Apartment holiday rentals in Oakwood Village

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Top-rated apartment rentals in Oakwood Village

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Top guest favourite
A cozy living area features a grey sofa and two matching armchairs, all positioned on a neutral area rug. A modern arc floor lamp provides soft lighting, while framed art adorns the walls. A small glass side table sits beside the sofa, enhancing the space's functionality.
Flat in Annex
4.93 out of 5 average rating, 221 reviews

Cute Private Apartment near University of Toronto

This cozy main floor apartment with private walk out patio, located on a quiet street in the beautiful Annex neighbourhood. Free parking Laundry in building Shared backyard 5 minute walk to subway (Christie Station) 5 minute walk to Bloor Street, the restaurants and bars of Korea Town, and historic Christie Pits Park. Walking distance to University of Toronto and George Brown College Casa Loma campus. There are a lot of great restaurants, bars and local grocery stores within a short walk.

Guest favourite
A warm and inviting living area features exposed brick walls and a large wooden dining table surrounded by black chairs. Soft lighting from a vintage chandelier casts a gentle glow over a cozy sofa and a stylish entertainment unit, creating a sense of comfort.
Flat in Annex
4.94 out of 5 average rating, 118 reviews

Luxurious Annex/Yorkville 1300 Sq Ft & Parking

Beautifully appointed, top quality furnishings & amenities , spacious Yorkville/Annex rental. Full 1300 sq foot. apartment located within a Heritage Victorian Brownstone! Exceptionally located, walking distance to subway, restaurants and all the sights! Walk to Casa Loma, Royal Ontario Museum & Yorkville. Parking, Wifi, Chromcast, Fibe TV, Local High Def TV included. Fully equipped gourmet kitchen. Air Conditioned. Digital safe for valuables. Treat yourself to pantry snacks, coffee & tea.

Top guest favourite
A cozy bedroom is highlighted by a spacious bed adorned with soft linens and a decorative pillow. Flanking the bed are two minimalist side tables, and stylish pendant lights hang above, providing a gentle glow. The window is covered with contemporary louvered shutters.
Flat in Christie Pits
4.96 out of 5 average rating, 28 reviews

Cozy & Chic Stay | Ossington Station

Welcome to your urban sanctuary in the heart of Toronto's vibrant Dovercourt Village. This bright and modern suite offers the perfect blend of city convenience and neighborhood charm. Guests rave about the stylish interiors, comfy furnishings, and the unbeatable location.​ Whether you're enjoying coffee in the sunlit living room, discovering local gems like Paradise Grapevine and Civil Liberties, or enjoying a stroll through Christie Pits or Bloor Street West, this is your ideal home base.

Superhost
A stylish living area showcases a yellow sofa adorned with decorative pillows, paired with a glass coffee table. Vibrant curtains framed by large windows enhance natural light. A flat-screen TV is mounted on the wall, and a wooden sideboard adds warmth to the space.
Flat in Earlscourt
4.79 out of 5 average rating, 57 reviews

Blue Haven- Beautiful home in perfect location

Relax in this spacious private retreat minutes to downtown. This stylish place to stay is perfect for those looking to experience life in a multi-cultural Toronto neighborhood. Located in the heart of the city's Corso Italia, this quiet, spacious home offers comfort and style. Experience life like a Toronto local, with stores, coffee shops, restaurants, bakeries, and parks at your doorstep. Explore Salsa on St. Clair, historic Casa Loma and Wychwood Barn Farmers Market. NO SMOKING NO PETS

Guest favourite
The entrance of the home features a set of steps leading up to a porch flanked by two lamp posts. A well-maintained garden with potted plants is visible along the pathway. The exterior showcases a combination of light-toned siding and dark accents.
Flat in Earlscourt
4.91 out of 5 average rating, 174 reviews

Spacious & Vibrant upstairs apartment

There are several shops and restaurants on St. Clair Ave W. Plenty of transit options north of you on the St. Clair line or the bus line on Dufferin. A dog within minutes from the home. The actual space is perfect. Opposite of the open concept apartment, this spacious one bedroom had a separate eat-in kitchen, separate living room, and bedroom. The apartment has the fastest wifi speed. The second floor back terrace has a lovely view with gorgeous sunsets. Parking ✅ Not a shared space.

