Holiday houses 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 $14 AUD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    310 of Oakwood Village holiday 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!

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

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

4.91 out of 5 average rating, 32 reviews
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.
Apartment in York

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.

4.96 out of 5 average rating, 163 reviews
Guest favourite
Home in Toronto

House w/ Free Parking | Backyard | BBQ | Piano

Stylish 2-level, 1,500 sq ft (139 m²) house with FREE parking, fast Wi-Fi, central AC, and a private patio with gazebo & BBQ. Enjoy a king bed, fully equipped kitchen, and 75” & 85” TVs with Netflix & Prime. Located in a lively, walkable area with groceries, cafés, restaurants, shops, parks, gym, library, FREE public pool, and 24-hour transit at your doorstep. Easy access to 3 subway stations; downtown/Bloor-Yonge is about 23 minutes by car. Close to Casa Loma, bike share & paid EV charging.

5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in York

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

4.83 out of 5 average rating, 124 reviews
Guest favourite
Guesthouse in York

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.

4.96 out of 5 average rating, 23 reviews
Guest favourite
Home in York

3BR/2BA - 2 min to Subway + Parking

Welcome to our updated 3 bedroom home, in the heart of Toronto. Just a 2-min walk to Oakwood or 10-min walk to Cedarvale 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 home 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

4.88 out of 5 average rating, 94 reviews
Guest favourite
The entrance of a charming home is surrounded by a vibrant garden. Colorful flowers bloom in the foreground, while a stone pathway leads to a welcoming front door. Lantern-style lights stand on either side of the entrance, enhancing the inviting atmosphere.
Home in York

Home Away from Home on St. Clair W./Corso Italia

This charming and beautiful 3-bedroom Century home, full of unique character and warmth, has been lovingly maintained to preserve its original charm with a modern touch. Nestled in a quiet neighbourhood just steps from Corso Italia and St. Clair Avenue West, it comfortably sleeps 6 guests. More than just a place to stay, it’s a true getaway where the vibrant city is at your doorstep, yet the peaceful front and back gardens offers a serene oasis that feels like an Italian villa for relaxation

4.96 out of 5 average rating, 47 reviews
Guest favourite
Home in York

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.

4.91 out of 5 average rating, 23 reviews
Guest favourite
An open living space is captured, featuring a modern kitchen with wooden cabinets and stainless steel appliances. A dining table with four chairs is positioned in the foreground, while a comfortable grey sofa faces the light-filled area. Two paintings adorn the wall beside the entrance.
Apartment in Midtown

Luxury Oasis l 3BR l Casa Loma l 1300 sf l Parking

Experience luxury at our recently renovated 3-bedroom apartment. The property has been professionally designed and features high-quality finishes including quartz countertops, stainless steel appliances, a 65-inch Smart TV with Netflix, and more. Whether you're in Toronto for business or pleasure, this is the ideal place to unwind and relax. Enjoy the peace of an upscale neighborhood and discover nearby attractions such as Casa Loma and everything this vibrant city has to offer!

4.87 out of 5 average rating, 47 reviews
Top 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

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!

4.92 out of 5 average rating, 189 reviews
Guest favourite
Apartment in York

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!

4.84 out of 5 average rating, 31 reviews
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

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!

4.91 out of 5 average rating, 122 reviews

Popular amenities for Oakwood Village holiday rentals