Holiday Rentals in Oakville

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Oakville holiday rentals
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Oakville holiday rentals: compare the best deals

Best family friendly Oakville holiday rentals

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

Cozy Basement Apartment In Oakville - Oakville
9.7 47 reviews
Oakville
07/23 – 09/14
HK$786/nightTotal: HK$41658 (53 )

Cozy Basement Apartment In Oakville

1 2
apartment , Toronto
This one-bedroom flat is situated in a peaceful residential area of Toronto, just a short walk from [insert specific landmarks or attractions]. It has received excellent ratings for user experience, location and cleanliness.
The apartment is comfortably furnished and can accommodate up to two guests. It comes equipped with a kitchen, a separate washer and dryer, and a dedicated workspace, making it suitable for both families and those working remotely.
4bed-luxury Home, Pool Table, Backyard, Sleeps 12 - Oakville
9.3 3 reviews
Oakville
06/25 – 06/28
HK$6769/nightTotal: HK$20307 (3 )

4bed-luxury Home, Pool Table, Backyard, Sleeps 12

4 4
apartment , Milton
This modern 4-bedroom house is located in a quiet subdivision in Oakville, 40 kilometres from the airport, offering a family-friendly base for those visiting Milton.
This spacious residence sleeps up to 12 guests, featuring a fully equipped kitchen with a dishwasher, air conditioning, a garden, and parking for up to four vehicles, with a game area for entertainment.
Modern-4 Car-king Bed-ping Pong-bbq-403/407/qew - Oakville
9.9 87 reviews
Oakville
07/23 – 09/14
HK$2076/nightTotal: HK$110028 (53 )

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

4 2
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.
3bed Bright Oakville Townhome With Balcony, Office - Oakville
9.0 2 reviews
Oakville
12/28 – 12/31
HK$1716/nightTotal: HK$5148 (3 )

3bed Bright Oakville Townhome With Balcony, Office

3 2
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.

Best Oakville holiday rentals with parking

Spacious And Luxurious 2br Suite With Huge Windows - Oakville
10 1 review
Oakville
07/01 – 07/31
HK$1860/nightTotal: HK$55800 (30 )

Spacious And Luxurious 2br Suite With Huge Windows

2 4
apartment , Toronto
This Mississauga apartment, located in the Erin Mills neighbourhood, is a 6.4km drive from the Oakville Entertainment Centre and iFLY Toronto Oakville.
This family-friendly 46-square-metre flat offers two bedrooms, one-and-a-half bathrooms, a fully equipped kitchen, in-unit laundry, free Wi-Fi, and parking, providing comfortable accommodation for up to four guests near various attractions including Putting Edge and Cineplex Winston Churchill cinemas.
Luxury 5 Br, Gym, Sauna, Thtr, Od Fp & Ktcn, Lake - Oakville
Oakville
12/28 – 12/31
HK$11195/nightTotal: HK$33585 (3 )

Luxury 5 Br, Gym, Sauna, Thtr, Od Fp & Ktcn, Lake

5 2
apartment , Hamilton
This newly built five-bedroom, four-bathroom residence is situated in Burlington, 14 kilometres from Hamilton city centre, offering proximity to the Oakville Art Society and Joseph Brant Museum.
This detached house accommodates up to ten guests and features air conditioning, a microwave oven, a dishwasher, a Jacuzzi, and parking, with cribs and baby gates available upon request.
Modern And Comfortable Basement Suite - Oakville
10 21 reviews
Oakville
07/10 – 07/15
HK$967/nightTotal: HK$4835 (5 )

Modern And Comfortable Basement Suite

1 2
apartment , Toronto
This self-contained two-bedroom basement flat in Toronto offers a private entrance and is conveniently located within walking distance of numerous shopping centres and a wide array of restaurants, making it an ideal base for families, couples, and business travellers. The accommodation is equipped with air conditioning, Wi-Fi, private laundry facilities, and off-street parking, comfortably accommodating up to four guests with one bathroom.
Private Executive 2br, Patio, Lake, Trails - Oakville
9.8 19 reviews
Oakville
08/28 – 09/04
HK$1146/nightTotal: HK$8022 (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 should a first-time visitor not miss in Oakville?

    You absolutely must visit the Oakville Museum, which showcases the town's history and art. For stunning views, take a stroll along the Oakville waterfront, where you can admire the lake and the beautiful gardens.
  • 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?

    The Old Oakville neighbourhood is charming with historic houses and shops, and is a great choice for a vacation rental. It's close to the waterfront and many restaurants.
  • 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?

    The Oakville Galleries is a great place to introduce kids to art, while the Oakville Public Library has fun events for families. For some outdoor fun, head to Coronation Park, which has a playground, splash pad, and a large green space.
  • 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 is during the shoulder seasons, from April to May or September to October, as the weather is still pleasant and the prices are lower.
  • What are the best rentals for families and kids in Oakville?

