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.

Beautiful And Cozy Detached House In Oakville - Oakville
9.7 19 reviews

Beautiful And Cozy Detached House In Oakville

apartment, Milton
This four-bedroom property is situated in Milton, close to the junction of Dundas Street and Neyagawa Boulevard, offering easy access to local amenities and the highway. The apartment has been awarded excellent ratings for location, cleanliness and overall user experience.
The spacious home features a modern open-plan design and can accommodate up to eight guests. Amenities include a fully equipped kitchen, air conditioning, a private garden, parking and internet access.
Oaknest | 2bedroom Suite | Free Parking | Licensed - Oakville
9.9 29 reviews

Oaknest | 2bedroom Suite | Free Parking | Licensed

apartment, Milton
This new luxury basement flat is situated in a peaceful Milton neighbourhood, offering easy access to the QEW, 403, and 407 motorways, the GO Station, and is approximately 32 kilometres from the airport and 56 kilometres from downtown Toronto.
This bright, open-plan two-bedroom flat accommodates up to four guests, featuring a fully equipped kitchen with a dishwasher, in-suite laundry, high-speed Wi-Fi, a smart TV, and a private entrance through the garden, with complimentary coffee and snacks provided alongside one dedicated parking space.
Entire Home In Oakville, Canada - Oakville
9.0 3 reviews

Entire Home In Oakville, Canada

house, Hamilton
This Oakville property, situated approximately 29 kilometres from Toronto Pearson International Airport and within a 39-kilometre radius of attractions such as BMO Field and Exhibition Place, offers a convenient base for exploring both Hamilton and Toronto.
This three-bathroom house sleeps fifteen guests, boasting a fully equipped kitchen, free Wi-Fi, private parking, and a balcony; nearby activities include exploring Oakville's suburban attractions.
Cozy Two Bedroom Basement Apartment - Oakville
9.0 4 reviews

Cozy Two Bedroom Basement Apartment

apartment, Toronto
This two-bedroom flat in Oakville offers a convenient base for exploring the Greater Toronto Area, situated 32 kilometres from Toronto Pearson International Airport and within driving distance of the Mississauga Convention Centre (30 kilometres) and BMO Field (40 kilometres).
This accommodation provides a fully equipped kitchen, air conditioning, complimentary WiFi, and free private parking, with a capacity for up to seven guests.

Best Oakville holiday rentals with parking

Lux 4br 3ba Home  Sunset Views & Ultimate Comfort - Oakville
9.9 50 reviews

Lux 4br 3ba Home Sunset Views & Ultimate Comfort

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.
Premium Oakville Executive Suite
2 Br + 2 Ba - Oakville
No reviews

Premium Oakville Executive Suite 2 Br + 2 Ba

apartment, Hamilton
This furnished two-bedroom flat is situated in Oakville, offering a peaceful setting approximately 45 kilometres from Hamilton's city centre.
This property accommodates up to four guests and features a fully equipped kitchen, air conditioning, parking, and complimentary high-speed Wi-Fi, making it ideal for professionals and extended stays.
Spacious Basement Apartment - Oakville
9.7 54 reviews

Spacious Basement Apartment

house, Toronto
This Toronto basement apartment is conveniently located near Mississauga (16km) and a GO train station (16km), offering easy access to both cities and public transport.
The self-contained unit sleeps four, features a modern kitchen with dishwasher, private laundry, and high ceilings, making it ideal for families visiting the Greater Toronto Area.
*Comfortable* 3 Bedroom Home In Safe Family Area - Oakville
No reviews

*Comfortable* 3 Bedroom Home In Safe Family Area

apartment, Hamilton
This Alton, Burlington flat offers convenient access, being a 2-minute drive to Bronte Creek Provincial Park and a 5-minute drive to Millcroft Golf Club.
This pet-friendly apartment boasts a fully equipped kitchen, air conditioning, complimentary Wi-Fi, and on-site parking, accommodating up to six guests with one bedroom and two bathrooms.

