Vacation rentals in Oakwood Village

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oakwood Village

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Guest favorite
Home in Eglinton West
4.84 out of 5 average rating, 70 reviews

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

An open-concept living area features a large sectional sofa facing a wall-mounted TV. Natural light floods in through expansive glass doors. A wooden coffee table sits in front, adorned with decorative items, while plants add a touch of greenery to the space.
Home in York
4.86 out of 5 average rating, 87 reviews

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.

Top guest favorite
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 favorite
A modern living area features a sleek white sofa adorned with yellow and gray pillows. A round black coffee table is positioned in front, displaying magazines. A vibrant artwork hangs on the wall, complemented by a floor lamp and a decorative lantern in the background.
Home in Oakwood Village
4.89 out of 5 average rating, 98 reviews

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.

Guest favorite
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

Top guest favorite
A bright living area is furnished with a light-colored sofa and a pair of wooden side tables. A textured area rug covers the hardwood floor, while natural light is allowed in through a nearby window. A small desk and chair are positioned against the wall.
Home in Earlscourt
5 out of 5 average rating, 72 reviews

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.

Guest favorite
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 favorite
A modern kitchen with dark wooden cabinetry is complemented by stainless steel appliances, including a refrigerator and microwave. A countertop provides space for meal preparation, while a neutral backsplash enhances the overall design. Natural light illuminates the wood-patterned floor, creating a welcoming environment.
Apartment in Oakwood Village
4.86 out of 5 average rating, 74 reviews

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.

Home in York
5 out of 5 average rating, 4 reviews

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

Superhost
Home in Oakwood Village
4.82 out of 5 average rating, 11 reviews

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.

Home in Wychwood
5 out of 5 average rating, 3 reviews

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.

Guest favorite
A comfortable living area features a plush sofa against a textured wall, complemented by a wooden coffee table. A small dining table with chairs is positioned nearby, and a window allows natural light to illuminate the space. Art pieces adorn the walls, adding visual interest.
Bungalow in Oakwood Village
4.94 out of 5 average rating, 50 reviews

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

When is the best time to visit Oakwood Village?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ235ﺩ.ﺇ228ﺩ.ﺇ231ﺩ.ﺇ242ﺩ.ﺇ264ﺩ.ﺇ283ﺩ.ﺇ308ﺩ.ﺇ323ﺩ.ﺇ316ﺩ.ﺇ286ﺩ.ﺇ305ﺩ.ﺇ253
Avg. temp-3°C-3°C2°C8°C14°C20°C23°C22°C18°C11°C5°C0°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!

  1. Airbnb
  2. Canada
  3. Ontario
  4. Toronto
  5. Oakwood Village