Compare Vacation Rentals & Airbnb in Oakville

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Oakville vacation rentals
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664 Rentals and Airbnb in Oakville

Best family friendly Oakville vacation rentals

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

Cozy & Clean, Eastlake Oakville 3 Bed 2.5 Bath - Oakville
10 7 reviews
Oakville
23/07 – 14/09
$369/nighttotal: $19557 (53 )

Cozy & Clean, Eastlake Oakville 3 Bed 2.5 Bath

1 2
apartment , Toronto
This spacious three-bedroom bungalow is situated in southeast Oakville, offering easy access to Highways 403 and QEW, and is a short drive (approximately 6-8 km) from Oakville GO station and the town centre.
The 3-bedroom, 2.5-bathroom property sleeps five guests and includes a fully equipped kitchen, garden, parking, Wi-Fi, and a washer/dryer; nearby attractions include a nature trail and lakeside access.
Welcome To Your Comfort Retreat By The Lake - Oakville
10 1 review
Oakville
09/08 – 14/08
$892/nighttotal: $4460 (5 )

Welcome To Your Comfort Retreat By The Lake

4 4
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.
Your Perfect Getaway Home - Oakville
9.3 48 reviews
Oakville
10/07 – 15/07
$437/nighttotal: $2185 (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.
Lux 4br 3ba Home • Sunset Views & Ultimate Comfort - Oakville
9.9 29 reviews
Oakville
28/08 – 04/09
$451/nighttotal: $3157 (7 )

Lux 4br 3ba Home • Sunset Views & Ultimate Comfort

4 3
apartment , Toronto
This spacious detached house is located in a quiet Oakville neighbourhood, approximately 8 kilometres from Oakville Place, dining options, and Sheridan College, with the Oakville GO Station for Toronto commutes also around 8 kilometres away.
Offering accommodation for up to 7 guests, this comfortable property features 3 bedrooms, 2 bathrooms, air conditioning, and includes a kitchen equipped with a fridge, freezer, microwave oven, and dishwasher, alongside on-site parking.

Best Oakville vacation rentals with parking

Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks - Oakville
Oakville
28/12 – 31/12
$270/nighttotal: $810 (3 )

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.
Luxury Oakville Home, Hot Tub, Fireplace (Upper) - Oakville
9.8 37 reviews
Oakville
28/08 – 04/09
$614/nighttotal: $4298 (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.
Cozy 2 Bedrooms Modern Basement Suite With Private Entrance, Kitchen And Parking - Oakville
9.1 16 reviews
Oakville
27/06 – 04/07
$297/nighttotal: $2079 (7 )

Cozy 2 Bedrooms Modern Basement Suite With Private Entrance, Kitchen And Parking

2 1
apartment , Toronto
This cosy Mississauga basement flat, located 18 kilometres from Toronto Pearson International Airport and within easy driving distance of attractions such as the Rogers Centre and CN Tower (both 35 kilometres away), offers convenient access to Toronto.
The 79-square-metre self-catering property sleeps nine guests, boasting two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, free Wi-Fi, air conditioning, and private parking.
Luxury Executive Studio In Prestigious Glen Abbey Oakville - Oakville
Oakville
01/08 – 31/10
$174/nighttotal: $15834 (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 vacation rentals in Oakville

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

    Oakville has a lot to offer, but for a first-timer, you shouldn't miss the waterfront. Stroll along the Oakville Harbour, visit the Oakville Museum, and maybe catch a show at the Oakville Centre for the Performing Arts.
  • 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?

    For a vacation rental, you might want to consider the Old Oakville neighbourhood. It's charming, with historic buildings and a vibrant atmosphere, and it's close to the waterfront and shops.
  • 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?

    For families, the Oakville Museum is a great place to start. Kids will love the hands-on exhibits, and the museum's location on the waterfront makes it even more appealing. Also, the Oakville Public Library is a great place to visit with children, with a variety of programs and events.
  • 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 a vacation rental in Oakville depends on your preferences. If you want to experience the summer festivals and outdoor activities, July and August are ideal. However, for a quieter getaway, spring or autumn might be better.
  • 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 throughout the year. The Oakville Jazz Festival in July is a popular event, and the Oakville Fall Fair in September is a great family-friendly event. You could also check out the Bronte Creek Provincial Park for events.
  • 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 Luxurious1 Br Condo In Downtown Mississauga .

