Vacation 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

4br Luxury Close To Lake, 30 Mins Toronto/niagara - Oakville
9.1 13 reviews
Oakville
01/07 – 31/07
A$323/nighttotal: A$9690 (30 )

4br Luxury Close To Lake, 30 Mins Toronto/niagara

1 2
apartment , Toronto
This luxurious bungalow is located in a prestigious neighbourhood in the Greater Toronto Area, just a short drive from Lake Ontario and within easy reach of both Toronto and Niagara Falls, making it an ideal base for exploring the region. The spacious property boasts three bedrooms, three bathrooms, and a large recreation room with a wet bar, comfortably accommodating up to ten guests and offering plenty of space for family gatherings.
Modern 2br Retreat | Renovated + Free Parking - Oakville
9.8 10 reviews
Oakville
01/07 – 31/07
A$174/nighttotal: A$5220 (30 )

Modern 2br Retreat | Renovated + Free Parking

1 2
apartment , Milton
This two-bedroom basement flat is situated in a new housing development in Oakville, Ontario, just a 10-kilometre drive from Milton and within easy reach of Toronto, Mississauga, and Niagara Falls. The property has received excellent ratings for cleanliness, location, and user experience, making it a great choice for travellers seeking a comfortable and convenient stay.
The flat can comfortably accommodate up to four guests and features a modern kitchen with stainless-steel appliances, a dedicated workspace with high-speed Wi-Fi, and a living area with a Roku TV and board games for entertainment. The flat also boasts a private entrance, free parking, and air conditioning, ensuring a relaxing and enjoyable stay.
Majestic 3br Oakville Home – Fifa World Cup - Oakville
9.3 9 reviews
Oakville
01/09 – 30/09
A$310/nighttotal: A$8990 (29 )

Majestic 3br Oakville Home – Fifa World Cup

1 4
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.
Beautiful Contemporary 4 Bed Oakville House! - Oakville
9.1 9 reviews
Oakville
01/09 – 30/09
A$201/nighttotal: A$5829 (29 )

Beautiful Contemporary 4 Bed Oakville House!

1 4
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.

Best Oakville holiday rentals with parking

The Croft House - 2 Bedroom 1 Bathroom Suite - Oakville
9.3 48 reviews
Oakville
28/12 – 31/12
A$146/nighttotal: A$438 (3 )

The Croft House - 2 Bedroom 1 Bathroom Suite

2 2
apartment , Hamilton
The Croft House - 2 Bedroom 1 Bathroom Suite is situated in Burlington, a suburb located 30 kilometres from Hamilton, offering a peaceful escape from the city centre. This apartment has received excellent ratings for its cleanliness, location and overall experience.
The 74 square metre apartment comfortably accommodates up to four guests in its two bedrooms and one bathroom. Guests can enjoy a private garden with an outdoor fireplace, a fully equipped kitchen, air conditioning, and a barbecue, making it a perfect choice for a relaxing stay.
Furnished 3000 Sqft 4 Bedrooms Home In Oakville - Oakville
10 16 reviews
Oakville
01/08 – 30/09
A$248/nighttotal: A$14880 (60 )

Furnished 3000 Sqft 4 Bedrooms Home In Oakville

1 4
house , Milton
This spacious townhome is conveniently located in Milton, close to local amenities and attractions. The property has consistently received excellent ratings for cleanliness, location and user experience.
The three-bedroom townhouse comfortably accommodates up to eight guests. It features modern design, a fully equipped kitchen, a private garden, parking, air conditioning, and internet access, making it ideal for families or groups.
Charming 2 Bedroom Basement With Private Entrance - Oakville
8.8 13 reviews
Oakville
01/07 – 31/10
A$82/nighttotal: A$10004 (122 )

Charming 2 Bedroom Basement With Private Entrance

2 2
apartment , Toronto
This basement apartment is located in Oakville, a suburb of Toronto, just a short distance from the lake, Oakville's downtown area, and several parks. It has received very good ratings for cleanliness and user experience, and an excellent rating for its location.
The apartment has two bedrooms, one bathroom, and can comfortably accommodate four guests. It is fully furnished and includes a well-equipped kitchen, a private entrance, and complimentary parking. Guests can enjoy a range of activities nearby, including exploring the lakefront, visiting local shops and restaurants, or relaxing in the nearby parks.
Charming Oakville Getaway - Oakville
Oakville
28/12 – 31/12
A$958/nighttotal: A$2874 (3 )

Charming Oakville Getaway

5 2
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.

Frequently asked questions about holiday rentals in Oakville

  • What are the top family-friendly attractions in Oakville?

    Oakville has a lot to offer families. The Oakville Children's Centre is a great place for kids to play and learn, and the Oakville Galleries has some fun interactive exhibits. You can also take a walk along the lakefront trail, which is perfect for a family picnic.
  • 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.

