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

Spacious & Lit Entire Suite With Full Kitchen - Oakville
9.8 44 reviews
Oakville
06/07 – 12/07
NZ$231/nighttotal: NZ$1386 (6 )

Spacious & Lit Entire Suite With Full Kitchen

1 2
apartment , Hamilton
This Burlington basement flat, a short drive from Appleby GO Station and approximately 19km from Hamilton, offers convenient access to Lake Ontario and downtown Burlington.
The self-contained apartment features a one-bedroom, one-bathroom layout sleeping up to three guests, complete with a kitchen (fridge, microwave), private washer/dryer, air conditioning, free parking, and self-serve entry via the garage; nearby amenities include a park with a splash pad.

Best Oakville Short term rentals with a jacuzzi

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

Whole House New Luxury Kitchen—5 Bedrooms 5 Baths - Oakville
10 1 review
Oakville
01/09 – 28/02
NZ$568/nighttotal: NZ$102240 (180 )

Whole House New Luxury Kitchen—5 Bedrooms 5 Baths

1 4
house , Milton
This recently renovated entire house is located in a residential area of Milton, offering easy access to local amenities and major routes.
This 5-bedroom, 5-bathroom accommodation sleeps up to 10 guests and features a brand-new kitchen, air conditioning, a Jacuzzi, and 5 dedicated parking spots.
Luxury Condo Stay That Feels Like Home - Oakville
10 2 reviews
Oakville
06/07 – 12/07
NZ$140/nighttotal: NZ$840 (6 )

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
10 135 reviews
Oakville
09/08 – 14/08
NZ$723/nighttotal: NZ$3615 (5 )

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.
Luxurious House With Pond View And Jacuzzi - Oakville
9.7 18 reviews
Oakville
04/07 – 10/07
NZ$830/nighttotal: NZ$4980 (6 )

Luxurious House With Pond View And Jacuzzi

1 8
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.

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

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.
2,800 Sq Ft Oakville Executive Home | 4br 4ba - Oakville
10 47 reviews
Oakville
01/09 – 30/09
NZ$525/nighttotal: NZ$15225 (29 )

2,800 Sq Ft Oakville Executive Home | 4br 4ba

1 4
apartment , Milton
This four-bedroom, three-bathroom house in Oakville, a short distance from Bronte Creek Provincial Park and the Oakville Centre for the Performing Arts, offers easy access to waterfront trails and Kerr Village.
The property sleeps eight guests and includes a gourmet kitchen, large laundry room with two professional-grade machines, a main-floor office convertible to a bedroom, parking for four cars (including a double garage), and a private garden.
2026 Fifa |40 Mins To Bmo Field |Oakville Go Train - Oakville
9.8 89 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.
Beautiful Contemporary 4 Bed Oakville House! - Oakville
9.1 9 reviews
Oakville
01/09 – 30/09
NZ$243/nighttotal: NZ$7047 (29 )

Beautiful Contemporary 4 Bed Oakville House!

1 4
apartment , Milton
This spacious Oakville house, a 4-bedroom, 3-bathroom dwelling, is conveniently located near Oakville's town centre and approximately 48 kilometres from Toronto Pearson International Airport.
The 2650 sq ft (246 sq m) property boasts an open-plan layout, sleeps six guests, and includes a fully equipped kitchen, garden, parking, and excellent internet access.

Best Oakville short term rentals with parking

Trafalgar - Oakville
9.0 5 reviews
Oakville
06/07 – 12/07
NZ$290/nighttotal: NZ$1740 (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.
Luxury 2br Suite | Private Entry |Oakville+parking - Oakville
9.6 10 reviews
Oakville
01/07 – 31/07
NZ$251/nighttotal: NZ$7530 (30 )

Luxury 2br Suite | Private Entry |Oakville+parking

2 3
B&B , Toronto
This private two-bedroom luxury suite is located in a quiet, upscale Oakville neighbourhood, offering swift access to major motorways, shopping centres, and dining establishments, situated approximately 29 kilometres southwest of downtown Toronto.
The self-contained accommodation sleeps up to five guests and features a spa-style bathroom, modern finishes, plush furnishings, fast Wi-Fi, and a smart TV, making it ideal for families or professionals seeking a comfortable and convenient stay with ample privacy.
Private Home : Kitchen-bath-laundry-gym-parking - Oakville
9.8 35 reviews
Oakville
01/09 – 30/09
NZ$134/nighttotal: NZ$3886 (29 )

Private Home : Kitchen-bath-laundry-gym-parking

1 1
apartment , Toronto
This basement flat is conveniently located just 1.5 kilometres from Sheridan College and White Oaks Secondary School, offering easy access to Superstore, Walmart, Tim Hortons, and bus stations. It has received excellent ratings for user experience, location, and cleanliness.
The flat comfortably accommodates two guests and features a separate entrance for complete privacy. The self-catering flat includes a fully equipped kitchen, laundry facilities, a dedicated exercise space, and free parking on the driveway. Multilingual services in English, Chinese, and Cantonese are available.
House In South Oakville - Close To Lake - Oakville
9.8 25 reviews
Oakville
28/08 – 04/09
NZ$974/nighttotal: NZ$6818 (7 )

House In South Oakville - Close To Lake

1 3
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.
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