Holiday rentals 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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Superhost

A cozy bedroom is presented with two comfortable beds adorned with quality linens. Soft lighting from recessed fixtures casts a gentle glow over the space. A television is positioned on a dark stand, and a piece of wall art adds a touch of color.

Home in Oakwood Village

4.92 out of 5 average rating, 38 reviews

Toronto Cozy Home Retreat

**Entire space**with kitchen and bathroom **Cozy Bedroom**: 2 comfy beds and quality linens. **Modern Bathroom**: A clean and updated bathroom equipped with fresh towels and toiletries. **Fully Stocked Kitchen**: Prepare meals with ease using our modern appliances and kitchenware. Includes a microwave, fridge, and stove. **Living Space**: A comfortable area with a desk and Wi-Fi, perfect for work or relaxation. **Fitness Corner**: Keep up with your fitness routine with the onsite exercise bike

Superhost

A bright living area is characterized by a white couch and a circular coffee table atop a soft, textured rug. A world map artwork is prominently displayed on the wall, surrounded by indoor plants in tasteful planters. Soft lighting from a modern chandelier enhances the inviting ambiance.

Private room in Jane and Finch

4.89 out of 5 average rating, 268 reviews

Superhost Self-Check-In Quiet Private Room #1

Your private room is in a clean & quiet guest home in Toronto North York, hosted by your liscenced professional Superhost Kuinai. We make sure your check-in/stays/checkout are smooth as always : ) √Easy self check-in/out by smart lock √Queen bed √Private key to the room √All toiletries included √1 parking is available for $10/night (Spots are limited, please inquiry) *Direct booking is offered to our returning guests only *Driveway 24-hours security camera *Not an underground basement : )

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

4.91 out of 5 average rating, 160 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!

Superhost

A narrow hallway leads to a living area, featuring light-colored walls and a smooth wooden floor. A small bench sits beside a large leafy plant in a pot. In the background, a neutral-toned couch is visible next to an adjoining bathroom.

Private room in North York

4.86 out of 5 average rating, 98 reviews

Charming Bedroom near Yorkdale, North York

10 minutes drive to Rogers Stadium at downview. ❇️Comfortable private bedroom ❇️Shared kitchenette and washroom ❇️Quiet neighbourhood in North York ❇️Great Location: - 1 minutes walk from bus - 10 minutes walk from Wilson Subway Station - 30 minutes to downtown - Near Yorkdale Mall and Costco - Right next to a highway for easy access ❇️Perfect For: - Students and workers - Travelers exploring Toronto - Anyone wanting an affordable, convenient stay

Guest favourite

The private bedroom is illuminated by soft lighting, featuring a spacious double bed with white linens and navy accents. Two nightstands hold lamps beside the bed. A desk and chair sit in the corner, complemented by a mirror. Decorative artwork adorns the wall.

Private room in Eglinton West

4.92 out of 5 average rating, 132 reviews

Bright Cozy Room | Kitchen, Parking | 5 Min Subway

Enjoy a private and bright bedroom in a clean home located in Midtown Toronto. This cozy space offers free parking and access to a lovely deck on the main floor. Perfectly situated, it’s within walking distance to Eglinton West Station, local restaurants, and conveniently close to major highways. The private, keyed bedroom includes a double bed, desk, chair, closet, and TV. Shared spaces include bathroom, kitchen, living room, and dining room.

Guest favourite

Private room in Earlscourt

4.95 out of 5 average rating, 124 reviews

Cozy private suite on 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

4.88 out of 5 average rating, 8 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.

Guest favourite

A spacious living area features a large gray sofa adorned with decorative pillows and a vibrant yellow throw. Warm lighting illuminates the wood-grain floor. A cozy blue chair sits to the side, while curtains divide the space from the kitchen area, visible in the background.

Flat in Earlscourt

4.84 out of 5 average rating, 90 reviews

Lovely 1-Bedroom Apartment in Corso Italia

The whole group will enjoy easy access to everything from this centrally located place. Fruit stands and restaurants and bars all at your footstep, with convenient transit to help you get anywhere in the city! Fully Private Apartment. Spacious 1 Bedroom Lower-Level Apartment, full kitchen and laundry all to yourself! Book confidently with an Airbnb Superhost with 80+ reviews.

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.

Flat in Oakwood Village

4.85 out of 5 average rating, 67 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. No parking available. Street parking permits available. No parties, smoking or loud groups.

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, 47 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.

Guest favourite

Private room in Earlscourt

4.91 out of 5 average rating, 116 reviews

Super Cozy Room in Corso-Italia

This is a super-cozy room located in the centre of Toronto. Great for solo travelers looking to stay on the cheap and to take advantage of the proximity to Corso-Italia, Bloordale and Little Italy. Just steps from the Dufferin bus that runs 24-7. Fantastic back patio with a stylish and simple living space.

Superhost

A wooden front door with a classic panel design is set against a backdrop of vertical wooden slats. A small stone step leads to the entrance, while a bench with storage sits to the side, surrounded by greenery.

Flat in Oakwood Village

4.81 out of 5 average rating, 16 reviews

Cozy & Cute 2-Bedroom Retreat in Oakwood Village

Welcome to your charming home-away-from-home in the heart of Toronto’s vibrant Oakwood Village! This delightful upper-level unit blends comfort, character, and a sprinkle of whimsy—perfect for couples, small groups, or solo travelers looking for a unique city stay.