
Vacation rentals in Oakwood Village
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Top-rated vacation rentals in Oakwood Village
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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

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.

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

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!

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

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.

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!

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.

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.

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

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

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
Other great vacation rentals in Oakwood Village

Bright and Modern Near Restaurants

Charming Apartment with Patio in Midtown Toronto

Modern Rustic Laneway Entire Home w/Patio

Midtown 4 bedroom home Free Wi-Fi and parking

Charming 5-Bedroom Forest Hill Home

Spacious Midtown 1BDRM-Great View/Parking/ Gym

Designer 2BR Home • Office & Deck • Wychwood Area

Cozy suite in Oakwood Village
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!
Destinations to explore
- Fitness-friendly rentals Oakwood Village
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- Private suite rentals Oakwood Village
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Union Station
- BMO Field
- The Danforth Music Hall
- Downsview Park
- Harbourfront Centre
- Toronto Eaton Centre
- Niagara Falls State Park
- Exhibition Place
- Toronto Zoo
- Scarborough Town Center
- Nike Square One Shopping Centre
- Trinity Bellwoods Park
- Niagara Falls
- Massey Hall
- Enercare Centre
- Casa Loma
- Yorkdale Shopping Centre
- York University
- Coca Cola Coliseum





