Compare Vacation Rentals & Airbnb in Oakville

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Oakville vacation rentals
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871 Rentals and Airbnb in Oakville

Best family friendly Oakville vacation rentals

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

House In South Oakville - Close To Lake - Oakville
9.8 33 reviews

House In South Oakville - Close To Lake

house, Toronto
This Oakville main floor apartment, ideally situated near Lake Ontario and Oakville's town centre, offers easy access to Toronto via nearby GO stations and major highways.
The three-bedroom, two-bathroom self-catering property sleeps six guests, boasting a fully furnished interior with modern appliances, high-speed Wi-Fi, dedicated parking, and a private garden.
Spacious Basement In Oakville - Oakville
9.9 114 reviews

Spacious Basement In Oakville

apartment, Toronto
This two-bedroom, one-bathroom apartment in Oakville, Ontario, is situated near Oakville Place shopping centre, offering easy access to public transport including a train station and local bus services.
The 4-guest property boasts a fully equipped kitchen with stainless steel appliances, a modern bathroom, and is close to recreational facilities such as bowling alleys, cinemas, nature trails, and various restaurants.
Feel At Home - Oakville
9.8 35 reviews

Feel At Home

apartment, Milton
This family-friendly, two-bedroom basement flat is situated in the Joshua Creek area of Oakville, approximately 6.4km from Oakville GO station, providing easy access to Toronto.
The 2-bedroom, 1-bathroom self-catering property sleeps up to 5 guests and features a well-equipped kitchen, high-speed Wi-Fi, driveway parking, and is close to Oakville Place shopping mall, Longo's and Metro supermarkets.
Cottage Style House With Hot Tub - Oakville
9.8 36 reviews

Cottage Style House With Hot Tub

cottage, Toronto
This five-bedroom Oakville apartment, seven minutes (approximately 11.3 kilometres) from downtown Oakville and Lake Ontario, offers easy access to Toronto attractions.
Sleeping up to twelve guests, this spacious property boasts a fully equipped kitchen, three large smart TVs, a private garden with hot tub, and free parking, making it ideal for families or large groups visiting the Toronto area.

Best Oakville vacation rentals with parking

2 Bed2 Wash Luxury Condo For Upto 6 Guests - Oakville
9.5 128 reviews

2 Bed2 Wash Luxury Condo For Upto 6 Guests

apartment, Milton
This charming bed and breakfast is situated in the desirable Oakville neighbourhood, just 4 kilometres from Walmart and Superstore and 7 kilometres from the train station. The accommodation has received excellent ratings for its cleanliness, location, and overall guest experience.
The B&B is part of a beautiful 2-bedroom condo and can accommodate up to 2 guests. Guests have access to a fully equipped kitchen, a spacious living/dining area, a TV, and high-speed internet, allowing for a comfortable and convenient stay.
Beautiful Condo In Oakville For Upto 6 People - Oakville
8.9 7 reviews

Beautiful Condo In Oakville For Upto 6 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.
Luxury Oakville Townhome | Free Parking & Wi-fi - Oakville
8.7 3 reviews

Luxury Oakville Townhome | Free Parking & Wi-fi

apartment, Milton
This private, self-contained two-level townhome suite is situated in a quiet residential area of Oakville, offering convenient access to the shopping and dining of Oakville, major motorways, and the waterfront attractions.
This two-bedroom, two-bathroom apartment accommodates up to four guests, featuring a fully equipped kitchen, dedicated workspace, in-suite laundry, fast WiFi, and a Smart TV, with complimentary driveway parking and self-check-in available.
Luxury Condo, Great Decor, Wheelchair Friendly!!! - Oakville
9.7 123 reviews

Luxury Condo, Great Decor, Wheelchair Friendly!!!

apartment, Toronto
This wheelchair-accessible luxury flat is situated in a prime area of Toronto, just a short walk from the city centre and its many attractions. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The property is spacious and tastefully furnished with two bedrooms, two bathrooms, and a balcony, comfortably accommodating two guests. It offers a range of amenities including a fully equipped kitchen, laundry facilities, a gym, and secure parking.

Frequently Asked Questions about vacation rentals in Oakville

  • What should a first-time visitor not miss in Oakville?

    Oakville has a lot to offer, but for a first-timer, you shouldn't miss the waterfront. Stroll along the Oakville Harbour, visit the Oakville Museum, and maybe catch a show at the Oakville Centre for the Performing Arts.
  • What are the best Airbnb and vacation rentals in Oakville?

    Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are the most popular Airbnb and vacation rentals in Oakville among travelers.

  • Which neighborhood in Oakville should you consider for a vacation rental?

    For a vacation rental, you might want to consider the Old Oakville neighbourhood. It's charming, with historic buildings and a vibrant atmosphere, and it's close to the waterfront and shops.
  • 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 top family-friendly attractions in Oakville?

