Vacation Rentals in Oakville

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Oakville holiday rentals
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871 Holiday rentals and Airbnb in Oakville

Superior Family-Friendly Holiday Rentals in Oakville, Canada

Give the entire crew plenty of space to relax and unwind after a busy day of sightseeing at family holiday rentals in Oakville, Canada.

4bed-luxury Home, Pool Table, Backyard, Sleeps 12 - Oakville
8.6 7 reviews

4bed-luxury Home, Pool Table, Backyard, Sleeps 12

apartment, Milton
This modern 4-bedroom house is located in a quiet subdivision in Oakville, 40 kilometres from the airport, offering a family-friendly base for those visiting Milton.
This spacious residence sleeps up to 12 guests, featuring a fully equipped kitchen with a dishwasher, air conditioning, a garden, and parking for up to four vehicles, with a game area for entertainment.
Spacious House With Pond View And Jacuuzi - Oakville
10 1 review

Spacious House With Pond View And Jacuuzi

apartment, Toronto
This four-bedroom, three-bathroom flat is located in Joshua Creek, Oakville, offering convenient access to major motorways (403, 407, QEW) and a brief drive to local amenities, approximately 25 kilometres west of downtown Toronto.
This spacious accommodation accommodates up to ten guests, featuring a gourmet kitchen with stainless steel KitchenAid appliances, a private patio with a hot Jacuzzi and BBQ, a laundry room with an LG washer and dryer, and parking for four vehicles, including a two-car garage.
South Oakville Bliss Haven - Oakville
9.7 43 reviews

South Oakville Bliss Haven

apartment, Toronto
This Toronto family-friendly house, sleeping six across three bedrooms and two bathrooms, offers a tranquil garden and parking, along with excellent guest ratings for cleanliness and location.
The property boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, internet access, and is ideally situated for exploring Toronto's attractions, although precise location and distances to landmarks remain unspecified.
Cozy 2 Bedrooms Modern Basement Suite With Private Entrance, Kitchen And Parking - Oakville
8.2 23 reviews

Cozy 2 Bedrooms Modern Basement Suite With Private Entrance, Kitchen And Parking

apartment, Toronto
This cosy Mississauga basement flat, located 18 kilometres from Toronto Pearson International Airport and within easy driving distance of attractions such as the Rogers Centre and CN Tower (both 35 kilometres away), offers convenient access to Toronto.
The 79-square-metre self-catering property sleeps nine guests, boasting two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, free Wi-Fi, air conditioning, and private parking.

Best Oakville holiday rentals with parking

Designer 4br Basement Suite  Oakville Entire Basement In Oakville, Canada - Oakville
No reviews

Designer 4br Basement Suite Oakville Entire Basement In Oakville, Canada

apartment, Milton
This 4-bedroom, 2.5-bathroom holiday home in Oakville is located 17.7 kilometres from Lake Ontario and 19.3 kilometres from Bronte Creek Provincial Park.
This property offers accommodation for 8 guests with internet, air conditioning, a dryer, and an iron, and is a short drive to Cinéplex Cinemas Winston Churchill, iFLY Toronto Oakville, Square One Shopping Centre and Toronto Premium Outlets.
Very Bright Basement Unit, Sep Entrance +Parking - Oakville
10 17 reviews

Very Bright Basement Unit, Sep Entrance +Parking

apartment, Toronto
This stylish city flat is located in a prime downtown Toronto district, offering immediate access to the city's core and close proximity to major landmarks such as the CN Tower, which is 1.5 kilometres away, and the Royal Ontario Museum, 2 kilometres away.
This modern apartment accommodates up to four guests and features a kitchen, air conditioning, and Wi-Fi, with pets welcome, making it an ideal base for exploring Toronto's attractions and public transport links.
Spacious Modern 4-bed Townhome With Cinema - Oakville
10 14 reviews

Spacious Modern 4-bed Townhome With Cinema

apartment, Milton
This contemporary townhome is situated in North Oakville, offering excellent access to the 403, 407, and QEW highways for convenient travel to Milton and surrounding areas.
This spacious property accommodates up to 8 guests, boasting 4 bedrooms, 3 bathrooms, ultra-fast 1.5 Gb/s internet, a dedicated home theatre with a 115-inch screen and Dolby Atmos sound system, two outdoor terraces, and ample parking for 4 vehicles.
Fully Furnished Basement Studio In Oakville - Oakville
No reviews

Fully Furnished Basement Studio In Oakville

apartment, Toronto
This basement studio flat is situated in Oakville's Westmount district, offering convenient access to the QEW and Bronte GO station within a 10-minute drive, and is a 12-minute drive from the lakefront.
This one-bedroom flat accommodates two guests, featuring a modern open-concept living area with a Smart TV and Wi-Fi, a kitchen with a fridge and microwave, air conditioning, separate entrance, and free parking, all within a peaceful neighbourhood with nearby trails and playgrounds.

