Oakville holiday homes

We found 738 holiday rentals — enter your dates for availability
Select from 57 houses, 25 apartments and other holiday rentals to find the perfect place for your stay in Oakville. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a hot tub. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Oakville

Showing deals for:9 Oct - 16 Oct

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  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Oakville

  • Urban-Nature Fusion: Enjoy scenic urban parks and nature reserves that offer a perfect blend of outdoor adventures and city experiences.
  • Historical Elegance: Discover the rich local history with museums and heritage sites that capture Oakville’s charming past.
  • Family-Friendly Vibes: Experience a welcoming, family-oriented atmosphere throughout the city’s diverse neighbourhoods.
  • Cultural Mix: Immerse yourself in a unique blend of classic charm and modern business energy.
  • Leisurely Strolls: Take leisurely walks through picturesque streets and vibrant public spaces.

Top attractions in and around Oakville

Explore the charm of Oakville, Ontario, where urban parks, nature reserves, and history museums provide a perfect blend of outdoor adventures and city experiences. Ideal for families and business themed holidays, the city offers a unique mix of cultural and natural attractions. Enjoy leisurely strolls through scenic parks and immerse yourself in the rich local history, all while experiencing the friendly, welcoming spirit of Oakville.

Things to do recommended for couples

Oakville offers a charming getaway for couples. Enjoy a leisurely walk along the picturesque waterfront, indulge in wine tasting at local vineyards, or explore the scenic gardens at Gairloch Gardens. For a memorable evening, dine at a romantic restaurant overlooking the lake, creating lasting memories together.

Things to do recommended for families

Your family will love exploring the scenic trails at Bronte Creek Provincial Park, perfect for picnics and nature walks. Don't miss the Oakville Museum for a glimpse into local history, and enjoy a day at the nearby beach at Oakville Harbour for some fun in the sun.

Things to do recommended for groups

Gather your crew for an adrenaline rush at Flamboro Speedway, a motorRacing venue 32km away from Oakville, offering thrilling sports and adventure vibes.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Oakville

No matter if you're travelling with a group, as a family, with your pets, or if you're seeking longer stays, be sure to apply the appropriate filters. Here are some top Vrbo booking tips just for you.

  • Traveling to Oakville with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily refine your search to include all of these options, and much more, on Vrbo.
  • Traveling to Oakville with young kids: Traveling with young ones can pose its challenges. You must prioritise their comfort and safety, ensuring there are child-friendly amenities such as a private pool. It’s also wise to consider how close you are to attractions that cater to families.
  • Taking your pets with you to Oakville: For many families, a trip wouldn’t feel complete without their furry companions. If this resonates with you, be sure to explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Oakville: If you're after holiday rentals offering discounts for stays of a month or more, you've come to the right spot. With the proper filter, you can effortlessly find and save on monthly rentals. Remember to include extras like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Oakville

Discover Oakville, where a blend of classic charm and modern business vibes awaits. Enjoy the historic elegance of Old Oakville, explore the welcoming streets of Central Oakville, and experience a family-friendly atmosphere on every corner. Oakville offers a rich mix of urban excitement and accessible leisure, making it a perfect destination for both business and family holidays.

  • Toronto: Toronto is a bustling metropolis and a short journey from Oakville, offering a dynamic mix of family, city-themed, and business experiences. Visitors can explore an array of shopping malls, centres, and theatres that cater to diverse tastes. The city is also home to renowned attractions including sports facility stadiums, lookout points, and modern towers, providing a vibrant urban setting. Toronto's extensive transportation network and cosmopolitan vibe make it a key destination for both leisure and professional ventures.
  • Mississauga: Located 14km from Oakville, Mississauga presents a lively city atmosphere with an emphasis on family, city-themed, and business-themed experiences. The city boasts bustling shopping mall centres, shopping centres, and even amusement parks for those seeking entertainment. Local landmarks such as sports facility stadiums, event conference venues, and convention centres add to its appeal. Mississauga's well-connected transit options and urban energy offer a well-rounded destination for visitors.
  • Great Lakes Waterfront Trail: The Great Lakes Waterfront Trail, situated 10km from Oakville, offers a scenic route primarily for footpath exploration. Ideal for outdoor, romantic, and family experiences, this trail is bordered by a shopping mall centre, recreational areas, and opportunities for body treatments. Its proximity to natural landmarks like lakes, family beaches, and sandy beaches provides a refreshing retreat into nature, perfect for leisurely strolls and quality time outdoors.

