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Vacation rentals in Oakwood Village

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Oakwood Village

  • Total vacation rentals

    Explore 290 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 9,510 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

    290 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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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 York
4.97 out of 5 average rating, 35 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
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
4.97 out of 5 average rating, 154 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
Home in York
4.81 out of 5 average rating, 112 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

Top guest favorite
Condo in Midtown
5 out of 5 average rating, 23 reviews

Luxury 1+Den w/ Parking | Downtown Toronto

Enjoy a stylish stay in this modern 1+Den condo in Downtown Toronto with free parking (rare for the area). Features a cozy living area, comfortable bedroom, and dedicated workspace—ideal for business or leisure stays. Minutes from Casa Loma, CN Tower, Rogers Centre, Scotiabank Arena, BMO Field, Exhibition Place, nightlife, restaurants, cafés, grocery stores, and a subway station just a 10-minute walk away. Clean, comfortable, and well-connected. Queen air mattress available upon request.

Top guest favorite
A modern living area features a sleek brown leather couch with decorative pillows, positioned across from a dark wooden coffee table. Bright natural light enters through large bay windows, complemented by light-filtering curtains. A decorative wall map and a large green plant add character to the space.
Home in York
4.99 out of 5 average rating, 211 reviews

Welcome to Greenhills, a Charming Home w/ Parking

Clean Open Concept, Sun-Filled 2 Bedroom main floor home with PARKING; Can sleep up to 4 people. Featuring simple modern décor, queen size beds, big beautiful windows with room darkening curtains, closet storage. Dedicated office desks in bedrooms Full kitchen, with oil, seasoning spices, toaster, hot water kettle, Keurig Coffee Machine and complimentary coffee+tea. Clean bathroom with shampoo+conditioner+body wash+lotion SMART TV 60” Fast internet Wifi Check-In: 3PM Check-Out: 11AM

Guest favorite
Home in York
4.93 out of 5 average rating, 14 reviews

Free Parking | 1 Bus to Downtown | Newly renovated

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
Apartment in York
4.87 out of 5 average rating, 23 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
Guesthouse in York
4.93 out of 5 average rating, 14 reviews

Handy Studio in Oakwood Village

Cosy midtown laneway studio is 440 square feet of private, quiet space, 75 ft from street parking. Easy access from Pearson. Large windows on north and south ends ensure great natural light. There are solar shades to keep out the summer heat while allowing the occupant to see out, and privacy curtains for times when they are 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.

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 Toronto
5 out of 5 average rating, 101 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
Apartment in York
5 out of 5 average rating, 4 reviews

Stylish Queen Basement with Free Parking

Stay in this bright and newly updated basement suite in a quiet residential neighbourhood, ideal for solo travellers or couples and comfortably sleeps 3. Relax in the cozy Queen bed, with a sleeper sofa for an extra guest after a day exploring the city. Enjoy Smart TVs, complimentary WiFi, and an in-suite washer and dryer. Easy transit access connects you to downtown, dining, parks, and nearby highlights like Cedarvale Park and Corso Italia. Book your stay today!

Guest favorite
Home in York
4.81 out of 5 average rating, 16 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
Home in Midtown
5 out of 5 average rating, 3 reviews

Brand New Designer Home Near Downtown

Welcome to our brand-new designer home, thoughtfully furnished for comfort and style. Enjoy a fully equipped kitchen, spacious living area, high-speed WiFi, and modern finishes throughout. Perfect for families, business travelers, and visitors looking for a relaxing stay near Downtown Toronto. Experience a clean, bright, and welcoming space designed to make you feel at home. Street parking is conveniently available on the rear street behind the property.

Popular amenities for Oakwood Village vacation rentals

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