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Holiday houses in Oakwood Village

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Oakwood Village

  • Total holiday rentals

    Explore 310 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 9,720 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    310 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!

Top-rated holiday rentals in Oakwood Village

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

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Guest favourite
Home in York

Renovated 2 Bed lower level apt- free parking

Welcome to this modern 2-bedroom basement apartment located in the vibrant Oakwood Village neighborhood. ideal for couples or small families. Located in one of Toronto’s most accessible pockets, steps from St. Clair Avenue West, featuring streetcar, local cafes, shops, parks, and grocery stores. Nearby amenities include Cedarvale Park, Oakwood Collegiate Institute, and the trendy Eglinton West dining strip, proximity to TTC bus routes, Yorkdale Mall, and easy access to Highway 401 via Allen Road

4.92 out of 5 average rating, 36 reviews
A comfortable living room is highlighted by neutral furnishings, including a spacious sofa with accent pillows and a pair of armchairs. Soft lighting is provided by lamps, while a round coffee table sits on a plush area rug. Large windows allow natural light to brighten the space.
Apartment in York

Classic Toronto 2 bedroom Apartment

Enjoy a stylishly decorated experience at this centrally located 2 bedroom unit. Self check-in at anytime, full stocked kitchen, lots of windows and lights. Professionally cleaned , High speed internet, 6 seater dining, Laundry, TV, high-end mattresses, comfortable living room and so much more. Centrally located for groceries, restaurants, bars and much more! Less than 1.5 km from subway station. Steps from public transport, malls, cafés, groceries, restaurants. 7 Years Super host in a row!

4.69 out of 5 average rating, 55 reviews
Guest favourite
Home in York

CHARMING 3 BEDROOM HOME IN THE CITY W FREE PARKING

Welcome to our clean, cozy 3 bedroom country style bungalow situated in the middle of the city. Close to anywhere you wish to go, but just far enough from all the hustle and bustle. Entire property with 3 bedrooms (1 King and 2 Queen size beds). - Free parking on a private lot for multiple vehicles - 2 televisions - Wifi - Netflix - Kitchen - 2 washrooms - Enclosed private patio and a backyard - Steps to TTC bus stop and 10 min walk to Oakwood Subway - High speed internet and working space

4.83 out of 5 average rating, 128 reviews
Guest favourite
Guesthouse in York

Handy Studio in Oakwood Village

Midtown laneway studio has 440 square feet of private, quiet space, 75 ft from street parking. As of Summer 2026, this propery has solar panels and is net zero. Windows on north and south ensure natural light. There are solar shades to keep out the summer heat while allowing the occupant to see out, with privacy curtains for times when privacy is needed. 4 minutes walk to TTC buses, 12 to subways. Full kitchen, fridge, dishwasher and stove. Wifi. Queen sized Murphy bed folds to maximize space.

4.96 out of 5 average rating, 26 reviews
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 York

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

4.87 out of 5 average rating, 68 reviews
Guest favourite
Home in York

Private Lower-Level Suite in Corso Italia

Private lower-level suite offering comfort, independence, and city convenience. Features a queen bed, private bathroom, and practical kitchenette for light meal preparation. Outdoor entrance and smart keyless lock provides full privacy . Located in Corso Italia, steps from 24/7 transit and walking distance to restaurants, cafes, bakeries, breweries and shops. Ideal for business, sightseeing, or a major city events. Rates may vary during special events or peak travel periods in Toronto.

4.91 out of 5 average rating, 58 reviews
Guest favourite
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.
Apartment in Toronto

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

4.84 out of 5 average rating, 75 reviews
Guest favourite
Home in York

Free Parking | Transit | Quartz Kitchen | Laundry

Beautifully renovated Toronto home in Corso Italia. Close to downtown and BMO field where FIFA world cup games will be, cafes, and restaurants. This bright, modern space features an open living area, quartz counters and stainless steel appliances, fast Wi-Fi, Smart TV, and in-suite laundry. Located on a quiet residential street with easy access to parks and transit. Perfect for couples, business travelers, or small groups seeking comfort, style, and convenience during their Toronto stay.

4.92 out of 5 average rating, 26 reviews
Top Guest favourite
Apartment in Toronto

Entire basement suite on Corso Italia

This stylish, cozy, clean basement unit offers a welcoming private space within a family home. The 1-bedroom suite has a Queen size bed, full bathroom, and full kitchen with everything you need for a comfortable stay. With a private entrance, guests can enjoy a peaceful residential neighbourhood close to multiple transit routes. Stores, cafés, grocers, restaurants, shops, and parks only a short walk away. As children live in the home above, occasional household noise may be heard.

5.0 out of 5 average rating, 16 reviews
Home in York

Stylish Walkout Basement & Backyard near Midtown

Private walkout basement suite with low ceilings in Toronto’s Little Jamaica near Dufferin & Eglinton. Step into your private entrance through the backyard. A cozy-chic space designed for comfort and convenience with unbeatable proximity to transit, cafes, restaurants, and shopping. Perfect for solo travelers, couples, or small families, this budget-friendly suite blends charm with practicality. 1-minute walk to 24-hour Dufferin bus route, 12-minute walk to Eglinton subway line.

4.8 out of 5 average rating, 20 reviews
Top 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 York

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, 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!

4.92 out of 5 average rating, 196 reviews
Guest favourite
Apartment in York

Urban Retreat Steps to Transit, Dining, & Shops

Welcome to your modern urban retreat in Toronto’s vibrant St. Clair West neighborhood! This bright, stylish 1 bedroom apartment sits in a lively area surrounded by cozy cafes, restaurants, local boutiques, and parks. Enjoy being just steps from express transit for quick access downtown or sites across the city. Our space is perfect for business trips, solo travelers, couples, small groups, or families looking for a home base in one of Toronto’s most vibrant neighborhoods!

4.85 out of 5 average rating, 33 reviews

Popular amenities for Oakwood Village holiday rentals