Oakville Short term rentals

531 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • 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

Spacious 2 Bedroom Apartment - Oakville. - Oakville
9.8 30 reviews
Oakville
08/07 – 07/08
SG$226/nighttotal: SG$6780 (30 )

Spacious 2 Bedroom Apartment - Oakville.

2 4
B&B , Milton
This spacious, two-bedroom basement flat in Milton offers convenient access to Oakville and Burlington town centres (approximately 18km away), and is within a 72km radius of Toronto and Niagara Falls.
The self-contained apartment, sleeping four, boasts a fully equipped kitchen, in-unit laundry, and private entrance; nearby amenities include shops, restaurants, and parks.

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
SG$237/nighttotal: SG$711 (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.
Luxurious House With Pond View And Jacuzzi - Oakville
Oakville
01/07 – 31/07
SG$389/nighttotal: SG$11670 (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.
Luxury 5 Br, Gym, Sauna, Thtr, Od Fp & Ktcn, Lake - Oakville
Oakville
27/06 – 04/07
SG$1574/nighttotal: SG$11018 (7 )

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.
Brand New Condo-bed+sofa Bed Bright Unit+parking - Oakville
9.4 7 reviews
Oakville
26/08 – 06/09
SG$214/nighttotal: SG$2354 (11 )

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.

Frequently asked questions about short term rentals in Oakville

  • What kind of weather can travelers expect in Oakville?

    Oakville has a humid continental climate. Summers are warm and humid, with average highs around 25°C. Winters are cold and snowy, with average lows around -5°C. You'll want to pack for all 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 lot of festivals and events throughout the year, but the most popular ones are the Oakville Jazz Festival, the Oakville Fall Fair, and the Oakville Christmas Market.
  • 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 stadiums or sports arenas, but you can catch a game at the nearby Rogers Centre in Toronto, which is home to the Toronto Blue Jays.
  • 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 close to some fantastic natural landmarks. The most popular is the Niagara Escarpment, which is a UNESCO World Biosphere Reserve. You can also visit the nearby Crawford Lake Conservation Area.
  • What are the best short term rentals for families and kids in Oakville?

  • What part of Oakville is ideal for finding lodging?

    The best place to find lodging in Oakville is near the waterfront in the downtown area, which is close to all the shops, restaurants, and attractions. The Old Oakville area is also a great choice for its charm and historic buildings.

Destinations nearby

Best family friendly Oakville Short term rentals

Among the 531 accommodations in Oakville, here are the 3 best family friendly rentals

Spacious And Luxurious 2br Suite With Huge Windows - Oakville
8.7 3 reviews
Oakville
23/07 – 31/07
SG$349/nighttotal: SG$2792 (8 )

Spacious And Luxurious 2br Suite With Huge Windows

2 4
apartment , Toronto
This Mississauga apartment, situated 19 kilometres from Toronto's downtown attractions including the BMO Field and Exhibition Place, offers convenient access to both the city and Pearson International Airport (18 kilometres).
This two-bedroom, two-bathroom flat boasts 46 square metres of space, comfortably accommodating up to nine guests and featuring free parking, Wi-Fi, and a fully equipped kitchen.
Luxury Modern Retreat: W/ Sauna & Modern Amenities - Oakville
10 2 reviews
Oakville
06/07 – 12/07
SG$870/nighttotal: SG$5220 (6 )

Luxury Modern Retreat: W/ Sauna & Modern Amenities

4 2
apartment , Toronto
This Mississauga Erin Mills holiday home, near Lake Ontario and The Riverwood Conservancy, offers easy access to Toronto, approximately 24 kilometres from the city centre.
This spacious 224 square metre property boasts a four-bedroom, four-bathroom layout sleeping up to ten guests, complete with a fully equipped kitchen, garden, parking, and air conditioning; nearby attractions include Benares Historic House and Playdium.
Oaknest | Luxury 2bedroom Suite | Free Parking - Oakville
9.8 8 reviews
Oakville
28/08 – 16/09
SG$210/nighttotal: SG$3990 (19 )

Oaknest | Luxury 2bedroom Suite | Free Parking

1 4
apartment , Milton
This new luxury basement flat is situated in a peaceful Milton neighbourhood, offering easy access to the QEW, 403, and 407 motorways, the GO Station, and is approximately 32 kilometres from the airport and 56 kilometres from downtown Toronto.
This bright, open-plan two-bedroom flat accommodates up to four guests, featuring a fully equipped kitchen with a dishwasher, in-suite laundry, high-speed Wi-Fi, a smart TV, and a private entrance through the garden, with complimentary coffee and snacks provided alongside one dedicated parking space.

Best Oakville short term rentals with parking

Bright, Spacious, Quiet 2 Bedroom - Licensed - Oakville
10 164 reviews
Oakville
10/07 – 15/07
SG$211/nighttotal: SG$1055 (5 )

Bright, Spacious, Quiet 2 Bedroom - Licensed

2 2
apartment , Toronto
This Toronto basement flat is located in a quiet, family-friendly neighbourhood offering easy access to major roadways, a hospital, recreation centres, and shopping, all within a few kilometres radius.
The self-contained apartment, sleeping up to four guests, boasts a private backyard entrance, soundproofing, fast WiFi, Netflix, a fully equipped kitchen, designated parking, and access to a shared patio and BBQ.
Serene High-celling Retreat In Upsacle And Safe Neighbourhood - Oakville
10 1 review
Oakville
08/08 – 03/10
SG$96/nighttotal: SG$5376 (56 )

Serene High-celling Retreat In Upsacle And Safe Neighbourhood

2 2
apartment , Toronto
This Glen Abbey holiday home in Oakville, Ontario, is situated within 2km of Saw-Whet Golf Course and Bronte Creek Provincial Park, and 3km from the Oakville Art Society.
The two-bedroom, one-bathroom property sleeps four guests and offers free Wi-Fi, a fully equipped kitchen including a dishwasher, in-home laundry facilities, and air conditioning.
Modern Studio W-kitchen - Parking Near Appleby Go - 40 Min To Toronto - Oakville
Oakville
08/08 – 03/10
SG$113/nighttotal: SG$6328 (56 )

Modern Studio W-kitchen - Parking Near Appleby Go - 40 Min To Toronto

1 2
studio , Hamilton
This modern studio apartment in Burlington offers convenient access to Hamilton, being approximately 43 kilometres from BMO Field and Budweiser Stage, and 39 kilometres from the Mississauga Convention Centre.
This self-contained unit provides free private parking, complimentary Wi-Fi, and a fully equipped kitchen, accommodating up to three guests with air conditioning for comfort.
Spacious Oakville 5 Bedroom Home - Sleeps 10 - Free Parking + Pet Friendly - Oakville
Oakville
28/08 – 04/09
SG$629/nighttotal: SG$4403 (7 )

Spacious Oakville 5 Bedroom Home - Sleeps 10 - Free Parking + Pet Friendly

5 3
apartment , Milton
This five-bedroom Oakville apartment, situated near parks and shopping, offers easy highway access for exploring attractions such as Lake Ontario, Erindale Park, Joshua Creek Heritage Art Centre, and Glen Abbey Golf Course; distances to Milton require separate calculation via online mapping services.
The self-catering property sleeps ten guests and features a modern open-plan layout, a fully equipped kitchen, air conditioning, internet access, and pet-friendly accommodation.
©2026 cozycozy.com