Oakville holiday rentals

We found 733 holiday rentals — enter your dates for availability
Select from 61 houses, 10 flats 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. 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 Club (1.8 mi / 2.9 km)
  • Glen Eden Ski and Snowboard Centre (13.1 mi / 21.1 km)
  • Chudleigh's Farm (13.7 mi / 22 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)

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:

  • Coronation Park (4.2 mi / 6.7 km)
  • Erindale Park (5.8 mi / 9.4 km)
  • Lakefront Promenade Park (9.4 mi / 15.1 km)
  • Rattlesnake Point (11.3 mi / 18.2 km)
  • Kelso Conservation Area (13 mi / 20.9 km)
  • Crawford Lake Indian Village (13.2 mi / 21.2 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?
When considering a holiday rental in Oakville, Ontario, the Bronte Village area stands out as a fantastic option. This charming neighbourhood is known for its picturesque waterfront along Lake Ontario, where you can enjoy scenic walks and relax at the local parks. Bronte Village is also home to a delightful selection of boutiques, cafes, and restaurants, making it a vibrant spot for visitors.Another noteworthy area is the Old Oakville district, which features beautiful historic homes and tree-lined streets. This neighbourhood offers a quaint, community feel while being close to the bustling downtown area. Here, you can explore the local shops and enjoy the lively option at various events held throughout the year. Additionally, the Oakville Museum and the nearby parks provide cultural and recreational opportunities for all ages.In terms of holiday rental options, both Bronte Village and Old Oakville have a variety of properties available, suiting different tastes and budgets.
Where are the best areas for renting a beach house in Oakville?
For renting a beach house in Oakville, the area around Bronte Creek and the waterfront along Lake Ontario offers some excellent options. The Bronte Harbour area is particularly appealing, with its picturesque marina and proximity to the beach. Many holiday rentals here come with amenities such as private balconies, outdoor seating areas, and access to communal gardens, providing an ideal setting for relaxation and entertaining.Along the lakeshore, you'll find charming cottages and larger homes that often feature modern kitchens, open-plan living spaces, and sometimes even private docks for those looking to enjoy water activities. The local parks, such as Bronte Creek Provincial Park, offer additional recreational opportunities, with hiking trails and picnic spots that enhance the beachside experience.In addition, the vibrant Bronte Village nearby provides a selection of restaurants and shops, making it convenient for guests to enjoy local dining and shopping options.
What is the most popular type of holiday rental accomodation in Oakville?
In Oakville, holiday houses are the most popular type of holiday rental, with approximately 232 options available throughout the town. These homes are often situated in residential neighbourhoods, providing a comfortable and spacious environment ideal for families or larger groups. Most holiday houses come equipped with multiple bedrooms, fully stocked kitchens, and outdoor areas such as gardens or patios for relaxation after a day of exploring.Apartments also feature in the rental market, with around 76 units available, typically located near local parks and vibrant shopping areas. These apartments generally include essential amenities like kitchen facilities, cosy living spaces, and some may even offer balconies for enjoying the surroundings. Additionally, there are about 28 condos available, which often provide modern furnishings and shared amenities such as pools or fitness centres.
Are there any family house rentals in Oakville?
In Oakville, Ontario, there are 18 family-friendly house rentals available, making it a splendid choice for families seeking a comfortable stay. This charming town is known for its picturesque waterfront along Lake Ontario and its proximity to various parks and recreational areas. Properties in neighbourhoods like Bronte and Glen Abbey often showcase spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor spaces ideal for children to play.Visitors can enjoy access to numerous amenities such as Wi-Fi, air conditioning, and sometimes even private gardens or patios for relaxation. Nearby attractions include Bronte Creek Provincial Park, where families can explore nature trails and picnic areas, as well as local shops and restaurants that offer a taste of the area's vibrant community.
Are there pet-friendly house rentals in Oakville?
In Oakville, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these properties are equipped with essential amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces, superb for both relaxation and entertaining.The neighbourhoods around Oakville, such as Bronte and Kerr Village, offer beautiful parks and trails, making them ideal for pet owners. Bronte Creek Provincial Park, for instance, features extensive walking paths where you can enjoy nature with your pets. Additionally, the local community is known for its pet-friendly cafes and shops, ideal for those travelling with animals.
