a small black table. Natural light enters through two high windows, enhancing the neutral-toned walls and wooden flooring.
Flat in Etobicoke
4.88 out of 5 average rating, 110 reviews

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.

Guest favourite
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
4.83 out of 5 average rating, 200 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 favourite
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
4.86 out of 5 average rating, 216 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 favourite
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, 105 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 favourite
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, 145 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.

Top guest favourite
A welcoming entryway featuring a light green wall. A wooden coat rack with hanging jackets is adjacent to a white door. A small table is visible, accompanied by a potted plant. The flooring is light-colored and there are mats at the doorway and stairs.
Home in Wychwood
4.93 out of 5 average rating, 147 reviews

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.

Top guest favourite
A modern living area features a spacious gray sectional sofa adorned with colorful throw pillows. Abstract artwork is displayed on the walls, while a round coffee table holds snacks. A large window allows natural light to fill the room, with a view of greenery outside.
Home in Annex
5 out of 5 average rating, 218 reviews

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

When is the best time to visit Oakwood Village?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€ 88€ 94€ 99€ 105€ 116€ 124€ 130€ 132€ 128€ 118€ 119€ 115
Avg. temp-3°C-3°C2°C8°C14°C20°C23°C22°C18°C11°C5°C0°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!

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