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

Apartment ∙ 2 Bedrooms ∙ 4 Guests - Oakville
No reviews

Apartment ∙ 2 Bedrooms ∙ 4 Guests

apartment, Milton
This two-bedroom flat in Halton offers convenient access to Oakville and Mississauga (both 32 kilometres away) and is 56 to 79 kilometres from downtown Toronto, with a GO station 630 metres from the property.
This modern apartment for four guests features a fully equipped kitchen with a dishwasher and microwave, air conditioning, a swimming pool, a jacuzzi, and private parking, providing a comfortable base for exploring the Greater Toronto Area.
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.
Private Home : Kitchen-bath-laundry-gym-parking - Oakville
9.8 35 reviews

Private Home : Kitchen-bath-laundry-gym-parking

apartment, Toronto
This basement flat is conveniently located just 1.5 kilometres from Sheridan College and White Oaks Secondary School, offering easy access to Superstore, Walmart, Tim Hortons, and bus stations. It has received excellent ratings for user experience, location, and cleanliness.
The flat comfortably accommodates two guests and features a separate entrance for complete privacy. The self-catering flat includes a fully equipped kitchen, laundry facilities, a dedicated exercise space, and free parking on the driveway. Multilingual services in English, Chinese, and Cantonese are available.
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.

Best Oakville holiday rentals with parking

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.
Luxury-5 Br-king Bed-2 Car-pond View-403/407/qew - Oakville
9.8 79 reviews

Luxury-5 Br-king Bed-2 Car-pond View-403/407/qew

apartment, Milton
This five-bedroom house, near the junction of the 403, 407 and QEW motorways, is situated approximately 10 km from Oakville GO station and within 8 km of shops including Walmart and Longo's supermarket in Oakville.
Offering self-check-in, this spacious property sleeps 12 guests and boasts a modern kitchen with dishwasher, two workspaces, a garden, parking, and ultra-high-speed internet (1 Gbps), plus two Smart TVs.
Comfortable Family Stay In Oakville - Oakville
No reviews

Comfortable Family Stay In Oakville

apartment, Toronto
This peaceful flat is located in a tranquil district of Toronto, offering a serene base for exploring the city's notable landmarks.
This apartment accommodates up to six guests and features a kitchen, air conditioning, and one bathroom, providing a restful stay with convenient access to Toronto's attractions.
Separate Walk-up Basement Apartment Oakville - Oakville
10 4 reviews

Separate Walk-up Basement Apartment Oakville

apartment, Hamilton
This private basement flat in a tranquil Oakville residential area provides straightforward access to main motorways and parks, situated approximately 72 kilometres from downtown Toronto and 160 kilometres from Niagara Falls.
This self-contained dwelling offers two bedrooms and space for four guests, featuring a full kitchen with a fridge, freezer, microwave, and dishwasher, as well as air conditioning, Wi-Fi, and on-site laundry facilities available upon request.

Frequently asked questions about holiday rentals in Oakville

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

    Oakville has a lot to offer, but you shouldn't miss the waterfront. Take a stroll along the Oakville Harbour, admire the beautiful sailboats, and enjoy the views of Lake Ontario. For a taste of history, visit the Oakville Museum, which showcases the town's past, and don't forget to check out the charming shops and restaurants in the historic downtown core.
  • 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.

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

    For a vibrant atmosphere, choose a vacation rental in the Old Oakville neighbourhood. It's close to the harbour, has plenty of restaurants and cafes, and is within walking distance of many attractions. If you prefer a quieter stay, consider Bronte Creek, a residential area with parks and trails, and easy access to the lakefront.
  • 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?

    Oakville has plenty for families. The Oakville Museum is a great place to learn about the town's history, and the Oakville Galleries is a fun spot for art lovers of all ages. For some outdoor fun, head to Coronation Park, which has a playground, splash pad, and a scenic walking trail.
  • What are the best holiday 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 is during the shoulder seasons, from April to May or September to October. The weather is still pleasant, the crowds are smaller, and the prices are often lower.
  • 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. The Oakville Jazz Festival in July brings world-class musicians to town, and the Oakville Fall Fair in September is a great family event with live music, food, and entertainment. For a unique experience, visit the Bronte Creek Provincial Park during their annual Renaissance Festival in August.
  • 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 Beautiful City View 1br High Rise Sq1 Condo 5-.

