Vacation Rentals in Oakville

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Oakville vacation rentals
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871 Vacation 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

Exquisite 3br Haven Near Bronte Harbour - Oakville
9.3 14 reviews

Exquisite 3br Haven Near Bronte Harbour

apartment, Toronto
This Oakville property, a three-bedroom house sleeping six, is situated minutes from Oakville's downtown core, Lakeside Park, and public transport.
The self-catering dwelling boasts a fully equipped kitchen, high-speed Wi-Fi, parking, and a modern bathroom; guests can enjoy nearby shopping and lakeside amenities.
Designer 4br Basement Suite  Oakville - Oakville
10 2 reviews

Designer 4br Basement Suite Oakville

apartment, Milton
This four-bedroom, two-bathroom flat in Oakville offers ample space for up to eight guests, featuring two full kitchens, a private gym, and keyless entry, with on-site parking and fast internet ideal for families or groups visiting Milton. Situated in a family-friendly neighbourhood, this property is conveniently located approximately 1.5 kilometers from the Milton Sports Centre and 3 kilometers from the historic Milton Town Hall, with easy access to local parks and shopping areas.
Sun-kissed 3br Family Home In A Quiet Neighborhood - Oakville
9.9 126 reviews

Sun-kissed 3br Family Home In A Quiet Neighborhood

apartment, Toronto
This spacious home is located in Oakville, a suburb 30 kilometres west of Toronto, and is close to Sheridan College, Walmart, Oakville Place mall, and the lakeshore. The property enjoys excellent user, location, and cleanliness ratings.
The detached house offers 3 bedrooms and 1.5 bathrooms, comfortably accommodating up to 6 guests. The house is fully equipped with a modern kitchen, a large garden, high-speed internet, free parking, and automated check-in and check-out.
*Top Rated In Oakville*luxurious Private Apartment - Oakville
9.9 20 reviews

*Top Rated In Oakville*luxurious Private Apartment

apartment, Toronto
This Glen Abbey, Oakville self-catering property is conveniently located near major roads, approximately 13km from Lake Ontario, and within a 16km radius of Glen Abbey Golf Course and Deer Creek Golf Course.
The spacious basement flat sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, in-unit laundry, Smart TV with streaming services, Xbox One with racing simulator, and private parking; enjoy nearby Oakville Place Shopping Centre, a short drive from Toronto (64km) and Niagara Falls (80km).

Best Oakville holiday rentals with parking

*Family Haven* Renovated 3br  Backyard  Parking - Oakville
8.3 8 reviews

*Family Haven* Renovated 3br Backyard Parking

apartment, Hamilton
This family-friendly townhome in Hamilton offers a prime location, just a short walk to grocery stores, restaurants, and shopping centres, and within 1 kilometre of the lakefront and Burlington Pier.
Boasting 185 square metres of living space, this 2-storey dwelling accommodates up to six guests with three bedrooms, 1.5 bathrooms, a fully equipped kitchen, dedicated workspace, in-unit laundry, and two driveway parking spots.
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.
Charming & Smart Boutique Suite - Private Entrance - Oakville
9.9 25 reviews

Charming & Smart Boutique Suite - Private Entrance

apartment, Milton
This private suite is located in a residential neighbourhood in Oakville, 1.6 kilometres from Oakville's Downtown Area, GO station, and lakeshore, and is situated across from a family-friendly park.
This one-bedroom flat accommodates up to three guests and features a private backyard with a patio, a fenced yard, a main floor bedroom with a Queen bed and ensuite, a basement living room with a pull-out sofa bed, a kitchenette with a mini fridge and microwave, and a dedicated workstation.
Modern 4br Oakville Townhouse - Oakville
8.9 19 reviews

Modern 4br Oakville Townhouse

apartment, Hamilton
This Oakville townhouse, located near Pavilion Path, offers convenient access to Pearson Airport (56 km), Oakville GO station (1.6 km) for transit to Hamilton, and Sheridan College (1.3 km), with major highways (403/QEW/407) providing regional exploration.
This family-friendly property accommodates up to nine guests in four bedrooms and three bathrooms, featuring air conditioning, Wi-Fi, a fully equipped kitchen with a dishwasher and microwave, a fireplace, and parking, ideal for visitors to Hamilton.

Frequently asked questions about holiday rentals in Oakville

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

    For a vacation rental, I'd recommend the Old Oakville neighbourhood. It's charming, with lots of Victorian architecture and a great selection of restaurants and shops. It's also within walking distance of the waterfront and the Oakville Museum.
  • 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.

