House holiday rentals in Oakwood Village

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Top-rated house rentals in Oakwood Village

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

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Top guest favourite
The exterior of the duplex house is shown, featuring a well-maintained front lawn with blooming flowers. The building has a brick façade with large windows framed by vibrant greenery. A small balcony is visible on the upper floor, adorned with potted plants.
Home in Deer Park
4.97 out of 5 average rating, 117 reviews

2-Bedroom House In Deer Park

Welcome to our charming 2-bedroom duplex house nestled in the beautiful Deer Park neighbourhood of Toronto! This cozy Airbnb is the perfect home away from home for your stay in the heart of the city, with subway, shops and parks within 10 minutes' walk. This newly renovated house is on the ground floor of a duplex and boasts an amazing sun-room, beautifully furnished living and dining rooms, a fully equipped modern kitchen and 2 comfortable bedrooms. Parking and laundry is available on request.

Guest favourite
A hot tub is illuminated with soft blue lighting, surrounded by wooden decking and adorned with lush greenery. Soft lighting strands are suspended nearby, creating a serene atmosphere during the evening hours. Brick walls add a warm texture to the space.
Home in Oakwood Village
4.97 out of 5 average rating, 110 reviews

Breathtaking Hot Tub Oasis 9 Guest 4BR 3WR Firepl

Relax and unwind in this downtown Toronto oasis. Trendy St. Clair West is a short 7 minute walk from your doorstep, and offers a wide range of excellent restaurants, bars, cafes, bespoke grocery stores, health food stores and shopping to suit every taste. On Saturdays, make your way to the bustling Wychwood Barns farmer's market for fresh goodies. Need a nature fix? A five minute walk brings you to Cedarvale Park, one of the city's best kept nature preserves. Bus stop located right outside.

Guest favourite
The spacious living area features a light-colored sectional sofa arranged around a circular coffee table. A large Smart TV is mounted on the wall, while abstract artwork adorns the walls. Natural light enters through double doors leading to the patio, complemented by a decorative plant.
Home in Markham
4.95 out of 5 average rating, 149 reviews

2BR+2Bath! 2queen beds! Luxury Private Quiet Clean

Fully renovated, modern, Bright, luxurious, and spacious ( over 1800 sq/ft) 2-bedroom, 2-bathroom high ceiling above ground apartment, separate entrance, and Patio for your next cozy home away from home! 5-star rated and top 5% of homes in AirBnB! As central as it gets in the GTA. You'll be close to Pearson Airport, Highway 401/404/407, shopping malls, grocery stores, and an array of trendy restaurants, movie theaters, parks, and bicycle/ hiking trails all around Book With Confidence!

Guest favourite
A modern living area features a sleek white sofa adorned with yellow and gray pillows. A round black coffee table is positioned in front, displaying magazines. A vibrant artwork hangs on the wall, complemented by a floor lamp and a decorative lantern in the background.
Home in Oakwood Village
4.89 out of 5 average rating, 97 reviews

Spacious 1 BD basement apartment

Forget your worries in this spacious and serene space. Peaceful neighborhood in central Toronto. This unit is everything you need. Perfect for couples. 700 sq ft, brand new furniture, transit-friendly and a 10 minute walk to a variety of restaurants and coffee shops. Transit will take you in Downtown in 20 min. Fresh linens, towels, Wi-Fi, coffee maker, toaster are provided. Guests have a private seperate entrance. I want people to feel comfortable in the space 6ft max height is recomended.

Guest favourite
The living room is enhanced by natural light from the windows, which are adorned with sheer curtains. A gray sofa faces a mounted flat-screen TV, and a sleek white entertainment unit is situated below it. Light hardwood flooring adds warmth to the cozy space.
Home in Dovercourt Village
4.91 out of 5 average rating, 106 reviews

Toronto Modern Haven: 1 BR w/ Queen Sofa Bed

Welcome to your urban oasis in the heart of Toronto located on the main floor! This modern retreat offers a fully equipped kitchen, a cozy living room with a sofa bed, and a bedroom with a queen-size bed. Immerse yourself in the vibrant energy of the city during the day, and relax in this peaceful haven at night. Indulge in local flavors at nearby eateries, discover hidden gems in eclectic neighborhoods, and soak in the city's iconic skyline views. Your perfect Toronto getaway starts here!

