This spacious Milton basement flat is conveniently located near a grocery store, medical clinic, and bus stop, offering easy access to Toronto Pearson International Airport (within a short driving distance). The 139 square metre self-contained property sleeps four, boasting two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, and parking; an additional bedroom is available on request.
10 2 reviews
Oakville
23/06 – 25/06
SG$105/nighttotal: SG$210 (2 )
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.
9.6 14 reviews
Oakville
21/06 – 21/08
SG$76/nighttotal: SG$4636 (61 )
Cozy Resort-like Stay With Pool
1 1
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.
9.9 20 reviews
Oakville
28/12 – 31/12
SG$128/nighttotal: SG$384 (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.
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.
Oakville
23/07 – 14/09
SG$374/nighttotal: SG$19822 (53 )
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.
Oakville
01/07 – 31/07
SG$263/nighttotal: SG$7890 (30 )
Four-seasons Serenity In The Heart Of Oakville Close To Lake Ontario
3 3
apartment , Toronto
This West Oakville property, a short drive (under 16km depending on traffic) from Toronto's attractions, is situated within 3km of the Oakville Art Society, Coronation Park, Bronte Heritage Park, Lake Ontario, and Bronte Harbour, and a 20-minute walk from Bronte station. The three-bedroom, one-bathroom house sleeps six, offering self-catering facilities including a washing machine, kitchen, and in-house amenities, and is ideal for exploring West Oakville's parks and the nearby Lake Ontario.
10 21 reviews
Oakville
23/06 – 25/06
SG$174/nighttotal: SG$348 (2 )
Modern And Comfortable Basement Suite
1 2
apartment , Toronto
This self-contained two-bedroom basement flat in Toronto offers a private entrance and is conveniently located within walking distance of numerous shopping centres and a wide array of restaurants, making it an ideal base for families, couples, and business travellers. The accommodation is equipped with air conditioning, Wi-Fi, private laundry facilities, and off-street parking, comfortably accommodating up to four guests with one bathroom.
Oakville
01/08 – 30/09
SG$110/nighttotal: SG$6600 (60 )
Bright Modern 2br Suite | Kerr Village, Walk To Go
1 4
apartment , Toronto
This private two-bedroom flat is located in Kerr Village, a 15-minute walk or 3-minute bus journey from Oakville GO Train station, offering a 30-40 minute commute to Downtown Toronto, and is steps from Kerr Village amenities, Downtown Oakville, and Lake Ontario. This self-catering apartment accommodates up to four guests and features a fully equipped kitchen with brand new appliances, in-suite laundry, a Smart TV, fast internet, and ample parking, with pets welcome.
8.8 17 reviews
Oakville
08/07 – 07/08
SG$248/nighttotal: SG$7440 (30 )
Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville
3 4
apartment , Milton
This 3-bedroom townhouse is located in Oakville, just 27 kilometres from Mississauga Convention Centre and Toronto Pearson International Airport, and 37 kilometres from BMO Field and Budweiser Stage. The property enjoys excellent location and cleanliness ratings, with guests consistently praising its comfort and convenience. The townhouse offers 172 square metres of space, comfortably accommodating up to 6 guests. A fully equipped kitchen, private terrace, air conditioning, free Wi-Fi, satellite TV, and parking are all provided for your enjoyment.
9.9 86 reviews
Oakville
31/07 – 31/08
SG$403/nighttotal: SG$12493 (31 )
Modern-4 Car-king Bed-ping Pong-bbq-403/407/qew
1 1
apartment , Toronto
This luxurious townhouse is located in the family-friendly Joshua Creek neighbourhood in Oakville, just a short drive from major highways and attractions like Bronte GO station, Lake Ontario and downtown Oakville. The property has received excellent ratings for location, cleanliness and user experience. The spacious three-bedroom townhouse can accommodate up to nine guests and features a dedicated office room and two workspaces. Guests can enjoy high-speed internet, two smart TVs with unlimited Netflix, a fully equipped kitchen, a ping pong table, a backyard with outdoor dining furniture, a BBQ, two garage parking spaces and two driveway parking spaces.
9.9 17 reviews
Oakville
06/07 – 06/08
SG$81/nighttotal: SG$2511 (31 )
009c Sunny View Room Ensuite Bathroom Kingsize Bed
1 1
house , Milton
This luxurious guest house is situated in Mississauga, near the Trafalgar/Dundas intersection, approximately 25 minutes' drive (40km) from Toronto Pearson International Airport and offering easy access to the 403, 407 and other major highways. The 4000 sq ft property features a fully equipped kitchen with Jenn-Air appliances, a large private bedroom with en-suite bathroom and walk-in wardrobe, accommodating two guests, and benefits from proximity to a community park with various recreational facilities; long-stay discounts apply.
Best Oakville luxury short term rentals
10 3 reviews
Oakville
01/09 – 28/02
SG$126/nighttotal: SG$22680 (180 )
Brand New Stylish 2br Condo In Oakville
1 4
apartment , Milton
This modern 2-bedroom, 2-bathroom flat is located at Dundas & Trafalgar in Oakville, providing easy access to Sixteen Mile Creek, Lake Ontario, beaches, and over 300 kilometers of nature trails. This stylish apartment offers accommodation for up to 4 guests, featuring an open-concept living space, a chef-inspired kitchen with quartz countertops, in-suite laundry, high-speed Wi-Fi, and one complimentary underground parking spot, all ideal for exploring the surrounding outdoor recreational opportunities.
