Find short term rentals in Oakville at the best prices
531 available short term rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Short term and Weekly rentals in Oakville
9.9 40 reviews
Oakville
26/08 – 06/09
$206/nighttotal: $2266 (11 )
Beautifully Upgraded One Bedroom And Den + Balcony
1 2
apartment , Milton
This centrally located Milton apartment offers easy walking access to major attractions, though precise distances to specific landmarks are not provided. The one-bedroom flat, including a versatile den, comfortably sleeps four guests and boasts a modern interior with a fully equipped kitchen, private balcony, underground parking, and access to a fitness centre.
10 10 reviews
Oakville
01/08 – 31/10
$131/nighttotal: $11921 (91 )
Free Parking, Full Kitchen/bath, Wrkspc, Sep Ent
1 3
apartment , Toronto
This basement flat is located in a convenient area of Toronto, less than 1 kilometre from a grocery store, pharmacy, bakery, and restaurants, and just an hour's drive from Niagara Falls. The apartment is ideal for couples or solo travellers seeking a comfortable and affordable base for exploring the city. The property offers a well-equipped kitchen with a fridge and microwave, a dedicated workspace for remote working, a comfortable living area with a TV, books, and games, and a bedroom with a queen-size bed. Guests can also enjoy the convenience of a washing machine and dryer, air conditioning, and free Wi-Fi.
Oakville
01/07 – 31/10
$68/nighttotal: $8296 (122 )
Modern Oakville Escape 温馨小窝
1 2
apartment , Toronto
This one-bedroom flat is located in a residential district of Toronto, offering a peaceful base with easy access to the city's amenities. This spacious 360 sqm residence accommodates two guests, featuring a fully equipped kitchen, private bathroom, and access to a garden, with a private parking garage available.
9.0 6 reviews
Oakville
01/07 – 31/10
$285/nighttotal: $34770 (122 )
💧Lakeshore Villa💧waterfront•pool•sunroom•5000sqf
3 2
apartment , Toronto
This luxurious waterfront property is located in Oakville, a short 6.4km drive from Bronte Harbour, offering breathtaking Lake Ontario views. The three-bedroom, two-bathroom house boasts a gourmet kitchen, inground pool, walk-out basement with entertainment facilities, and accommodates up to 12 guests, with access to optional luxury services including private chefs and chauffeur service.
9.9 20 reviews
Oakville
28/12 – 31/12
$139/nighttotal: $417 (3 )
Charming & Smart Boutique Suite - Private Entrance
1 2
apartment , Milton
This private suite is located in a residential neighbourhood in Oakville, 1.6 kilometres from Oakville's Downtown Area, GO station, and lakeshore, and is situated across from a family-friendly park. This one-bedroom flat accommodates up to three guests and features a private backyard with a patio, a fenced yard, a main floor bedroom with a Queen bed and ensuite, a basement living room with a pull-out sofa bed, a kitchenette with a mini fridge and microwave, and a dedicated workstation.
10 1 review
Oakville
09/08 – 14/08
$452/nighttotal: $2260 (5 )
Lovely Home Top Location- Shopping & Lake
1 4
apartment , Toronto
This South Oakville bungalow, a short walk (approximately 1.6 km) from Lake Ontario and local shops, offers easy access to Oakville GO station and major highways for convenient travel to Toronto and beyond. The three-bedroom, one-bathroom property sleeps six, boasting a fully equipped kitchen with stainless steel appliances, a private fenced backyard with BBQ, two parking spaces, unlimited high-speed internet, and a 60" FireTV.
10 9 reviews
Oakville
01/09 – 28/02
$71/nighttotal: $12780 (180 )
Budget 2 Bedroom Basement In Oakville
1 4
B&B , Toronto
This Oakwood Airbnb, a basement flat in a renovated house, is situated in Toronto's Oakwood neighbourhood, approximately 3.2km from Lake Ontario's parks and beaches. The self-contained apartment sleeps five guests in two queen-sized beds, offering a private kitchenette with an electric stove, fridge, microwave, and a private bathroom, plus in-unit laundry and shared garden access.
9.5 4 reviews
Oakville
08/07 – 07/08
$348/nighttotal: $10440 (30 )
Charming House Near The Lake And Shopping Centre
4 4
apartment , Toronto
This four-bedroom, two-bathroom house is situated in the exclusive South Oakville neighbourhood, a short drive (distances unspecified) from Lake Ontario and offering easy access to Toronto via the Oakville GO Station. The property, suitable for up to eight guests, boasts a fully equipped kitchen, air conditioning, parking, internet access, and is pet-friendly; nearby attractions include Oakville's shops and restaurants, plus easy access to the Niagara region and Mississauga.
