Photo by Jerrah Biggerstaff

Oakwood Village vacation rentals

We found 82 vacation rentals — enter your dates for availability

Discover a selection of 18 homes and other vacation rentals in Oakwood Village that are perfect for your trip. Whether you're going on vacation with family or friends, vacation homes have the best amenities for hanging out with the people that matter most, which might include WiFi and a fireplace. You're sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

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Find out more about Oakwood Village

Find out more about Oakwood Village

Why visit Oakwood Village

  1. Rich Cultural Atmosphere: Immerse yourself in the vibrant local culture with artistic flair and friendly locals.
  2. Family-Friendly Activities: Enjoy a variety of attractions suitable for all ages, perfect for a fun day out with loved ones.
  3. Urban Parks: Explore beautiful parks that offer a refreshing escape within the city, ideal for relaxation and outdoor fun.
  4. Diverse Accommodation Options: Choose from a range of vacation rentals, including stylish apartments and private homes.
  5. Authentic Urban Experience: Discover a blend of history and modernity in this budget-friendly gem of a neighbourhood.

Popular types of accommodation around Oakwood Village

Discover the charm of Oakwood Village with our selection of vacation rentals, including private homes, apartments, and condos. Whether you're exploring Oakwood Avenue or looking for stylish apartments in Oakwood Village, we have the perfect option for you. Our listings feature a variety of apartment rentals, including those in Oakwood Village York, ensuring you find a comfortable stay tailored to your needs. Experience the best of Oakwood Village with our transparent and reassuring booking process.

  • Houses: The top choice for visitors in Oakwood Village, offering spacious and comfortable stays for families, friends, or couples.
  • Apartments: A popular option for those seeking a home-like experience, perfect for short or extended stays in the area.
  • Condos: Well-liked among travellers, these modern living spaces provide convenience and amenities for a pleasant vacation.
  • Villas: Ideal for larger groups, these luxurious properties offer privacy and stunning surroundings.
  • Cottages: A charming choice for those looking for a cozy getaway with a touch of nature.**

Top attractions around Oakwood Village

Oakwood Village is a fantastic destination for a city-themed, family-friendly vacation, offering a blend of outdoor and cultural experiences. Visitors can explore urban parks, art museums, and event venues that cater to various interests. Whether you’re looking to immerse yourself in local culture or enjoy a day out with family, Oakwood Village provides a delightful array of attractions and activities that promise to enrich your travel experience.

  1. University of Toronto - St. George Campus: A historic institution with stunning architecture and vibrant campus life, offering a rich cultural atmosphere where you can explore galleries, libraries, and serene green spaces.
  2. Royal Ontario Museum: A premier destination for history and culture, featuring diverse exhibits ranging from natural history to world cultures, providing an engaging experience for all ages.
  3. Casa Loma: A magnificent Gothic Revival mansion with beautiful gardens, offering a glimpse into Toronto's past through its stunning architecture and intriguing exhibits.

Things to do recommended for couples

Discover romance in Oakwood Village with a visit to Roy Thomson Hall for a captivating concert, or enjoy a thrilling day at Earl Bales Ski and Snowboard Centre. For a cozy dinner, Spin Toronto offers a charming atmosphere perfect for couples seeking a delightful culinary experience.

Things to do recommended for families

Families will love the excitement at Rogers Centre and Scotiabank Arena, both offering thrilling sports experiences just 6.4km from Oakwood Village. For some icy fun, head to George Bell Arena, located only 3.2km away, perfect for ice skating and adventure!

Things to do recommended for groups

Explore the CF Toronto Eaton Centre for shopping and entertainment, savour local flavours at St. Lawrence Market, and enjoy a performance at the Four Seasons Centre. Each venue offers a unique vibe, perfect for creating memorable moments with your group in Oakwood Village.

What do I need to keep in mind when booking a vacation around Oakwood Village

If you're planning a trip with a group, family, pets, or are seeking longer accommodations, it's important to prioritize your preferences. Here are some helpful tips for booking on Vrbo.

  • Traveling to Oakwood Village with a group: Think about how many bedrooms you'll require, along with amenities like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these features and more on Vrbo.
  • Traveling to Oakwood Village with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oakwood Village: For many, a family vacation isn't truly fulfilling without their furry companion by their side. If this resonates with you, consider exploring Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Oakwood Village: If you're in search of vacation rentals that offer special deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay around Oakwood Village

Discover the vibrant charm of Oakwood Village, a delightful neighbourhood in Toronto, perfect for family-friendly adventures and urban exploration. Stroll through its lively streets, where you'll encounter friendly locals, artistic flair, and a rich cultural atmosphere. Venture into nearby sub-neighbourhoods to experience a blend of history and modernity, making this area a budget-friendly gem for any traveller seeking an authentic urban experience.

  • Saint Clair West Village: Located a mere 1.1km from Oakwood Village, Saint Clair West Village is a vibrant neighbourhood that attracts visitors seeking a family-friendly atmosphere and urban experiences. This area is known for its bustling shopping mall centres and local boutiques. Stroll along the charming streets, where you can find an array of shops and eateries. The urban parks provide a perfect spot for relaxation and leisure, making it an ideal location for families to explore and enjoy the outdoors.
  • Humewood-Cedarvale: Also situated 1.1km from Oakwood Village, Humewood-Cedarvale is a delightful neighbourhood offering a mix of city life and outdoor adventure. This area is perfect for families looking to engage in recreational activities, with access to shopping centres and lively parks. The local urban park and nearby stadium provide fantastic opportunities for sports enthusiasts and families alike. Visitors can immerse themselves in the community's vibrant spirit while enjoying a variety of outdoor experiences.
  • Cedarvale: Cedarvale, located 1.1km from Oakwood Village, is a family-friendly neighbourhood that combines city living with nature's charm. Here, you'll find shopping mall centres and recreational parks that cater to both leisure and business needs. The picturesque urban park and serene river add to the area's appeal, making it a perfect spot for family outings and exploration. Cedarvale's welcoming atmosphere invites visitors to discover its hidden gems and enjoy the local community vibe.

