Vacation rentals in Oakwood Village

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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
Apartment in Yorkville
5 out of 5 average rating, 15 reviews

City Views in Yorkville with Gym, Near Subway

Two-bedroom Yorkville condo with floor-to-ceiling windows showcasing stunning Toronto skyline views. Enjoy the convenience of an in-suite washer and dryer and access to a fully equipped building gym for a seamless stay. Steps from the Royal Ontario Museum, Bloor Street's luxury shopping, fine dining, and Bay subway station, this prime location places the best of Toronto at your doorstep. Ideal for professionals, families, and extended-stay guests seeking a refined urban experience in one of the

Guest favorite
Condo in Davisville Village
4.94 out of 5 average rating, 31 reviews

Modern 2BR/2BA • Breathtaking Views • Parking Spot

Enjoy executive living in this stylish 2-bedroom, 2-bath condo with an open-concept layout and abundant natural light. Relax in the spacious living area with two sofas and a large flat-screen TV. The modern dining area seats four, and the sleek kitchen is fully equipped. The primary bedroom features a king-size bed, and the second offers a cozy queen. Includes in-suite laundry, a dedicated desk, high-speed Wi-Fi, and a large private balcony with stunning panoramic city views. Parking included.

Guest favorite
Home in York
4.81 out of 5 average rating, 110 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 favorite
A spacious living area features a large, sectional sofa covered in neutral fabric, complemented by a glass coffee table. Natural light pours in through expansive windows, offering views of the skyline. A piece of minimalist wall art adds a subtle touch to the concrete walls.
Loft in Liberty Village
4.95 out of 5 average rating, 107 reviews

Sun-Filled Two-Storey Loft | 15 Minute FIFA Walk!

Welcome to our two-storey loft in the heart of entertainment! You have the place to yourself, and location strikes the perfect balance of quiet, yet close to the action. Most popular booking reasons: access to concert venues, conference centres, downtown core, waterfront and all professional sports. Work from home is ideal with a dedicated work space. The balcony gets lots of sun light; it's a cozy place to relax, have a drink and read a book. Make yourself at home and enjoy the area!

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, 210 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

Superhost
A welcoming living area features a plush circular ottoman at the center, surrounded by two vibrant blue armchairs. A comfortable blue sofa is positioned against a wall of large windows, offering ample natural light. A decorative area rug adds warmth, while soft lighting enhances the inviting space.
Home in York
4.94 out of 5 average rating, 16 reviews

Spacious 3BR Home • Backyard • Great Location

Welcome to a spacious 3-bedroom home—perfect for remote work, or family getaways. With a fully equipped kitchen, large dining area, and cozy living room, there's plenty of room to relax. The lower-level features a big-screen TV, loaded bookshelf, games, and an office desk. Each bedroom offers comfortable sleeping arrangements with fresh linens. Enjoy the private backyard, fast Wi-Fi, and in-suite laundry. A well-designed space that feels like home—whether you're staying a week or a month.

Top guest favorite
Apartment in York
4.95 out of 5 average rating, 19 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!

Superhost
Apartment in Junction Triangle
4.89 out of 5 average rating, 28 reviews

Toronto Junction | Walk to Cafés, Shops & Dining

Welcome to our newly renovated suite in Toronto’s vibrant Junction neighbourhood! Just steps from the UP Express (airport to Union Station) and subway, getting around is effortless. Surrounded by top restaurants, breweries, parks, and shops, you’re minutes from the buzzing Dundas St. West. This bright, charming space offers comfort and convenience, making it perfect for exploring the city with ease. Sleeps 4 guests comfortably on Queen bed + sofa bed.

Superhost
A modern kitchen features sleek white cabinetry and stainless steel appliances. A round dining table with light grey upholstered chairs is positioned in the center, complemented by a decorative bowl. Soft lighting adds warmth to the space.
Apartment in Midtown
4.9 out of 5 average rating, 79 reviews

Bright Luxurious 2 Bdrm Apartment

Nestled near little Portugal and Corso Italia neighborhoods. Experience and enjoy this 2 Bedroom Luxury Boutique apt of a newly built (2023) building. Centrally located within a 3-minute walk to TTC station and minutes walk away to trendy cafes, and restaurants on Geary Avenue, Toronto's hidden gem for food and drinks. Our home features high ceilings and large windows and is the perfect retreat for anyone wanting to visit the city! Free Parking.

Top guest favorite
A contemporary living space features exposed brick walls and industrial accents. A sleek kitchen island with black stools complements the modern design. Natural light filters through the softly draped windows, highlighting the comfortable sofa and coffee table arranged on a patterned rug.
Home in Downtown Toronto
4.98 out of 5 average rating, 44 reviews

Designer 3-Storey Loft w/ Balcony + CN Tower View

1860's designer 3-Storey-Loft in the heart of Little Italy. Safe, walkable neighbourhood. A stone's throw from cafes, restaurants, bars, Kensington Market, Koreatown, Annex/Harbord Village. The loft boasts luxury high ceilings, private balcony + stunning wrap-around deck. Enjoy rooftop views of the Toronto skyline + CN Tower. Fast Fiber Optic WIFI. Central AC

Top guest favorite
An open-concept living space features large floor-to-ceiling windows, allowing natural light to fill the area. A dark accent sofa is arranged around a circular coffee table, with an artful piece displayed on the wall and a laid-back patterned area rug beneath. A lush plant is visible through the windows.
Home in Toronto
5 out of 5 average rating, 21 reviews

Luxury Retreat • Casper King Beds • Private patio

Celebrities Favourite! Brand new modern luxury custom laneway house in downtown Toronto comes with a free parking spot. It has 14-foot ceilings and floor-to-ceiling windows that fill the space with natural light. Both bedrooms feature Casper king mattresses for a restful night's sleep. Private backyard with modern outdoor furniture

Guest favorite
Apartment in Little Portugal
4.99 out of 5 average rating, 76 reviews

Sunny Private Patio Retreat • Walk to Everything

Spacious, bright, and stylish unite right in Downtown Toronto. Steps away from public transportation. And 3 minute's walk to Queen Street West. Voted by Vogue Magazine as one of the 15 coolest neighbourhoods in the world. Steps from some of the highest-rated restaurants, cafes, and retail stores this city has to offer.

Popular amenities for Oakwood Village vacation rentals

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!

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