  • What events or festivals should visitors check out in and around Oakville?

    The Oakville Jazz Festival in July is a highlight, featuring live music and food stalls. In August, the Oakville Waterfront Festival offers a variety of activities, from boat shows to live entertainment.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakville?

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

    Take a walk or bike ride along the waterfront trail, which offers stunning views of Lake Ontario. You can also visit the Oakville Public Library, which has free events and exhibitions.
  • What are the best restaurants with local dishes in Oakville?

    Try the fish and chips at The Captain's Boil, or enjoy a classic Canadian meal at The Keg Steakhouse + Bar. For something a bit more unique, check out the menu at The Oakville Bistro, which features modern Canadian cuisine.
  • 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. For a more challenging ride, try the Oakville Creek Trail, which winds its way through the Oakville Creek.
  • Are there pet-friendly attractions in Oakville?

    Yes, many parks in Oakville are dog-friendly, including Coronation Park and Bronte Creek Provincial Park. You can also find dog-friendly patios at some restaurants.
  • 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, making them ideal for families or longer stays.
  • What are the top sports attractions and facilities in Oakville?

    The Oakville Soccer Club offers various programs for all ages. The Oakville Golf Club is a popular destination for golfers, and the Oakville Tennis Club has courts for both casual and competitive players.

Destinations nearby

Best Oakville holiday rentals with a balcony

*Family Haven* Renovated 3br  Backyard  Parking - Oakville
Oakville
08/28 – 09/04
HK$2540/nightTotal: HK$17780 (7 )

*Family Haven* Renovated 3br Backyard Parking

3 3
apartment , Hamilton
This spacious 186-square-metre, two-storey townhome is situated in Burlington, a short drive from Hamilton's attractions, and is within walking distance of local shops and restaurants.
This pet-friendly residence accommodates up to six guests with three bedrooms and two bathrooms, offering a fully equipped kitchen, a formal dining area for eight, in-unit laundry, air conditioning, a terrace, and two driveway parking spaces, with high-speed WiFi suitable for remote work.
Luxury Oakville Home, Hot Tub, Fireplace, New Home - Oakville
10 1 review
Oakville
07/05 – 07/12
HK$4974/nightTotal: HK$34818 (7 )

Luxury Oakville Home, Hot Tub, Fireplace, New Home

4 10
house , Milton
This luxurious property is situated in Oakville, just 24 kilometres from the Mississauga Convention Centre, 35 kilometres from BMO Field, and 37 kilometres from Budweiser Stage. The home has received excellent ratings for its location, cleanliness, and overall user experience.
This four-bedroom home is spacious and comfortable, with a floor area of 229 square metres and a guest capacity of 10. The property offers a range of amenities, including a private hot tub, outdoor dining area, fireplace, fully equipped kitchen, free Wi-Fi, washer and dryer, and a peaceful garden.
Cozy 3 Bedroom Bungalow With Bright Basement Suit. - Oakville
Oakville
07/23 – 09/14
HK$1268/nightTotal: HK$67204 (53 )

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.
South Oakville Bliss Haven Monthly Stays Only - Oakville
8.5 2 reviews
Oakville
09/01 – 09/30
HK$2538/nightTotal: HK$73602 (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
07/01 – 07/31
HK$526/nightTotal: HK$15780 (30 )

Charming 2 Bedroom Basement With Private Entrance

1 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.
Cozy 2 Bedrooms Modern Basement Suite With Private Entrance, Kitchen And Parking - Oakville
9.1 16 reviews
Oakville
08/28 – 09/04
HK$1549/nightTotal: HK$10843 (7 )

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

2 3
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.
2 Bedroom - Apartment - Close To Lake Ontario - Oakville
Oakville
12/28 – 12/31
HK$1096/nightTotal: HK$3288 (3 )

2 Bedroom - Apartment - Close To Lake Ontario

1 2
apartment , Toronto
This basement flat in Toronto offers proximity to the lake and scenic walking trails, situated a short distance from waterfront activities.
This accommodation sleeps up to five guests and features two bedrooms, a fully equipped kitchen, a washroom, air conditioning, internet, and a living area with a theatre-like experience, allowing pets.
Contemporary 2br Condo Ev Charger: Fifa World Cup - Oakville
10 25 reviews
Oakville
08/28 – 09/16
HK$1737/nightTotal: HK$33003 (19 )

Contemporary 2br Condo Ev Charger: Fifa World Cup

2 4
apartment , Milton
This two-bedroom, two-bathroom flat is situated in Milton's downtown district, a short 500-metre walk from the historic Market Square and near the Milton Art Gallery.
This individualistic apartment accommodates up to five guests and includes air conditioning, Wi-Fi, a kitchen, and parking, with a fitness centre available on-site.
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