Holiday Rentals in Oakville

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Oakville holiday rentals
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Oakville holiday rentals: compare the best deals

Best family friendly Oakville holiday rentals

Among the 664 accommodations in Oakville, here are the 4 best family friendly rentals

Spacious And Luxurious 2br Suite With Huge Windows - Oakville
8.7 3 reviews
Oakville
07/06 – 07/12
HK$2255/nighttotal: HK$13530 (6 )

Spacious And Luxurious 2br Suite With Huge Windows

2 2
apartment , Toronto
This Mississauga apartment, situated 19 kilometres from Toronto's downtown attractions including the BMO Field and Exhibition Place, offers convenient access to both the city and Pearson International Airport (18 kilometres).
This two-bedroom, two-bathroom flat boasts 46 square metres of space, comfortably accommodating up to nine guests and featuring free parking, Wi-Fi, and a fully equipped kitchen.
Serene Oakville Retreat - Modern 2-bedroom Apartment - Oakville
Oakville
12/28 – 12/31
HK$1443/nighttotal: HK$4329 (3 )

Serene Oakville Retreat - Modern 2-bedroom Apartment

2 2
apartment , Milton
This two-bedroom flat is situated in Halton, offering convenient access to Oakville (32 kilometres), Mississauga (32 kilometres), and Toronto (56-77 kilometres), with a GO Station a mere 7-minute drive away.
This family-friendly apartment, accommodating up to four guests, boasts a fully equipped kitchen, air conditioning, a jacuzzi, and private parking, and is located within a 15-minute drive of Oakville Place, Toronto Premium Outlet, and Erin Mills Town Centre.
Your Perfect Getaway Home - Oakville
9.3 48 reviews
Oakville
07/10 – 07/15
HK$2452/nighttotal: HK$12260 (5 )

Your Perfect Getaway Home

1 2
apartment , Toronto
This Oakville house, ideally located near the Queen Elizabeth Way highway, offers easy access to downtown Oakville, local parks, and Lake Ontario.
The three-bedroom property sleeps eight, boasting a well-equipped kitchen, a solarium, a large garden with patio furniture and barbecue, and ample parking; nearby attractions include numerous parks and the lake.
Luxury Oakville Home, Hot Tub, Fireplace, New Home - Oakville
10 1 review
Oakville
07/05 – 07/12
HK$4974/nighttotal: HK$34818 (7 )

Luxury Oakville Home, Hot Tub, Fireplace, New Home

4 10
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 holiday rentals with parking

Private One Bedroom Suite. B And B On Main Floor - Oakville
Oakville
07/31 – 08/31
HK$468/nighttotal: HK$14508 (31 )

Private One Bedroom Suite. B And B On Main Floor

1 1
apartment , Milton
This female-only guesthouse is situated in Oakville, a short drive from the Oakville GO station and the University of Toronto Mississauga campus, making it a convenient base for exploring the surrounding area. The property offers a private back yard entrance leading to a spacious, comfortable bedroom with a queen bed, oversized windows, and a 50-inch TV.
The basement kitchen is fully equipped with a fridge, stove, microwave, dishwasher, and washer/dryer, allowing guests to prepare their own meals. Guests also have access to free Wi-Fi and Netflix, as well as private parking for a monthly fee.
Luxe Furnished Home In Oakville - Oakville
Oakville
07/08 – 08/07
HK$1499/nighttotal: HK$44970 (30 )

Luxe Furnished Home In Oakville

4 4
apartment , Toronto
This four-bedroom, four-bathroom Oakville apartment rental in West Oak Trails offers easy access to Bronte Creek Provincial Park (approx. 5 km) and Glen Abbey Golf Course (approx. 8 km).
The self-catering property sleeps seven, includes a fully equipped kitchen with dishwasher, in-unit laundry, parking, and smart TV with Wi-Fi, and is close to further attractions such as Saw-Whet Golf Course and the Canadian Golf Hall of Fame.
Modern And Comfortable Basement Suite - Oakville
10 21 reviews
Oakville
06/23 – 06/24
HK$981/nightfor 1 night

Modern And Comfortable Basement Suite

1 2
apartment , Toronto
This self-contained two-bedroom basement flat in Toronto offers a private entrance and is conveniently located within walking distance of numerous shopping centres and a wide array of restaurants, making it an ideal base for families, couples, and business travellers. The accommodation is equipped with air conditioning, Wi-Fi, private laundry facilities, and off-street parking, comfortably accommodating up to four guests with one bathroom.
Luxury Executive Studio In Prestigious Glen Abbey Oakville - Oakville
Oakville
08/01 – 10/31
HK$974/nighttotal: HK$88634 (91 )

Luxury Executive Studio In Prestigious Glen Abbey Oakville

1 3
studio , Toronto
This one-bedroom apartment is located in the prestigious Glen Abbey community of Oakville, approximately 40 kilometres southwest of Toronto and within easy reach of Bronte Creek Provincial Park.
The 93 square metre studio flat offers a comfortable stay for up to four guests and features a fully equipped kitchen, a king-sized bed, a 55-inch television, and a private patio, perfect for relaxing after a day exploring the surrounding area.

