Oakville holiday lettings

We found 746 holiday rentals — enter your dates for availability

Discover a selection of 55 homes, 20 apartments and other holiday rentals in Oakville that are perfect for your trip. 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:5 Dec - 12 Dec
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Find out more about Oakville

Find out more about Oakville

Why visit Oakville

  • Charming neighbourhoods: Oakville boasts picturesque areas that invite exploration and provide a friendly atmosphere.
  • Outdoor adventures: Enjoy beautiful parks and beach access, perfect for leisurely strolls or family outings.
  • Family-friendly activities: A variety of attractions cater to families, ensuring enjoyable experiences for all ages.
  • Vibrant city life: Experience a lively urban environment with shopping, dining, and cultural events.
  • Diverse accommodation options: Choose from charming private homes, modern apartments, or stylish condos for a comfortable stay.

Popular types of accommodation in Oakville

If you're pondering what type of accommodation awaits you in Oakville, look no further. Our most sought-after options include charming houses, modern apartments, and stylish condos. Whether you're searching for house rentals or holiday rentals in Oakville, we have a variety of choices to suit your needs for a delightful getaway.

  • Houses: The top choice for accommodation in Oakville, offering a homely feel perfect for families or groups.
  • Apartments: A popular option for couples and solo travellers looking for convenience and comfort during their stay.
  • Condos: A stylish alternative providing modern amenities, ideal for those wanting a touch of luxury.
  • Cottages: Quaint and charming, these are perfect for a tranquil escape close to nature.
  • Villas: Spacious and luxurious, ideal for those seeking an upscale holiday experience.**

Top attractions near Oakville

Oakville, Ontario, is an excellent destination for family, city, or business-themed holidays. Visitors can explore a variety of attractions, including urban parks, event and conference venues, and modern colleges and universities. Whether you seek outdoor adventures, family-friendly activities, or a vibrant city experience, Oakville offers a delightful mix of points of interest to suit every traveller's needs.

  • University of Toronto Mississauga: Nestled in a vibrant urban setting, this modern university boasts striking architecture and lush green spaces, creating a perfect blend of academia and nature. Explore its contemporary facilities and enjoy the dynamic atmosphere.
  • Bronte Creek Provincial Park: A haven for outdoor enthusiasts, this national park features picturesque trails, picnicking spots, and scenic vistas. Engage in activities like hiking, cycling, and wildlife watching amid its stunning natural beauty.
  • Mississauga Celebration Square: This lively landmark serves as a community hub, where friendly locals gather for events and festivals. Enjoy the family-friendly vibe, with ample space for relaxation, entertainment, and cultural experiences.

Things to do recommended for couples

For a romantic getaway in Oakville, consider an exhilarating indoor skydiving experience at iFLY Toronto. Alternatively, enjoy a day of skiing at Glen Eden Ski and Snowboard Centre or challenge each other to a fun round of mini golf at Putting Edge Mississauga, both a short drive away.

Things to do recommended for families

During your family vacation in Oakville, you can experience the excitement at Paramount Fine Foods Centre for sports, enjoy thrilling games at Playdium, and let the kids explore the outdoor fun at Amazing Adventures Playland, all within a short drive from your accommodation.

Things to do recommended for groups

Groups visiting Oakville can indulge in retail therapy at the nearby Square One Shopping Centre, enjoy a round of golf at Glen Abbey Golf Course, or immerse themselves in the arts at the Living Arts Centre, all while experiencing the vibrant local culture.

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

If you're travelling with a group, family, pets, or seeking extended stays, it's essential to apply the appropriate filters to meet your needs. Here are some helpful Vrbo booking tips 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. Thankfully, you can easily refine your search for all of these options, and plenty more, on Vrbo.
  • Traveling to Oakville with young kids: Travelling with young children can be quite demanding. It's essential to prioritise 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 Oakville: For many, a family holiday wouldn’t be the same without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oakville: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Oakville

Oakville, Ontario, offers a delightful blend of family-friendly activities and vibrant city life, making it an ideal holiday destination. With its charming neighbourhoods and beautiful beach access, visitors can enjoy a relaxing atmosphere while exploring the local culture. Just a short journey from Southern Ontario's attractions, Oakville provides a perfect base for excursions, whether you're seeking business opportunities or leisure time with loved ones. Discover the warmth of this friendly community during your stay.

  • Mississauga: Situated approximately 5.6km from Oakville, Mississauga is a bustling city offering a rich blend of family-friendly activities and business opportunities. Known for its impressive shopping centres and malls, visitors can enjoy a vibrant retail experience. The city is home to notable landmarks such as the impressive sports facility stadium and a state-of-the-art convention centre, making it an ideal spot for both leisure and corporate events. With a diverse culinary scene and numerous parks, Mississauga presents a dynamic atmosphere that caters to all types of travellers.
  • Sheridan: Located about 2.5km from Oakville, Sheridan is a charming neighbourhood that appeals to families and professionals alike. It is renowned for its educational institutions, including a modern college university, which attracts students from various backgrounds. The area boasts several shopping centres, providing ample opportunities for retail therapy. Additionally, Sheridan features a prominent sports facility stadium, offering exciting events throughout the year. Its picturesque residential streets and community vibe make it a lovely place to explore, relax, and enjoy local amenities.
  • Clarkson: Also situated around 2.5km from Oakville, Clarkson is a delightful neighbourhood known for its family-oriented atmosphere and cultural attractions. The area features vibrant shopping centres and is often buzzing with music concerts and community events. Noteworthy landmarks include a historic place and a sports facility stadium, which host various events and activities. Clarkson's charming streets and friendly community make it a perfect destination for those looking to enjoy a blend of history, culture, and modern amenities.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient platform for you to plan new getaways, refine your arrangements, or manage your existing bookings. The properties you've saved or reserved are neatly categorised into Potential, Upcoming, or Current Trips for your ease of access. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/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. 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)
  • IFLY Toronto Oakville (3.1 mi / 5 km)
  • Toronto Golf Club (11.1 mi / 17.9 km)
  • Royal Woodbine Golf Club (15.4 mi / 24.8 km)
  • Mohawk Racetrack (15.6 mi / 25.2 km)
  • Wild Waterworks (15.7 mi / 25.2 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:

  • Lakefront Promenade Park (9.8 mi / 15.7 km)
  • Rattlesnake Point (11.3 mi / 18.2 km)
  • Centennial Park (13.8 mi / 22.2 km)
  • Humber Bay Park West (14.8 mi / 23.8 km)
  • Humber Bay Park East (15 mi / 24.2 km)
  • Royal Botanical Gardens (15.5 mi / 25 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 rental?
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 rental accommodation in Oakville?
The most sought-after types of holiday rentals in Oakville are houses. Searching for something different? Vrbo 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 rental 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 Vrbo holiday rentals offer amazing value.
How much does it cost to rent a beach house in Oakville?
The average price for a holiday 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 holiday 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 holiday rental in Oakville?
The minimum age can differ across properties on Vrbo, so double-check the rules of the holiday rental in Oakville you want. But typically, it's 16, 18 or 21.
How long can I rent a holiday 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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