Holiday Rentals in Oakville

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Oakville holiday rentals
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871 Holiday Rentals and Airbnb in Oakville

Best family friendly Oakville holiday rentals

Among the 871 accommodations in Oakville, here are the 4 best family friendly rentals

Beautiful Pond View Town - Oakville
No reviews

Beautiful Pond View Town

apartment, Milton
This four-bedroom Milton house, ideally located near the bus stop and within easy walking distance of local shops and restaurants, offers convenient access to the 401, 403, and 407 highways, Costco, Walmart, and Square One Shopping Centre.
The self-catering property sleeps eight guests, boasting three bathrooms (two en-suite), a full kitchen with stainless steel appliances, and a garden; Coronation Park is a short drive away (approx. 5-10km depending on the specific location within Milton).
Beautiful Contemporary 4 Bed Oakville House! - Oakville
9.1 9 reviews

Beautiful Contemporary 4 Bed Oakville House!

apartment, Milton
This spacious Oakville house, a 4-bedroom, 3-bathroom dwelling, is conveniently located near Oakville's town centre and approximately 48 kilometres from Toronto Pearson International Airport.
The 2650 sq ft (246 sq m) property boasts an open-plan layout, sleeps six guests, and includes a fully equipped kitchen, garden, parking, and excellent internet access.
Designer 4br Basement Aymond Suites Oakville - Oakville
No reviews

Designer 4br Basement Aymond Suites Oakville

apartment, Milton
This Oakville flat is located 22.5 kilometres from Toronto Pearson International Airport and 20.9 kilometres from the Mississauga Convention Centre, offering convenient access for travellers.
This spacious 177 square metre apartment accommodates up to 17 guests with one bedroom and two bathrooms, featuring a fully equipped kitchen, kitchenette, in-unit washing machine, complimentary WiFi, air conditioning, and access to an on-site fitness room and an electric vehicle charging station, with nearby hiking trails for outdoor pursuits.
South Oakville Apartment Near Lake (Basement) - Oakville
9.6 18 reviews

South Oakville Apartment Near Lake (Basement)

apartment, Toronto
This Oakville basement flat, a 15-minute walk from Lake Ontario and near the QEW and Trafalgar GO Station, offers easy access to both Toronto (30-minute drive) and downtown Oakville.
The self-contained one-bedroom suite, sleeping two, features a fully equipped kitchen, private laundry, high-speed Wi-Fi, a 55-inch Smart TV, dedicated parking, and was newly furnished in 2025.

Best Oakville holiday rentals with parking

Beautiful Condo In Oakville For Upto 4 People - Oakville
10 4 reviews

Beautiful Condo In Oakville For Upto 4 People

apartment, Milton
This two-bedroom flat in Milton offers an unrivalled central location, providing immediate access to the town's main attractions and essential services, making it ideal for families exploring the area.
This centrally located flat includes internet, a kitchen, air conditioning, a fitness centre, and parking, accommodating up to four guests and serving as a convenient base for discovering local landmarks and activities.
Beautiful Apartment For Friends And Family - Oakville
No reviews

Beautiful Apartment For Friends And Family

apartment, Milton
This two-bedroom, two-bathroom flat in Oakville, Milton, is located approximately 32 kilometres from Square One Shopping Centre and Toronto Premium Outlets, and close to Lake Ontario.
This apartment offers accommodation for up to four guests, featuring modern amenities including air conditioning, heating, and WiFi, alongside a fully equipped kitchen, and is ideally situated for visiting the Oakville Centre for the Performing Arts and Putting Edge.
Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville - Oakville
No reviews

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville

apartment, Milton
This 3-bedroom townhouse is located in Oakville, just 27 kilometres from Mississauga Convention Centre and Toronto Pearson International Airport, and 37 kilometres from BMO Field and Budweiser Stage. The property enjoys excellent location and cleanliness ratings, with guests consistently praising its comfort and convenience.
The townhouse offers 172 square metres of space, comfortably accommodating up to 6 guests. A fully equipped kitchen, private terrace, air conditioning, free Wi-Fi, satellite TV, and parking are all provided for your enjoyment.
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.

Frequently asked questions about holiday rentals in Oakville

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

    The Oakville Public Library is a great place to take the kids, with lots of fun activities and events. The Oakville Museum also has a children's section with interactive exhibits. For outdoor fun, you can go to Coronation Park, which has a playground, splash pad, and plenty of green space.
  • 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 depends on your preferences. If you want warm weather and outdoor activities, then July and August are popular months. For a quieter and more affordable experience, consider booking in the shoulder seasons, like spring or autumn.
  • 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 are the best budget-friendly activities in Oakville?

    Oakville has plenty of free or low-cost activities to enjoy. You can take a stroll along the waterfront, visit the Oakville Museum, or explore the many parks and green spaces. You can also check out the farmers market on Saturdays for fresh produce and local crafts.
  • 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, try the Oakville Fish Market, which serves fresh seafood. The Queen's Plate Restaurant is also a popular spot for traditional Canadian dishes. If you're looking for something a bit more casual, the Oakville Farmers Market has a variety of food vendors offering local produce and baked goods.
  • 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.

