Oakville Short term rentals

531 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Oakville short term rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Oakville

Best Oakville luxury short term rentals

Luxury Basement Apartment In Oakville Monthly Stays Only - Oakville
9.5 23 reviews
Oakville
08/07 – 07/08
A$180/nighttotal: A$5400 (30 )

Luxury Basement Apartment In Oakville Monthly Stays Only

1 4
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.

Best Oakville Short term rentals with a jacuzzi

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

Luxurious House With Pond View And Jacuzzi - Oakville
9.7 18 reviews
Oakville
01/08 – 30/09
A$565/nighttotal: A$33900 (60 )

Luxurious House With Pond View And Jacuzzi

1 4
apartment , Milton
This four-bedroom, three-bathroom townhouse is located in the Joshua Creek neighbourhood of Oakville, conveniently situated near major highways (403, 407, and QEW), offering easy access to Milton and other nearby attractions.
The property boasts a modern open-plan layout, sleeping up to seven guests and featuring a fully equipped kitchen with KitchenAid appliances, a Jacuzzi, a private patio, and a fitness centre, all within a short distance of local walking trails and parks.
Luxury Condo Stay That Feels Like Home - Oakville
10 2 reviews
Oakville
28/12 – 31/12
A$119/nighttotal: A$357 (3 )

Luxury Condo Stay That Feels Like Home

1 2
apartment , Toronto
This one-bedroom flat in Oakville offers direct train access to Toronto, situated just steps from Oakville GO station and Kerr Village, placing you 30 kilometres southwest of the city centre with proximity to lakeside amenities. Guests can enjoy luxury condo amenities including a swimming pool, sauna, and gym, alongside a private washroom and access to a shared kitchen for a comfortable stay.
Modern Executive Townhome W/ Rooftop Hot Tub Oasis - Oakville
10 133 reviews
Oakville
01/07 – 31/07
A$513/nighttotal: A$15390 (30 )

Modern Executive Townhome W/ Rooftop Hot Tub Oasis

1 4
apartment , Milton
This stylish townhouse is located in Oakville, just a short distance from Milton, and is conveniently situated near three major highways. The property has received excellent ratings for its cleanliness, location and overall experience.
The two-bedroom townhouse can comfortably accommodate up to four guests and features spacious living areas perfect for relaxing or socialising. Enjoy the private rooftop terrace with a Jacuzzi hot tub, a fully equipped kitchen with complimentary Nespresso, coffee, decaf, and tea options, and ultra-fast internet with a Roku TV and Crave TV.
Luxury 5 Br, Gym, Sauna, Thtr, Od Fp & Ktcn, Lake - Oakville
Oakville
04/08 – 12/08
A$1801/nighttotal: A$14408 (8 )

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

5 3
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.

Frequently asked questions about short term rentals in Oakville

  • What kind of weather can travelers expect in Oakville?

    Oakville has a humid continental climate, so you can expect warm summers and cold winters. You can expect temperatures to range from -15°C to 30°C. Spring and autumn are generally mild, but can be unpredictable. Don't forget to pack layers, especially if you're visiting during the shoulder seasons.
  • 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 bustling events calendar throughout the year. You can check out the Oakville Jazz Festival in July, the Oakville Fall Fair in September, and the Oakville Christmas Market in December. These events bring the town alive with music, food, and entertainment.
  • What are the best short term rentals with a pool in Oakville?

  • What notable natural landmarks are near Oakville?

    Oakville is surrounded by some beautiful natural areas. Just a short drive away, you can find the picturesque Dundas Peak and the scenic Crawford Lake Conservation Area. These are great spots for hiking, camping, and enjoying the outdoors.
  • 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 part of Oakville is ideal for finding lodging?

    The downtown core of Oakville, near the waterfront, is a great place to find hotels and restaurants. However, you can also find some charming bed and breakfasts in the historic Old Oakville neighbourhood. The area around the Oakville GO station is also a convenient place to stay, as it has good access to public transportation.
  • 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

Modern-4 Car-king Bed-ping Pong-bbq-403/407/qew - Oakville
9.9 86 reviews
Oakville
01/09 – 28/02
A$269/nighttotal: A$48420 (180 )

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.
*Top Rated In Oakville*luxurious Private Apartment - Oakville
9.9 20 reviews
Oakville
23/06 – 25/06
A$420/nighttotal: A$840 (2 )

*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).
3bd 2.5bth House W/ Pool Table, Swing, Outdoor Bbq - Oakville
9.8 184 reviews
Oakville
01/07 – 05/07
A$502/nighttotal: A$2008 (4 )

3bd 2.5bth House W/ Pool Table, Swing, Outdoor Bbq

1 3
apartment , Toronto
This apartment is located in a quiet neighbourhood in Oakville, just 15 kilometres from downtown Toronto and less than 80 kilometres from Niagara Falls. It has consistently received excellent ratings for cleanliness, location, and user experience.
The three-bedroom home is perfect for families or groups of up to nine guests and offers a spacious layout with a large backyard. Guests can enjoy amenities like a fully equipped kitchen, a pool table, a foosball table, a quiet workstation, and a private garage.
Cozy Basement Apartment In Oakville - Oakville
9.7 47 reviews
Oakville
31/07 – 31/08
A$133/nighttotal: A$4123 (31 )

Cozy Basement Apartment In Oakville

1 1
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.

Best Oakville short term rentals with parking

2026 Fifa |40 Mins To Bmo Field |Oakville Go Train - Oakville
9.8 89 reviews
Oakville
23/06 – 25/06
A$494/nighttotal: A$988 (2 )

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

1 2
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.
Luxurious House With Pond View And Jacuzzi - Oakville
Oakville
22/06 – 22/07
A$421/nighttotal: A$12630 (30 )

Luxurious House With Pond View And Jacuzzi

4 1
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.
Serene High-celling Retreat - Oakville
9.8 19 reviews
Oakville
01/09 – 30/09
A$141/nighttotal: A$4089 (29 )

Serene High-celling Retreat

2 1
apartment , Toronto
This Oakville apartment, situated approximately 32-45 kilometres from Toronto attractions such as the CN Tower and Rogers Centre, offers a peaceful retreat from the city centre.
The 56-square-metre flat features two bedrooms, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, free Wi-Fi, and private parking.
Spacious And Luxurious 2br Suite With Huge Windows - Oakville
10 1 review
Oakville
01/07 – 31/07
A$332/nighttotal: A$9960 (30 )

Spacious And Luxurious 2br Suite With Huge Windows

2 2
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.
©2026 cozycozy.com