Holiday rentals in Oakwood Village

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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
An open living area features a light-colored sofa covered with a protective cover, a coffee table, and a flat-screen TV mounted on the wall. Natural light enters through large windows dressed with sheer curtains, complementing the warm wood tones of the flooring.
Guest suite in Oakwood Village
4.91 out of 5 average rating, 58 reviews

Chic Midtown Toronto Suite / Newly Renovated

Welcome to our stylish and newly renovated suite located in the trendy St. Clair Avenue West area of Midtown Toronto! The suite features a spacious bedroom with a plush queen-sized bed, a fully equipped kitchen with brand-new appliances, and a sleek bathroom with a luxurious rain shower. Enjoy the convenience of being just steps away from top restaurants, cafes, and shopping in one of Toronto’s most vibrant neighbourhoods. 20 minutes walk to St. Clair West station, 5 minutes to the streetcar.

Guest favourite
Home in Eglinton West
4.84 out of 5 average rating, 69 reviews

3BDRM/2Bath near subway/Toronto w/parking

Welcome to our newly renovated 3 bedroom home, in the heart of Toronto. With just a 10-min walk to your nearest subway/metro station, commute to the city is a breeze. A quick 15-20 min drive to the vibrant Downtown Toronto or Toronto Pearson airport. Our location offers convenience & accessibility. Restaurants, shops, cafes, groceries & transit are nearby. * 3 bedroom / 2 bath– Sleeps 6 * Free Wifi * Fully equipped kitchen * Washer & dryer * Professionally Cleaned * Private Parking: 3 cars

Top guest favourite
A Mid-Century Modern themed bedroom features a queen bed with crisp white linens and decorative pillows in warm tones. Floral artwork adorns the walls above the bed. A nightstand holds a lamp and a small vase with flowers, adding a touch of color to the space.
Guest suite in Earlscourt
4.95 out of 5 average rating, 147 reviews

Midtown Mid-Mod

Bright, clean and spacious lower-level guest suite located in Mid-Town’s trendy St. Clair West neighbourhood. Our suite is best suited for adults who want to explore the city and take in the sites, business travelers who want privacy and a comfortable workspace or families visiting relatives. We offer the amenities you’d need and some you wouldn’t expect. Mid-mod inspired bedroom with Queen bed makes for a great place to rest your head after a visiting one of our many trendy local restaurants.

Flat in York
5 out of 5 average rating, 3 reviews

Cozy Toronto Midtown Basement Apartment

Welcome to our cozy basement apartment in the heart of Midtown Toronto! This fully furnished space features a comfortable bedroom, a stylish living area, a well-equipped kitchenette, and a modern bathroom. Enjoy high-speed Wi-Fi, a smart TV, and convenient access to public transportation, shops, and restaurants. Ideal for solo travelers or couples looking for a quiet retreat in a vibrant neighborhoods. Babies are welcome too. Book your stay today and experience the best of Toronto living!

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 Earlscourt
5 out of 5 average rating, 71 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
A modern kitchen with dark wooden cabinetry is complemented by stainless steel appliances, including a refrigerator and microwave. A countertop provides space for meal preparation, while a neutral backsplash enhances the overall design. Natural light illuminates the wood-patterned floor, creating a welcoming environment.
Flat in Oakwood Village
4.86 out of 5 average rating, 74 reviews

1 x Bedroom Modern Apartment (2xBeds)

Enjoy the bright 1 x bedroom and business friendly basement apartment with complete separate entrance. Newly renovated space. 8ft Ceilings throughout. Centrally located for easy access to downtown and uptown. In suite laundry & wifi and Netflix as well. It is a basement apartment so people live in the unit above. The apartment has been built to code with acoustic insulation. No parking available. Street parking permits available. No parties, smoking or loud groups.

