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Vacation rentals in Oakwood Village

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Oakwood Village

  • Total vacation rentals

    Explore 310 vacation rentals in Oakwood Village

  • Nightly prices starting at

    Oakwood Village vacation rentals start at ﺩ.ﺇ 37 per night before taxes and fees

  • Verified guest reviews

    Over 9,720 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    310 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!

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
A cozy living area features a neutral-colored sofa and a single lounge chair, complemented by a decorative coffee table. A large television stands on a modern metallic stand. Natural light enters through a glass door, casting a warm glow on the vibrant area rug.
Home in Midtown
4.98 out of 5 average rating, 93 reviews

Private Full Height Suite Near TTC - Salem Gallery

Enjoy our bright, stylish private basement apartment suite, just a few minutes from the Bloor subway line 2 in Bloorcourt Village. This one-bedroom is fully renovated and features heated floors, full-height ceilings, and original artwork from various local Toronto artists. Our space is a perfect jumping-off point for work, sightseeing or visiting family. Whether you've had a long day sightseeing our beautiful city, or a long day at work, wind down at the spot you wish you knew about sooner.

Top guest favorite
A compact bedroom is furnished with a spacious bed dressed in striped linens. Artwork is displayed on the walls, and a mirrored closet adds depth to the space. Natural light enters through partially covered windows, while soft bedside lamps provide illumination.
Apartment in York
4.97 out of 5 average rating, 155 reviews

Cozy 1-bdm suite filled with amenities & parking

A whimsically decorated basement apartment with a separate entrance that welcomes all. The exposed brick gives it a unique character and the location means you're not too far from downtown, close to public transportation and away from congestion. Enjoy amenities such as a kitchenette with all the fixings for a continental breakfast, plentiful snacks and refreshments. The kitchen offers an induction cooktop & toaster oven instead of a stove. Guests can enjoy Netflix, Wifi, and free parking.

Guest favorite
Home in York
4.81 out of 5 average rating, 112 reviews

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

Guest favorite
Condo in Midtown
5 out of 5 average rating, 28 reviews

Luxury 1+Den w/ Parking | Downtown Toronto

Enjoy a stylish stay in this modern 1+Den condo in Downtown Toronto with free parking (rare for the area). Features a cozy living area, comfortable bedroom, and dedicated workspace—ideal for business or leisure stays. Minutes from Casa Loma, CN Tower, Rogers Centre, Scotiabank Arena, BMO Field, Exhibition Place, nightlife, restaurants, cafés, grocery stores, and a subway station just a 10-minute walk away. Clean, comfortable, and well-connected. Queen air mattress available upon request.

Guest favorite
Home in York
4.93 out of 5 average rating, 14 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 favorite
Apartment in York
4.83 out of 5 average rating, 24 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!

Top guest favorite
Guesthouse in York
4.94 out of 5 average rating, 16 reviews

Handy Studio in Oakwood Village

Cosy midtown laneway studio is 440 square feet of private, quiet space, 75 ft from street parking. Easy access from Pearson. Large windows on north and south ends ensure great natural light. There are solar shades to keep out the summer heat while allowing the occupant to see out, and privacy curtains for times when they are 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 favorite
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, 117 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!

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 Toronto
5 out of 5 average rating, 103 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
Guesthouse in York
4.97 out of 5 average rating, 70 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.

Superhost
Home in Midtown
5 out of 5 average rating, 4 reviews

Brand New Designer Home Near Downtown

Welcome to our brand-new designer home, thoughtfully furnished for comfort and style. Enjoy a fully equipped kitchen, spacious living area, high-speed WiFi, and modern finishes throughout. Perfect for families, business travelers, and visitors looking for a relaxing stay near Downtown Toronto. Experience a clean, bright, and welcoming space designed to make you feel at home. Street parking is conveniently available on the rear street behind the property.

Superhost
Guest suite in York
4.96 out of 5 average rating, 157 reviews

Mid Town MidMod | Stylish 1BR w/ Full Kitchen

Bright, clean and spacious lower-level guest suite located in Mid-Town's trendy St. Clair West neighbourhood. Our suite is best suited for adults exploring the city, business travelers seeking privacy and a comfortable workspace, or families visiting relatives. Our private 1-bedroom suite features a queen bed, separate futon, full kitchen, and all the amenities you need for a comfortable stay. Walk to great restaurants, cafés, shops, and transit.

Popular amenities for Oakwood Village vacation rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Toronto
  5. Oakwood Village