    For families, the Oakville Museum is a great place to start. Kids will love the hands-on exhibits, and the museum's location on the waterfront makes it even more appealing. Also, the Oakville Public Library is a great place to visit with children, with a variety of programs and events.
  • What are the best vacation rentals with a pool 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 to experience the summer festivals and outdoor activities, July and August are ideal. However, for a quieter getaway, spring or autumn might be better.
  • 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 events or festivals should visitors check out in and around Oakville?

    Oakville has a lively events calendar throughout the year. The Oakville Jazz Festival in July is a popular event, and the Oakville Fall Fair in September is a great family-friendly event. You could also check out the Bronte Creek Provincial Park for events.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakville?

    The best vacation 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 .

  • What are the best budget-friendly activities in Oakville?

    Oakville has plenty of free and budget-friendly activities. A walk along the waterfront is always enjoyable, and you can explore the many parks and green spaces. You can also visit the Oakville Public Library, which offers free events and programs.
  • What are the best restaurants with local dishes in Oakville?

    For local dishes, try the Oakville Fish Market for fresh seafood, or The Oakville Chop House for a classic Canadian steakhouse experience. For something a bit more casual, The Oakville Brewing Company serves up delicious pub fare.
  • What are the best walking or cycling routes in Oakville?

    The Waterfront Trail is a popular choice for walking and cycling, offering scenic views of Lake Ontario. The Oakville Creek Trail is another great option, winding through the town's natural areas. You can also check out the trails at Bronte Creek Provincial Park.
  • Are there pet-friendly attractions in Oakville?

    Many parks and green spaces in Oakville are pet-friendly, including the Oakville Harbour. You can also find dog-friendly patios at some restaurants and cafes.
  • What are the benefits of choosing a vacation rental in Oakville?

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

    Oakville has several sports facilities, including the Oakville Soccer Club, the Oakville Tennis Club, and the Oakville Golf Club. The town also hosts a variety of sporting events throughout the year.

Popular destinations

Best Oakville vacation 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.
5br New Detached 4500sq  Brand Newhome |13guests  | Oakville ( Creek Side Home) - Oakville
9.8 6 reviews

5br New Detached 4500sq Brand Newhome |13guests | Oakville ( Creek Side Home)

apartment, Milton
This spacious 5-bedroom detached house in Oakville is situated near Lake Ontario, offering convenient access to Square One Shopping Centre and Toronto Premium Outlets, approximately 12 kilometres away.
This family-friendly residence spans 418 square metres, accommodates up to 10 guests, and features a dedicated workspace, a large garden with a patio, a basement rec room with a projector, and parking for up to 4 cars, including an EV charger.
Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville - Oakville
No reviews

Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville

house, Toronto
House rental. You will be based in Toronto.
Services and facilities: a terrace, a fridge and a dish washer.
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.

Best Oakville vacation rentals with air conditioning

New Basement Apartment | 2 Bedrooms With Parking - Oakville
9.7 38 reviews

New Basement Apartment | 2 Bedrooms With Parking

apartment, Milton
This spacious Milton basement flat is conveniently located near a grocery store, medical clinic, and bus stop, offering easy access to Toronto Pearson International Airport (within a short driving distance).
The 139 square metre self-contained property sleeps four, boasting two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, and parking; an additional bedroom is available on request.
Stylish Oakville Condo To Call Home - Oakville
No reviews

Stylish Oakville Condo To Call Home

apartment, Milton
This Oakville condo, situated near the Dundas and Trafalgar intersection, offers easy access to shops, restaurants, and local attractions such as the Oakville Museum and Lake Ontario.
The one-bedroom, one-bathroom apartment sleeps three, features a fully equipped kitchen with microwave and dishwasher, in-suite laundry, and a private balcony; nearby Erindale Park provides further recreational opportunities.
Spacious Urban Oasis:stylish 2 Bed, 2 Bath Getaway - Oakville
9.7 83 reviews

Spacious Urban Oasis:stylish 2 Bed, 2 Bath Getaway

apartment, Toronto
This Oakville condo, approximately 64km from Toronto, offers stunning views of a pond and Lake Ontario from its enclosed balcony, providing easy access to both Oakville's amenities and Toronto.
The spacious 84 square metre, two-bedroom, two-bathroom apartment sleeps four, featuring a modern condominium complex with elevator access, queen-size beds, and a walk-in closet in the master bedroom.
South Oakville Bliss Haven: Spacious 3 Bedroom Home With Kitchen And Terrace - Oakville
No reviews

South Oakville Bliss Haven: Spacious 3 Bedroom Home With Kitchen And Terrace

apartment, Toronto
This West Oakville flat is located approximately 32 kilometres from Toronto Pearson International Airport and 36 kilometres from BMO Field, offering a residential setting with straightforward access to city attractions.
This spacious accommodation, ideal for up to 10 guests, features five bedrooms, three bathrooms, two kitchens, air conditioning, free Wi-Fi, and is situated near family-friendly activities and a local mini-market.
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