Frequently asked questions about holiday rentals in Oakville

  • What are the top family-friendly attractions in Oakville?

    Oakville has a lot to offer families. The Oakville Children's Centre is a great place for kids to play and learn, and the Oakville Galleries has some fun interactive exhibits. You can also take a walk along the lakefront trail, which is perfect for a family picnic.
  • What are the best Airbnb and holiday rentals in Oakville?

    Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are among the best Airbnb and holiday rentals in Oakville.

  • When is the best time to book a vacation rental in Oakville?

    The best time to book a vacation rental in Oakville is during the shoulder seasons, from April to June and September to October. You'll avoid the crowds and get better rates, but the weather is still pleasant.
  • What are the most popular Airbnbs in Oakville?

    Among the Airbnbs in Oakville, Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are the most popular ones.

  • What events or festivals should visitors check out in and around Oakville?

    Oakville's got a great calendar of events, including the Oakville Jazz Festival in July and the Oakville Fall Fair in September. If you're looking for something a little different, check out the Bronte Creek Provincial Park, which hosts a number of events throughout the year.
  • What are the best holiday rentals with a pool in Oakville?

  • What are the best restaurants with local dishes in Oakville?

    For a taste of local cuisine, head to The Oakville Chop House for a classic steak or The Queen's Plate Restaurant for a more casual dining experience. Both offer delicious and authentic dishes.
  • What are the best rentals for families and kids in Oakville?

    The best rentals for families and kids in Oakville are Home Away From Home (Basement Apartment), Pathway Suites and Cozy & Beautiful Basement Apartment.

  • What are the best walking or cycling routes in Oakville?

    The Waterfront Trail is a great option for both walking and cycling. It stretches along the lakefront and offers stunning views. For a shorter walk, try the Bronte Creek Provincial Park, which has a variety of trails for all levels.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakville?

    The best holiday rentals or Airbnb with a jacuzzi in Oakville are Pathway Suites, Beautiful Cozy 1 Br Condo Steps To Sq1 and Luxurious1 Br Condo In Downtown Mississauga .

  • Are there pet-friendly attractions in Oakville?

    Yes, Oakville is a very pet-friendly city. You can bring your furry friend to many of the parks and trails, including Coronation Park and the Waterfront Trail. Many restaurants also have outdoor patios that welcome dogs.
  • What are the benefits of choosing a vacation rental in Oakville?

    Vacation rentals offer more space and privacy than hotels, and often come with amenities like kitchens and laundry facilities. They can also be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Oakville?

    Oakville has a number of sports facilities, including the Oakville Soccer Club, the Oakville Tennis Club, and the Oakville Golf Club. The town is also home to the Oakville Hornets, a junior hockey team.

Popular destinations

Holiday Rentals with a Balcony in Oakville, Canada

Relax outdoors and watch the town come alive from the elevated vantage of holiday rentals with a balcony in Oakville, Canada.

Luxury Oakville Home, Hot Tub, Fireplace, New Home - Oakville
10 1 review

Luxury Oakville Home, Hot Tub, Fireplace, New Home

house, Milton
This luxurious property is situated in Oakville, just 24 kilometres from the Mississauga Convention Centre, 35 kilometres from BMO Field, and 37 kilometres from Budweiser Stage. The home has received excellent ratings for its location, cleanliness, and overall user experience.
This four-bedroom home is spacious and comfortable, with a floor area of 229 square metres and a guest capacity of 10. The property offers a range of amenities, including a private hot tub, outdoor dining area, fireplace, fully equipped kitchen, free Wi-Fi, washer and dryer, and a peaceful garden.
*Family Haven* Renovated 3br  Backyard  Parking - Oakville
No reviews

*Family Haven* Renovated 3br Backyard Parking

apartment, Hamilton
This spacious 186-square-metre, two-storey townhome is situated in Burlington, a short drive from Hamilton's attractions, and is within walking distance of local shops and restaurants.
This pet-friendly residence accommodates up to six guests with three bedrooms and two bathrooms, offering a fully equipped kitchen, a formal dining area for eight, in-unit laundry, air conditioning, a terrace, and two driveway parking spaces, with high-speed WiFi suitable for remote work.
The Oakville House - Oakville
No reviews