Best Oakville Short term rentals with a jacuzzi
Among the 531 accommodations in Oakville, here are the 4 best rentals with a jacuzzi
9.5 4 reviews
Oakville
31/07 – 31/08
SG$181/nighttotal: SG$5611 (31 )
Brand New Condo-bed+sofa Bed Bright Unit+parking
1 1
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.
10 133 reviews
Oakville
01/07 – 31/07
SG$464/nighttotal: SG$13920 (30 )
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
01/08 – 30/09
SG$510/nighttotal: SG$30600 (60 )
Luxurious House With Pond View And Jacuzzi
1 4
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.
Oakville
04/07 – 10/07
SG$333/nighttotal: SG$1998 (6 )
Hot Tub Oasis · Park Backyard · Near Lake
1 8
apartment , Toronto
This spacious four-bedroom flat, ideal for up to ten guests, is located in a peaceful residential area between Toronto and Niagara Falls, just a short walk from Lake Ontario. Guests can enjoy a private hot tub in the park-like garden, a secondary kitchen in the walkout suite, and exterior security cameras for added safety.
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 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?
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 4 best family friendly rentals
9.0 2 reviews
Oakville
26/08 – 06/09
SG$256/nighttotal: SG$2816 (11 )
Spacious Basement In Oakville
2 2
apartment , Toronto
This spacious Oakville basement flat, approximately 26-35 km from Toronto attractions such as the CN Tower and Rogers Centre, offers a peaceful alternative to the city centre. The 79 square metre, two-bedroom property sleeps seven, includes a fully equipped kitchen with dishwasher, free Wi-Fi, private parking, and a washing machine; Toronto Pearson International Airport is 27 km away.
Oakville
01/08 – 31/10
SG$272/nighttotal: SG$24752 (91 )
Spacious, Bright 4-bed Modern Home In Oakville - Prime Location
4 3
apartment , Toronto
This four-bedroom, three-bathroom flat in Oakville offers proximity to Lake Ontario (a 10-minute drive), Lions Valley Park (a 8-minute drive), Oakville Centre for the Performing Arts (an 8-minute drive), and Glen Abbey Golf Club (a 6-minute drive), making it ideal for exploring the surrounding areas. With a guest capacity of eight, this residence features an on-site laundry facility and is conveniently situated for access to shopping centres like Square One and local amenities.
9.1 13 reviews
Oakville
01/07 – 31/07
SG$261/nighttotal: SG$7830 (30 )
4br Luxury Close To Lake, 30 Mins Toronto/niagara
1 3
apartment , Toronto
This luxurious bungalow is located in a prestigious neighbourhood in the Greater Toronto Area, just a short drive from Lake Ontario and within easy reach of both Toronto and Niagara Falls, making it an ideal base for exploring the region. The spacious property boasts three bedrooms, three bathrooms, and a large recreation room with a wet bar, comfortably accommodating up to ten guests and offering plenty of space for family gatherings.
9.9 29 reviews
Oakville
10/07 – 15/07
SG$403/nighttotal: SG$2015 (5 )
Lux 4br 3ba Home • Sunset Views & Ultimate Comfort
4 2
apartment , Toronto
This spacious detached house is located in a quiet Oakville neighbourhood, approximately 8 kilometres from Oakville Place, dining options, and Sheridan College, with the Oakville GO Station for Toronto commutes also around 8 kilometres away. Offering accommodation for up to 7 guests, this comfortable property features 3 bedrooms, 2 bathrooms, air conditioning, and includes a kitchen equipped with a fridge, freezer, microwave oven, and dishwasher, alongside on-site parking.
Best Oakville short term rentals with parking
9.3 8 reviews
Oakville
01/08 – 30/09
SG$155/nighttotal: SG$9300 (60 )
Serene Retreat - Cozy + Private!
1 4
apartment , Toronto
This Toronto apartment, located on Grand Oak, offers a private lower-level unit with parking, ideal for exploring the city's attractions; the precise distance to landmarks requires further clarification. The two-bedroom, one-bathroom flat sleeps five guests and features a fully equipped kitchen, air conditioning, and exclusive outdoor access.
9.9 76 reviews
Oakville
06/07 – 12/07
SG$297/nighttotal: SG$1782 (6 )
Contemporary, Quite Two Bedroom Home !
2 2
apartment , Toronto
This two-bedroom flat is located in Mississauga, just 4 kilometres from Oakville and easily accessible via the 403 Highway and public transport. The property has received excellent ratings for its cleanliness, location, and overall experience. The flat is ideal for families or groups of up to four people, offering a comfortable living space with a fully equipped kitchen, a spacious living area, and two modern bathrooms. Guests can enjoy a range of amenities including air conditioning, a washing machine and dryer, and a garden, making it a convenient and enjoyable base for exploring Toronto.
9.4 3 reviews
Oakville
01/07 – 05/07
SG$329/nighttotal: SG$1316 (4 )
Cozy 2-bedroom Apartment With Wifi, Separate Entrance And Parking
2 3
apartment , Toronto
This Mississauga apartment, situated in the Erin Mills neighbourhood, is 5 minutes from Erin Mills Town Centre, 10 minutes from the University of Toronto Mississauga and Square One Shopping Centre, and an 18-minute drive from Toronto Pearson International Airport. The 74-square-metre (800 sq ft) property sleeps up to five guests in two queen beds and a sofa bed, and includes WiFi, a fully equipped kitchen with dishwasher, a washing machine, air conditioning, parking, and is close to various attractions including Putting Edge and iFLY Toronto Oakville.
Oakville
01/08 – 30/09
SG$96/nighttotal: SG$5760 (60 )
Serene High-celling Retreat In Upsacle And Safe Neighbourhood
2 4
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.