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Holiday houses 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
A modern dining area features a long wooden table surrounded by various chairs. A colorful artwork decorates one wall, while large windows allow natural light to brighten the space. The kitchen can be seen in the background, showcasing a clean and contemporary design.
Home in Trinity-Bellwoods
4.92 out of 5 average rating, 66 reviews

Big Bright Artist’s Own Victorian - Modern Scandi

Enjoy charm and style in this artist’s own spacious and bright 1 bdrm. This restored Victorian home features a modern Scandinavian kitchen with Cambria quartz counters and Bosch appliances. Unwind with in-ceiling speakers and movie nights on a 65” Frame TV. Walk to trendy Dundas & Ossington district, known for its top restaurants, lively nightlife, cafés, and boutiques. Stroll through nearby Trinity Bellwoods Park. Transit and bike share steps away. Private entrance and foyer. True urban oasis!

Top Guest favourite
A compact bedroom is furnished with a spacious bed dressed in striped linens. Artwork is displayed on the walls, and a mirrored closet adds depth to the space. Natural light enters through partially covered windows, while soft bedside lamps provide illumination.
Apartment in Oakwood Village
4.96 out of 5 average rating, 139 reviews

Cozy 1-bdm suite filled with amenities & parking

A whimsically decorated basement apartment with a separate entrance that welcomes all. The exposed brick gives it a unique character and the location means you're not too far from downtown, close to public transportation and away from congestion. Enjoy amenities such as a kitchenette with all the fixings for a continental breakfast, plentiful snacks and refreshments. The kitchen offers an induction cooktop & toaster oven instead of a stove. Guests can enjoy Netflix, Wifi, and free parking.

Top 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, 138 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
An open-concept basement suite is shown, featuring a spacious bed with fresh linens. A large smart television is mounted on the wall, and a kitchenette with modern appliances, including a fridge and coffee maker, is visible in the background. Light wood flooring enhances the room's brightness.
Guest suite in Earlscourt
4.92 out of 5 average rating, 167 reviews

A cozy suite in transit friendly Corso Italia.

A newly, hotel inspired, renovated cozy basement suite in the transit-friendly neighbourhood of Corso Italia. The suite includes an open-concept living, kitchenette, high-speed internet and everything you need for a perfect stay in Toronto. Less than a 10 minute walk from a variety of restaurants, a park, and shops on St. Claire avenue. With public transportation steps away( 1 minute to a bus stop), it's a perfect base for exploring the neighbourhood and the city. Parking is available!

Superhost
A modern living room features a light grey sectional couch with decorative pillows, centered on a patterned area rug. A round coffee table holds a small plant and magazines. Natural light floods the space through the open layout, highlighting the restored brick wall and wooden flooring.
Home in Oakwood Village
4.87 out of 5 average rating, 68 reviews

Modern Rustic Laneway Entire Home w/Patio

This cozy historic house is an area that many years ago used to be the apple orchard of John Oakwood, of Oakwood Ave. This rustic brick laneway home is where the apple pickers used to live and a perfect getaway. - A Queen & twin size bed, 3 ppl -A/C -Kitchen -Nespresso/ Frother -Bathroom -Backyard /patio -BBQ -2 Smart TV's -Free Wi-Fi -Laundry - 2 min to closest paid street parking Parking Info Download GreenP App Parking Rates: Day Max (7am – 6pm): $4.50 Night Max (6pm – 7am): $2.50

Top Guest favourite
Guest suite in York
4.94 out of 5 average rating, 81 reviews

Spacious suite with 8 foot ceilings.

Spacious and clean suite. Short walk to bus stops with routes south to Keele, Ossington and Dundas West stations. Easy travel to north to Humber River Hospital, York University and Yorkdale Shopping Mall. Close to cafés, restaurants and Stockyards Shopping Centre. Eleven kilometers from Pearson airport. Note: My Airbnb is not downtown in the city centre. Please take note of the area in proximity to tourist attractions, so you can plan accordingly. Registration number: STR-2312-GSGRVT

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, 75 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 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.
Apartment in Oakwood Village
4.87 out of 5 average rating, 76 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.

Guest favourite
A modern living area features a comfortable gray couch positioned near a low white coffee table. A decorative shelving unit displays various sculptures and vases, while light streams in through two small windows above. A neat sleeping area is visible in the background, separated by the shelving.
Guest suite in Eglinton West
4.86 out of 5 average rating, 216 reviews

BRIGHT MODERN STUDIO WITH TERRACE

Bright, airy, modern and new unit with private entrance in midtown Toronto. One minute to transportation, supermarket, bakeries, pharmacies, and all other conveniences. Thirty minutes to downtown and 25 minutes to Yonge and Eglinton by public transport. The space is recently renovated with a small terrace for outdoor space. The unit is self contained with a private kitchen, bathroom and laundry. Sorry, there is no smoking on the property.

Superhost
Home in Oakwood Village
4.75 out of 5 average rating, 12 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.

Guest favourite
A comfortable living area features a plush sofa against a textured wall, complemented by a wooden coffee table. A small dining table with chairs is positioned nearby, and a window allows natural light to illuminate the space. Art pieces adorn the walls, adding visual interest.
Bungalow in Oakwood Village
4.94 out of 5 average rating, 50 reviews

Comfy Bungalow in Midtown TO

You and your guests will enjoy this cozy, spacious bungalow in the heart of Toronto. Located in Humewood/Oakwood, it’s easy to get around from here to all parts of the city. The house is tidy and well-maintained with lovely landscaping and artful touches. A great spot for you to enjoy in your downtime visiting the city.

Popular amenities for Oakwood Village holiday rentals

When is the best time to visit Oakwood Village?

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Avg. price$111 NZD$108 NZD$110 NZD$115 NZD$125 NZD$134 NZD$146 NZD$153 NZD$150 NZD$136 NZD$145 NZD$120 NZD
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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 $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 9,980 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wi-Fi availability

    300 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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