Top guest favourite
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, 199 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

Top guest favourite
A spacious sleeping area is highlighted by a comfortable bed adorned with patterned bedding. A bright seating area features a vibrant red couch and a blue chair, complemented by natural light from large windows. A flat-screen TV stands on a modern media console.
Home in Bedford Park
4.91 out of 5 average rating, 183 reviews

Uptown Separate Bright Suite ( Free Parking )

Great private and quiet bright furnished basement suite(just 6 steps under street level) with separate entrance in a classy and safe Bedford Park neighborhood in central Toronto,12 min walk to Lawrence subway station,2 min to bus station,3 min to Loblaws(best Canadian grocery store), 2 min walk to Yonge street with shops, bars and the best restaurants ,18 min drive to Pearson int airport and tennis courts nearby. Our place is perfect for couples, solo adventurers and business travelers.

Top guest favourite
The living area features a modern design with a comfortable sofa accented by patterned pillows. A marble dining table is surrounded by elegant chairs. A striking chandelier hangs above, while a large round mirror reflects the ambient light from windows dressed in soft curtains.
Home in Corktown
4.99 out of 5 average rating, 238 reviews

Stylish 1870s Home near Distillery District & Old Toronto

“Rated a Top 10 listing by BlogTO and frequently featured as a must-stay in Toronto. Love thoughtful details? You’ll find them here in this stylishly remodeled 1870s rowhouse. Start your day at St. Lawrence Market, wander through the pedestrian-friendly Distillery District, and explore nearby cafés, restaurants, and bars. In the evening, retreat to the plush, charcoal-hued bedroom and drift off under the glow of a tiered Restoration chandelier. The perfect Toronto stay awaits.”

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, 68 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
An inviting sleeping area is highlighted by a spacious bed with neatly arranged pillows. A stylish lamp provides warm lighting, while a full-length mirror is positioned beside the wall. A cozy throw blanket is draped over the bed, and a magazine rests on the bedside table.
Home in York
4.83 out of 5 average rating, 200 reviews

Cozy and Chic Gem in the City

Entire lower level unit. Very clean and cozy unit in a great friendly neighborhood. The unit is bright and airy. The bathroom and kitchen is yours to use. Separate entrance through the side door of the house. Closet space to store your luggage and clothes. Coffee machine with pods and kettle are at your disposable. Extra blankets and pillows are available upon request. While the unit offers a private setup, the main house may also be accessed or shared as per your needs.

Guest favourite
A living area features a sleek black futon and a modern television on a low-profile media console. A glass coffee table is placed in front of the seating, while a small dining table with black chairs is positioned against the blue wall. Decorative wall art adds subtle interest.
Home in Mississauga
4.89 out of 5 average rating, 118 reviews

Mississauga Bsmt Apartment off of Bloor St!

Basement apartment with seperate entrance and complete privacy, located in Mississauga bordering Toronto. A minute walk to Bloor Street which goes directly to downtown Toronto. For people taking public transportation there is a great connection on Bloor St to the Kipling Subway station and to Square One Mall. If looking to visit downtown Toronto by public transportation, it will take about 50 minutes. Parks and lots of attractions near by. New Baby and Toddler in house.

Top guest favourite
An open-concept living area showcases a comfortable sofa and modern furnishings on a patterned area rug. Natural light streams through large windows, illuminating the space. A wooden floating staircase leads to the upper floor, while a stylish dining space and kitchen are visible in the background.
Home in Oakwood Village
4.9 out of 5 average rating, 212 reviews

Family Home Near St Clair W and Public Transport

Steps away from vibrant St Clair West with great dining, access to public transport and shopping. A real family home with space and amenities for everyone. Free parking for 2 cars. Open-concept living & dining, well-equipped kitchen. Sunny back deck. 3 comfortable bedrooms. Spa bathroom with heated floor. Perfect for families who are in town for reunions, weddings, birthday parties and visiting. Quiet hours after 10pm - not suitable for groups in town ‘to party’.

Popular amenities for house rentals in Oakwood Village

When is the best time to visit Oakwood Village?

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Avg. price$81 SGD$74 SGD$80 SGD$82 SGD$90 SGD$97 SGD$104 SGD$108 SGD$102 SGD$94 SGD$103 SGD$84 SGD
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Quick stats about house rentals in Oakwood Village

  • Total holiday rentals

    Explore 190 holiday rentals in Oakwood Village

  • Nightly prices starting at

    Oakwood Village holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wifi availability

    190 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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