Oakville Short term rentals

531 available short term rental offers

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Oakville short term rentals
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Best Short term and Weekly rentals in Oakville

Best Oakville luxury short term rentals

2026 Fifa |40 Mins To Bmo Field |Oakville Go Train - Oakville
9.7 91 reviews
Oakville
09/08 – 14/08
NZ$698/nighttotal: NZ$3490 (5 )

2026 Fifa |40 Mins To Bmo Field |Oakville Go Train

1 4
apartment , Toronto
This five-bedroom, three-bathroom house in Uptown Oakville offers self-catering for up to ten guests, conveniently located within 1.6km of Oakville Place shopping centre, 0.96km from Sheridan College, and 0.8km from a drive-in cinema.
The property features a fully equipped kitchen, a spacious living room with a 65" smart TV, two workspaces, a private enclosed garden, and family-friendly amenities including a high chair, children's books and toys; self check-in is available.

Best Oakville Short term rentals with a jacuzzi

Among the 531 accommodations in Oakville, here are the 4 best rentals with a jacuzzi

Apartment ∙ 2 Bedrooms ∙ 4 Guests - Oakville
Oakville
28/12 – 31/12
NZ$317/nighttotal: NZ$951 (3 )

Apartment ∙ 2 Bedrooms ∙ 4 Guests

2 2
apartment , Milton
This two-bedroom flat in Halton offers convenient access to Oakville and Mississauga (both 32 kilometres away) and is 56 to 79 kilometres from downtown Toronto, with a GO station 630 metres from the property.
This modern apartment for four guests features a fully equipped kitchen with a dishwasher and microwave, air conditioning, a swimming pool, a jacuzzi, and private parking, providing a comfortable base for exploring the Greater Toronto Area.
Brand New Condo-bed+sofa Bed Bright Unit+parking - Oakville
9.4 7 reviews
Oakville
31/07 – 02/08
NZ$418/nighttotal: NZ$836 (2 )

Brand New Condo-bed+sofa Bed Bright Unit+parking

1 2
apartment , Milton
This one-bedroom flat is located in a central Milton district, providing easy access to local amenities.
This flat accommodates up to three guests and includes essential amenities such as air conditioning, a kitchen, and parking, making it ideal for both business and leisure stays.
Luxary Villa W/ Pool, Sauna, Hot Tub | Sleeps 12 - Oakville
Oakville
28/08 – 04/09
NZ$1706/nighttotal: NZ$11942 (7 )

Luxary Villa W/ Pool, Sauna, Hot Tub | Sleeps 12

5 9
apartment , Toronto
This luxury spa villa is located in an accessible area of Toronto with direct GO train access, providing a journey of approximately 64 kilometres to BMO Field.
This spacious 5-bedroom, 3-bathroom flat accommodates up to 12 guests, featuring a private backyard with a pool, hot tub, sauna, and cold plunge, alongside an EV charger for convenience.
Luxurious House With Pond View And Jacuzzi - Oakville
Oakville
01/07 – 31/07
NZ$521/nighttotal: NZ$15630 (30 )

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.

Frequently asked questions about short term rentals in Oakville

  • What kind of weather can travelers expect in Oakville?

    Oakville has a humid continental climate, with warm summers and cold winters. Expect temperatures ranging from -10°C to 30°C throughout the year. Pack for all seasons, especially if you're visiting during spring or autumn when the weather can be unpredictable.
  • What are the best short term rentals in Oakville?

    Among the short term rentals in Oakville, Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are the most popular ones.

  • What are the most popular festivals and events in Oakville?

    Oakville has a lively events calendar. The Oakville Jazz Festival is a popular summer event, attracting music lovers from across the region. The Oakville Fall Fair is another highlight, showcasing local produce and entertainment.
  • What are the best short term rentals with a pool in Oakville?

  • Are there any famous stadiums or sports arenas in Oakville?

    Oakville doesn't have any major professional sports stadiums or arenas. The town is mainly known for its beautiful scenery and its focus on community events rather than big-league sports.
  • What are the best short term rentals with a jacuzzi in Oakville?

    The best short term rentals with a jacuzzi in Oakville are Planurstay - Luxury Suites Mississauga Downtown, Pathway Suites and Beautiful Cozy 1 Br Condo Steps To Sq1 .

  • What notable natural landmarks are near Oakville?