Are there any remote work holiday rentals in Oakville?
In Oakville, Ontario, there are numerous remote work-friendly holiday rentals available, with around 256 options to choose from. This charming town offers a blend of suburban comfort and proximity to natural beauty, making it an ideal location for those working remotely. Many properties come equipped with essential amenities such as high-speed internet, free Wi-Fi, dedicated work desks, and desk chairs, ensuring a conducive work environment. Some rentals even provide access to printers, making it easier for guests to manage their professional needs while enjoying their stay.Oakville is known for its picturesque waterfront along Lake Ontario, where visitors can unwind after a day of work. The town also features lovely parks, shops, and restaurants, providing ample opportunities to explore the local culture during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Oakville?
In Oakville, popular rental amenities include onsite parking, which is a significant convenience for travellers. Most holiday rentals are equipped with kitchens, allowing guests to prepare their meals and enjoy the comfort of dining in. Additionally, many properties offer coffee and tea makers for that morning brew and paper towels for everyday needs. For those travelling with furry companions, it's worth noting that pets are permitted in some rentals, making Oakville a welcoming destination for pet owners.
When is the best time to visit Oakville for a holiday rental?
The best time to visit Oakville for a holiday rental is during the peak season from July to September. This vibrant period draws in families and leisure travellers who flock to the area to enjoy its beautiful waterfront, charming parks, and engaging local festivals. With warm temperatures averaging around 25 to 30 degrees Celsius, it's an ideal time for outdoor activities, from relaxing on the beaches to strolling along the scenic trails.July, in particular, stands out as the most popular month, bringing a lively option filled with events and activities. You can immerse yourself in the local culture by attending summer festivals or enjoying outdoor dining at one of the many waterfront restaurants. The pleasant weather enhances sightseeing opportunities, allowing you to explore Oakville's historic downtown and picturesque harbours with ease.For those seeking a more budget-friendly experience, consider visiting in November. Although this month falls outside the peak tourist season, it offers a unique charm with fewer crowds and the opportunity to explore the area's fall landscapes. This quieter time is great for discovering local shops and enjoying a peaceful retreat.Ultimately, your choice of when to visit Oakville will depend on whether you prefer the bustling energy of summer or the tranquil beauty of autumn.
What are the top attractions in Oakville?
In Oakville, visitors can enjoy a variety of attractions that showcase the town's natural beauty and vibrant community. The picturesque waterfront along Lake Ontario is a highlight, particularly at Bronte Creek Provincial Park, where outdoor enthusiasts can partake in hiking, picnicking, and birdwatching. The nearby Oakville Harbour offers scenic views and opportunities for sailing and kayaking.Downtown Oakville boasts charming boutiques, art galleries, and a selection of cafes and restaurants, making it an ideal spot for leisurely strolls and dining. The Oakville Centre for the Performing Arts hosts a range of cultural events, including theatre performances and concerts, providing entertainment for all tastes.For those interested in history, the Erchless Estate, home to the Oakville Museum, offers insights into the town's past and features beautiful gardens to explore. Additionally, the Sixteen Mile Creek runs through the town, offering serene trails great for walking and cycling.
Are all fees included in the Oakville holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Oakville holiday homes with parking?
Stayz offers a wide selection of holiday homes in Oakville with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Oakville holiday homes?
You can find great discounts on holiday homes in Oakville on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Oakville holiday home booking on Stayz?
To find Oakville holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Oakville?
A long-stay holiday home in Oakville is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Oakville holiday home?
Book your Oakville holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oakville?
Prices for holiday homes in Oakville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Oakville to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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