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House holiday rentals in Oakwood Village

Find and book unique houses on Airbnb

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, 118 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
A modern kitchen area features smooth gray cabinetry and stainless-steel appliances. A wooden table is set for dining, with simple dinnerware arranged on top. A plush brown sofa is positioned nearby, complemented by decorative elements on the wall and a stylish clock.
Home in Wychwood
4.96 out of 5 average rating, 136 reviews

Amazing 1BR Suite Near Downtown!

A private one bedroom luxury basement suite in popular Wychwood has it all: amazing kitchen; open living area with oversized sofa - watch Netflix or cable on the wide-screen TV; dine at a reclaimed wood table; sleep great on a queen size Sealy Posturepedic mattress in the bedroom, 8ft ceilings, private entrance; new washer/dryer! Public transit is steps away. Visit famous Wychwood Barns or shop on St. Clair West - less than 10 min walking. High speed unlimited wifi, premium cable TV, and more!

Guest favourite
A well-lit living area features a large window allowing natural light to flow in. Seating is provided by a dark sofa and a dining table with two white chairs. Decorative curtains add a touch of warmth, complemented by a mounted television on the wall.
Home in Oakwood Village
4.82 out of 5 average rating, 101 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. Designed to host visiting families or multiple couples. 3 bedrooms (1 King and 2 Queen size beds). Free parking. 2 televisions, Wifi, Netflix all included for your entertainment. Kitchen, 2 washrooms, enclosed private patio and a backyard. Laundry washer available on site. High speed internet and working space

Top Guest favourite
A dining table is elegantly set with two decorative plates, glasses of varying sizes, and utensils arranged symmetrically. A soft glow is provided by a small candle flickering in a metallic holder, creating a subtle ambiance for mealtime.
Home in Vaughan
4.99 out of 5 average rating, 377 reviews

Adorable — One Bedroom Guest Unit in Vaughan, ON

Enjoy a stylish and peaceful stay at this centrally located one-bedroom lower-level unit, perfect for both leisure and business travelers. With your private entrance, parking, and all the essentials, it’s your ideal home away from home. Features include a full kitchen, bathroom, internet, smart TV, one Queen and one sofa bed, and a functional workspace. Steps from FreshCo, Walmart, restaurants, and services. Minutes to Vaughan Mills, Canada’s Wonderland, Cortellucci Hospital and transit.

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, 202 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, 185 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
A bright living room is highlighted by a cozy sofa and a sleek coffee table. Two yellow chairs face large windows, allowing natural light to fill the space. A flat-screen TV is mounted on the wall, and a decorative plant adds a touch of greenery.
Home in Roncesvalles
4.99 out of 5 average rating, 176 reviews

Luxury modern Victorian - private parking included

This recently renovated gem has all of the comforts of home, with a fully appointed kitchen that has everything you need to cook a great meal. Nespresso coffee and a selection of teas are also included. Two Smart TVs and a Bluetooth speaker for entertainment. Two comfortable beds and a spacious spa bathroom will make your stay feel like home. A work remote work set up is available for those who require it. The private backyard includes a gas BBQ and private parking is included.

Top Guest favourite
An outdoor seating area is showcased, featuring a comfortable couch adorned with patterned cushions. Flanking the couch, two red chairs face a wooden fence, while a decorative lantern and potted plants add touches of greenery, highlighting the inviting atmosphere of this private space.
Home in Cabbagetown
4.94 out of 5 average rating, 588 reviews

Comfy Oasis In Historic Downtown Neighborhood

According to Airbnb, we are "One of the most beloved homes on Airbnb". Now in the top 5% of all listings on AIRBNB. Superhosts for 10 years! This renovated guest house features an open-plan kitchen, a spiral staircase to a beautiful and open loft suite, with custom furniture and decorating accessories (1 bed + 1 sofabed). Enjoy the beautiful garden in the summer, and sip any of the more than 15 different complimentary teas and coffees we offer. This guest house is FULLY equipped.

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.

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, 213 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’.

Top Guest favourite
Home in Corktown
4.99 out of 5 average rating, 240 reviews

Stylish 1870s Home near Distillery District & Old Toronto

Named a Top 10 Toronto stay by BlogTO, this beautifully restored 1870s rowhouse blends historic charm with modern refinement. Thoughtfully designed throughout, it’s steps from St. Lawrence Market, the Distillery District, and some of the city’s best cafés and restaurants. In the evening, unwind in the serene, charcoal-toned bedroom beneath the warm glow of a statement chandelier—your refined Toronto retreat awaits

Popular amenities for Oakwood Village house rentals

When is the best time to visit Oakwood Village?

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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 $17 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    190 of Oakwood Village holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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