Oakville holiday rentals

We found 759 holiday rentals — enter your dates for availability

Select from 59 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.
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Why visit Oakville

  • Charming Historic District: Explore the picturesque streets of Old Oakville, filled with quaint shops and rich heritage.
  • Beautiful Urban Parks: Enjoy the stunning lakeside views and recreational activities in Oakville's serene parks and nature reserves.
  • Vibrant Local Markets: Experience the lively atmosphere of local markets showcasing fresh produce and artisanal goods.
  • Engaging Cultural Heritage: Discover enlightening history museums that highlight the city's unique past and community spirit.
  • Family-Friendly Atmosphere: Oakville offers a welcoming environment perfect for families and those seeking a balanced holiday experience.

Popular types of accommodation in Oakville

Welcome to Oakville, Ontario, a charming city offering a delightful blend of scenic lakeside views, heritage attractions, and a vibrant local culture. Whether you're seeking cosy private holiday homes, contemporary apartments, or stylish condos, Oakville’s diverse selection of holiday rentals, including oakville apartment rentals and bedroom rentals, ensures a memorable stay for all. Explore the town’s unique landmarks and immerse yourself in its warm, inviting atmosphere during your next getaway.

  • Private Holiday Homes: Enjoy the comfort and privacy of your own space, perfect for families or groups seeking a home-like atmosphere during their stay in Oakville.
  • Apartments: Ideal for those looking for a convenient and self-sufficient option, apartments offer a blend of comfort and accessibility in the heart of the city.
  • Condos: Experience modern living with amenities, condos are a popular choice for travellers wanting a stylish and comfortable retreat.
  • Cottages: Embrace a quaint and charming atmosphere with cottages, often nestled in serene locations, perfect for a relaxing getaway.
  • Villas: For a touch of luxury, villas provide spacious living and upscale amenities, ideal for those seeking a lavish escape.**

Top attractions in and around Oakville

Oakville, Ontario, is a charming city perfect for family, urban, and business-themed holidays. Visitors can enjoy its beautiful urban parks, serene nature reserves, and enlightening history museums. The attractions in Oakville cater to those seeking outdoor adventures and enriching experiences, making it an ideal destination for travellers looking to explore the city's vibrant culture and natural beauty.

  • Coronation Park: A delightful urban park nestled in Oakville, perfect for families and outdoor enthusiasts. It boasts scenic views, ample green space for picnics, and recreational facilities, making it an ideal spot for relaxation and enjoyment.
  • Mississauga Celebration Square: While slightly outside Oakville, this vibrant landmark is renowned for its community events and friendly atmosphere. It's a great place for families to gather and enjoy various activities throughout the year.
  • Erindale Park: A picturesque nature reserve that offers a serene escape with lovely walking trails and lush landscapes. This park is family-friendly, making it perfect for leisurely strolls and enjoying the outdoors.

Things to do recommended for couples

In Oakville, immerse yourselves in a romantic lakeside stroll at Bronte Creek Provincial Park, or indulge in a candlelit dinner at a charming local bistro. Don't miss the stunning sunset views over Lake Ontario; it’s the perfect backdrop for a memorable couple's getaway.

Things to do recommended for families

Families visiting Oakville can explore the scenic Bronte Creek Provincial Park, where children can enjoy nature trails and a petting farm. The Oakville Museum offers engaging exhibits for all ages, while the local splash pads provide a perfect spot for kids to cool off during sunny days.

Things to do recommended for groups

Groups visiting Oakville can experience the thrill of Flamboro Speedway, a motor racing venue located 32km away, perfect for those seeking sports and adventure vibes. Enjoy the excitement and camaraderie as your group witnesses high-speed races and the vibrant atmosphere of the track.

*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

When you’re planning a trip, whether it’s with a group, family, pets, or for an extended stay, be sure to prioritise your preferences when filtering your options. Here are some helpful booking tips for Stayz.

  • Traveling to Oakville with a group: Consider how many bedrooms will be required and whether you need extras like a fully-equipped kitchen or an outdoor area suitable for group gatherings. Fortunately, you can use Stayz to filter for these features and many others.
  • Traveling to Oakville with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Oakville: For many, a family holiday is not complete without the company of a furry companion. If this resonates with you, explore Stayz properties that welcome pets. The majority of these 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 Oakville: If you’re in search of holiday rentals with offers 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 rentals. It’s also worth considering additional features in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay in Oakville

Discover Oakville’s unique charm as you stroll through its historic Old Oakville, explore vibrant local markets, and experience the warm, family-friendly spirit. The city’s blend of business and leisure atmospheres offers an engaging mix of urban life and local heritage, perfect for a balanced holiday experience. Enjoy the authentic life in Oakville and its inviting, close-knit community.

  • Toronto: Toronto, a bustling metropolis, offers an exciting mix of cultural experiences and urban adventures. Located within close proximity to Oakville, this vibrant city is perfect for those seeking family-friendly activities, business opportunities, or city-themed excursions. Visitors can explore iconic shopping centres, catch a performance at a local theatre, or enjoy a day at one of the many sports stadiums. With landmarks such as the CN Tower and various modern skyscrapers, Toronto is a city where the skyline tells its own story. The diverse neighbourhoods offer a rich tapestry of dining, entertainment, and cultural experiences, making it an essential stop during your visit.
  • Mississauga: Situated approximately 14km from Oakville, Mississauga is a dynamic city known for its family-oriented attractions and thriving business scene. This urban landscape is home to expansive shopping malls and the popular amusement park, providing endless entertainment for visitors of all ages. Key landmarks include the event conference venues and convention centre, which host a variety of events year-round. With its well-planned parks and recreational facilities, Mississauga offers a balanced blend of urban life and leisurely activities, making it a great destination for a day trip.
  • Clarkson-Lorne Park: Just 8km away from Oakville, the charming neighbourhood of Clarkson-Lorne Park is ideal for those seeking a family-friendly and outdoor-oriented experience. This area boasts beautiful recreational spaces and shopping centres that cater to both relaxation and leisure. Visitors can enjoy local parks, ideal for picnics or leisurely strolls, as well as various sports facilities. Clarkson-Lorne Park provides a serene escape from the hustle and bustle, allowing you to savour the natural beauty and community spirit of the region.

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. Peak season runs from July to September, while off-peak times, like October to December tend to have fewer bookings and better deals.

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

Booking with Stayz is a breeze

Looking to save on your upcoming holiday? Consider a flexible approach to your travel dates, as prices can differ significantly. Moreover, opting for a longer stay often results in substantial savings. To discover the ideal Stayz property that meets your budget, simply utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board provides a convenient platform for you to plan new trips, refine your existing plans, or manage your bookings with ease. The properties you've saved or reserved are thoughtfully categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/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)
  • Royal Woodbine Golf Club (15.4 mi / 24.8 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)
  • Gairloch Gardens (2.1 mi / 3.3 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)
  • Ashbridge s Bay Park (10.9 mi / 17.6 km)
  • Marie Curtis Park (10.9 mi / 17.6 km)
  • Rattlesnake Point (11.3 mi / 18.2 km)
  • Colonel Sam Smith Park (12.3 mi / 19.7 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? Stayz 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 Stayz 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 Stayz 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 Stayz 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 Stayz, 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 Stayz 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.