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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 cozy backyard space is presented, featuring comfortable seating surrounding a glass table with a fire pit. Soft lighting and a large umbrella create an inviting atmosphere. Greenery and decorative elements enhance the serene environment, with a charcoal grill visible in the background.
Home in Oakwood Village
4.96 out of 5 average rating, 27 reviews

Modern Basement Apartment

Stay in style and comfort at our centrally located Toronto Airbnb basement apartment. Just steps from the #90 bus, which takes you on a short 15-minute ride to St. Clair West subway station, or enjoy a pleasant walk to the station. Exploring Toronto has never been easier. This apartment has two bedrooms and three beds, ensuring ample space for you and your guests to relax in comfort. After a day of sightseeing, unwind in the fenced-in backyard, providing a serene oasis in the heart of the city.

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.

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

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
4.88 out of 5 average rating, 99 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.

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 spacious living area is furnished with a large blue couch and a comfortable beige armchair. A patterned area rug is centered on the wooden floor, while framed artwork and photographs decorate the walls. Natural light floods in through large windows, enhancing the cozy environment.
Home in Earlscourt
4.97 out of 5 average rating, 29 reviews

Boutique Toronto Home near Downtown

Charming Toronto Retreat – Steps to Shops, Dining & Transit Welcome to a cozy and stylish home located in Toronto’s vibrant York neighborhood. Surrounded by beautiful local restaurants, and boutiques, just minutes from downtown and steps from transit. Cozy & Comfortable: – Bright, inviting spaces – Fully equipped kitchen – Peaceful backyard Short walk to St. Clair West, parks and groceries Perfect for a city getaway, work trip, or family stay, enjoy comfort and in a quiet, central spot.

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, 78 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.
Apartment in Oakwood Village
4.87 out of 5 average rating, 77 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.

Top Guest favourite
A spacious living area is featured with a dark sectional sofa adorned with textured cushions. A round coffee table, topped with a decorative bowl and books, complements the soft area rug beneath. Natural light filters through large windows, illuminating the neutral walls and decor.
Apartment in Wychwood
4.95 out of 5 average rating, 73 reviews

Modern 1-Bedroom Loft

Experience the city like a local in this unique professionally designed space. This large, bright, airy space boasts 14 ft ceilings and has in-suite heating and AC. We are centrally located (steps away from Casa Loma and downtown) with plenty of options for food, drinks, and local shops. The area has excellent walkability and great transit access. 24km from/to Pearson Airport and 6km from/to Billy Bishop Airport

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.

Top Guest favourite
A dining area is presented with a wooden table set for meals. A textured vase holds an arrangement of greenery and foliage. Black-framed photographs adorn the wall, creating an artistic backdrop, while a pendant light offers soft illumination.
Apartment in Wychwood
4.97 out of 5 average rating, 97 reviews

Renovated Modern 2 Bedroom Suite w/ City Views

Experience the city like a local in this newly renovated two-bedroom suite. This ample, bright, airy space has beautiful city line views. We are centrally located (steps away from Casa Loma and downtown) with plenty of options for food, drinks, and local shops. The area has excellent walkability and great transit access. 24km from/to Pearson Airport and 6km from/to Billy Bishop Airport

Top Guest favourite
A welcoming entryway features a stone staircase leading to a pair of wooden double doors. Flanking the entrance, potted plants add greenery, while large windows provide views of the surrounding yard. The roof is tiled, and a well-maintained lawn adds to the home's appeal.
Place to stay in Etobicoke
4.94 out of 5 average rating, 80 reviews

The Snug Oasis - Burrow (Near Airport)

Make some memories at this enchanting, family-friendly ranch style estate. Welcomed by old Oak trees and classic stone facades, your suite is on the ground floor. A warm wooden chamber abundant in antique charm, it overlooks the gorgeous garden and resort size pool. Birds chirping, bunnies visiting; nearby restaurants and poolside barbecues make it the perfect retreat!

Popular amenities for Oakwood Village holiday rentals

When is the best time to visit Oakwood Village?

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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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