Holiday Rentals in Oakville

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Oakville holiday rentals
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664 Holiday rentals and Airbnb in Oakville

Best family friendly Oakville holiday rentals

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

Executive Townhouse Next To Popular Provincial Park, 10 Minutes Walk - Oakville
8.0 1 review
Oakville
27/06 – 31/12
109 €/nighttotal: 20383 € (187 )

Executive Townhouse Next To Popular Provincial Park, 10 Minutes Walk

4 2
apartment , Toronto
This Oakville family home, situated in the West Oak Trails neighbourhood, is approximately 32 kilometres southwest of Toronto, close to Glen Abbey Golf Course and the Canadian Golf Hall of Fame.
The four-bedroom property, sleeping seven guests, boasts three bathrooms, a fully equipped kitchen, in-house laundry, smart TVs, air conditioning, a terrace, garden, and parking; nearby recreational activities are available.
Luxury Modern Retreat: W/ Sauna & Modern Amenities - Oakville
10 2 reviews
Oakville
01/07 – 31/07
350 €/nighttotal: 10500 € (30 )

Luxury Modern Retreat: W/ Sauna & Modern Amenities

4 2
apartment , Toronto
This Mississauga Erin Mills holiday home, near Lake Ontario and The Riverwood Conservancy, offers easy access to Toronto, approximately 24 kilometres from the city centre.
This spacious 224 square metre property boasts a four-bedroom, four-bathroom layout sleeping up to ten guests, complete with a fully equipped kitchen, garden, parking, and air conditioning; nearby attractions include Benares Historic House and Playdium.
Luxury Oakville Home, Hot Tub, Fireplace, New Home - Oakville
Oakville
06/07 – 12/07
578 €/nighttotal: 3468 € (6 )

Luxury Oakville Home, Hot Tub, Fireplace, New Home

1 2
house , Milton
Book this Holiday rental. You will be located in Milton.
Services and facilities: free parking, air conditioning and a dish washer. This is a family-friendly house!
Luxury Basement Apartment In Oakville Monthly Stays Only - Oakville
9.5 23 reviews
Oakville
08/07 – 07/08
109 €/nighttotal: 3270 € (30 )

Luxury Basement Apartment In Oakville Monthly Stays Only

1 4
apartment , Milton
This luxury basement flat is located in Oakville, just 35 kilometres from both BMO Field and Budweiser Stage in Toronto, offering easy access to the city's attractions. It has received excellent ratings for location, cleanliness and user experience.
The self-catering flat, with a floor area of 11 square metres, can accommodate up to four guests. It offers a range of amenities, including a fully equipped kitchen, a washing machine, free Wi-Fi, a satellite flat-screen TV, a fireplace, a seating area, access to darts and tennis, a fitness room, and outdoor play equipment.

Best Oakville holiday rentals with parking

Luxury Oakville Home, Hot Tub, Fireplace (Upper) - Oakville
9.8 38 reviews
Oakville
28/08 – 04/09
380 €/nighttotal: 2660 € (7 )

Luxury Oakville Home, Hot Tub, Fireplace (Upper)

1 9
apartment , Milton
This Oakville house, near quality restaurants and parks, is under 48km from Pearson Airport and 53km from Toronto city centre.
The four-bedroom, three-bathroom property sleeps ten, boasting a fully equipped kitchen, jacuzzi, garden, and parking; summer BBQs are possible using the grill.
Basement Studio In Mississauga - Oakville
10 8 reviews
Oakville
27/06 – 04/07
119 €/nighttotal: 833 € (7 )

Basement Studio In Mississauga

1 2
apartment , Toronto
This private basement studio is located in Clarkson, a short 1.2 kilometre drive from the lake and within easy reach of entertainment venues such as iFLY, Cineplex, and Dave & Buster's.
This self-contained apartment offers accommodation for two guests with one bedroom and one bathroom, featuring essential amenities including internet, a kitchen, air conditioning, and dedicated parking.
Bromsgrove Hideaway - Oakville
10 1 review
Oakville
23/07 – 14/09
162 €/nighttotal: 8586 € (53 )

Bromsgrove Hideaway

4 2
apartment , Toronto
This Clarkson-Lorne Park holiday home in Toronto is situated 1.4 km from Scooter's Roller Palace, within 5 km of Benares Historic House and Oakville Entertainment Centre, and a 15-minute walk from Clarkson Station.
This two-bedroom, two-bathroom property sleeps three guests and offers a fully equipped kitchen, free Wi-Fi, air conditioning, a terrace, garden, spa, fitness centre, and parking; nearby attractions include family-friendly activities and convenient public transport links.
Spacious 2 Bedrooms 2 Bathrooms With Cozy Charm Plus 1 Parking - Oakville
Oakville
01/09 – 30/09
154 €/nighttotal: 4466 € (29 )

Spacious 2 Bedrooms 2 Bathrooms With Cozy Charm Plus 1 Parking

1 1
apartment , Milton
This Mississauga apartment, situated 24km from the Mississauga Convention Centre and 40km from Toronto attractions including BMO Field and Exhibition Place, offers convenient access to major landmarks. This one-bedroom flat, boasting 8 square metres of floor space, features a fully equipped kitchen, private parking, and a balcony; accommodating one guest.

