Oakville vacation rentals

We found 715 vacation rentals — enter your dates for availability

Discover a selection of 47 homes, 18 apartments, and other vacation rentals in Oakville that are perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, such as WiFi and cable TV. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Oakville

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Enjoy a vibrant lakeside setting in Oakville

Perched on the north-western shore of shimmering Lake Ontario, just 30 minutes by car from downtown Toronto, Oakville is among the province’s most picturesque and prosperous towns. Its bustling downtown area is awash with cutting-edge galleries, chic fashion boutiques, and eclectic eateries, and from spring to fall you can shop for fabulously fresh seasonal produce at colorful farmers’ markets. A jam-packed year-round program of events and festivals ensures that there’s always something new to see and do, from free live music to open-air art exhibitions. And with an array of centrally located Oakville vacation rentals to choose from, you can stay right in the heart of the action.

Oakville’s awesome arts scene

If you’re after a culture fix within easy reach of your Oakville vacation rental, look no further than the Oakville Galleries. Operating out of 2 pristine venues, this cherished local organization expertly curates an ever-rotating program of thought-provoking contemporary art exhibitions. Meanwhile, the Oakwood Museum, housed in a beautifully preserved historical home set in lush gardens, tells the story of the town through ethnological artifacts, local arts and crafts, and all manner of quirky antiques and everyday objects. Oakville is also home to the Canadian Golf Hall of Fame and Museum, a must-visit for any fan of the sport.

Fabulous summer festivals in Oakville

Oakville’s annual festivals draw visitors from all over Ontario and beyond. Each June, the Oakville Family Ribfest serves up lip-smacking, award-winning ribs alongside equally hefty helpings of kid-friendly fun. Meanwhile in July, the whole town takes to the streets for Midnight Madness, an evening-long, open-air extravaganza with live entertainment, street food, and shopping. Oakville’s lakeside location makes it a haven for lovers of the great outdoors, particularly in the warm summer months. Hire a sail boat, embark on a fishing expedition or bracing hike, or simply lounge around on the sandy shoreline and soak up some rays.

Sunny summer days in Oakville

The high summer season of June to August is the most popular time to book Oakville vacation rentals. Days are long, sunny, and pleasantly warm, although rainfall is fairly consistent throughout the year, so be sure to pack something waterproof. If you want to enjoy the town in the company of fewer visitors, late spring and early fall are good options. Winters are milder than in many other regions of Canada, but temperatures are often below freezing from December until March.

Exploring the natural landscape of Oakville

Whether you're looking for fun outdoor activities or just want to take in the scenery, Oakville is a great place to spend some time outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Bronte Creek Provincial Park (6 mi / 9.6 km)
  • Centennial Park (13.8 mi / 22.2 km)
  • Royal Botanical Gardens (15.5 mi / 25 km)
  • High Park (17 mi / 27.3 km)
  • RBC Echo Beach (17.8 mi / 28.7 km)
  • Trinity Bellwoods Park (18.5 mi / 29.7 km)

Traveling to and around Oakville

Fly into Toronto Pearson Intl. Airport (YYZ), the closest airport, located 15.3 mi (24.6 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Billy Bishop Toronto City Airport (YTZ), which is 18.5 mi (29.8 km) away.

If you'd rather travel by train, make your way to Oakville Station or Bronte Station and explore the city from there.

Frequently asked questions

What is the best area to stay in Oakville when booking a vacation rental?
If you’re planning a break in Oakville, Bronte is among the most popular destinations to stay. No matter your travel style, Vrbo is sure to have a vacation rental here that’s just right for you.
What is the most popular type of vacation rental accommodation in Oakville?
Apartments are the most popular style of vacation rental in Oakville, according to our data. Even if you have something a little different in mind, Vrbo has properties in loads of sizes and shapes. Browse our many options to find your perfect fit.
How much does it cost to rent a vacation rental in Oakville?
Length of stay, property type and season are among the factors that can influence the price of a vacation home. Simply add your travel dates to find the ultimate escape. From comfy cabins to expansive villas, all Vrbo vacation rentals offer unbeatable value.
How much does it cost to rent a beach house in Oakville?
Prices for beach houses in Oakville may vary depending on the type and size of the property and when you’re traveling. All you have to do is enter your travel dates into Vrbo and the number of guests to view your rental options and prices. From there you can use the filters to refine your search results by nearby activities, amenities, ratings and more.
Are there pet-friendly vacation rentals in Oakville?
Yes, there are. You’ll have your pick of five vacation rentals that cater to pets in Oakville. Several of our pet-friendly vacation rentals even have space outdoors for your fur baby to have fun in, complimentary treats, special dog beds and proximity to parks. Apply the “Pets allowed” filter to find a vacation home on Vrbo that’s pawfect.
Can I rent a house with a pool in Oakville?
Dig out your swimwear and inflatable flamingo, because there are two houses with a private pool in Oakville. Settle in at one of these superb vacation homes and let every day be a pool day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find the perfect place for a splashing good time!
What are popular rental amenities in Oakville?
When it comes to rental amenities that people are searching for in Oakville, tennis, a swimming pool and a balcony are the most popular. With Vrbo vacation homes, there are options to fit your taste and style, whether you’re traveling with your partner, your friends or even pets.
Are there vacation rentals in Oakville that welcome kids?
With five family-friendly vacation properties to select from in Oakville, now is a great time to introduce the little ones to the excitement of travel. Check our “Properties good for families” filter box to locate stays that come with conveniences ideal for families on the move, such as dining rooms, pools, entertainment units and bunk beds.
What are the top attractions for families in Oakville?
There are tons of fabulous things to see and do with the family in Oakville, such as:

  • Oakville Centre for the Performing Arts
  • Glen Abbey Golf Course
  • Oakville Entertainment Centrum

Are there vacation rentals with WiFi in Oakville?
Whether you’d like to keep up with the headlines, make a video call or update your social media, there are four vacation homes with WiFi in Oakville. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How old do you have to be to rent a vacation rental in Oakville?
The age limit can differ across properties on Vrbo, so double-check the rules of the vacation rental in Oakville you’re interested in. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Oakville for?
How long you can book a vacation rental in Oakville is down to the property. Just enter your preferred dates to display a list of options offering extended stays. With plenty of features like air conditioning and full kitchens, as well as some offering discounted weekly or monthly prices, you’re sure to discover somewhere perfect to call your home away from home in Oakville.
Does Vrbo offer discounts for vacation homes in Oakville?
On Vrbo, we’ve got some fantastic discounts and deals for Oakville. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re after a weekend getaway or a longer stay, Vrbo has a variety of options for all budgets and styles.

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