Home in York
5 out of 5 average rating, 4 reviews

brand new city oasis

Be among the first to stay in this brand-new home, perfectly located for easy access to Toronto’s top spots. Just minutes from public transit, shopping centres, Yorkdale Mall, and Downsview Park. Enjoy quick trips downtown, to York University, or anywhere in the city with easy access to Highways 401 and 400. Designed for comfort and style, it’s ideal for families, friends, or business travellers looking for a modern retreat in a prime location

An open-concept living area features a large sectional sofa facing a wall-mounted TV. Natural light floods in through expansive glass doors. A wooden coffee table sits in front, adorned with decorative items, while plants add a touch of greenery to the space.
Home in York
4.86 out of 5 average rating, 87 reviews

Luxury Modern House: Hot Tub, Gym & Steam Shower

Luxury residence in Humewood/Cedervale neighbourhood. Modern and contemporary open concept house in amazing location offers a relaxing vibe with a ravine nearby. Over 2800 square feet of living space, 11 foot ceilings in entertainment room, vaulted ceiling in master bedroom, luxury towels, linens and robes for your convenience. Amenities: - Steam Shower - Hot Tub - Heated Floors in Master Ensuite - Wood Burning Fireplace - Gym

Superhost
A clean private room features a full-size bed with neatly arranged white linens and two rolled towels placed at the foot. A small desk and chair are situated by a window, allowing natural light to brighten the space.
Private room in Toronto
4.91 out of 5 average rating, 139 reviews

#2 Private room close to Lansdowne Subway Station

Clean Private room that locate close to Lansdowne subway station. This room for 1 person only. if you have an extra guest, please book room 1 or 3. A 8 minute walk or 2 mins with Bus (3 stops away) from Lansdowne station. No Kitchen. Full size bed, wifi, shared washroom, towel, Shampoo and bodywash Bathroom will be clean daily. Street parking only (midnight - 7AM need permit) for parking options, please check "other details"

Top guest favourite
A bright and spacious room features a neat single bed with a simple white cover. A small bedside table holds a soft lamp, and a piece of wall art adds a touch of color. A closet is visibly integrated into the design, providing storage options.
Private room in North York
4.9 out of 5 average rating, 268 reviews

FREE parking- cozy, inexpensive room in bsmt

Enjoy your place in our cozy place at very convenient location. This apartment is prepared especially for you, . We have free Wifi with fiber optic cable and more than 4 parking space so that you can enjoy your stay. We provide breakfast with cereal, breads, milk, tea, coffee with many flavors to choose. If you need iron, shampoo, or any travel essentials, we got them all for free. Note: *PLEASE REMOVE SHOES AT THE ENTRANCE

Superhost
Home in Oakwood Village
4.8 out of 5 average rating, 10 reviews

Casa del Jo | Boho 2BR Retreat + Free Parking

Stylish boho 2BR main-floor suite tucked in a quiet, walkable neighbourhood — just 1 bus to downtown Toronto, Entertainment District, and Financial District! Enjoy a luxury renovated bathroom, cozy king + queen beds, fast WiFi, and free parking. Ideal for professionals, mature students, or digital nomads on longer stays. Close to transit, St. Clair, Casa Loma, George Brown, Yorkdale & more.

Top guest favourite
Home in Earlscourt
5 out of 5 average rating, 10 reviews

4BR home - Patio, BBQ & Parking in St Clair West

Stay in a stylish and spacious four-bedroom home in Toronto’s vibrant St. Clair West Village, steps from Corso Italia. This home has comfy queen beds, two full bathrooms, a bright living room and dining room, a backyard with a BBQ, and free parking. Walk to great restaurants, shops, and parks. Public transit is nearby, so you can get around the city easily.

Popular amenities for Oakwood Village holiday rentals

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Quick stats about holiday rentals in Oakwood Village

  • Total holiday rentals

    Explore 300 holiday rentals in Oakwood Village

  • Nightly prices starting at

    Oakwood Village holiday rentals start at £8 per night before taxes and fees

  • Verified guest reviews

    Over 9,520 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wifi availability

    300 of Oakwood Village holiday rentals include wifi 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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