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.

Destinations nearby

Best Oakville holiday rentals with a balcony

3bed Bright Oakville Townhome With Balcony, Office - Oakville
9.0 2 reviews
Oakville
01/09 – 30/09
170 €/nighttotal: 4930 € (29 )

3bed Bright Oakville Townhome With Balcony, Office

3 4
house , Toronto
This Oakville townhouse is located 26 kilometres from Toronto Pearson International Airport, providing a suburban base with reasonable access to Toronto's attractions.
This property offers free Wi-Fi, private parking, a fully equipped kitchen, and a private balcony, accommodating up to 11 guests with 2 bathrooms and air conditioning.
Charming Oakville Getaway - Oakville
Oakville
09/08 – 14/08
200 €/nighttotal: 1000 € (5 )

Charming Oakville Getaway

5 4
apartment , Milton
This five-bedroom, four-bathroom serviced apartment in Oakville offers convenient access to Milton, situated 23 kilometres from the Mississauga Convention Centre and 33 kilometres from Toronto's BMO Field, Budweiser Stage, and Exhibition Place.
The spacious accommodation provides a fully equipped kitchen, air conditioning, a terrace, balcony, free Wi-Fi, and private parking, with a guest capacity of 17.
*Cozy* 1 Bedroom Home Near Waterfront/trails - Oakville
Oakville
28/12 – 31/12
227 €/nighttotal: 681 € (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.
Luxary Villa With Pool, Sauna, Hot Tub Sleeps 12 - Oakville
Oakville
28/12 – 31/12
738 €/nighttotal: 2214 € (3 )

Luxary Villa With Pool, Sauna, Hot Tub Sleeps 12

1 2
house , Toronto
This luxury villa in Oakville is situated approximately 35 kilometres from the Mississauga Convention Centre and Toronto Pearson International Airport, with major Toronto attractions such as BMO Field and Rogers Centre located within a 40-42 kilometre radius.
This spacious 279 square metre dwelling accommodates up to 27 guests, featuring one separate bedroom, four bathrooms, a fully equipped kitchen, air conditioning, a private swimming pool, sauna, hot tub, and direct terrace access, with complimentary WiFi and private parking including an electric vehicle charging station.

Best Oakville holiday rentals with air conditioning

Oakville Bright&airy 4-bdrm Home! Close To Highway 403&qew! - Oakville
Oakville
23/07 – 14/09
180 €/nighttotal: 9540 € (53 )

Oakville Bright&airy 4-bdrm Home! Close To Highway 403&qew!

4 2
apartment , Milton
This luxury townhome in Oakville offers tranquil pond views and is located approximately 5 kilometres from Benares Historic House and Oakville Museum, with convenient access to attractions such as Putting Edge and Glen Abbey Golf Course.
This spacious 232 square metre residence features four bedrooms, three and a half bathrooms, and accommodates up to eight guests, with amenities including air conditioning, internet, and private two-car garage parking.
Spacious Two Floor House - Oakville
9.2 10 reviews
Oakville
15/08 – 04/09
152 €/nighttotal: 3040 € (20 )

Spacious Two Floor House

3 2
apartment , Toronto
This Toronto house rental, ideal for families or groups, offers comfortable accommodation in a residential area with easy access to public transport.
The property features four bedrooms, three bathrooms, and parking for guests, along with a fully equipped kitchen and workspace.
Family Basement Suite (For 3) In Gta, Ont., Canada - Oakville
9.8 46 reviews
Oakville
10/07 – 15/07
114 €/nighttotal: 570 € (5 )

Family Basement Suite (For 3) In Gta, Ont., Canada

1 2
apartment , Toronto
This modern basement flat is situated in Clarkson, Mississauga, a short 8-kilometre drive from Clarkson GO station and the Queen Elizabeth Way (QEW), offering easy access to Toronto.
The self-contained unit sleeps two guests, features a fully equipped kitchen, in-suite laundry, high-speed Wi-Fi, and a spacious living area with a large television; nearby attractions include the Clarkson Community Centre.
Clean Modern One Br Condo | Full Kitchen, Laundry - Oakville
Oakville
27/06 – 04/07
125 €/nighttotal: 875 € (7 )

Clean Modern One Br Condo | Full Kitchen, Laundry

1 1
apartment , Toronto
This conveniently located flat offers a peaceful retreat in a safe neighbourhood, just 500 metres from Ridgeway Plaza's amenities and close to Highways 403 and 407, with downtown Toronto a 48-kilometre drive away.
This furnished one-bedroom apartment accommodates two guests and features air conditioning, in-suite laundry, free parking, a queen bed, a fully equipped kitchen, and fast WiFi, making it ideal for remote workers.
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