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

    You can enjoy Oakville without breaking the bank. Take a walk or cycle along the waterfront trail, visit the free Oakville Museum, or explore the many parks and green spaces. For a picnic lunch, grab some fresh produce from the Oakville Farmers' Market.
  • What are the best restaurants with local dishes in Oakville?

    Oakville boasts a diverse culinary scene. For a taste of local seafood, try the fresh oysters at The Fish House. If you're craving a delicious burger, head to The Oakville Grill. For a more casual dining experience, enjoy the classic Canadian dishes at The Old Mill.
  • What are the best walking or cycling routes in Oakville?

    Oakville offers beautiful walking and cycling routes. The Waterfront Trail is a popular choice, offering stunning views of Lake Ontario. The Bronte Creek Provincial Park has several scenic trails for all levels, and the Oakville Trafalgar Trail is a great option for a longer ride.
  • Are there pet-friendly attractions in Oakville?

    Oakville is a dog-friendly town. Many parks, like Coronation Park and Bronte Creek Provincial Park, welcome well-behaved dogs on leash. The waterfront trail is also a great option for a walk with your furry friend.
  • What are the benefits of choosing a vacation rental in Oakville?

    Vacation rentals offer more space and privacy than hotels. They often come with amenities like kitchens and laundry facilities, making them ideal for families or longer stays. You can also find rentals in different locations, allowing you to choose the neighbourhood that best suits your needs.

Popular destinations

Best Oakville holiday rentals with a balcony

Cozy Park View Suit In Oakville - Oakville
10 1 review

Cozy Park View Suit In Oakville

apartment, Toronto
This Oakville flat provides park views and is located a 10-minute walk from commercial amenities, near a golf course and cultural attractions such as the Joshua Creek Heritage Art Centre.
This private walk-out basement suite accommodates up to three guests, featuring a newly renovated interior with a separate entrance, air conditioning, Wi-Fi, a fully equipped kitchen, and laundry facilities, with Oakville's shops and restaurants within easy reach.
Cozy 3 Bedroom Bungalow With Bright Basement Suit. - Oakville
No reviews

Cozy 3 Bedroom Bungalow With Bright Basement Suit.

apartment, Toronto
This cosy bungalow is located in West Oakville, offering proximity to Bronte Creek Provincial Park and Rattray Marsh Conservation Area, with cultural sites such as the Canadian Golf Hall Of Fame nearby.
This apartment provides accommodation for up to 10 guests with 3 bedrooms and 1 bathroom, featuring air conditioning and internet, and is situated in a quiet, family-friendly neighbourhood ideal for relaxation.
2 Bedroom Private Suite-parking-near Hospital And Airport - Oakville
No reviews

2 Bedroom Private Suite-parking-near Hospital And Airport

apartment, Milton
Apartment. You will stay in Milton.
Facilities and services: a terrace, a washing machine and a barbecue.
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.

Best Oakville holiday rentals with air conditioning

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.
4 Bedroom / 2.5 Bath House - Oakville
10 2 reviews

4 Bedroom / 2.5 Bath House

apartment, Milton
This Milton flat is located in a district offering ample space for family enjoyment, with convenient access to local attractions.
This four-bedroom dwelling accommodates up to eight guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, alongside air conditioning and a fitness centre.
Windfield Coach House - Oakville
9.3 21 reviews

Windfield Coach House

house, Toronto
This Toronto studio apartment, situated in a private and quiet location above a garage, offers seclusion yet convenient access to the city.
The 330 sq ft (approximately 31 sq m) self-contained unit features a king-size bed, double pull-out sofa, full bathroom with washer/dryer, and a well-equipped kitchenette, comfortably sleeping up to four guests.
Luxury Stay, Cozy & Bright, Nature's Art - Oakville
9.9 41 reviews

Luxury Stay, Cozy & Bright, Nature's Art

apartment, Toronto
This five-bedroom, three-bathroom Oakville apartment, a short drive from Toronto, offers easy access to local amenities; precise distances to Toronto landmarks are not specified.
Sleeping up to twelve guests, this spacious property boasts a fully equipped kitchen, air conditioning, parking, and excellent internet access; bird feeders outside provide a tranquil setting.
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