The Oakville House

apartment, Milton
This spacious three-bedroom flat is located in Oakville, 24 kilometres from the Mississauga Convention Centre and 24 kilometres from Toronto Pearson International Airport, offering city views from its patio.
The 232 square metre residence accommodates up to 11 guests with air conditioning, a kitchen equipped with a fridge and dishwasher, a terrace with garden views, and private parking, with proximity to the Budweiser Stage, Exhibition Place, Rogers Centre, and CN Tower within a 38 kilometre radius.
Premium 3br Oakville /Pool, Gym And Parking, Close To All Hwys & Shops - Oakville
No reviews

Premium 3br Oakville /Pool, Gym And Parking, Close To All Hwys & Shops

apartment, Toronto
This three-bedroom flat in Oakville offers convenient access to major motorways and shopping centres such as Square One and Toronto Premium Outlets, with Lake Ontario situated a short distance away.
This residence provides on-site Wi-Fi, air conditioning, a pool, and a gym, along with practical amenities like a clothes dryer and towels, making it suitable for travellers seeking a serviced apartment in the Toronto area.

Best Oakville holiday rentals with air conditioning

Condo In Oakville - Oakville
9.6 92 reviews

Condo In Oakville

apartment, Milton
This newly renovated Oakville condo, a 30-minute (48km) drive from Toronto city centre and 6 minutes (approx. 4km) from Oakville GO station, offers easy access to Toronto and Niagara Falls (approx. 100km).
The two-bedroom, one-bathroom apartment sleeps five comfortably, boasting a queen bed, double bed, pull-out sofa, in-unit laundry, underground parking, balcony, and access to a fitness centre; nearby amenities include Walmart, Canadian Superstore, and various restaurants.
Spacious Basement Apartment - Oakville
9.7 54 reviews

Spacious Basement Apartment

house, Toronto
This Toronto basement apartment is conveniently located near Mississauga (16km) and a GO train station (16km), offering easy access to both cities and public transport.
The self-contained unit sleeps four, features a modern kitchen with dishwasher, private laundry, and high ceilings, making it ideal for families visiting the Greater Toronto Area.
Relaxing Home Base | Quiet Area & Cozy Living - Oakville
10 2 reviews

Relaxing Home Base | Quiet Area & Cozy Living

apartment, Toronto
This flat is situated in Mississauga's Erin Mills Stadium district, a 4-minute drive from Oakville Entertainment Centrum and Erin Mills Town Centre, offering convenient access to shopping and entertainment venues.
This one-bedroom flat accommodates up to four guests and features a fully equipped kitchen, in-suite laundry, Wi-Fi, and a dedicated workspace, with nearby attractions including the Bradley Museum and Riverwood Conservancy.
Oakville Fully Furnished 3 Bedroom Entiretownhome! - Oakville
9.1 30 reviews

Oakville Fully Furnished 3 Bedroom Entiretownhome!

house, Milton
This newly furnished house is located in Milton, just a short distance from the town centre and within easy reach of the Milton Historical Society Museum. The property has received excellent ratings for its cleanliness, location and overall experience.
The house has three bedrooms, sleeping up to six guests, making it ideal for families or groups of friends. Guests can enjoy modern furnishings, a comfortable living space with a TV and free Wi-Fi, a fully equipped kitchen for self-catering, and a peaceful garden.

Uncover Exclusive Holiday Rentals in Oakville, Canada

Treat yourself to high-end design, smart home features, and curated artwork at luxury holiday rentals in Oakville, Canada.

Executive Townhouse Next To Popular Provincial Park, 10 Minutes Walk - Oakville
8.0 1 review

Executive Townhouse Next To Popular Provincial Park, 10 Minutes Walk

apartment, Toronto

Downtown Holiday Rentals in Oakville, Canada

Spend less time on public transport and more time visiting nearby sights from centrally located holiday rentals in Oakville, Canada.

New 2bd Furnished Townhome Location - Oakville
9.8 11 reviews

New 2bd Furnished Townhome Location

house, Toronto
Sun-kissed 3br Family Home In A Quiet Neighborhood - Oakville
9.9 134 reviews

Sun-kissed 3br Family Home In A Quiet Neighborhood

apartment, Toronto
Bright & Spacious 2br/2ba Condo In Prime Location - Oakville
10 6 reviews

Bright & Spacious 2br/2ba Condo In Prime Location

apartment, Toronto
Cozy Modern Studio In Oakville | Free Parking - Oakville
9.6 173 reviews

Cozy Modern Studio In Oakville | Free Parking

apartment, Toronto
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