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

*Top Rated In Oakville*luxurious Private Apartment - Oakville
9.9 20 reviews
Oakville
28/12 – 31/12
SG$278/nighttotal: SG$834 (3 )

*Top Rated In Oakville*luxurious Private Apartment

1 2
apartment , Toronto
This Glen Abbey, Oakville self-catering property is conveniently located near major roads, approximately 13km from Lake Ontario, and within a 16km radius of Glen Abbey Golf Course and Deer Creek Golf Course.
The spacious basement flat sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, in-unit laundry, Smart TV with streaming services, Xbox One with racing simulator, and private parking; enjoy nearby Oakville Place Shopping Centre, a short drive from Toronto (64km) and Niagara Falls (80km).
Luxury Stay, Cozy & Bright, Nature's Art - Oakville
9.8 38 reviews
Oakville
15/08 – 04/09
SG$552/nighttotal: SG$11040 (20 )

Luxury Stay, Cozy & Bright, Nature's Art

1 2
apartment , Toronto
This five-bedroom, three-bathroom Oakville apartment, a short drive from Toronto, offers easy access to local amenities; precise distances to Toronto landmarks are not specified.
Sleeping up to twelve guests, this spacious property boasts a fully equipped kitchen, air conditioning, parking, and excellent internet access; bird feeders outside provide a tranquil setting.
2 Bedroom Private Suite-parking-near Hospital And Airport - Oakville
9.2 23 reviews
Oakville
23/07 – 31/07
SG$236/nighttotal: SG$1888 (8 )

2 Bedroom Private Suite-parking-near Hospital And Airport

2 4
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.
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.

Best Oakville holiday rentals with parking

Free Parking, Full Kitchen/bath, Wrkspc, Sep Ent - Oakville
10 11 reviews
Oakville
23/07 – 14/09
SG$122/nighttotal: SG$6466 (53 )

Free Parking, Full Kitchen/bath, Wrkspc, Sep Ent

1 2
apartment , Toronto
This basement flat is located in a convenient area of Toronto, less than 1 kilometre from a grocery store, pharmacy, bakery, and restaurants, and just an hour's drive from Niagara Falls. The apartment is ideal for couples or solo travellers seeking a comfortable and affordable base for exploring the city.
The property offers a well-equipped kitchen with a fridge and microwave, a dedicated workspace for remote working, a comfortable living area with a TV, books, and games, and a bedroom with a queen-size bed. Guests can also enjoy the convenience of a washing machine and dryer, air conditioning, and free Wi-Fi.
Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville - Oakville
10 3 reviews
Oakville
28/12 – 31/12
SG$329/nighttotal: SG$987 (3 )

Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville

2 2
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.
Cozy 2 Bedrooms Modern Basement Suite With Private Entrance, Kitchen And Parking - Oakville
9.1 16 reviews
Oakville
28/12 – 31/12
SG$294/nighttotal: SG$882 (3 )

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

2 2
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.
Trafalgar - Oakville
9.0 5 reviews
Oakville
05/07 – 11/07
SG$217/nighttotal: SG$1302 (6 )

Trafalgar

2 2
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.

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

Stylish 3br 2.5 Bath Townhouse With Patio And Parking - Oakville
Oakville
23/07 – 14/09
SG$601/nighttotal: SG$31853 (53 )

Stylish 3br 2.5 Bath Townhouse With Patio And Parking

3 2
house , Toronto
This townhouse is situated in Streetsville, approximately 16 kilometres from the Mississauga Convention Centre and 19 kilometres from Toronto Pearson International Airport.
This property offers 125 square metres of living space with three bedrooms and two bathrooms, accommodating up to nine guests with amenities including a dishwasher, microwave oven, fridge, air conditioning, a terrace, balcony, and free private parking.
3bed Bright Oakville Townhome With Balcony, Office - Oakville
9.0 2 reviews
Oakville
28/08 – 16/09
SG$269/nighttotal: SG$5111 (19 )