10 1 review
Oakville
06/07 – 12/07
$204/nighttotal: $1224 (6 )
Beautiful Condo In Oakville For Upto 4 People
1 2
apartment , Milton
This two-bedroom flat in Milton offers an unrivalled central location, providing immediate access to the town's main attractions and essential services, making it ideal for families exploring the area. This centrally located flat includes internet, a kitchen, air conditioning, a fitness centre, and parking, accommodating up to four guests and serving as a convenient base for discovering local landmarks and activities.
Oakville
09/08 – 14/08
$337/nighttotal: $1685 (5 )
Designer 4br Basement Suite – Oakville
4 4
apartment , Milton
This four-bedroom, two-bathroom flat in Oakville offers ample space for up to eight guests, featuring two full kitchens, a private gym, and keyless entry, with on-site parking and fast internet ideal for families or groups visiting Milton. Situated in a family-friendly neighbourhood, this property is conveniently located approximately 1.5 kilometers from the Milton Sports Centre and 3 kilometers from the historic Milton Town Hall, with easy access to local parks and shopping areas.
10 4 reviews
Oakville
01/07 – 01/10
$151/nighttotal: $13892 (92 )
Executive 1bd+den Suite|perfect For Extended Stay
1 1
apartment , Milton
This luxury one-bedroom plus den flat is located in Oakville, offering direct access to the 407, QEW/403, and 401 motorways, with the Oakville GO Station just 10 minutes away for a 30-minute commute to Toronto's Union Station. This family-friendly apartment includes a private balcony, a fully equipped kitchen with a Ninja blender and Keurig coffee machine, an indoor gym, a party room, an outside lounge with a barbecue area, and underground parking with EV charging, accommodating up to two guests.
Oakville
28/12 – 31/12
$238/nighttotal: $714 (3 )
Relaxing Home Base | Quiet Area & Cozy Living
1 2
apartment , Toronto
This flat is situated in Mississauga's Erin Mills Stadium district, a 4-minute drive from Oakville Entertainment Centrum and Erin Mills Town Centre, offering convenient access to shopping and entertainment venues. This one-bedroom flat accommodates up to four guests and features a fully equipped kitchen, in-suite laundry, Wi-Fi, and a dedicated workspace, with nearby attractions including the Bradley Museum and Riverwood Conservancy.
Best Oakville luxury short term rentals
9.8 44 reviews
Oakville
06/07 – 12/07
$188/nighttotal: $1128 (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
9.8 37 reviews
Oakville
05/07 – 12/07
$612/nighttotal: $4284 (7 )
Luxury Oakville Home, Hot Tub, Fireplace (Upper)
1 10
apartment , Milton
This Oakville house, near quality restaurants and parks, is under 48km from Pearson Airport and 53km from Toronto city centre. The four-bedroom, three-bathroom property sleeps ten, boasting a fully equipped kitchen, jacuzzi, garden, and parking; summer BBQs are possible using the grill.
Oakville
10/07 – 15/07
$158/nighttotal: $790 (5 )
Walk To The Lake Park, 30min Train To Fifa
2 2
apartment , Toronto
This two-bedroom flat is located in a prosperous lakeside neighbourhood, offering a 30-minute commute by train to central Toronto and the FIFA grounds, with restaurants and groceries within walking distance. This property features a post-modern industrial interior with high ceilings, air conditioning, a Jacuzzi, a garden with BBQ facilities, a Mac, and an electric piano, accommodating up to four guests.
10 1 review
Oakville
27/06 – 04/07
$112/nighttotal: $784 (7 )
Warm Family Home Filled With Love And Comfort.
1 1
apartment , Hamilton
This one-bedroom flat is located in a friendly Hamilton neighbourhood, providing straightforward access to local conveniences and green areas, with parks and community centres a short distance away. The accommodation offers a comfortable stay with a kitchen, air conditioning, a jacuzzi, and parking, ensuring a memorable experience beyond just accommodation with its serene garden and inviting atmosphere.
10 2 reviews
Oakville
28/12 – 31/12
$117/nighttotal: $351 (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.
Frequently Asked Questions about short term rentals in Oakville
Which top landmarks you shouldn't miss in Oakville?
Oakville has some lovely landmarks. You've got to see the Oakville Harbour, it's beautiful, especially in the summer. Then there's the Oakville Museum, which is great for learning about the town's history. And you can't miss the Oakville Centre for the Performing Arts, it's a stunning building and they put on some great shows.
What kind of weather can travelers expect in Oakville?
Oakville has a humid continental climate, which means you can expect hot summers, with temperatures reaching around 25°C, and cold winters with temperatures dropping to around -5°C. It can get pretty snowy in the winter, so pack accordingly!
