Oakville vacation rentals

We found 558 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of 25 homes, 11 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.

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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?

Bronte is among the more in-demand neighborhoods for a vacation property in Oakville. Make yourself at home here to enjoy the relaxation and comfort that comes with having an entire place to yourself.

What is the most popular type of vacation rental accommodation in Oakville?

The most sought-after types of vacation rentals in Oakville are houses. Searching for something different? Vrbo has plenty of options to match our guests' requirements, so you'll see vacation homes in all shapes and sizes, and for all budgets. The ideal home away from home is waiting for you — snap up yours today.

How much does it cost to rent a vacation rental in Oakville?

Season, property type and length of stay are among the factors that can determine the price of a vacation home. Simply add your travel dates to find your perfect fit. From cozy country cottages to expansive luxury villas, all Vrbo vacation rentals offer amazing value.

How much does it cost to rent a beach house in Oakville?

The average price for a vacation rental by the beach in Oakville depends on when you're going and the style and size of property you're looking for. You can easily find prices on Vrbo by entering your destination and travel dates. Then use our handy filter tool to choose the number of bedrooms and amenities important to you, like air conditioning, WiFi and a hot tub.

What are popular rental amenities in Oakville?

When it comes to rental amenities that guests look for in Oakville, a fireplace, free WiFi and an oven rank highest. With Vrbo vacation rentals, you'll find options to fit your taste and style, whether you're going on a trip with your partner, your family or even pets.

What are the top attractions for families in Oakville?

There are tons of cool things to see and do with the family in Oakville, such as:

  • Playdium
  • Putting Edge
  • Oakville Museum

How old do you have to be to rent a vacation rental in Oakville?

The minimum age can differ across properties on Vrbo, so double-check the rules of the vacation rental in Oakville you want. But typically, it's 16, 18 or 21.

How long can I rent a vacation rental in Oakville for?

It all depends on the Oakville property. To look at a list of options offering extended stays, just type your travel dates and number of people into the Vrbo search page. You can look forward to having the whole property to yourself, along with amenities such as a fully-equipped kitchen, air conditioning and an outdoor space where the kids can run around and play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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