Oakville 2br: Central, Comfy & Close To Everything
1 2
apartment , Toronto
This Oakville apartment, ideally situated near the Walmart Superstore, Shoppers Drug Mart, Oakville Place shopping centre, and Toronto Premium Outlets, offers easy access to major highways, public transport, and the train station. The two-bedroom, one-bathroom flat sleeps six guests and boasts a modern design, including a fully equipped kitchen with dishwasher, air conditioning, a garden, fitness centre, and parking; day trips to Toronto are easily facilitated by its excellent transport links.
Oakville
28/08 – 16/09
NZ$369/nighttotal: NZ$7011 (19 )
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.
This charming bed and breakfast is situated in the peaceful West Oak Trails neighbourhood of Oakville, a short drive from Toronto, offering easy access to the city's attractions. The property has consistently received excellent ratings for its cleanliness, location, and overall guest experience. The basement apartment provides complete privacy for up to four guests, with a separate entrance and dedicated parking. Amenities include a comfortable living area with a queen bed, a pull-out couch, a small kitchenette, a mini-library, and a TV, ensuring a relaxing and enjoyable stay.
10 4 reviews
Oakville
01/09 – 28/02
NZ$146/nighttotal: NZ$26280 (180 )
Modern Luxury Condo In North Oakville!
1 4
apartment , Milton
This North Oakville flat offers convenient access to Oakville Trafalgar High School, Sixteen Mile Sports Complex, Sheridan College (a 7-minute drive), and the UTM Campus (a 15-minute drive). This stylish one-bedroom plus den apartment, equipped with air conditioning, parking, and a kitchen featuring a fridge, microwave, and dishwasher, can accommodate up to five guests and boasts an open-concept design.
10 3 reviews
Oakville
09/08 – 14/08
NZ$209/nighttotal: NZ$1045 (5 )
Separate Walk-up Basement Apartment Oakville
1 4
apartment , Hamilton
This private basement flat in a tranquil Oakville residential area provides straightforward access to main motorways and parks, situated approximately 72 kilometres from downtown Toronto and 160 kilometres from Niagara Falls. This self-contained dwelling offers two bedrooms and space for four guests, featuring a full kitchen with a fridge, freezer, microwave, and dishwasher, as well as air conditioning, Wi-Fi, and on-site laundry facilities available upon request.
8.0 1 review
Oakville
27/06 – 04/07
NZ$326/nighttotal: NZ$2282 (7 )
Cozy Getaway In Mississauga
1 2
apartment , Toronto
This Mississauga flat, located in Clarkson, offers direct access to Clarkson GO Station, facilitating a 30-minute rail journey to Toronto, with Erin Mills Mall and Lakeside within a 7-minute and 15-minute drive respectively. This two-bedroom apartment accommodates up to six guests, featuring a fully equipped kitchen with modern appliances, in-house laundry, two parking spaces, and a Smart TV, ideal for exploring the Greater Toronto Area.
9.9 91 reviews
Oakville
01/07 – 01/10
NZ$73/nighttotal: NZ$6716 (92 )
Relax & Work: Spacious Queen Room On First Floor
1 1
apartment , Toronto
This charming bed and breakfast is located in a friendly neighbourhood in Toronto, just a short walk from open malls, restaurants like Scaddabush and Cafe Demetre, and attractions such as iFLY and bowling alleys. The property has consistently received excellent ratings for its cleanliness, location, and user experience. The guesthouse has one bedroom and one bathroom, accommodating one guest. Guests can enjoy a fully equipped kitchen, a shared living room, a garden, and a welcome kit including masks, hand sanitizer, and a hairdryer.
10 1 review
Oakville
28/12 – 31/12
NZ$661/nighttotal: NZ$1983 (3 )
Welcome To Your Comfort Retreat By The Lake
1 2
apartment , Toronto
This Burlington residence, located approximately 40 kilometres from the Mississauga Convention Centre and 45 kilometres from Toronto's BMO Field and Budweiser Stage, offers convenient access to the lakefront. This spacious 300 square metre flat accommodates up to 15 guests, featuring four bathrooms, air conditioning, a well-equipped kitchen, complimentary Wi-Fi, and private parking, with a private swimming pool available for use.
Oakville
01/07 – 31/10
NZ$84/nighttotal: NZ$10248 (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.
Oakville
27/06 – 04/07
NZ$227/nighttotal: NZ$1589 (7 )
Welcome To This Brand-new, Fully Detached House
1 2
apartment , Toronto
This detached dwelling in Toronto offers complete privacy with no shared walls, featuring dedicated private bedrooms, bathrooms, and a kitchen, plus free street parking. This exclusive Toronto residence accommodates two guests, providing a peaceful and organised environment with convenient access to local amenities and attractions.
Oakville
01/09 – 28/02
NZ$161/nighttotal: NZ$28980 (180 )
Serene 2-bedroom Basement Apartment With Ac In Oakville
2 4
apartment , Milton
This Oakville flat, near Lake Ontario and Bronte Creek Provincial Park (approximately 16km from each), offers easy access to Milton and its surrounding attractions, including Square One Shopping Centre (22km away). The two-bedroom, one-bathroom property sleeps four guests and includes Wi-Fi, air conditioning, and essential amenities; nearby activities include Glen Abbey Golf Course (13km) and Putting Edge mini golf.
Oakville
01/07 – 01/10
NZ$49/nighttotal: NZ$4508 (92 )
Private Room In Clarkson 1
1 1
apartment , Toronto
This one-bedroom flat in Toronto offers convenient access to transport links, with a bus stop directly outside and Clarkson GO Station a short walk away, facilitating travel across the city and to Pearson Airport, which is 32 kilometres distant. This basement flat provides a comfortable queen bed, a dedicated workspace with a charging station, high-speed WiFi, and is situated 200 metres from Food Basics for grocery shopping, making it ideal for solo travellers or couples.
Best Oakville luxury short term rentals
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
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.
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.
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.
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 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?
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?
Among the 531 accommodations in Oakville, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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.
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.
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.