
Vacation rentals in Oakwood Village
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Top-rated vacation rentals in Oakwood Village
Guests agree: these stays are highly rated for location, cleanliness, and more.

3BDRM/2Bath near subway/Toronto w/parking
Welcome to our newly renovated 3 bedroom home, in the heart of Toronto. With just a 10-min walk to your nearest subway/metro station, commute to the city is a breeze. A quick 15-20 min drive to the vibrant Downtown Toronto or Toronto Pearson airport. Our location offers convenience & accessibility. Restaurants, shops, cafes, groceries & transit are nearby. * 3 bedroom / 2 bath– Sleeps 6 * Free Wifi * Fully equipped kitchen * Washer & dryer * Professionally Cleaned * Private Parking: 3 cars

Modern House w/ Amazing Location: Hot Tub & Gym
Welcome to your 4 bedroom home away from home. Beautifully located house in the charming Humewood/Cedervale neighbourhood of Toronto. Perfect for couples, solo travelers, families w/ young children or professionals, this property offers comfort, privacy, and easy access to everything the city has to offer. Nestled on a quiet, tree-lined street, you’ll enjoy a peaceful stay while still being minutes from vibrant local shops, cafes, parks, and convenient transit connections to downtown Toronto.

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.

Spacious 1 BD basement apartment
Forget your worries in this spacious and serene space. Peaceful neighborhood in central Toronto. This unit is everything you need. Perfect for couples. 700 sq ft, brand new furniture, transit-friendly and a 10 minute walk to a variety of restaurants and coffee shops. Transit will take you in Downtown in 20 min. Fresh linens, towels, Wi-Fi, coffee maker, toaster are provided. Guests have a private seperate entrance. I want people to feel comfortable in the space 6ft max height is recomended.

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

Cozy and Modern Lower-Level Suite in Corso Italia
Welcome to your home away from home! This newly updated, bright and cozy suite is nestled in Toronto’s buzzing Corso Italia neighbourhood. This apartment offers the perfect blend of comfort, privacy, and convenience. Whether you're here for a short stay or a longer getaway, you'll enjoy a comfortable retreat in this recently renovated and thoughtfully designed space. You will have access to the entire apartment accessible via a separate entrance located in the backyard.

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.

1 x Bedroom Modern Apartment (2xBeds)
Enjoy the bright 1 x bedroom and business friendly basement apartment with complete separate entrance. Newly renovated space. 8ft Ceilings throughout. Centrally located for easy access to downtown and uptown. In suite laundry & wifi and Netflix as well. It is a basement apartment so people live in the unit above. The apartment has been built to code with acoustic insulation. No parking available. Street parking permits available. No parties, smoking or loud groups.

brand new city oasis
Be among the first to stay in this brand-new home, perfectly located for easy access to Toronto’s top spots. Just minutes from public transit, shopping centres, Yorkdale Mall, and Downsview Park. Enjoy quick trips downtown, to York University, or anywhere in the city with easy access to Highways 401 and 400. Designed for comfort and style, it’s ideal for families, friends, or business travellers looking for a modern retreat in a prime location

Casa del Jo | Boho 2BR Retreat + Free Parking
Stylish boho 2BR main-floor suite tucked in a quiet, walkable neighbourhood — just 1 bus to downtown Toronto, Entertainment District, and Financial District! Enjoy a luxury renovated bathroom, cozy king + queen beds, fast WiFi, and free parking. Ideal for professionals, mature students, or digital nomads on longer stays. Close to transit, St. Clair, Casa Loma, George Brown, Yorkdale & more.

Stunning 3B+Garden Oasis @ Wychwood. Top location.
Fully renovated 3BR home in vibrant St. Clair West. Bright, open layout with full kitchen, private garden with BBQ, and sunroom with dedicated workspace. Sleeps up to 7 with 3 bedrooms + sofa bed in the lower level. Walk to top restaurants, shops, and transit. Ideal for families & professionals. Quiet, stylish, and entirely yours — the perfect Toronto stay.

Comfy Bungalow in Midtown TO
You and your guests will enjoy this cozy, spacious bungalow in the heart of Toronto. Located in Humewood/Oakwood, it’s easy to get around from here to all parts of the city. The house is tidy and well-maintained with lovely landscaping and artful touches. A great spot for you to enjoy in your downtime visiting the city.
Popular amenities for Oakwood Village vacation rentals
Other great vacation rentals in Oakwood Village

Comfy, Spacious and Clean Mid-Toronto Stay

Clean, cozy home just 6 min from Yorkdale Center.

Cozy 2-Bed w/ Kitchen & Patio in Midtown Toronto

Stylish Private Room in Midtown Toronto + Netflix

York Private Room • Easy Downtown

SuperHost Repost: Self Check-in Private Bedroom #2

Beautiful Oasis: Private Bedroom/Bathroom

Cozy Corner
When is the best time to visit Oakwood Village?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ235 | ﺩ.ﺇ228 | ﺩ.ﺇ231 | ﺩ.ﺇ242 | ﺩ.ﺇ264 | ﺩ.ﺇ283 | ﺩ.ﺇ308 | ﺩ.ﺇ323 | ﺩ.ﺇ316 | ﺩ.ﺇ286 | ﺩ.ﺇ305 | ﺩ.ﺇ253 |
| 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 in Oakwood Village

Total vacation rentals
Explore 300 vacation rentals in Oakwood Village

Nightly prices starting at
Oakwood Village vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 9,520 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wi-Fi availability
300 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
- Family-friendly rentals Oakwood Village
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- Apartment rentals Oakwood Village
- 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




