
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.

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!

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.

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!

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!

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

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

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.

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.

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.

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.

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.

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.
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When is the best time to visit Oakwood Village?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
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!
Destinations to explore
- Pet-friendly rentals Oakwood Village
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Nike Square One Shopping Centre
- Bay Station
- BMO Field
- Harbourfront Centre
- Exhibition Place
- Toronto Zoo
- Toronto Eaton Centre
- Trinity Bellwoods Park
- Financial District
- Massey Hall
- Niagara Falls State Park
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- Toronto City Hall