  • 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, like spring or autumn. You'll avoid the crowds and the prices are usually lower.
  • 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 has a lot of great events throughout the year. In the summer, there's the Oakville Jazz Festival, which is always a big hit. And in the fall, there's the Oakville Fall Fair, which is a great place to experience local culture. If you're looking for something a bit different, you could check out the Bronte Creek Provincial Park, they have a lot of events throughout the year.
  • What are the best vacation rentals with a pool in Oakville?

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

    If you're looking for local dishes, I'd recommend checking out The Oakville Chop House. They're known for their steaks and their Canadian-inspired menu. Another great option is The Stone House, they have a great selection of local seafood.
  • 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?

    Oakville has a lot of great walking and cycling routes. The Waterfront Trail is a popular option, it stretches for kilometers along the lake. You could also try the Oakville Creek Trail, it's a bit more off the beaten path, but it's really scenic.
  • 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 .

  • Are there pet-friendly attractions in Oakville?

    Yes, Oakville is quite pet-friendly. You can bring your dog to Coronation Park, they have a designated off-leash area. And most of the restaurants along the waterfront have outdoor patios where you can enjoy a meal with your furry friend.
  • What are the benefits of choosing a vacation rental in Oakville?

    Vacation rentals offer a lot of benefits, like more space and privacy compared to a hotel. You can also often find rentals with amenities like a kitchen and laundry facilities, which can be very convenient. And of course, you'll have the chance to experience local life in a more authentic way.

Popular destinations

Best Oakville holiday rentals with a balcony

2 Bedroom Private Suite-parking-near Hospital And Airport - Oakville
8.9 25 reviews

2 Bedroom Private Suite-parking-near Hospital And Airport

apartment, Milton
This Oakville apartment, situated 22.5km from the Mississauga Convention Centre and 37km from both BMO Field and the Budweiser Stage, offers a peaceful retreat near Milton.
The 19-square-metre, two-bedroom flat sleeps seven, boasting a fully equipped kitchen, terrace, garden, parking, and free Wi-Fi.
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.
Escarpment Views - Luxury 1br Condo - Resort-style Amenities In North Burlington - Oakville
8.0 1 review

Escarpment Views - Luxury 1br Condo - Resort-style Amenities In North Burlington

apartment, Hamilton
This Burlington flat, offering escarpment views, is situated approximately 32 kilometres from John Munro Hamilton International Airport and 34 kilometres from the Mississauga Convention Centre.
This one-bedroom flat for up to three guests features a modern kitchen with a fridge, microwave, and dishwasher, air conditioning, free WiFi, a private terrace, balcony, and access to a communal garden and barbecue area, alongside an on-site sauna.
Entire Home In Oakville, Canada - Oakville
9.0 3 reviews

Entire Home In Oakville, Canada

house, Hamilton
This Oakville property, situated approximately 29 kilometres from Toronto Pearson International Airport and within a 39-kilometre radius of attractions such as BMO Field and Exhibition Place, offers a convenient base for exploring both Hamilton and Toronto.
This three-bathroom house sleeps fifteen guests, boasting a fully equipped kitchen, free Wi-Fi, private parking, and a balcony; nearby activities include exploring Oakville's suburban attractions.

Best Oakville holiday rentals with air conditioning

Luxury Corner Home Near Restaurants, Parks & Shops - Oakville
9.6 67 reviews

Luxury Corner Home Near Restaurants, Parks & Shops

house, Milton
This four-bedroom, three-bathroom Oakville townhouse, near Dundas Street East and Trafalgar Road, offers easy access to Uptown Oakville's amenities, including Walmart, and is approximately 6–10 km from Oakville's lakeshore and Ridgeway Plaza.
The property sleeps ten guests, boasts a full kitchen with modern appliances, high-speed internet (500 Mbps), and Rogers Ignite streaming, plus two master bedrooms for added privacy.
Luxury 4br Retreat With Pool, Piano, Spa & Games - Oakville
8.8 6 reviews

Luxury 4br Retreat With Pool, Piano, Spa & Games

apartment, Toronto
This four-bedroom, five-bathroom flat is situated in the Clarkson-Lorne Park district of Mississauga, offering convenient access to Square One Shopping Centre (approximately 5 kilometres away), Lake Ontario, and High Park, with Woodbine Racetrack and Famous People Players Dinner Theatre also within reach.
This fully renovated apartment accommodates eight guests and features a private heated pool and a large garden, alongside luxury bedding and spa-style bathrooms, with a spacious living room complete with a piano and a family room boasting a large television.
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.
Relaxing Home Base | Quiet Area & Cozy Living - Oakville
10 1 review

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.
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