Holiday rentals in Oakwood Village

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Quick stats about holiday rentals in Oakwood Village

  • Total holiday rentals

    Explore 310 holiday rentals in Oakwood Village

  • Nightly prices starting at

    Oakwood Village holiday rentals start at £7 per night before taxes and fees

  • Verified guest reviews

    Over 9,720 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wifi availability

    310 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!

Top-rated holiday rentals in Oakwood Village

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

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Guest favourite
Home in York
4.91 out of 5 average rating, 32 reviews

Renovated 2 Bed lower level apt- free parking

Welcome to this modern 2-bedroom basement apartment located in the vibrant Oakwood Village neighborhood. ideal for couples or small families. Located in one of Toronto’s most accessible pockets, steps from St. Clair Avenue West, featuring streetcar, local cafes, shops, parks, and grocery stores. Nearby amenities include Cedarvale Park, Oakwood Collegiate Institute, and the trendy Eglinton West dining strip, proximity to TTC bus routes, Yorkdale Mall, and easy access to Highway 401 via Allen Road

Top guest favourite
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 York
4.94 out of 5 average rating, 90 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 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 York
4.96 out of 5 average rating, 163 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.

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

Bright Garden Retreat with Fireplace & Kitchen

Enjoy a bright, self-contained private suite featuring a comfortable double bedroom, a fireplace, and abundant natural light from large windows overlooking a beautiful garden. The unit includes a full kitchen, a private bathroom, a washer & dryer, and an elegant heated granite floor for year-round comfort. It is within walking distance of Toronto’s Line 1 & Line 5 subway stations and just a few blocks from city amenities & beautiful Cedarvale Park, with its extensive walking and cycling trails.

Guest favourite
Home in York
4.83 out of 5 average rating, 124 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. Entire property with 3 bedrooms (1 King and 2 Queen size beds). - Free parking on a private lot for multiple vehicles - 2 televisions - Wifi - Netflix - Kitchen - 2 washrooms - Enclosed private patio and a backyard - Steps to TTC bus stop and 10 min walk to Oakwood Subway - High speed internet and working space

Guest favourite
Guest house in York
4.95 out of 5 average rating, 22 reviews

Handy Studio in Oakwood Village

Midtown laneway studio has 440 square feet of private, quiet space, 75 ft from street parking. As of Summer 2026, this propery has solar panels and is net zero. Windows on north and south ensure natural light. There are solar shades to keep out the summer heat while allowing the occupant to see out, with privacy curtains for times when privacy is needed. 4 minutes walk to TTC buses, 12 to subways. Full kitchen, fridge, dishwasher and stove. Wifi. Queen sized Murphy bed folds to maximize space.

Guest favourite
Home in York
4.91 out of 5 average rating, 22 reviews

Free Parking | Transit | Quartz Kitchen | Laundry

Beautifully renovated Toronto home in Corso Italia. Close to downtown and BMO field where FIFA world cup games will be, cafes, and restaurants. This bright, modern space features an open living area, quartz counters and stainless steel appliances, fast Wi-Fi, Smart TV, and in-suite laundry. Located on a quiet residential street with easy access to parks and transit. Perfect for couples, business travelers, or small groups seeking comfort, style, and convenience during their Toronto stay.

Guest favourite
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 York
4.92 out of 5 average rating, 189 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, 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!

Guest favourite
Flat in York
4.87 out of 5 average rating, 30 reviews

Urban Retreat Steps to Transit, Dining, & Shops

Welcome to your modern urban retreat in Toronto’s vibrant St. Clair West neighborhood! This bright, stylish 1 bedroom apartment sits in a lively area surrounded by cozy cafes, restaurants, local boutiques, and parks. Enjoy being just steps from express transit for quick access downtown or sites across the city. Our space is perfect for business trips, solo travelers, couples, small groups, or families looking for a home base in one of Toronto’s most vibrant neighborhoods!

Guest favourite
A cozy living space features a blue sofa with patterned cushions and a wooden coffee table. A round mirror hangs on the wall, reflecting natural light. A floor lamp provides additional lighting, and a small chair is positioned nearby. A plant adds a touch of greenery.
Home in Midtown
4.91 out of 5 average rating, 122 reviews

Spacious Mid Century w/Patio

Adorable Historic Home with Private Patio & BBQ. ♡ 3 bedroom & 1.5 bath (1 King & 2 Queens) ♡ Hotel Inspired Home with Super Fast WIFI ♡ Automated Check in & Check Out ♡ Steps from St. Clair transit line / connects to Subway ♡ 90/100 Walk Score ♡ 100/100 Transit Score ♡ Walking distance to Casa Loma | Rated #1 by BlogTO of Places to Visit in Toronto ♡ Flexible Check in Check out - Message for Details ♡ A/C ♡ Laundry ♡ BBQ & Fully Equipped Kitchen ❤ Book today!

Top guest favourite
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 Toronto
5.0 out of 5 average rating, 109 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
Guest suite in Toronto
5.0 out of 5 average rating, 15 reviews

Lovely Basement Suite

Enjoy your time at my centrally located private apartment. It's a very stylish basement apartment. It has all the amenities of a home with a kitchen, private entrance, laundry,and a full bathroom. It sleeps 4 with 1 double bed and a double pull out sofa bed. There is permit street parking available You will be close to many restaurants,grocery stores,bars etc Only 15 minutes to the downtown core whether by bus,street car, Uber or subway.

Popular amenities for Oakwood Village holiday rentals