Frequently asked questions about holiday rentals in Oakville

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

    You absolutely must visit the Oakville Museum, which showcases the town's history and art. For stunning views, take a stroll along the Oakville waterfront, where you can admire the lake and the beautiful gardens.
  • 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?

    The Old Oakville neighbourhood is charming with historic houses and shops, and is a great choice for a vacation rental. It's close to the waterfront and many restaurants.
  • 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?

    The Oakville Galleries is a great place to introduce kids to art, while the Oakville Public Library has fun events for families. For some outdoor fun, head to Coronation Park, which has a playground, splash pad, and a large green space.
  • 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 is during the shoulder seasons, from April to May or September to October, as the weather is still pleasant and the prices are lower.
  • What are the best rentals for families and kids in Oakville?

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

    The Oakville Jazz Festival in July is a highlight, featuring live music and food stalls. In August, the Oakville Waterfront Festival offers a variety of activities, from boat shows to live entertainment.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakville?

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

    Take a walk or bike ride along the waterfront trail, which offers stunning views of Lake Ontario. You can also visit the Oakville Public Library, which has free events and exhibitions.
  • What are the best restaurants with local dishes in Oakville?

    Try the fish and chips at The Captain's Boil, or enjoy a classic Canadian meal at The Keg Steakhouse + Bar. For something a bit more unique, check out the menu at The Oakville Bistro, which features modern Canadian cuisine.
  • 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. For a more challenging ride, try the Oakville Creek Trail, which winds its way through the Oakville Creek.
  • Are there pet-friendly attractions in Oakville?

    Yes, many parks in Oakville are dog-friendly, including Coronation Park and Bronte Creek Provincial Park. You can also find dog-friendly patios at some restaurants.
  • 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, making them ideal for families or longer stays.
  • What are the top sports attractions and facilities in Oakville?

    The Oakville Soccer Club offers various programs for all ages. The Oakville Golf Club is a popular destination for golfers, and the Oakville Tennis Club has courts for both casual and competitive players.

Destinations nearby

Best Oakville holiday rentals with a balcony

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville - Oakville
8.8 17 reviews
Oakville
07/01 – 07/31
HK$1510/nighttotal: HK$45300 (30 )

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville

3 2
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.
*Cozy* 1 Bedroom Home Near Waterfront/trails - Oakville
Oakville
12/28 – 12/31
HK$2057/nighttotal: HK$6171 (3 )

*Cozy* 1 Bedroom Home Near Waterfront/trails

1 2
apartment , Hamilton
This newly renovated one-bedroom flat is situated in Burlington, a short drive from the lakefront and Burlington Pier, offering convenient access to amenities.
This private suite accommodates two guests and features a fully equipped kitchen, high-speed WiFi, in-unit laundry, and two driveway parking spaces, with pets welcome.
2 Bedroom Private Suite-parking-near Hospital And Airport - Oakville
9.2 23 reviews
Oakville
06/23 – 06/25
HK$1616/nighttotal: HK$3232 (2 )

2 Bedroom Private Suite-parking-near Hospital And Airport

2 2
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.
The Oakville House - Oakville
Oakville
08/01 – 09/30
HK$6558/nighttotal: HK$393480 (60 )

The Oakville House

3 4
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.

Best Oakville holiday rentals with air conditioning

Spacious Oakville 5 Bedroom Home - Sleeps 10 - Free Parking + Pet Friendly - Oakville
Oakville
08/26 – 09/06
HK$3650/nighttotal: HK$40150 (11 )

Spacious Oakville 5 Bedroom Home - Sleeps 10 - Free Parking + Pet Friendly

5 2
apartment , Milton
This five-bedroom Oakville apartment, situated near parks and shopping, offers easy highway access for exploring attractions such as Lake Ontario, Erindale Park, Joshua Creek Heritage Art Centre, and Glen Abbey Golf Course; distances to Milton require separate calculation via online mapping services.
The self-catering property sleeps ten guests and features a modern open-plan layout, a fully equipped kitchen, air conditioning, internet access, and pet-friendly accommodation.
Modern 4br Oakville Townhouse - Oakville
9.1 14 reviews
Oakville
06/21 – 08/21
HK$2395/nighttotal: HK$146095 (61 )

Modern 4br Oakville Townhouse

1 1
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.
Sun-kissed 3br Family Home In A Quiet Neighborhood - Oakville
9.9 120 reviews
Oakville
08/26 – 09/06
HK$1465/nighttotal: HK$16115 (11 )

Sun-kissed 3br Family Home In A Quiet Neighborhood

1 2
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.
Brand New Modern 4 Bedroom Home In Prestigious Oakville Community - Oakville
Oakville
07/08 – 08/07
HK$1660/nighttotal: HK$49800 (30 )

Brand New Modern 4 Bedroom Home In Prestigious Oakville Community

4 4
apartment , Toronto
This four-bedroom, three-and-a-half-bathroom apartment in the West Oak Trails neighbourhood of Oakville, Ontario, is situated approximately 5 km from Bronte Creek Provincial Park and 8 km from Glen Abbey Golf Course.
The self-catering property sleeps eight guests and includes a fully equipped kitchen with microwave and dishwasher, Wi-Fi, a Smart TV, washer/dryer, and all linens; nearby attractions include Square One Shopping Centre and Toronto Premium Outlets.
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