Holiday Rentals in Oakville

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Oakville holiday rentals
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Best Holiday rentals and Airbnb offers in Oakville

Best family friendly Oakville holiday rentals

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

Modern-4 Car-king Bed-ping Pong-bbq-403/407/qew - Oakville
9.9 87 reviews
Oakville
08/07 – 07/08
SG$323/nighttotal: SG$9690 (30 )

Modern-4 Car-king Bed-ping Pong-bbq-403/407/qew

1 4
apartment , Toronto
This luxurious townhouse is located in the family-friendly Joshua Creek neighbourhood in Oakville, just a short drive from major highways and attractions like Bronte GO station, Lake Ontario and downtown Oakville. The property has received excellent ratings for location, cleanliness and user experience.
The spacious three-bedroom townhouse can accommodate up to nine guests and features a dedicated office room and two workspaces. Guests can enjoy high-speed internet, two smart TVs with unlimited Netflix, a fully equipped kitchen, a ping pong table, a backyard with outdoor dining furniture, a BBQ, two garage parking spaces and two driveway parking spaces.
Beautiful Contemporary 4 Bed Oakville House! - Oakville
9.1 9 reviews
Oakville
01/09 – 30/09
SG$181/nighttotal: SG$5249 (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.
Luxary Villa With Pool, Sauna, Hot Tub Sleeps 12 - Oakville
Oakville
28/12 – 31/12
SG$1097/nighttotal: SG$3291 (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.
Beautiful And Cozy Detached House In Oakville - Oakville
9.6 17 reviews
Oakville
01/09 – 30/09
SG$265/nighttotal: SG$7685 (29 )

Beautiful And Cozy Detached House In Oakville

1 1
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.

Best Oakville holiday rentals with parking

Park View In Oakville - Oakville
Oakville
01/08 – 31/10
SG$90/nighttotal: SG$8190 (91 )

Park View In Oakville

1 3
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.
Lux 4br 3ba Home • Sunset Views & Ultimate Comfort - Oakville
9.9 29 reviews
Oakville
28/08 – 04/09
SG$415/nighttotal: SG$2905 (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.
Modern 2br Retreat | Renovated + Free Parking - Oakville
9.8 10 reviews
Oakville
01/07 – 31/07
SG$141/nighttotal: SG$4230 (30 )

Modern 2br Retreat | Renovated + Free Parking

1 3
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.
Private Executive 2br, Patio, Lake, Trails - Oakville
9.8 19 reviews
Oakville
28/08 – 04/09
SG$188/nighttotal: SG$1316 (7 )

Private Executive 2br, Patio, Lake, Trails

2 3
house , Toronto
This luxurious lower level apartment is situated in a prestigious area of Oakville, a suburb of Toronto, within walking distance of the lake, grocery stores, and various amenities. The property has received excellent ratings for its cleanliness, location, and overall experience.
The self-contained basement apartment offers a private entrance, patio, and ample parking, comfortably accommodating up to four guests. The kitchen is fully equipped with a fridge, freezer, microwave oven, and dishwasher, and the bathroom features a soaker tub, a glass shower, and an integrated laundry set.

Frequently asked questions about holiday rentals in Oakville

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

    For families, the Oakville Museum is a great place to visit. The kids will love exploring the exhibits, and there's often a special event or activity going on. Another great option is the Oakville Harbour. There's a playground, a splash pad, and plenty of space to run around. If you're looking for something a little more active, the Oakville Soccer Centre is a great place to let the kids run around and burn off some energy.
  • 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.

  • 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, in spring or autumn. The weather is still pleasant, but the crowds are smaller and the prices are lower. You'll get the best of both worlds.
  • 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 has a lot of great events and festivals throughout the year. The Oakville Jazz Festival is a popular event in the summer, and the Oakville Fall Fair is a fun way to experience the local culture. There's also the Oakville Waterfront Festival in the summer, which is a great way to enjoy the waterfront. And, if you're looking for something a little different, check out the Oakville Art Crawl, which takes place in the fall.
  • What are the best vacation rentals with a pool in Oakville?

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

    For local dishes, you can't go wrong with The Oakville Bistro. They offer a wide variety of dishes, all made with fresh, local ingredients. Another great option is The Oakville Grill. They're known for their delicious burgers and fries, and their atmosphere is always lively. If you're looking for something a little more upscale, try The Oakville Club. They have a fantastic menu, and the service is impeccable.
  • 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?

    Oakville has a great network of walking and cycling trails. The Oakville Waterfront Trail is a popular choice for a scenic stroll or bike ride. It runs along the waterfront and offers stunning views of Lake Ontario. Another great option is the Bronte Creek Provincial Park Trail. It's a longer trail, but it's worth the effort for the beautiful scenery.
  • 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 Beautiful City View 1br High Rise Sq1 Condo 5-.