Best time to go to Oakwood Village

If you're planning a trip to Oakwood Village, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.2°F (-3.8°C)Light RainMostly CloudySlightly LowSlightly Low
February25.2°F (-3.8°C)Light RainMostly CloudySlightly LowSlightly Low
March33.3°F (0.7°C)Light RainMostly CloudyAverageAverage
April42.6°F (5.9°C)Light RainMostly CloudyAverageSlightly Low
May54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
June64.4°F (18.0°C)Light RainMostly SunnySlightly HighSlightly High
July71.6°F (22.0°C)Light RainMostly SunnySlightly HighSlightly High
August71.2°F (21.8°C)Light RainMostly SunnySlightly HighSlightly High
September65.1°F (18.4°C)Light RainMostly SunnyAverageAverage
October53.4°F (11.9°C)Light RainMostly SunnyAverageAverage
November41.5°F (5.3°C)Light RainMostly SunnyAverageAverage
December32.9°F (0.5°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate significantly. Furthermore, opting for a longer stay can result in substantial savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, and manage your travel arrangements with ease. You can easily access the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Oakwood Village?
In Oakwood Village, both vacation houses and apartments are popular choices, each offering a variety of amenities suited to different traveller needs. The area features several vacation houses, which typically provide spacious rooms ideal for families or larger groups. These homes often include multiple bedrooms, fully equipped kitchens, and private outdoor spaces for relaxation and socialising.
Are there any beach house rentals in Oakwood Village?
In Oakwood Village, Ontario, there are beach house rentals available, although they are relatively limited in number. Most of these properties are situated near the scenic shores of Lake Ontario, offering a tranquil escape from the city. The beach houses typically feature amenities such as spacious living areas, fully equipped kitchens, and outdoor patios that provide stunning views of the lake. Many also include additional conveniences like barbecue facilities and private access to the beach, making them ideal for families or groups looking to enjoy a relaxing getaway.
How much does it cost to rent a vacation home in Oakwood Village?
Prices for vacation rentals in Oakwood Village vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oakwood Village to more spacious homes.
Are there any discounts for Oakwood Village vacation house rentals?
You can find great discounts on house rentals in Oakwood Village on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Oakwood Village?
In Oakwood Village, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals conveniently. Many properties also feature coffee and tea makers for those who enjoy a warm beverage at any time of the day. Onsite parking is a significant advantage for travellers with vehicles, providing easy access and peace of mind. Additionally, rentals often come with blenders, suiting guests who prefer smoothies or other blended drinks. Many accommodations also boast decks or patios, offering outdoor space to relax and enjoy the surroundings.
Are there any family house rentals in Oakwood Village?
In Oakwood Village, Ontario, there are several family-friendly house rentals available. This suburban area is known for its friendly atmosphere and proximity to various parks, making it an ideal spot for families. Many of these properties offer spacious living areas, full kitchens for preparing meals, and outdoor spaces where children can play safely.
Are there any Oakwood Village vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Oakwood Village with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there pet-friendly vacation rentals in Oakwood Village?
In Oakwood Village, there are several pet-friendly vacation rentals available for travellers seeking to enjoy this charming area. Many of these accommodations offer amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can play. The rentals often come with convenient features like laundry facilities and parking, making them suitable for longer stays.
Can I find long-stay vacation rentals in Oakwood Village?
A long-stay vacation rental in Oakwood Village is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Oakwood Village for a vacation rental?
The best time to visit Oakwood Village for a vacation rental is during the vibrant summer months of June to August. This peak season attracts travellers, who flock to the area to enjoy the warm weather, local festivals, and community events. With temperatures often reaching the low 20s Celsius, it's an ideal time for outdoor activities such as exploring nearby parks, picnicking, or simply soaking up the sun.

July stands out as the most popular month, bringing a lively atmosphere to Oakwood Village. Expect bustling streets filled with people enjoying the various summer activities, which may include outdoor concerts and local markets. This is a wonderful time for those who appreciate a sense of community and a range of entertainment options.

For those seeking a more budget-friendly option, consider planning your visit in October. This month not only offers a quieter experience but also showcases the beauty of autumn as the foliage transforms into stunning shades of red, orange, and yellow. The crisp air makes for pleasant walks through the parks, and you can enjoy local harvest festivals without the summer crowds.
Are there any remote work vacation rentals in Oakwood Village?
In Oakwood Village, Ontario, there are several remote work vacation rentals available, with approximately 11 options to choose from. These properties are well-equipped to accommodate remote workers, featuring essential amenities such as reliable Wi-Fi, dedicated workspaces with desks, and comfortable desk chairs. This makes it easy for travellers to maintain productivity while enjoying a change of scenery. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Oakwood Village vacation rental?
Book your Oakwood Village vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oakwood Village?
In Oakwood Village, visitors can enjoy a blend of local charm and natural beauty. The area is known for its proximity to parks such as Oakwood Park and Westmount Park, which offer green spaces, walking trails, and playgrounds, making it ideal for families and outdoor enthusiasts. The nearby Humber River provides additional opportunities for hiking and cycling along its scenic paths.
Can I change or cancel my Oakwood Village home rental booking on Vrbo?
To find Oakwood Village vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Oakwood Village vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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