Holiday houses in Oakwood Village

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Quick stats about holiday rentals in Oakwood Village

  • Total holiday rentals

    Explore 290 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 9,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wi-Fi availability

    290 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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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
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.

Superhost
Apartment in York
5 out of 5 average rating, 4 reviews

Private Basement Apt • Transit to Downtown • 1–4

This comfortable basement apartment is perfect for solo travelers, couples, or business guests. Whether you want to explore Little Jamaica’s Caribbean flavours, shop at Yorkdale Mall, or head downtown, you’ll be perfectly located for an amazing Toronto experience! ✔ Self Check-In ✔ Queen Bed ✔ Fully Equipped Kitchen ✔ WiFi & Smart TV (Netflix included) ✔ Steps from Public Transit Enjoy this charming space with reading material, warm lighting, and all the essentials in a vibrant neighborhood!

Guest favourite
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 favourite
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.

Guest favourite
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 favourite
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!

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 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.

Guest favourite
The living room showcases a comfortable sofa paired with accent pillows, positioned near expansive floor-to-ceiling windows. A modern coffee table and a sleek side table complement the space. A large smart TV occupies the wall, and city views are visible through the windows.
Apartment in Downtown Toronto
4.9 out of 5 average rating, 62 reviews

Sleek Downtown Condo | Panoramic Skyline Views

Welcome to your cozy urban retreat in the heart of Toronto! This modern and stylish 2-bedroom condo is situated in the vibrant entertainment district, offering you the perfect blend of comfort, convenience, and contemporary living. The living room is tastefully furnished with a comfortable sofa, perfect for unwinding after a day of exploring the city. Enjoy your favourite shows or movies on the 65" smart flat-screen TV equipped with streaming apps for your convenience.

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.

Guest favourite
A cozy bedroom features a spacious, unmade bed adorned with pillows in a neutral color palette. Natural light enters through two windows, with sheer curtains gently diffusing the sunlight. An antique dresser occupies one side, complemented by a wooden chair and a floral arrangement.
Loft in Little Portugal
4.97 out of 5 average rating, 34 reviews

The Wanderly Suite

A whimsy apartment in an 18th century building, the Wanderly Suite is curated with rustic antique furnishings and merged with modern amenities. Located above our store ~The Wanderly~ the apartment is conveniently situated amongst Little Portugal's best vintage shops + cafés/restaurants! The space features an open concept kitchen/living room + bedroom, complete with a patio off the back. The perfect jumping off point for your next Toronto stay!

Guest favourite
Guest suite in Toronto
5 out of 5 average rating, 9 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.

Top Guest favourite
Guest suite in York
5 out of 5 average rating, 15 reviews

Cozy Greenhills Stay - Close to Subway

A unique and tranquil getaway only 8 minutes away from Keelesdale subway station making it very easy to travel around Toronto. There are beautiful parks in the area, as well as York Recreation Centre with ammenities such as swimming pool and gym (free). It's also very easy and convinient to get to from the Airport on the UP Express train (this train also goes to Union station). We can't wait to have you!

Popular amenities for Oakwood Village holiday rentals

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