Vacation rentals in Oakwood Village

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oakwood Village

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

1 of 1 pages1 / 1
Top guest favorite
A modern, multi-story house features a mixture of light stone and dark siding. The structure includes multiple large windows and decorative balconies, surrounded by neatly manicured landscaping. A driveway leads to a garage located beneath the home.
Apartment in York
4.97 out of 5 average rating, 60 reviews

Bloor/Jane Gem

WELCOME TO Modern Luxury ~ studio apt. in Bloor West Village - FIFA FANS ~ 5 min. walk to subway - minutes to Gardiner Expressway & QEW ~ park FREE on driveway ~ private entry ~ private patio ~ 10 ft. ceiling ~ KING BED ~ separate glassed-in shower ~ kitchenette ~ toaster, drip coffee maker, microwave, tea kettle, dishes ~ mini fridge ~ 55” TV ~WI-Fi ~HEATED floor ~ walk to restaurants, sportbars , shops ~ minutes to Old Mill Inn and Humber River

Superhost
Apartment in York
5 out of 5 average rating, 3 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 favorite
A spacious living area features a comfortable dark leather sectional sofa positioned in front of a flat-screen television. A window allows natural light to fill the room, while light purple walls add a touch of warmth. A small coffee table completes the inviting space.
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

Top guest favorite
A bright and airy living space features large corner windows that offer expansive views of the city. A modern sectional couch is paired with a light rug, while a flat-screen television is mounted on the wall. Lush green plants add a touch of nature to the inviting décor.
Condo in Yorkdale
5 out of 5 average rating, 143 reviews

The Penty: Luxurious Penthouse with Pool, Hot Tub

Welcome to our modern & luxurious corner penthouse! Stylishly designed with lush greenery and upscale touches, this bright space offers comfort, elegance, and a relaxed tropical vibe. Take in stunning panoramic city views and unwind with premium amenities including an outdoor pool, hot tub, and steam room sauna. Just a 15-min drive to downtown. Public transit at the doorstep. 10-min drive to Rogers Stadium. Perfect for discerning guests seeking an elevated stay in Toronto’s vibrant urban core

Guest favorite
A modern building featuring a glass facade stands prominently along a tree-lined street. The architecture showcases a blend of contemporary and traditional design, with a mix of vehicles parked and moving along the road, indicating a vibrant urban atmosphere.
Apartment in Yorkville
4.75 out of 5 average rating, 71 reviews

Cozy 1+1 Condo in Yorkville + free parking

Formerly a Four Seasons hotel suite, now fully renovated, this 1 bedroom plus 1 office/den condo with free parking is in the most luxurious area of Toronto: Yorkville. Walking distance to U of T, high end restaurants, cafes, bars and shopping stores, Royal Ontario Museum, and the subway. Smart TV, Bell Fibe, Netflix,& Wifi. Large windows with a breathtaking view and tons of natural light. Walk in Closet for Storage, Washer & Dryer Don’t miss out on this elegant and unforgettable stay!

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

Guest favorite
A spacious living area features large windows allowing ample natural light. A modern grey sofa is accompanied by a stylish armchair, while a round coffee table sits at the center. Decorative art pieces enhance the minimalist design, creating an inviting place for relaxation.
Condo in Toronto
4.94 out of 5 average rating, 51 reviews

2 min to the subway | Patio | Parking | HWY

Stylish townhouse is perfect for both business and leisure travellers. → Easy commute to FIFA WORLD CUP ⚽️ → Easy access to Rodgers Stadium → Spacious roof-top terrace with outdoor furniture → 2 min walk to the subway (TTC) → 20 min subway ride or drive to downtown core → 200m access to major Toronto highways → Short distance from luxurious Yorkdale Mall Enjoy shopping at Yorkdale Mall, a few blocks away or explore the city with easy access to Toronto. subway and all major highways

Guest favorite
An open-concept living area features a light-colored sofa and a chic coffee table, complemented by a neutral rug. A staircase leads to the upper floor, while a dining area is visible in the background near large windows allowing natural light.
Home in Islington
4.92 out of 5 average rating, 132 reviews

Luxury Home - 5 min from airport, 15 to downtown

The stunning house in Etobicoke is only a few minutes from the Airport and City Centre. This spacious open concept, rare luxury modern home, is beautifully designed and decorated. It is a fully stocked home and will have everything you could ever wish for a short-term stay. Perfect for large families and groups! min age 25 yrs to book. Room 1 king bed Room 2 queen Room 3 twin and another twin roll out Room 4 queen no party policy or excessive noise. this is a quiet listing

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
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
Home in Toronto
4.98 out of 5 average rating, 98 reviews

Bright & Cheerful Laneway Home

The Laneway suite is my home and was built in 2022 as my dream home in behind an investment property. I’ve equipped my laneway home with all the modern amenities and have tried to give it a real homey feel. I am an artist and my own art is displayed on the walls. I love music so I’ve equipped it with a nice surround sound system. I travel often for work but I’m always reachable through the airbnb messaging system.

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!

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