3bed Bright Oakville Townhome With Balcony, Office

3 4
house , Toronto
This Oakville townhouse is located 26 kilometres from Toronto Pearson International Airport, providing a suburban base with reasonable access to Toronto's attractions.
This property offers free Wi-Fi, private parking, a fully equipped kitchen, and a private balcony, accommodating up to 11 guests with 2 bathrooms and air conditioning.
Luxurious House With Pond View And Jacuzzi - Oakville
Oakville
08/08 – 03/10
SG$350/nighttotal: SG$19600 (56 )

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.
South Oakville Bliss Haven Monthly Stays Only - Oakville
8.5 2 reviews
Oakville
01/09 – 30/09
SG$416/nighttotal: SG$12064 (29 )

South Oakville Bliss Haven Monthly Stays Only

5 4
house , Toronto
This five-bedroom house, ideal for large groups, is situated in South Oakville, approximately 32-37 kilometres from Toronto attractions including the Mississauga Convention Centre, BMO Field, Budweiser Stage, and Exhibition Place.
The 13-square-metre property boasts three bathrooms, a fully equipped kitchen, private parking, Wi-Fi, and a balcony with barbecue facilities, comfortably accommodating up to 19 guests.

Best Oakville holiday rentals with air conditioning

Charming 2 Bedroom Basement With Private Entrance - Oakville
8.8 13 reviews
Oakville
08/08 – 03/10
SG$78/nighttotal: SG$4368 (56 )

Charming 2 Bedroom Basement With Private Entrance

2 2
apartment , Toronto
This basement apartment is located in Oakville, a suburb of Toronto, just a short distance from the lake, Oakville's downtown area, and several parks. It has received very good ratings for cleanliness and user experience, and an excellent rating for its location.
The apartment has two bedrooms, one bathroom, and can comfortably accommodate four guests. It is fully furnished and includes a well-equipped kitchen, a private entrance, and complimentary parking. Guests can enjoy a range of activities nearby, including exploring the lakefront, visiting local shops and restaurants, or relaxing in the nearby parks.
Beautiful 2 Bed 2 Wash Corner Suite! Tons Of Light - Oakville
Oakville
27/06 – 31/12
SG$124/nighttotal: SG$23188 (187 )

Beautiful 2 Bed 2 Wash Corner Suite! Tons Of Light

1 2
apartment , Milton
This spacious 2-bedroom, 2-bathroom corner flat is located in a well-lit area of Milton, offering convenient access to local amenities.
This furnished or unfurnished residence accommodates up to 4 guests and includes internet, air conditioning, a kitchen, fitness centre, and parking.
Modern Luxury Condo In North Oakville! - Oakville
10 5 reviews
Oakville
01/09 – 30/09
SG$118/nighttotal: SG$3422 (29 )

Modern Luxury Condo In North Oakville!

1 1
apartment , Milton
This North Oakville flat offers convenient access to Oakville Trafalgar High School, Sixteen Mile Sports Complex, Sheridan College (a 7-minute drive), and the UTM Campus (a 15-minute drive).
This stylish one-bedroom plus den apartment, equipped with air conditioning, parking, and a kitchen featuring a fridge, microwave, and dishwasher, can accommodate up to five guests and boasts an open-concept design.
Relaxing Home Base | Quiet Area & Cozy Living - Oakville
Oakville
28/08 – 04/09
SG$180/nighttotal: SG$1260 (7 )

Relaxing Home Base | Quiet Area & Cozy Living

1 3
apartment , Toronto
This flat is situated in Mississauga's Erin Mills Stadium district, a 4-minute drive from Oakville Entertainment Centrum and Erin Mills Town Centre, offering convenient access to shopping and entertainment venues.
This one-bedroom flat accommodates up to four guests and features a fully equipped kitchen, in-suite laundry, Wi-Fi, and a dedicated workspace, with nearby attractions including the Bradley Museum and Riverwood Conservancy.
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