Guest favourite
Flat in North York
4.97 out of 5 average rating, 189 reviews

Keele off 401 (1.4km to Humber River Hospital)

Welcome to our cozy private one-bedroom basement apartment! Situated in the basement of our home, this space features a bedroom, a bathroom, a kitchen, and a combined living and dining area. Please note that our apartment is located on Keele Street, a main road, so it may not be suitable for light sleepers. Proximity to/from Pearson International Airport: 15 minute drive Proximity to/from Downtown Toronto: 50 minute drive Proximity to/from Humber River Hospital: 2 minute drive

Guest favourite
The spacious living area features a cozy sectional sofa facing a wall-mounted television. A dining table is set for four, with design elements visible in framed art. A colorful striped rug adds vibrancy, while a small coffee table sits at the center.
Flat in York
4.95 out of 5 average rating, 92 reviews

Lovely 2 bedroom, 2 washroom and living room

* Sleeps 6 with 1 King bed in a private room, 1 Queen bed in a private room and a hideaway Queen-size couch bed in the den. * Newly Built Legal 2 Bedroom, 2 Washroom Basement w Den * 1000 Square Feet * Newly renovated & spacious * Separate private entrance * 8-foot ceilings * TTC is 5 houses away, 10 minutes to St. Clair West subway station. * Beautiful parks and green spaces are close by. * New appliances * Very bright and sunny apartment with large windows

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, 350 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 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.
Flat in Wychwood
4.97 out of 5 average rating, 94 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 entrance features a large set of double doors framed by decorative wreaths. A covered porch is supported by white columns, with steps leading to the front door. Lush greenery and potted flowers enhance the inviting entryway.
Flat in Etobicoke
4.99 out of 5 average rating, 85 reviews

Casa Savoia

Cozy and bright bedroom/with private entrance, , 3-piece bathroom, laundry available if staying for three nights or more. Beautiful outdoor patio and free parking. Very centrally located - 2 minute walk to subway, restaurants, coffee shops, grocery stores - 15 minute drive to downtown Toronto and to Pearson International Airport. Established and safe neighbourhood

Guest favourite
A charming two-story brick facade displays a combination of stone and wood elements, featuring a welcoming entrance with steps leading to the front door. Lush greenery surrounds the property, enhancing the inviting atmosphere of the home.
Flat in Corso Italia
4.86 out of 5 average rating, 81 reviews

Stay like a Real Torontonian on trendy St Clair W!

Come stay like a true Torontonian on trendy St Clair Avenue West in our newly-renovated basement apartment; steps from amazing restaurants, bars, parks, markets and the streetcar that will easily connect you to your adventures elsewhere in the city!. We're sure you'll love our neighborhood as much as we do!

Superhost
A corner of a cozy living area features a softly upholstered couch adorned with a light throw and decorative pillows. A whimsical fish mural adds a pop of color to the white wall. The adjoining kitchen area is equipped with modern appliances and decorative shelving.
Flat in Oakwood Village
4.81 out of 5 average rating, 27 reviews

Cute Getaway in Toronto’s Oakwood Village

Welcome to your charming home-away-from-home in the heart of Toronto’s vibrant Oakwood Village! This beautifully maintained cute unit blends cozy comfort, playful charm, and city convenience—ideal for couples, solo travelers, small groups, or remote workers looking for a unique Toronto stay.

Popular amenities for Oakwood Village apartment rentals

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Avg. price$78 SGD$81 SGD$91 SGD$101 SGD$104 SGD$116 SGD$118 SGD$121 SGD$125 SGD$112 SGD$111 SGD$98 SGD
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Quick stats about flat rentals in Oakwood Village

  • Total holiday rentals

    Explore 70 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 2,030 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 of Oakwood Village holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oakwood Village rentals

  • 4.7 Average rating

    Oakwood Village stays receive an average rating of 4.7 out of 5 from guests

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