Find short term rentals in Oakville at the best prices

720 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

Our Lakefront Shared Room - Oakville
10 1 review

Our Lakefront Shared Room

apartment, Toronto
This flat is located in the Bronte district, directly opposite the lake and next to Bronte Creek Provincial Park, with Bronte Harbour and its pier a short walk away.
This pet-friendly apartment accommodates two guests and features a kitchen with a fridge, freezer, microwave, and dishwasher, alongside a fitness centre and garden, with Bronte Creek Provincial Park offering outdoor activities and sunrise views over the lake from the beach.

Best Oakville Short term rentals with a jacuzzi

Among the 720 accommodations in Oakville, here are the 4 best rentals with a jacuzzi

Oakville Premium 3br | Pool, Gym & Parking - Oakville
No reviews

Oakville Premium 3br | Pool, Gym & Parking

apartment, Toronto
This furnished executive townhome is situated in a sought-after Oakville community, offering convenient walking access to local amenities and quick access to major highways including the QEW, 403, and 407, facilitating travel across the Greater Toronto Area.
This spacious 3-bedroom, 2-bathroom property accommodates up to 6 guests, featuring a double garage, access to a swimming pool and fitness centre, and is ideally positioned for exploring Oakville and commuting to Toronto.
Whimsical House On Watson In South Oakville! - Oakville
No reviews

Whimsical House On Watson In South Oakville!

apartment, Toronto
This three-bedroom, three-bathroom apartment is situated in a quiet residential area of South Oakville, approximately 30-40km west of Toronto, offering easy access to the major highways leading to Toronto Pearson International Airport.
The spacious property boasts two fully equipped kitchens, two washer/dryer sets, a jacuzzi, parking, and comfortably accommodates six guests, ideal for families or groups visiting Toronto.
Cottage Style House With Hot Tub - Oakville
9.9 32 reviews

Cottage Style House With Hot Tub

cottage, Toronto
This five-bedroom Oakville apartment, seven minutes (approximately 11.3 kilometres) from downtown Oakville and Lake Ontario, offers easy access to Toronto attractions.
Sleeping up to twelve guests, this spacious property boasts a fully equipped kitchen, three large smart TVs, a private garden with hot tub, and free parking, making it ideal for families or large groups visiting the Toronto area.
Brand New Luxury 2 Bedroom Oakville Townhouse With King Bed! - Oakville
No reviews

Brand New Luxury 2 Bedroom Oakville Townhouse With King Bed!

apartment, Milton
This two-bedroom townhouse is situated in North Oakville, just 15 minutes by train from Milton's historic downtown. It's a convenient location with easy access to the GO station, major highways, and local amenities.
The property offers ample space for up to four guests, and features a modern design with engineered hardwood floors and stainless steel appliances. Enjoy the outdoor space on one of the two private patios, and take advantage of the in-suite laundry, master bedroom with ensuite bathroom, and a fully equipped kitchen with a fridge, microwave, and dishwasher.

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 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 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?

    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?

    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.

Popular destinations

Best family friendly Oakville Short term rentals

Among the 720 accommodations in Oakville, here are the 4 best family friendly rentals

Lovely Home Top Location- Shopping & Lake - Oakville
10 1 review

Lovely Home Top Location- Shopping & Lake

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.
Free Parking, Full Kitchen/bath, Wrkspc, Sep Ent - Oakville
9.8 12 reviews

Free Parking, Full Kitchen/bath, Wrkspc, Sep Ent

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.
Luxury Executive Studio - Oakville
10 7 reviews

Luxury Executive Studio

studio, Toronto
This Oakville luxury apartment is situated approximately 40-45 kilometres west of Toronto's major attractions, including the CN Tower, Rogers Centre, and Exhibition Place, offering a peaceful retreat whilst remaining easily accessible by car.
The 93 square metre self-catering studio sleeps three, boasting a fully equipped kitchen with dishwasher and oven, air conditioning, free Wi-Fi, on-site parking, and access to a tennis court and water park.
Spacious And Luxurious 2br Suite With Huge Windows - Oakville
10 1 review

Spacious And Luxurious 2br Suite With Huge Windows

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.

Best Oakville lodging with parking

South Oakville Bliss Haven - Oakville
9.7 43 reviews

South Oakville Bliss Haven

apartment, Toronto
This Toronto family-friendly house, sleeping six across three bedrooms and two bathrooms, offers a tranquil garden and parking, along with excellent guest ratings for cleanliness and location.
The property boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, internet access, and is ideally situated for exploring Toronto's attractions, although precise location and distances to landmarks remain unspecified.
Lovely House Fully Equipped Lake & Shopping - Oakville
No reviews

Lovely House Fully Equipped Lake & Shopping

apartment, Toronto
This 3-bedroom bungalow in prime South Oakville offers convenient access to Lake Ontario and the Oakville GO station, with commutes to downtown Toronto taking approximately 30-40 minutes.
This property accommodates up to six guests and features a fully equipped kitchen, a fenced garden with outdoor dining, unlimited high-speed internet, and two driveway parking spaces, with optional cleaning services available.
4bed-luxury Home, Pool Table, Backyard, Sleeps 12 - Oakville
9.6 5 reviews

4bed-luxury Home, Pool Table, Backyard, Sleeps 12

apartment, Milton
This modern 4-bedroom house is located in a quiet subdivision in Oakville, 40 kilometres from the airport, offering a family-friendly base for those visiting Milton.
This spacious residence sleeps up to 12 guests, featuring a fully equipped kitchen with a dishwasher, air conditioning, a garden, and parking for up to four vehicles, with a game area for entertainment.
The Oakville Comfort And Modern Stay - Oakville
9.6 29 reviews

The Oakville Comfort And Modern Stay

apartment, Toronto
This three-bedroom house in Oakville offers a peaceful, family-friendly base, located a 5-minute drive from Oakville GO station for convenient travel to Toronto, and is also within easy reach of major highways including the QEW, 403, and 407.
This fully renovated dwelling accommodates up to four guests and features a private workstation and an EV charger, with a children's park situated directly in front of the property and the shores of Lake Ontario a short distance away.
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