Vacation Rentals in Oakville

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Oakville holiday rentals
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871 Holiday rentals and Airbnb in Oakville

Superior Family-Friendly Holiday Rentals in Oakville, Canada

Give the entire crew plenty of space to relax and unwind after a busy day of sightseeing at family holiday rentals in Oakville, Canada.

Cozy Basement Apartment In Oakville - Oakville
9.7 121 reviews

Cozy Basement Apartment In Oakville

apartment, Milton
This Oakville basement flat, situated in a quiet neighbourhood near restaurants and grocery stores, is approximately 16-24 km from Toronto Pearson International Airport (YYZ) and 10-15 minutes from Oakville GO Station.
The self-catering apartment offers two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus parking and air conditioning.
Oakville 2 Bedroom Apartment - South Shell Beach - Oakville
No reviews

Oakville 2 Bedroom Apartment - South Shell Beach

apartment, Toronto
This Oakville flat is located on Admiral Drive, approximately 35 kilometres from John C. Munro Hamilton International Airport.
This 93 square metre residence accommodates up to six guests with two bedrooms and one bathroom, featuring a kitchenette, air conditioning, and complimentary WiFi, and is suitable for families and pets.
Comfortable Luxury Home In Oakville - Oakville
9.9 75 reviews

Comfortable Luxury Home In Oakville

house, Milton
This spacious four-bedroom apartment is ideally located in a sought-after area of Toronto, just a short distance from highways, grocery stores, and bars. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment is perfect for families, accommodating up to nine guests comfortably. It features a well-equipped kitchen, a dedicated office space, a separate family room, a private garden, a fitness centre, and secure parking.
Luxury Basement Apartment In Oakville Monthly Stays Only - Oakville
9.6 23 reviews

Luxury Basement Apartment In Oakville Monthly Stays Only

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

Spacious Urban Oasis:stylish 2 Bed, 2 Bath Getaway - Oakville
9.7 83 reviews

Spacious Urban Oasis:stylish 2 Bed, 2 Bath Getaway

apartment, Toronto
This Oakville condo, approximately 64km from Toronto, offers stunning views of a pond and Lake Ontario from its enclosed balcony, providing easy access to both Oakville's amenities and Toronto.
The spacious 84 square metre, two-bedroom, two-bathroom apartment sleeps four, featuring a modern condominium complex with elevator access, queen-size beds, and a walk-in closet in the master bedroom.
Oakville Fully Furnished 3 Bedroom Entiretownhome! - Oakville
9.1 30 reviews

Oakville Fully Furnished 3 Bedroom Entiretownhome!

house, Milton
This newly furnished house is located in Milton, just a short distance from the town centre and within easy reach of the Milton Historical Society Museum. The property has received excellent ratings for its cleanliness, location and overall experience.
The house has three bedrooms, sleeping up to six guests, making it ideal for families or groups of friends. Guests can enjoy modern furnishings, a comfortable living space with a TV and free Wi-Fi, a fully equipped kitchen for self-catering, and a peaceful garden.
Spacious 2 Br Basement Suite | Private Entrance - Oakville
10 1 review

Spacious 2 Br Basement Suite | Private Entrance

apartment, Milton
This three-bedroom, one-bathroom flat, offering space for six guests, is located in the North Oakville district, a mere 500 meters from Oakville Hospital and within easy reach of major motorways, shopping centres, diverse eateries, and recreational parks.
This self-contained dwelling provides a private entrance, a fully equipped kitchen, in-suite laundry, high-speed Wi-Fi, air conditioning, and free parking, ensuring a comfortable and convenient stay for those visiting Milton.
Modern & Spacious 2-bedroom Basement Suite - Oakville
No reviews

Modern & Spacious 2-bedroom Basement Suite

apartment, Toronto
This private basement flat in Toronto offers a secure, residential setting with easy access to shops, restaurants, parks, public transport, and major roads.
This two-bedroom, one-bathroom flat accommodates up to four guests and features a fully equipped kitchen, in-suite laundry, fast Wi-Fi, a Smart TV, and free parking.

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.

Popular destinations

Holiday Rentals with a Balcony in Oakville, Canada

Relax outdoors and watch the town come alive from the elevated vantage of holiday rentals with a balcony in Oakville, Canada.