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.

Cozy Park View Suit In Oakville - Oakville
10 1 review

Cozy Park View Suit In Oakville

apartment, Toronto
This Oakville flat provides park views and is located a 10-minute walk from commercial amenities, near a golf course and cultural attractions such as the Joshua Creek Heritage Art Centre.
This private walk-out basement suite accommodates up to three guests, featuring a newly renovated interior with a separate entrance, air conditioning, Wi-Fi, a fully equipped kitchen, and laundry facilities, with Oakville's shops and restaurants within easy reach.
Serene Stays - Oakville (3 Beds, 2 Baths, 1 Parking) - Oakville
No reviews

Serene Stays - Oakville (3 Beds, 2 Baths, 1 Parking)

apartment, Hamilton
This two-bedroom flat in Oakville offers convenient access to Hamilton, with the Sixteen Mile Sports Complex and Lions Valley Park just a short distance away, alongside Oakville Place for shopping and several golf clubs including Glen Abbey.
This pet-friendly apartment accommodates up to six guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a private patio, a dedicated workspace with high-speed internet, and access to shared condo amenities such as a gym and yoga room.
Luxurious House With Pond View And Jacuzzi - Oakville
No reviews

Luxurious House With Pond View And Jacuzzi

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 With Sauna & Modern Amenities - Oakville
10 1 review

Luxury Modern Retreat With Sauna & Modern Amenities

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.

Best Oakville holiday rentals with air conditioning

Private One Bedroom Suite.   B And B On Main Floor - Oakville
9.7 43 reviews

Private One Bedroom Suite. B And B On Main Floor

house, Milton
This comfortable one-bedroom property is located in Oakville, just 5 kilometres from the Oakville GO station, providing easy access to Toronto and other destinations. The property has received excellent ratings for cleanliness, location and user experience.
The self-catering property sleeps one guest and features a private back yard entrance, an en-suite bathroom, a full kitchen in the basement, and a spacious living area with a 50-inch TV. The property also benefits from a private back yard, free parking, and is close to major highways, shopping centres, grocery stores, Oakville Hospital, Sheridan College, and the University of Toronto Mississauga campus.
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.
Modern 2 Br Basement Suite In Oakville + Parking! - Oakville
8.9 9 reviews

Modern 2 Br Basement Suite In Oakville + Parking!

apartment, Milton
This 2-bedroom flat, ideal for travellers to Milton, is situated in Oakville, a well-regarded, family-friendly suburb of Toronto, just 200 metres from local parks and offering excellent links to the city centre.
This secure and peaceful accommodation sleeps up to four guests and provides essential amenities including air conditioning, a kitchen, and parking, making it a convenient base for exploring the surrounding area.
Modern & Cozy Walkout Basement With Scenic Views - Oakville
9.8 37 reviews

Modern & Cozy Walkout Basement With Scenic Views

apartment, Milton
This Milton apartment, perfect for families, offers two bedrooms, one bathroom, and sleeps four guests; further details regarding its precise location within Milton and proximity to local attractions are unavailable.
The property includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, garden, and parking; information on the apartment's size, specific interior design, and nearby activities is currently lacking.

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.

Oakville Lakeside Retreat - 2br Apartment - Oakville
No reviews

Oakville Lakeside Retreat - 2br Apartment

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 Retreat In Oakville - Oakville
9.5 141 reviews

Cozy Retreat In Oakville

apartment, Toronto
Mainfloor Unit, 3 Beds,2 Bath, 2parking,1 Laundry - Oakville
10 1 review

Mainfloor Unit, 3 Beds,2 Bath, 2parking,1 Laundry

apartment, Toronto
Sun-kissed 3br Family Home In A Quiet Neighborhood - Oakville
9.9 134 reviews

Sun-kissed 3br Family Home In A Quiet Neighborhood

apartment, Toronto
Spacious Basement In Oakville - Oakville
9.9 114 reviews

Spacious Basement In Oakville

apartment, Toronto
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