  • Are there pet-friendly attractions in Oakville?

    Yes, many of Oakville's parks and green spaces are pet-friendly. You can also take your furry friend for a walk along the waterfront or visit the Oakville Museum, which welcomes well-behaved dogs.
  • 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 Beautiful City View 1br High Rise Sq1 Condo 5-.

  • What are the benefits of choosing a vacation rental in Oakville?

    Vacation rentals offer more space and privacy than hotels, and they can be a great option for families or groups. They also often come with amenities like kitchens and laundry facilities, which can save you money on dining out and laundry costs.
  • 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. You can also catch a hockey game at the Oakville Hawks, the town's junior hockey team.

Popular destinations

Best Oakville holiday rentals with a balcony

Modern Luxury Designer Home The Poshest Neighbourhood In Canada - Oakville
No reviews

Modern Luxury Designer Home The Poshest Neighbourhood In Canada

apartment, Toronto
This designer townhouse is situated in West Oakville, offering proximity to Lake Ontario and a 48-64 kilometre drive to Toronto's city centre.
This luxurious four-bedroom, three-bathroom property accommodates up to eight guests and features a private backyard with a swimming pool, a barbecue, and is equipped with air conditioning, high-speed internet, and five parking spaces.
Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks - Oakville
10 2 reviews

Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks

house, Toronto
This modern luxe residence is situated in Oakville, 26 kilometres from the Mississauga Convention Centre and 32-35 kilometres from Toronto landmarks such as BMO Field, Rogers Centre, and the CN Tower, with Toronto Pearson International Airport located 26 kilometres away.
This property offers free WiFi, private parking, air conditioning, a kitchen, and a balcony, accommodating up to seven guests with a check-out time of 11:00 AM.
Stylish 3br 2.5 Bath Townhouse With Patio And Parking - Oakville
No reviews

Stylish 3br 2.5 Bath Townhouse With Patio And Parking

house, Toronto
This townhouse is situated in Streetsville, approximately 16 kilometres from the Mississauga Convention Centre and 19 kilometres from Toronto Pearson International Airport.
This property offers 125 square metres of living space with three bedrooms and two bathrooms, accommodating up to nine guests with amenities including a dishwasher, microwave oven, fridge, air conditioning, a terrace, balcony, and free private parking.
Luxurious House With Pond View And Jacuzzi - Oakville
No reviews

Luxurious House With Pond View And Jacuzzi

apartment, Milton
This Oakville holiday home, an 11-minute (17.7km) drive from Lake Ontario and a 13-minute (20.9km) drive from Square One Shopping Centre, offers convenient access to Oakville's attractions.
Sleeping eight guests, the property boasts four bedrooms, four bathrooms, a fully equipped kitchen including a dishwasher and lobster pot, a jacuzzi, and covered parking; nearby activities include Putting Edge mini golf and Glen Abbey Golf Course.

Best Oakville holiday rentals with air conditioning

Modern Oakville Townhouse - Oakville
10 10 reviews

Modern Oakville Townhouse

apartment, Milton
This newly built four-bedroom townhouse in Oakville is located in a family-friendly neighbourhood, just a few minutes from Hays Blvd Plaza, offering convenient access to Downtown Oakville and the waterfront.
This property features a unique third-floor loft, a well-equipped kitchen with a Keurig coffee maker, and a basement retreat with a dining table for six, comfortably accommodating up to eight guests with central heating and air conditioning.
Luxury Condo In Heart Of Oakville 2br/2 Bath - Oakville
9.9 21 reviews

Luxury Condo In Heart Of Oakville 2br/2 Bath

apartment, Milton
This two-bedroom condo in Oakville is situated 8 kilometres from downtown Oakville, 56 kilometres from Toronto, and 80 kilometres from Niagara Falls, with Sheridan College campus located 800 metres away.
This modern apartment offers accommodation for five guests with a fully equipped kitchen, two bathrooms, air conditioning, and access to a fitness centre and rooftop terrace, being conveniently located 15 kilometres from Milton and close to the Ridgeway Plaza Mississauga food street.
@Oakville - Cozy Private Studio Unit In Basement - Oakville
No reviews

@Oakville - Cozy Private Studio Unit In Basement

apartment, Toronto
This newly renovated private basement studio offers a tranquil retreat in a quiet Toronto neighbourhood, providing easy access to local amenities.
This self-contained flat features a kitchenette, a home-theatre setup, exclusive backyard space, and complimentary on-site parking, accommodating up to two guests with a private entrance for added convenience.
Oakville's Gem! - Oakville
10 10 reviews

Oakville's Gem!

apartment, Milton
This luxurious four-bedroom house, situated in Oakville, offers easy access to Milton's amenities; a short drive (distance unspecified) connects the property to Milton's attractions.
The spacious property features a state-of-the-art Hoist Home Gym, a fully equipped kitchen including a dishwasher, and accommodates up to six guests, with one bedroom adaptable as an office.
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