Vacation rentals in Oakwood Village

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Quick stats about vacation rentals in Oakwood Village

  • Total vacation rentals

    Explore 310 vacation rentals in Oakwood Village

  • Nightly prices starting at

    Oakwood Village vacation rentals start at ﺩ.ﺇ 37 per night before taxes and fees

  • Verified guest reviews

    Over 9,720 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    310 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!

Top-rated vacation rentals in Oakwood Village

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

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Guest favorite
Home in York
4.93 out of 5 average rating, 30 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

Guest favorite
Home in Toronto
5.0 out of 5 average rating, 10 reviews

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.

Guest favorite
Guesthouse 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 favorite
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
4.96 out of 5 average rating, 46 reviews

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

Guest favorite
A stylish living area showcases a yellow sofa adorned with decorative pillows, paired with a glass coffee table. Vibrant curtains framed by large windows enhance natural light. A flat-screen TV is mounted on the wall, and a wooden sideboard adds warmth to the space.
Apartment in Toronto
4.83 out of 5 average rating, 71 reviews

Blue Haven- Beautiful home in perfect location

Relax in this spacious private retreat minutes to downtown. This stylish place to stay is perfect for those looking to experience life in a multi-cultural Toronto neighborhood. Located in the heart of the city's Corso Italia, this quiet, spacious home offers comfort and style. Experience life like a Toronto local, with stores, coffee shops, restaurants, bakeries, and parks at your doorstep. Explore Salsa on St. Clair, historic Casa Loma and Wychwood Barn Farmers Market. NO SMOKING NO PETS

Guest favorite
Home in York
4.95 out of 5 average rating, 19 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 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 York
4.92 out of 5 average rating, 186 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 favorite
Apartment 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 favorite
Home in York
4.86 out of 5 average rating, 22 reviews

Casa del Jo | Boho 2BR + Parking + Workspace

☀️ Summer Stays in Toronto! Stylish boho 2BR main-floor suite in a quiet, walkable neighbourhood with easy access to downtown, the Entertainment District, and top Toronto attractions. Relax with fast WiFi, Smart TV, a newly renovated spa-like bathroom, dedicated workspace, and free parking. Featuring cozy king + queen beds, in-suite laundry, and thoughtful touches throughout. Perfect for couples, friends, professionals, remote workers, or longer stays.

Superhost
Guest suite in Toronto
5.0 out of 5 average rating, 14 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.

The living area features comfortable gray sofas positioned around a light-colored coffee table. A small dining area with a white table and chairs is visible in the background. Natural light enters through large windows, illuminating a modern wall art piece with soft green hues.
Home in York
4.82 out of 5 average rating, 155 reviews

Bright and Modern Near Restaurants

Elegant 2-bedroom apartment, each with a private bathroom. The main suite features a queen bed with a 12" Beautyrest World Class mattress, walk-in closet, and 70" TV. The second bedroom offers a cozy queen bed and plenty of storage. Open-concept living area with a 50" smart TV and fully equipped kitchen, your perfect Toronto home base. Laundry after 7 p.m. by request · Smoke-free property · Paid on-street parking available

Top guest favorite
A spacious living area features a large sectional sofa adorned with bright pillows. A small side table sits next to the sofa, and a decorative rug covers the wooden floor. In the background, a softly lit doorway leads to the bedroom and kitchenette.
Guest suite in York
5.0 out of 5 average rating, 42 reviews

Modern Clean Midtown Private Suite free parking

✨Welcome to a modern, super-clean basement suite in Toronto! Perfect for couples, solo travellers, or small families and groups, this quiet retreat is just a short stroll to Cidervale Subway and steps from the LRT, with grocery stores, cafés, and restaurants nearby. Across the street, enjoy a family-friendly park with a playground, splash pad, and Beltline Trail. This is great for morning walks or a quick bike ride.

Popular amenities for Oakwood Village vacation rentals