  • 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 June and September to October. You'll avoid the crowds and get better rates, but the weather is still pleasant.
  • 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's got a great calendar of events, including the Oakville Jazz Festival in July and the Oakville Fall Fair in September. If you're looking for something a little different, check out the Bronte Creek Provincial Park, which hosts a number of events throughout the year.
  • What are the best holiday rentals with a pool in Oakville?

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

    For a taste of local cuisine, head to The Oakville Chop House for a classic steak or The Queen's Plate Restaurant for a more casual dining experience. Both offer delicious and authentic dishes.
  • 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?

    The Waterfront Trail is a great option for both walking and cycling. It stretches along the lakefront and offers stunning views. For a shorter walk, try the Bronte Creek Provincial Park, which has a variety of trails for all levels.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakville?

    The best holiday 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 a very pet-friendly city. You can bring your furry friend to many of the parks and trails, including Coronation Park and the Waterfront Trail. Many restaurants also have outdoor patios that welcome dogs.
  • What are the benefits of choosing a vacation rental in Oakville?

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

    Oakville has a number of sports facilities, including the Oakville Soccer Club, the Oakville Tennis Club, and the Oakville Golf Club. The town is also home to the Oakville Hornets, a junior hockey team.

Destinations nearby

Best Oakville holiday rentals with a balcony

Modern Townhouse Rooftop Vibes - Oakville
Oakville
23/07 – 31/07
A$252/nighttotal: A$2016 (8 )

Modern Townhouse Rooftop Vibes

1 4
house , Milton
This Milton house, sleeping seven guests, offers one bedroom and three bathrooms within an 111 square metre space and includes free private parking; its precise location within Milton requires further clarification to determine proximity to local landmarks.
The property boasts a fully equipped kitchen, free Wi-Fi, a terrace/balcony, air conditioning, and an outdoor fireplace, perfect for relaxing evenings.
Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks - Oakville
Oakville
26/08 – 06/09
A$288/nighttotal: A$3168 (11 )

Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks

2 2
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.
Trafalgar - Oakville
9.0 5 reviews
Oakville
28/12 – 31/12
A$248/nighttotal: A$744 (3 )

Trafalgar

2 2
apartment , Milton
This two-bedroom flat in Oakville, Trafalgar, is approximately 22.5 kilometres from the Mississauga Convention Centre and between 33.8 and 35.4 kilometres from Toronto landmarks such as BMO Field, Rogers Centre, and the CN Tower.
This 999 square metre residence accommodates up to four guests with two bathrooms, a fully equipped kitchen, air conditioning, a balcony, and complimentary private parking, offering free high-speed WiFi.
The Oakville House - Oakville
Oakville
28/08 – 04/09
A$1226/nighttotal: A$8582 (7 )

The Oakville House

3 3
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

Stylish 2-bed Oakville Home With Free Parking + Wifi - Oakville
10 1 review
Oakville
23/07 – 31/07
A$349/nighttotal: A$2792 (8 )

Stylish 2-bed Oakville Home With Free Parking + Wifi

2 4
apartment , Milton
This self-contained side unit in Oakville, located 1.5 kilometres from Lake Ontario and 2.1 kilometres from Bronte Creek Provincial Park, offers convenient access to amenities and natural attractions for those visiting Milton. This two-bedroom flat accommodates up to four guests and features a fully equipped kitchen, in-unit laundry, air conditioning, and dedicated parking, with an office area suitable for business travellers.
Comfy Condo, Can Sleep 5, Close To Stores, Park - Oakville
9.8 20 reviews
Oakville
01/08 – 30/09
A$175/nighttotal: A$10500 (60 )

Comfy Condo, Can Sleep 5, Close To Stores, Park

1 4
apartment , Toronto
This Toronto apartment rental offers a peaceful, central location, though precise distances to specific landmarks remain unspecified.
The two-bedroom, one-bathroom flat sleeps four guests and includes a kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, garden, and parking.
*Top Rated In Oakville*luxurious Private Apartment - Oakville
9.9 20 reviews
Oakville
10/08 – 15/08
A$530/nighttotal: A$2650 (5 )

*Top Rated In Oakville*luxurious Private Apartment

1 2
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).
Basement Apartment  ( Separate Entrance) - Oakville
9.8 255 reviews
Oakville
23/07 – 14/09
A$118/nighttotal: A$6254 (53 )

Basement Apartment ( Separate Entrance)

1 2
apartment , Toronto
This basement flat is conveniently located near major roads and public transport, making it easy to explore Toronto and its surroundings. The property has received excellent ratings for location, cleanliness, and overall user experience.
The self-contained accommodation is suitable for two guests and features a queen-size bed, a sofa bed, and a kitchenette with a fridge, microwave, toaster, and coffee maker. Guests can also enjoy free high-speed Wi-Fi, a private entrance, one parking space, and access to gym equipment.
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