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

Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville - Oakville
10 3 reviews
Oakville
01/09 – 30/09
A$246/nighttotal: A$7134 (29 )

Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville

2 1
house , Toronto
This modern bungalow is located in Oakville, a suburb of Toronto, situated around 40 kilometres from downtown attractions like BMO Field and Budweiser Stage. The property has received excellent ratings for location, cleanliness, and overall experience, making it a comfortable and convenient choice for travellers.
The two-bedroom, two-bathroom house can comfortably accommodate up to four guests. The fully equipped kitchen, private garden, free Wi-Fi, and parking make it easy to relax and enjoy your stay.
Spacious And Luxurious 2br Suite With Huge Windows - Oakville
8.7 3 reviews
Oakville
01/07 – 31/07
A$361/nighttotal: A$10830 (30 )

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.
Luxury Modern Retreat With Sauna & Modern Amenities - Oakville
Oakville
01/07 – 31/07
A$982/nighttotal: A$29460 (30 )

Luxury Modern Retreat With Sauna & Modern Amenities

4 4
house , Toronto
This Mississauga property, situated 19 kilometres from Toronto Pearson International Airport and 18 kilometres from the Mississauga Convention Centre, offers convenient access to major attractions.
The 250 square metre modern home boasts four bedrooms, four bathrooms, sleeps nineteen guests, and includes a fully equipped kitchen, sauna, garden, terrace, parking, and Wi-Fi.
Luxurious Apartment With King Bed - Oakville
10 8 reviews
Oakville
10/08 – 15/08
A$289/nighttotal: A$1445 (5 )

Luxurious Apartment With King Bed

1 2
apartment , Toronto
This one-bedroom flat is located in a quiet, fashionable district of Toronto, a short walk from major attractions and entertainment venues.
This family-friendly apartment offers a fully equipped kitchen, air conditioning, Wi-Fi, and on-site parking, with a guest capacity of two.

Best Oakville holiday rentals with parking

Stylish 2-bed Oakville Home With Free Parking + Wifi - Oakville
10 1 review
Oakville
01/09 – 30/09
A$276/nighttotal: A$8004 (29 )

Stylish 2-bed Oakville Home With Free Parking + Wifi

2 1
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.
Luxury Condo, Great Decor, Wheelchair Friendly!!! - Oakville
9.7 112 reviews
Oakville
28/12 – 31/12
A$295/nighttotal: A$885 (3 )

Luxury Condo, Great Decor, Wheelchair Friendly!!!

2 2
apartment , Toronto
This wheelchair-accessible luxury flat is situated in a prime area of Toronto, just a short walk from the city centre and its many attractions. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The property is spacious and tastefully furnished with two bedrooms, two bathrooms, and a balcony, comfortably accommodating two guests. It offers a range of amenities including a fully equipped kitchen, laundry facilities, a gym, and secure parking.
Luxurious House With Pond View And Jacuzzi - Oakville
Oakville
23/07 – 14/09
A$414/nighttotal: A$21942 (53 )

Luxurious House With Pond View And Jacuzzi

4 2
apartment , Milton
This Oakville holiday home, an 11-minute (17.7km) drive from Lake Ontario and a 13-minute (20.9km) drive from Square One Shopping Centre, offers convenient access to Oakville's attractions.
Sleeping eight guests, the property boasts four bedrooms, four bathrooms, a fully equipped kitchen including a dishwasher and lobster pot, a jacuzzi, and covered parking; nearby activities include Putting Edge mini golf and Glen Abbey Golf Course.
Luxury Modern Retreat: W/ Sauna & Modern Amenities - Oakville
10 2 reviews
Oakville
01/07 – 31/07
A$572/nighttotal: A$17160 (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.

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

Charming Oakville Getaway - Oakville
Oakville
26/08 – 06/09
A$281/nighttotal: A$3091 (11 )

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.
Spacious 2 Bedrooms 2 Bathrooms With Cozy Charm Plus 1 Parking - Oakville
Oakville
01/09 – 30/09
A$253/nighttotal: A$7337 (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.
*Family Haven* Renovated 3br  Backyard  Parking - Oakville
Oakville
28/12 – 31/12
A$628/nighttotal: A$1884 (3 )

*Family Haven* Renovated 3br Backyard Parking

3 2
apartment , Hamilton
This spacious 186-square-metre, two-storey townhome is situated in Burlington, a short drive from Hamilton's attractions, and is within walking distance of local shops and restaurants.
This pet-friendly residence accommodates up to six guests with three bedrooms and two bathrooms, offering a fully equipped kitchen, a formal dining area for eight, in-unit laundry, air conditioning, a terrace, and two driveway parking spaces, with high-speed WiFi suitable for remote work.
Luxury Oakville Home, Hot Tub, Fireplace, New Home - Oakville
10 1 review
Oakville
06/07 – 12/07
A$951/nighttotal: A$5706 (6 )

Luxury Oakville Home, Hot Tub, Fireplace, New Home

4 2
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 air conditioning

Tim Allen's Santa Clause House - Oakville
10 1 review
Oakville
27/06 – 04/07
A$2205/nighttotal: A$15435 (7 )

Tim Allen's Santa Clause House

1 2
apartment , Oakville
This luxurious Oakville townhouse, a former filming location for 'The Santa Clause', is situated close to Lake Ontario, offering scenic views and convenient access to local attractions.
The two-bedroom, two-bathroom property sleeps four guests and boasts a modern kitchen, fitness centre, and on-site yoga studio, celebrating the film's 30th anniversary with a unique holiday experience.
Modern 1 Bedroom Oakville Suite  Parking  Private  Pets Allowed - Oakville
Oakville
10/08 – 15/08
A$256/nighttotal: A$1280 (5 )

Modern 1 Bedroom Oakville Suite Parking Private Pets Allowed

1 2
apartment , Milton
This private, self-contained side unit of a duplex in Oakville offers a comfortable stay for up to two guests, with convenient access to Lake Ontario and Bronte Creek Provincial Park, and is situated approximately 1.5 kilometres from Glen Abbey Golf Course and Cameron's Brewing Company.
This one-bedroom flat includes a full kitchen, 1.5 bathrooms, an in-unit washer and dryer, and free on-site driveway parking for one vehicle, ensuring a convenient and well-equipped stay for visitors to Milton.
Welcome To Your Comfort Retreat By The Lake - Oakville
10 1 review
Oakville
06/07 – 12/07
A$1106/nighttotal: A$6636 (6 )

Welcome To Your Comfort Retreat By The Lake

4 2
apartment , Toronto
This Burlington residence, located approximately 40 kilometres from the Mississauga Convention Centre and 45 kilometres from Toronto's BMO Field and Budweiser Stage, offers convenient access to the lakefront.
This spacious 300 square metre flat accommodates up to 15 guests, featuring four bathrooms, air conditioning, a well-equipped kitchen, complimentary Wi-Fi, and private parking, with a private swimming pool available for use.
Feel At Home - Oakville
9.9 28 reviews
Oakville
26/08 – 06/09
A$235/nighttotal: A$2585 (11 )

Feel At Home

2 2
apartment , Milton
This family-friendly, two-bedroom basement flat is situated in the Joshua Creek area of Oakville, approximately 6.4km from Oakville GO station, providing easy access to Toronto.
The 2-bedroom, 1-bathroom self-catering property sleeps up to 5 guests and features a well-equipped kitchen, high-speed Wi-Fi, driveway parking, and is close to Oakville Place shopping mall, Longo's and Metro supermarkets.
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