What are the best short term rentals with a pool in Oakville?
What are the most popular festivals and events in Oakville?
Oakville has a great events calendar. The Oakville Jazz Festival is a big one, happening every July. The Oakville Fall Fair is another popular event, with lots of fun for all ages. And don't forget the Oakville Christmas Market, it's lovely in December with lots of festive cheer.
What are the best short term rentals with a jacuzzi in Oakville?
There are some lovely natural spots near Oakville. The most famous is probably the Bronte Creek Provincial Park, which is a great spot for hiking and exploring nature. You could also head to the Rattlesnake Point Conservation Area, which offers some incredible views of the Niagara Escarpment.
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 really depends on what you're looking for. If you want to be close to the lake and the action, then the downtown area is a good choice. But if you're looking for something quieter, then the Old Oakville area is lovely, with lots of charming bed and breakfasts.
Destinations nearby
Best family friendly Oakville Short term rentals
Among the 531 accommodations in Oakville, here are the 4 best family friendly rentals
9.9 15 reviews
Oakville
23/07 – 14/09
$104/nighttotal: $5512 (53 )
The Refined Oak-cozy Lower Retreat Room 2
1 2
apartment , Milton
This Oakville guesthouse is conveniently located near Oakville GO station, Oakville Trafalgar Hospital, and the Highway 403, approximately 24km from Pearson Airport and 16km from Sheridan College. Offering one ensuite bedroom with a queen-sized bed, this self-catering property sleeps two guests and includes free Wi-Fi, parking, and a shared kitchenette with a fridge and microwave.
Oakville
09/08 – 14/08
$450/nighttotal: $2250 (5 )
Stylish Garden Home | 4 Br | Mississauga | Parking
1 4
apartment , Toronto
This four-bedroom, three-bathroom flat in Clarkson offers convenient access to downtown Toronto, being just a short distance from the Clarkson GO Train station for swift journeys and within easy reach of BMO Field and venues for Toronto Blue Jays games. This family-friendly residence accommodates up to seven guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, and a garden, providing a comfortable base for exploring Toronto's attractions, enjoying day trips to Niagara Falls, or relaxing at Jack Darling Park.
9.6 14 reviews
Oakville
01/07 – 31/07
$94/nighttotal: $2820 (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.
9.3 48 reviews
Oakville
10/07 – 15/07
$437/nighttotal: $2185 (5 )
Your Perfect Getaway Home
1 2
apartment , Toronto
This Oakville house, ideally located near the Queen Elizabeth Way highway, offers easy access to downtown Oakville, local parks, and Lake Ontario. The three-bedroom property sleeps eight, boasting a well-equipped kitchen, a solarium, a large garden with patio furniture and barbecue, and ample parking; nearby attractions include numerous parks and the lake.
Best Oakville lodging with parking
9.8 27 reviews
Oakville
31/07 – 02/08
$220/nighttotal: $440 (2 )
Cozy Parkview Suite In Oakville
1 2
B&B , Toronto
This private basement suite in Toronto offers a peaceful retreat near a commercial area, a 10-minute walk (1.6km) from banks, Walmart, restaurants and Starbucks. The self-contained apartment, sleeping two guests, features a bedroom, living room, kitchen, bathroom, office area, laundry facilities, and provides disposable amenities; enjoy park views from its private backyard entrance.
Oakville
08/07 – 07/08
$321/nighttotal: $9630 (30 )
Modern 3br Home With Office And Parking And Wifi
1 4
apartment , Toronto
This modern 3-bedroom house is situated in a quiet, family-friendly neighbourhood in Oakville, a short 3-kilometre drive from Lake Ontario and major highways for convenient access to the Greater Toronto Area. This residence offers ample parking for four cars, high-speed Wi-Fi, in-home laundry, and a 65-inch Smart TV with Roku, comfortably accommodating up to six guests with easy access to Oakville Place Shopping Centre and nearby walking trails.
9.6 10 reviews
Oakville
01/07 – 31/07
$204/nighttotal: $6120 (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.
10 1 review
Oakville
26/08 – 06/09
$356/nighttotal: $3916 (11 )
Stylish 2-bed Oakville Home With Free Parking + Wifi
2 2
apartment , Milton
This self-contained side unit in Oakville, located 1.5 kilometres from Lake Ontario and 2.1 kilometres from Bronte Creek Provincial Park, offers convenient access to amenities and natural attractions for those visiting Milton. This two-bedroom flat accommodates up to four guests and features a fully equipped kitchen, in-unit laundry, air conditioning, and dedicated parking, with an office area suitable for business travellers.