  • Are there pet-friendly attractions in Oakville?

    Oakville is a very dog-friendly town. Many of the parks and trails are dog-friendly, and there are a number of restaurants and shops that welcome furry friends. The Oakville Harbour is a great place to take your dog for a walk, and they're even allowed on the beach.
  • What are the benefits of choosing a vacation rental in Oakville?

    Choosing a vacation rental in Oakville gives you more space and privacy than a hotel. You can also enjoy the convenience of having a kitchen and laundry facilities. Plus, you'll often find that vacation rentals are more affordable than hotels, especially for families or groups.
  • What are the top sports attractions and facilities in Oakville?

    Oakville is a great place for sports enthusiasts. The Oakville Soccer Centre is a popular destination for soccer fans, and the Oakville Tennis Club offers a variety of courts and programs. For those who prefer to watch sports, the Oakville Hornets are a local hockey team that plays in the Ontario Junior Hockey League.

Destinations nearby

Best Oakville holiday rentals with a balcony

2 Bedroom Private Suite-parking-near Hospital And Airport - Oakville
9.2 23 reviews
Oakville
23/07 – 14/09
SG$231/nighttotal: SG$12243 (53 )

2 Bedroom Private Suite-parking-near Hospital And Airport

2 2
apartment , Milton
This Oakville apartment, situated 22.5km from the Mississauga Convention Centre and 37km from both BMO Field and the Budweiser Stage, offers a peaceful retreat near Milton.
The 19-square-metre, two-bedroom flat sleeps seven, boasting a fully equipped kitchen, terrace, garden, parking, and free Wi-Fi.
*Cozy* 1 Bedroom Home Near Waterfront/trails - Oakville
Oakville
28/12 – 31/12
SG$337/nighttotal: SG$1011 (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.
Spacious 2 Bedrooms 2 Bathrooms With Cozy Charm Plus 1 Parking - Oakville
Oakville
01/09 – 30/09
SG$229/nighttotal: SG$6641 (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.
Charming Oakville Getaway - Oakville
Oakville
28/08 – 16/09
SG$243/nighttotal: SG$4617 (19 )

Charming Oakville Getaway

5 4
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.

Best Oakville holiday rentals with air conditioning

2 Bedroom $80/night Mississauga (30 Days Booking) - Oakville
9.6 104 reviews
Oakville
01/07 – 31/07
SG$124/nighttotal: SG$3720 (30 )

2 Bedroom $80/night Mississauga (30 Days Booking)

1 2
apartment , Toronto
This basement flat is located in a suburb of Toronto, a 35-minute drive or train ride from the city centre and a 25-minute drive from the airport. The property has received excellent ratings for cleanliness, location and user experience.
This self-contained apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. It includes modern amenities such as air conditioning, heating, a TV with Lodge, a fully equipped kitchen, free WiFi, and Netflix, as well as a shared parking space and a coin laundry.
Brand New Muskoka-syle Home | Near Toronto & Lake! - Oakville
Oakville
28/08 – 04/09
SG$810/nighttotal: SG$5670 (7 )

Brand New Muskoka-syle Home | Near Toronto & Lake!

1 9
apartment , Toronto
This seven-bedroom, six-bathroom Muskoka-style apartment is situated a short distance from Toronto, offering easy access to the highway and a nearby lake perfect for water activities.
The property sleeps ten guests and boasts a fully equipped kitchen, fast Wi-Fi, and ample parking, making it ideal for families or groups visiting the Toronto area.
Hot Tub Oasis · Park Backyard · Near Lake - Oakville
Oakville
04/07 – 10/07
SG$333/nighttotal: SG$1998 (6 )

Hot Tub Oasis · Park Backyard · Near Lake

1 8
apartment , Toronto
This spacious four-bedroom flat, ideal for up to ten guests, is located in a peaceful residential area between Toronto and Niagara Falls, just a short walk from Lake Ontario.
Guests can enjoy a private hot tub in the park-like garden, a secondary kitchen in the walkout suite, and exterior security cameras for added safety.
Stylish Oakville Studio! Work Desk + Wifi +Free Parking + Pet Friendly - Oakville
Oakville
10/08 – 15/08
SG$153/nighttotal: SG$765 (5 )

Stylish Oakville Studio! Work Desk + Wifi +Free Parking + Pet Friendly

1 2
studio , Milton
This private, self-contained studio apartment is located in Oakville, a short distance from the Oakville Museum and Benares Historic House, offering convenient access to local attractions.
This accommodation sleeps two guests and features a kitchenette with a fridge and microwave, air conditioning, free parking, and high-speed WiFi, making it suitable for remote work or study.
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