    Oakville is surrounded by beautiful natural landmarks. The nearby Bronte Creek Provincial Park is a great spot for hiking, fishing, and camping. For a scenic drive, head to the Niagara Escarpment, a breathtaking geological formation that offers stunning views.
  • What are the best short term rentals for families and kids in Oakville?

Destinations nearby

Best family friendly Oakville Short term rentals

Among the 531 accommodations in Oakville, here are the 4 best family friendly rentals

House In South Oakville - Close To Lake - Oakville
9.8 25 reviews
Oakville
23/07 – 31/07
NZ$595/nighttotal: NZ$4760 (8 )

House In South Oakville - Close To Lake

1 4
apartment , Toronto
This Oakville main floor apartment, ideally situated near Lake Ontario and Oakville's town centre, offers easy access to Toronto via nearby GO stations and major highways.
The three-bedroom, two-bathroom self-catering property sleeps six guests, boasting a fully furnished interior with modern appliances, high-speed Wi-Fi, dedicated parking, and a private garden.
Luxury-5 Br-king Bed-2 Car-pond View-403/407/qew - Oakville
9.8 79 reviews
Oakville
01/07 – 31/07
NZ$631/nighttotal: NZ$18930 (30 )

Luxury-5 Br-king Bed-2 Car-pond View-403/407/qew

1 2
apartment , Milton
This five-bedroom house, near the junction of the 403, 407 and QEW motorways, is situated approximately 10 km from Oakville GO station and within 8 km of shops including Walmart and Longo's supermarket in Oakville.
Offering self-check-in, this spacious property sleeps 12 guests and boasts a modern kitchen with dishwasher, two workspaces, a garden, parking, and ultra-high-speed internet (1 Gbps), plus two Smart TVs.
Cozy Resort-like Stay With Pool - Oakville
9.6 14 reviews
Oakville
01/07 – 31/07
NZ$115/nighttotal: NZ$3450 (30 )

Cozy Resort-like Stay With Pool

1 2
apartment , Toronto
This charming bed and breakfast is situated in a peaceful residential neighbourhood of Toronto, within easy walking distance of Sixteen Mile Creek, Lions Valley, and Neyagawa Park. The property has received excellent ratings for its cleanliness, location, and overall experience.
The guest house is set up in a basement, providing a quiet and private stay for up to two guests. Guests can enjoy a spacious living area, a well-equipped kitchen, a modern bathroom, a private garden, and access to a swimming pool.
Private Basement Bedrooms In Oakville - Oakville
Oakville
27/06 – 04/07
NZ$165/nighttotal: NZ$1155 (7 )

Private Basement Bedrooms In Oakville

1 2
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Best Oakville short term rentals with parking

Luxury Basement Apartment In Oakville Monthly Stays Only - Oakville
9.5 23 reviews
Oakville
23/07 – 14/09
NZ$205/nighttotal: NZ$10865 (53 )

Luxury Basement Apartment In Oakville Monthly Stays Only

1 2
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.
Brand New Stylish 2br Condo In Oakville - Oakville
Oakville
08/08 – 03/10
NZ$304/nighttotal: NZ$17024 (56 )

Brand New Stylish 2br Condo In Oakville

2 2
apartment , Milton
This apartment is situated in North Oak, Oakville, a short distance from Sixteen Mile Creek, Lake Ontario, and over 300 kilometres of nature trails, offering convenient access to major highways and Sheridan College.
This stylish 67 square metre flat provides accommodation for up to 4 guests with 2 bedrooms, 2 bathrooms, a fully equipped kitchen including a dishwasher, air conditioning, Wi-Fi, and one complimentary underground parking space, plus in-suite laundry facilities.
Quiet And Comfortable Homestay - Oakville
8.4 351 reviews
Oakville
27/06 – 04/07
NZ$124/nighttotal: NZ$868 (7 )

Quiet And Comfortable Homestay

1 2
B&B , Toronto
Quiet and Comfortable Homestay is located 18 miles from Mississauga Convention Center and Toronto Pearson International Airport, and 22 miles from BMO Field and Budweiser Stage, offering a peaceful retreat from the city centre. This guest house has received very good ratings for location, cleanliness, and overall experience.
The accommodation features a bedroom and bathroom, along with a shared lounge area. Amenities include a terrace, garden, kitchen with a fridge and microwave, free Wi-Fi, and private parking.
*Cozy* 1 Bedroom Home Near Waterfront/trails - Oakville
Oakville
28/12 – 31/12
NZ$451/nighttotal: NZ$1353 (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.
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