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

    Oakville has plenty of free and budget-friendly activities. A walk along the waterfront is always enjoyable, and you can explore the many parks and green spaces. You can also visit the Oakville Public Library, which offers free events and programs.
  • What are the best restaurants with local dishes in Oakville?

    For local dishes, try the Oakville Fish Market for fresh seafood, or The Oakville Chop House for a classic Canadian steakhouse experience. For something a bit more casual, The Oakville Brewing Company serves up delicious pub fare.
  • 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. The Oakville Creek Trail is another great option, winding through the town's natural areas. You can also check out the trails at Bronte Creek Provincial Park.
  • Are there pet-friendly attractions in Oakville?

    Many parks and green spaces in Oakville are pet-friendly, including the Oakville Harbour. You can also find dog-friendly patios at some restaurants and cafes.
  • 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, which can be convenient for families or longer stays. They can also be a more affordable option, especially for larger groups.
  • What are the top sports attractions and facilities in Oakville?

    Oakville has several sports facilities, including the Oakville Soccer Club, the Oakville Tennis Club, and the Oakville Golf Club. The town also hosts a variety of sporting events throughout the year.

Destinations nearby

Best Oakville vacation rentals with a balcony

*Cozy* 1 Bedroom Home Near Waterfront/trails - Oakville
Oakville
28/12 – 31/12
$367/nighttotal: $1101 (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.
Cozy 3 Bedroom Bungalow With Bright Basement Suit. - Oakville
Oakville
01/07 – 31/07
$229/nighttotal: $6870 (30 )

Cozy 3 Bedroom Bungalow With Bright Basement Suit.

3 2
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.
Luxary Villa With Pool, Sauna, Hot Tub Sleeps 12 - Oakville
Oakville
28/12 – 31/12
$1193/nighttotal: $3579 (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.
Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville - Oakville
8.8 17 reviews
Oakville
01/09 – 30/09
$269/nighttotal: $7801 (29 )

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville

3 1
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.

Best Oakville vacation rentals with air conditioning

New Basement Apartment | 2 Bedrooms With Parking - Oakville
9.8 26 reviews
Oakville
28/12 – 31/12
$165/nighttotal: $495 (3 )

New Basement Apartment | 2 Bedrooms With Parking

1 2
apartment , Milton
This spacious Milton basement flat is conveniently located near a grocery store, medical clinic, and bus stop, offering easy access to Toronto Pearson International Airport (within a short driving distance).
The 139 square metre self-contained property sleeps four, boasting two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, and parking; an additional bedroom is available on request.
Modern 2br Townhome | King Bed • Parking • Pets - Oakville
8.7 11 reviews
Oakville
01/09 – 30/09
$227/nighttotal: $6583 (29 )

Modern 2br Townhome | King Bed • Parking • Pets

2 1
house , Milton
This spacious two-bedroom, two-bathroom townhouse in North Oakville offers easy access to major highways and the GO station, with the precise distance to Milton needing clarification depending on the exact location.
The 1300+ sq ft property, sleeping four, boasts a modern kitchen with stainless steel appliances, in-suite laundry, two private patios, and underground parking.
Cozy Basement Apartment In The Heart Of Oakville - Oakville
9.7 126 reviews
Oakville
01/09 – 30/09
$104/nighttotal: $3016 (29 )

Cozy Basement Apartment In The Heart Of Oakville

2 1
apartment , Toronto
This two-bedroom flat is located just a short distance from Oakville Place shopping mall and the Oakville GO station, in a quiet and safe neighbourhood. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers a private entrance and full privacy, with access to the entire basement, excluding a locked storage room. Guests can enjoy a fully furnished living space, including a kitchen with a fridge and microwave, as well as a washer and dryer available on weekends.
Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville - Oakville
10 3 reviews
Oakville
01/09 – 30/09
$242/nighttotal: $7018 (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.
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