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Vacation rentals in Oakwood Village

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Top-rated vacation rentals in Oakwood Village

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

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Top guest favorite
An open living area features a light-colored sofa covered with a protective cover, a coffee table, and a flat-screen TV mounted on the wall. Natural light enters through large windows dressed with sheer curtains, complementing the warm wood tones of the flooring.
Guest suite in Oakwood Village
4.93 out of 5 average rating, 55 reviews

Chic Midtown Toronto Suite / Newly Renovated

Welcome to our stylish and newly renovated suite located in the trendy St. Clair Avenue West area of Midtown Toronto! The suite features a spacious bedroom with a plush queen-sized bed, a fully equipped kitchen with brand-new appliances, and a sleek bathroom with a luxurious rain shower. Enjoy the convenience of being just steps away from top restaurants, cafes, and shopping in one of Toronto’s most vibrant neighbourhoods. 20 minutes walk to St. Clair West station, 5 minutes to the streetcar.

Guest favorite
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, 165 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!

Guest favorite
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
4.89 out of 5 average rating, 97 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.

Guest favorite
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
4.95 out of 5 average rating, 19 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 favorite
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, 68 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 favorite
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
4.86 out of 5 average rating, 73 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 favorite
A clean private room features a full-size bed with neatly arranged white linens and two rolled towels placed at the foot. A small desk and chair are situated by a window, allowing natural light to brighten the space.
Private room in Toronto
4.92 out of 5 average rating, 136 reviews

#2 Private room close to Lansdowne Subway Station

Clean Private room that locate close to Lansdowne subway station. This room for 1 person only. if you have an extra guest, please book room 1 or 3. A 8 minute walk or 2 mins with Bus (3 stops away) from Lansdowne station. No Kitchen. Full size bed, wifi, shared washroom, towel, Shampoo and bodywash Bathroom will be clean daily. Street parking only (midnight - 7AM need permit) for parking options, please check "other details"

Guest favorite
Private room in Oakwood Village
4.93 out of 5 average rating, 143 reviews

Toronto-seperate apartment, free parking &laundry

**Free Parking* ***seperate entrance, keypad*** Explore Midtown Toronto on foot, by bus or streetcar; 2 minute walk to the Dufferin bus, 8 minute walk to the Oakwood bus or take a stroll, and walk 20 minutes south to St. Clair. On St. Clair, ride the streetcar or walk east and west. St. Clair offers a variety of shops, restaurants, bars and pubs. Then return home to relax and wind down in this cozy space.

Guest favorite
Private room in Earlscourt
4.95 out of 5 average rating, 127 reviews

Cozy private suite in Corso

Private basement suite in Corso Italia! A cozy, relaxed and quiet space to wind down with your own entrance, bathroom, and kitchenette. Perfect for a solo traveller or couple. Access to downtown west end Toronto by public transit: 4 bus routes 2min, 8min, 9min and 10min walk away. Food and drink nearby on St Clair, cool bars on Geary, Dupont, and Bloor. Beautiful walks nearby in Prospect Cemetery.

Superhost
Home in Oakwood Village
4.78 out of 5 average rating, 9 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 favorite
Private room in Davisville Village
5 out of 5 average rating, 178 reviews

Mid town Toronto LGBTQ Friendly Chic & Comfortable

This urban chic place is perfect for solo, or couples/friends on vacation or business. Centrally located in mid-town Toronto between two subway stops (St Clair and Davisville on Line 1) plus 24 hour bus service, you are only 15 minutes from downtown or a 8 minute drive. On street parking is free! I look forward to hosting you in Toronto, the world’s most multicultural city !

Guest favorite
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, 49 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 vacation rentals

When is the best time to visit Oakwood Village?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$13,381 GYDG$12,963 GYDG$13,172 GYDG$13,799 GYDG$15,054 GYDG$16,099 GYDG$17,563 GYDG$18,399 GYDG$17,981 GYDG$16,308 GYDG$17,354 GYDG$14,426 GYD
Avg. temp-3°C-3°C2°C8°C14°C20°C23°C22°C18°C11°C5°C0°C

Quick stats about vacation rentals in Oakwood Village

  • Total vacation rentals

    Explore 300 vacation rentals in Oakwood Village

  • Nightly prices starting at

    Oakwood Village vacation rentals start at G$2,091 GYD per night before taxes and fees

  • Verified guest reviews

    Over 9,520 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wi-Fi availability

    300 of Oakwood Village vacation rentals include wi-fi 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!

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