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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.

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Top guest favorite
A cozy backyard space is presented, featuring comfortable seating surrounding a glass table with a fire pit. Soft lighting and a large umbrella create an inviting atmosphere. Greenery and decorative elements enhance the serene environment, with a charcoal grill visible in the background.
Home in Oakwood Village
4.96 out of 5 average rating, 27 reviews

Modern Basement Apartment

Stay in style and comfort at our centrally located Toronto Airbnb basement apartment. Just steps from the #90 bus, which takes you on a short 15-minute ride to St. Clair West subway station, or enjoy a pleasant walk to the station. Exploring Toronto has never been easier. This apartment has two bedrooms and three beds, ensuring ample space for you and your guests to relax in comfort. After a day of sightseeing, unwind in the fenced-in backyard, providing a serene oasis in the heart of the city.

Top guest favorite
An open living area features a light-colored sofa covered with a protective cover, a coffee table, and a flat-screen TV mounted on the wall. Natural light enters through large windows dressed with sheer curtains, complementing the warm wood tones of the flooring.
Guest suite in Oakwood Village
4.92 out of 5 average rating, 61 reviews

Chic Midtown Toronto Suite / Newly Renovated

Welcome to our stylish and newly renovated suite located in the trendy St. Clair Avenue West area of Midtown Toronto! The suite features a spacious bedroom with a plush queen-sized bed, a fully equipped kitchen with brand-new appliances, and a sleek bathroom with a luxurious rain shower. Enjoy the convenience of being just steps away from top restaurants, cafes, and shopping in one of Toronto’s most vibrant neighbourhoods. 20 minutes walk to St. Clair West station, 5 minutes to the streetcar.

Top guest favorite
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.
Apartment 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.

Guest favorite
An open-concept basement suite is shown, featuring a spacious bed with fresh linens. A large smart television is mounted on the wall, and a kitchenette with modern appliances, including a fridge and coffee maker, is visible in the background. Light wood flooring enhances the room's brightness.
Guest suite in Earlscourt
4.92 out of 5 average rating, 167 reviews

A cozy suite in transit friendly Corso Italia.

A newly, hotel inspired, renovated cozy basement suite in the transit-friendly neighbourhood of Corso Italia. The suite includes an open-concept living, kitchenette, high-speed internet and everything you need for a perfect stay in Toronto. Less than a 10 minute walk from a variety of restaurants, a park, and shops on St. Claire avenue. With public transportation steps away( 1 minute to a bus stop), it's a perfect base for exploring the neighbourhood and the city. Parking is available!

Superhost
A modern living room features a light grey sectional couch with decorative pillows, centered on a patterned area rug. A round coffee table holds a small plant and magazines. Natural light floods the space through the open layout, highlighting the restored brick wall and wooden flooring.
Home in Oakwood Village
4.87 out of 5 average rating, 68 reviews

Modern Rustic Laneway Entire Home w/Patio

This cozy historic house is an area that many years ago used to be the apple orchard of John Oakwood, of Oakwood Ave. This rustic brick laneway home is where the apple pickers used to live and a perfect getaway. - A Queen & twin size bed, 3 ppl -A/C -Kitchen -Nespresso/ Frother -Bathroom -Backyard /patio -BBQ -2 Smart TV's -Free Wi-Fi -Laundry - 2 min to closest paid street parking Parking Info Download GreenP App Parking Rates: Day Max (7am – 6pm): $4.50 Night Max (6pm – 7am): $2.50

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
4.88 out of 5 average rating, 101 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.

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, 81 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.

Superhost
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
4.82 out of 5 average rating, 201 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
4.87 out of 5 average rating, 78 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.

Guest favorite
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, 217 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.

Top guest favorite
A bright entryway showcases a spacious seating area with a light-colored couch. Decorative plants are placed strategically, beside a standing mirror and a flat-screen TV mounted on the wall. Soft lighting illuminates the modern design, leading to a glimpse of the bedroom area in the background.
Apartment in Stockyards District
4.98 out of 5 average rating, 356 reviews

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.

Top guest favorite
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, 148 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.

Popular amenities for Oakwood Village vacation rentals

When is the best time to visit Oakwood Village?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$13,367 GYDG$12,949 GYDG$13,158 GYDG$13,784 GYDG$15,038 GYDG$16,082 GYDG$17,544 GYDG$18,379 GYDG$17,961 GYDG$16,917 GYDG$16,291 GYDG$16,708 GYD
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 G$2,089 GYD per night before taxes and fees

  • Verified guest reviews

    Over 9,980 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 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!

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