Holiday rentals in Oakwood Village

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Oakwood Village

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

%{current} / %{total}1 / 1
Top guest favourite
The exterior of a charming cottage apartment is framed by vibrant orange lilies and lush greenery. Large windows with white trim mark the front, under a gently sloped roof covered in moss. A sturdy wooden door is centrally positioned, welcoming guests to the inviting space.
Guest suite in Centre Island
5 out of 5 average rating, 27 reviews

Island Getaway

Toronto Island cottage apartment Two bedroom, newly renovated, furnished with full kitchen Adjacent to park and beaches, easy access to the downtown, public transit, the Rogers Centre, CN tower, the aquarium, harbour front The island is a car free community accessible in 8 min by ferry or water taxi and does not have grocery stores although there are several restaurants and cafes to eat at. My island retreat is a 2 min walk from the Wards ferry. Winter guests note last City ferry is at 11:15 pm

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.
Flat in Oakwood Village
4.96 out of 5 average rating, 140 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 Mid-Century Modern themed bedroom features a queen bed with crisp white linens and decorative pillows in warm tones. Floral artwork adorns the walls above the bed. A nightstand holds a lamp and a small vase with flowers, adding a touch of color to the space.
Guest suite in Earlscourt
4.95 out of 5 average rating, 151 reviews

Midtown Mid-Mod

Bright, clean and spacious lower-level guest suite located in Mid-Town’s trendy St. Clair West neighbourhood. Our suite is best suited for adults who want to explore the city and take in the sites, business travelers who want privacy and a comfortable workspace or families visiting relatives. We offer the amenities you’d need and some you wouldn’t expect. Mid-mod inspired bedroom with Queen bed makes for a great place to rest your head after a visiting one of our many trendy local restaurants.

Guest favourite
An inviting corner features a rich brick wall, accented by a decorative white antler mount. A plush armchair with a soft throw sits beside a small round table, on which a vintage lamp provides gentle illumination. A circular shelf displays decorative items, enhancing the cozy atmosphere.
Home in Carleton Village
4.97 out of 5 average rating, 70 reviews

Home in Carleton Village

Welcome and feel perfectly at home in our bright and spacious main floor unit with a cozy basement bedroom on a peaceful tree-lined street in the heart of the city. We are conveniently located, nestled between the Junction and St. Clair West, next door to a beautiful large park. Steps away you’ll find St. Clair West parks, shops, and restaurants, Junction shopping and breweries, and the West Toronto Railpath and the Bloor UP station, for quick and easy transit to Pearson airport or Downtown.

Top guest favourite
A serene bedroom features a spacious bed adorned with a light blue quilt. Two bedside lamps provide gentle illumination beside the bed, which is positioned against a wall of windows allowing natural light to fill the room. A mirror reflects the calming space.
Apartment in Yorkville
4.96 out of 5 average rating, 76 reviews

City center/luxury amenities condo in Yorkville

--Safe, well-managed luxury building in a prestigious area, check in with building staff anytime after 4 pm. --Max for 4, 2 Queen beds, inquire about early check-in, late check-out, parking, and DISCOUNT for long-term renting -- Indoor swimming pool, jacuzzi, steam room, gym are open to guests --Steps away from UofT, ROM, subway stations, and bus stops, grocery stores(Whole Food, City Market, Eataly) --Surrounded by luxury brand stores, museums, internet-famous coffee shops, and restaurants

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!

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 Toronto
4.99 out of 5 average rating, 204 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

Guest favourite
A modern kitchen area features stainless steel appliances and sleek cabinetry, complemented by a glass dining table with two chairs. Wooden flooring adds warmth to the space, while a glass partition allows views of the adjoining bedroom.
Apartment in Harbourfront
4.92 out of 5 average rating, 267 reviews

Luxury Downtown Waterfront Condo + Free Parking

Luxury 1BR downtown condo, steps to Scotiabank Arena, Rogers Centre & Harbourfront. Ideal for business trips, couples & Toronto getaways. Located in Toronto’s Entertainment & Financial District, this modern waterfront condo puts you near top attractions, transit, restaurants, and nightlife. Enjoy 5-star building amenities, a spotless, well-designed space, and a comfortable hotel-style stay. Perfect for business travelers, couples, and tourists looking for a central downtown Toronto stay.

Top guest favourite
A bright entryway showcases a spacious seating area with a light-colored couch. Decorative plants are placed strategically, beside a standing mirror and a flat-screen TV mounted on the wall. Soft lighting illuminates the modern design, leading to a glimpse of the bedroom area in the background.
Flat in Stockyards District
4.98 out of 5 average rating, 359 reviews

Modern Retreat in Trendy JUNCTION Neighbourhood

A newly renovated, hotel-inspired lower level suite nestled in Toronto’s buzzing Junction neighbourhood. This vibrant, bright basement, brought to life by its charming and colourful accents, is a quick stroll from a variety of restaurants, breweries, parks, and shops. With public transportation steps away, it's the perfect base for exploring the neighbourhood and the city beyond. And, of course, for unwinding afterward.

Top guest favourite
A comfortable sofa, accented with a variety of cushions in soft tones, is positioned against a plain wall. A round glass coffee table sits in front, holding a few stacked books, creating a cozy seating area.
Townhouse in Roncesvalles
4.95 out of 5 average rating, 160 reviews

New Luxury Suite off Sterling Rd

Early risers will enjoy the morning light that streams through the window, while the night owls will appreciate the black out curtains. We offer a Keyless entry, a gorgeous and spacious walk in shower, extra high ceilings, a Nespresso coffee machine, smart TV, wifi, and a super comfy queen sized bed that is actually a Murphy bed, and can be easily be turned into a sofa!

Top guest favourite
A modern living area features a spacious gray sectional sofa adorned with colorful throw pillows. Abstract artwork is displayed on the walls, while a round coffee table holds snacks. A large window allows natural light to fill the room, with a view of greenery outside.
Home in Annex
5 out of 5 average rating, 220 reviews

Annex Garden Coach House

Welcome to the Annex Garden Coach House! Well suited for solo and family travellers alike, seeking a centrally located, quiet little house, surrounded by backyard trees, in the leafy Annex neighbourhood. You're able to park for free at your private front door, and it's a quick walk to your choice of three nearby subway stations.

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?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$82 SGD$79 SGD$81 SGD$85 SGD$92 SGD$99 SGD$108 SGD$113 SGD$110 SGD$104 SGD$100 SGD$103 SGD
Avg. temp-3°C-3°C2°C8°C14°C20°C23°C22°C18°C11°C5°C0°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 $13 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wifi availability

    300 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!

  1. Airbnb
  2. Canada
  3. Ontario
  4. Toronto
  5. Oakwood Village