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 $14 AUD 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, 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!

Top-rated holiday rentals in Oakwood Village

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

1 of 1 pages1 / 1
Guest favourite
Home in York
4.93 out of 5 average rating, 30 reviews

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

Guest favourite
Guesthouse in York
4.95 out of 5 average rating, 22 reviews

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.

Guest favourite
The entrance of a charming home is surrounded by a vibrant garden. Colorful flowers bloom in the foreground, while a stone pathway leads to a welcoming front door. Lantern-style lights stand on either side of the entrance, enhancing the inviting atmosphere.
Home in York
4.96 out of 5 average rating, 46 reviews

Home Away from Home on St. Clair W./Corso Italia

This charming and beautiful 3-bedroom Century home, full of unique character and warmth, has been lovingly maintained to preserve its original charm with a modern touch. Nestled in a quiet neighbourhood just steps from Corso Italia and St. Clair Avenue West, it comfortably sleeps 6 guests. More than just a place to stay, it’s a true getaway where the vibrant city is at your doorstep, yet the peaceful front and back gardens offers a serene oasis that feels like an Italian villa for relaxation

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
4.83 out of 5 average rating, 72 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
Home in York
4.95 out of 5 average rating, 21 reviews

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.

Guest favourite
Apartment in York
4.87 out of 5 average rating, 30 reviews

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!

Guest favourite
Apartment in Toronto
4.9 out of 5 average rating, 196 reviews

Spacious & Vibrant

Stay comfortably in this spacious 2-apartment in vibrant Corso Italia, perfect for couples, friends or small groups of friends. Enjoy a bright and private second-floor unit with plenty of space to relax after exploring Toronto. Step outside to enjoy your private patio, or take advantage of convenient parking. With transit just steps away, you’ll have easy access to downtown, Toronto’s attractions, restaurants, and entertainment. Parking is available for up to 2 vehicles.

Guest favourite
A cozy living space features a blue sofa with patterned cushions and a wooden coffee table. A round mirror hangs on the wall, reflecting natural light. A floor lamp provides additional lighting, and a small chair is positioned nearby. A plant adds a touch of greenery.
Home in Midtown
4.91 out of 5 average rating, 121 reviews

Spacious Mid Century w/Patio

Adorable Historic Home with Private Patio & BBQ. ♡ 3 bedroom & 1.5 bath (1 King & 2 Queens) ♡ Hotel Inspired Home with Super Fast WIFI ♡ Automated Check in & Check Out ♡ Steps from St. Clair transit line / connects to Subway ♡ 90/100 Walk Score ♡ 100/100 Transit Score ♡ Walking distance to Casa Loma | Rated #1 by BlogTO of Places to Visit in Toronto ♡ Flexible Check in Check out - Message for Details ♡ A/C ♡ Laundry ♡ BBQ & Fully Equipped Kitchen ❤ Book today!

Guest favourite
Guesthouse in York
4.96 out of 5 average rating, 76 reviews

Junction Private Laneway Suite with Backyard

Welcome to a modern loft-style laneway suite nestled in the vibrant Junction Stockyards neighbourhood of Toronto, just a stone's throw away from downtown's hustle and bustle. Experience the perfect blend of convenience & local charm in the Stockyards. Our Airbnb is centrally situated; downtown Toronto a quick drive or easy transit ride away. Within a 10-minute walk, you'll find the lively Junction area, brimming with diverse restaurants, trendy shops, and cozy cafes.

Guest favourite
Home in York
4.86 out of 5 average rating, 22 reviews

Casa del Jo | Boho 2BR + Parking + Workspace

☀️ Summer Stays in Toronto! Stylish boho 2BR main-floor suite in a quiet, walkable neighbourhood with easy access to downtown, the Entertainment District, and top Toronto attractions. Relax with fast WiFi, Smart TV, a newly renovated spa-like bathroom, dedicated workspace, and free parking. Featuring cozy king + queen beds, in-suite laundry, and thoughtful touches throughout. Perfect for couples, friends, professionals, remote workers, or longer stays.

Superhost
Guest suite in Toronto
5.0 out of 5 average rating, 14 reviews

Lovely Basement Suite

Enjoy your time at my centrally located private apartment. It's a very stylish basement apartment. It has all the amenities of a home with a kitchen, private entrance, laundry,and a full bathroom. It sleeps 4 with 1 double bed and a double pull out sofa bed. There is permit street parking available You will be close to many restaurants,grocery stores,bars etc Only 15 minutes to the downtown core whether by bus,street car, Uber or subway.

Top Guest favourite
A spacious living area features a large sectional sofa adorned with bright pillows. A small side table sits next to the sofa, and a decorative rug covers the wooden floor. In the background, a softly lit doorway leads to the bedroom and kitchenette.
Guest suite in York
5.0 out of 5 average rating, 42 reviews

Modern Clean Midtown Private Suite free parking

✨Welcome to a modern, super-clean basement suite in Toronto! Perfect for couples, solo travellers, or small families and groups, this quiet retreat is just a short stroll to Cidervale Subway and steps from the LRT, with grocery stores, cafés, and restaurants nearby. Across the street, enjoy a family-friendly park with a playground, splash pad, and Beltline Trail. This is great for morning walks or a quick bike ride.

Popular amenities for Oakwood Village holiday rentals