Stylish Three-level Oakville Townhome Near Toronto With Parking And Balconies - Oakville
8.0 4 reviews

Stylish Three-level Oakville Townhome Near Toronto With Parking And Balconies

apartment, Toronto
This spacious three-level townhome in Oakville's residential area offers a quiet base, with easy access to Toronto, located approximately 30 to 45 kilometres away depending on traffic.
This pet-friendly residence accommodates up to six guests and features a fully equipped kitchen with a microwave and dishwasher, in-unit laundry, air conditioning, a terrace, parking, and two bathrooms, including a luxurious penthouse ensuite.
Premium Furnished 1br Near Clarkson Go With Parking - Oakville
No reviews

Premium Furnished 1br Near Clarkson Go With Parking

apartment, Toronto
This Mississauga flat offers convenient access to Toronto Pearson International Airport, located 22.5 kilometres away, and is situated close to Clarkson GO station for straightforward public transport connections.
This 66 square metre one-bedroom flat accommodates up to seven guests and features a fully equipped kitchen, air conditioning, a balcony, and access to building amenities including a swimming pool, sauna, and hot tub, with private on-site parking also provided.
Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville - Oakville
No reviews

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville

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.
Trafalgar - Oakville
8.5 12 reviews

Trafalgar

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.

Best Oakville holiday rentals with air conditioning

Luxury & Modern 2 Bedroom W/parking - Oakville
9.0 2 reviews

Luxury & Modern 2 Bedroom W/parking

apartment, Milton
This two-bedroom flat in Oakville offers excellent access to Milton, being just minutes from major motorways and providing a direct 40-minute GO Train journey to downtown Toronto.
This modern apartment, suitable for four guests, boasts a fully equipped kitchen with a fridge, freezer, and microwave, air conditioning, in-suite laundry, high-speed Wi-Fi, and complimentary parking, with a welcome pack including coffee and snacks.
Luxury 2br Suite | Free Parking | Private Entrance - Oakville
9.6 74 reviews

Luxury 2br Suite | Free Parking | Private Entrance

apartment, Milton
This excellent, family-friendly basement flat in a prestigious Milton neighbourhood is conveniently located near the GO station, Walmart, and Canadian Superstore.
The two-bedroom, one-bathroom self-catering apartment sleeps five, boasts a fully equipped kitchen including a dishwasher, high-speed Wi-Fi, Netflix, and parking, offering comfortable accommodation near Lakeshore and Milton town centre.
Spacious 2 Bedroom Home W/ Parking & Laundry - Oakville
10 42 reviews

Spacious 2 Bedroom Home W/ Parking & Laundry

apartment, Toronto
This Toronto apartment rental, ideally located in [Insert Specific Toronto Neighbourhood, e.g., Yorkville], is approximately 2 km from the Royal Ontario Museum and offers easy access to public transport.
Sleeping four guests comfortably in two bedrooms and one bathroom, this property boasts a fully equipped kitchen including fridge, freezer, and microwave, air conditioning, parking, and excellent guest reviews.
One Bedroom And One Washroom - Oakville
No reviews

One Bedroom And One Washroom

apartment, Milton
This Oakville flat is situated on a quiet street opposite a park, with banks, grocery stores, restaurants, Bronte Creek Provincial Park, and the Oakville Museum all within a 3-5 kilometre drive.
This one-bedroom flat for two guests offers complimentary WiFi, air conditioning, and on-site driveway parking, with the option of house-made Indian vegetarian or non-vegetarian meals for breakfast and dinner.

Uncover Exclusive Holiday Rentals in Oakville, Canada

Treat yourself to high-end design, smart home features, and curated artwork at luxury holiday rentals in Oakville, Canada.

Relaxing Home Base | Quiet Area & Cozy Living - Oakville
10 2 reviews

Relaxing Home Base | Quiet Area & Cozy Living

apartment, Toronto

Downtown Holiday Rentals in Oakville, Canada

Spend less time on public transport and more time visiting nearby sights from centrally located holiday rentals in Oakville, Canada.

Cozy Modern Studio In Oakville | Free Parking - Oakville
9.6 173 reviews

Cozy Modern Studio In Oakville | Free Parking

apartment, Toronto
@Oakville - Cozy Private Studio - Oakville
10 2 reviews

@Oakville - Cozy Private Studio

apartment, Toronto
Yaras Nest - Oakville
10 2 reviews

Yaras Nest

apartment, Toronto
3bed Bright Oakville Townhome With Balcony, Office - Oakville
10 3 reviews

3bed Bright Oakville Townhome With Balcony, Office

house, Toronto
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