Best time to go to Oakville

If you're planning a trip to Oakville, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.3°F (-3.7°C)Light RainMostly CloudyAverage
February25.5°F (-3.6°C)Light RainMostly CloudyAverage
March33.8°F (1.0°C)Light RainMostly CloudyAverage
April43.3°F (6.3°C)Light RainMostly CloudyAverage
May55.2°F (12.9°C)Light RainMostly SunnyAverage
June64.8°F (18.2°C)Light RainMostly SunnyAverage
July71.6°F (22.0°C)Light RainMostly SunnySlightly High
August71.1°F (21.7°C)Light RainMostly SunnySlightly High
September64.9°F (18.3°C)Light RainMostly SunnySlightly High
October53.2°F (11.8°C)Light RainMostly SunnySlightly Low
November41.5°F (5.3°C)Light RainMostly SunnySlightly Low
December32.9°F (0.5°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is a breeze

Looking to save on your next adventure? Being flexible with your travel dates can really make a difference, as prices often fluctuate. You might also enjoy substantial savings by booking a longer stay. To find a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's pioneering Trip Board offers you a dedicated space to design fresh trips, pick up where you last stopped, or review and arrange your travel plans. Saved and booked properties are now neatly categorised as Potential, Upcoming, or Current Trips. To access your Trip Boards, please visit: https://www.bookabach.co.nz/trips

**Based on Vrbo properties bookings.

Travel to lively Oakville

Enjoy the area's musicals, theatre scene and entertainment with a rental holiday home in Oakville. This city's wildlife, restaurants and university setting draw many visitors. Square One Shopping Centre and RBC Amphitheatre are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Oakville

Are you looking for things to do while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Oakville a fun place to get away to. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Glen Abbey Golf Course (1.8 mi / 2.9 km)
  • Toronto Golf Club (11.1 mi / 17.9 km)
  • Wild Waterworks (15.7 mi / 25.2 km)
  • Ontario Place (17.8 mi / 28.7 km)
  • Wet 'n' Wild Toronto (19.1 mi / 30.8 km)
  • IFLY Toronto Oakville (3.1 mi / 5 km)

Exploring the natural landscape of Oakville

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Oakville is a great place to get out in nature. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Erindale Park (5.8 mi / 9.4 km)
  • Lakefront Promenade Park (9.8 mi / 15.7 km)
  • Colonel Sam Smith Park (12.3 mi / 19.7 km)
  • Kelso Conservation Area (13 mi / 20.9 km)
  • Centennial Park (13.8 mi / 22.2 km)
  • Hilton Falls (14.1 mi / 22.7 km)

Travelling to and around Oakville

Fly into Toronto, ON (YYZ-Pearson Intl.), the closest airport, located 15.3 mi (24.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Toronto, ON (YTZ-Billy Bishop Toronto City), which is 18.5 mi (29.8 km) away.

If you're travelling 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 holiday home?
Bronte is among the more in-demand neighbourhoods for a holiday 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 holiday home accommodation in Oakville?
The most sought-after types of holiday homes in Oakville are houses. Searching for something different? Bookabach has plenty of options to match our guests' requirements, so you'll see holiday 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 holiday home in Oakville?
Season, property type and length of stay are among the factors that can determine the price of a holiday home. Simply add your travel dates to find your perfect fit. From cosy country cottages to expansive luxury villas, all Bookabach holiday homes offer amazing value.
How much does it cost to rent a beach house in Oakville?
The average price for a holiday home 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 Bookabach 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 home amenities in Oakville?
When it comes to home amenities that guests look for in Oakville, a fireplace, free WiFi and an oven rank highest. With Bookabach holiday homes, 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 holiday home in Oakville?
The minimum age can differ across properties on Bookabach, so double-check the rules of the holiday home in Oakville you want. But typically, it's 16, 18 or 21.
How long can I rent a holiday home 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 Bookabach 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.