Oakville Short term rentals

720 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Oakville short term rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Oakville

Discover Central Short-Term Rentals in Oakville

Find yourself moments from popular independent bistros and transit links at central short-term rentals in Oakville.

Modern 1 Bdr Suite | Sleep 4 | Pvt Entry | Near Go - Oakville
9.8 11 reviews

Modern 1 Bdr Suite | Sleep 4 | Pvt Entry | Near Go

apartment, Toronto
This newly renovated one-bedroom flat is situated in a quiet Oakville neighbourhood, offering excellent connectivity to the Oakville GO Station for straightforward journeys into Toronto, and is conveniently positioned near major routes like the QEW and 403, as well as local amenities such as Oakville Mall and various restaurants.
This family-friendly apartment provides private entrance, a dedicated workspace with Wi-Fi, soundproofing, a full kitchen with cooking range and microwave, an in-suite washer and dryer, a smart TV with fireplace, and a Bose music system, accommodating up to five guests.
Modern Luxe Home | 2br | Balcony | Parking - Oakville
10 9 reviews

Modern Luxe Home | 2br | Balcony | Parking

apartment, Toronto
This Oakville flat provides convenient access to Toronto, situated approximately 30 kilometres southwest of the city centre, with local shops and restaurants within 500 metres.
This two-bedroom apartment accommodates up to four guests, featuring a modern kitchen with a dishwasher, in-unit laundry, high-speed Wi-Fi, air conditioning, and a private balcony, with parking available.
Mainfloor Unit, 3 Beds,2 Bath, 2parking,1 Laundry - Oakville
10 1 review

Mainfloor Unit, 3 Beds,2 Bath, 2parking,1 Laundry

apartment, Toronto
This Toronto flat is located in a quiet district, offering a peaceful base with easy access to the city's attractions.
This accommodation for 8 guests features 3 bathrooms, air conditioning, and a kitchen, with internet provided, making it suitable for family stays.
Pool Retreat In Oakville - Oakville
9.5 136 reviews

Pool Retreat In Oakville

apartment, Toronto
This four-bedroom house is situated in Oakville, a prestigious suburb of Toronto, just 3 kilometres from the highway and a short walk from the Kerr Village with its fine dining options. The property has received excellent ratings for its cleanliness, location, and overall experience.
The house can comfortably accommodate up to nine guests and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher. Guests can enjoy a private garden, a swimming pool, and parking, as well as a dedicated home office space.

Best Family-Friendly Holiday Rentals in Oakville

Family stays in Oakville work best when there is space and city attractions within easy reach.

Luxury Executive Studio - Oakville
No reviews

Luxury Executive Studio

B&B, Toronto
B&B rental. Your accommodation will be based in Toronto.
Services and facilities include an iron, a dish washer and a kitchen. Take advantage of the Free Parking with this accommodation.
Large 2bdrm Bsmt Apt, Furnished, Laundry, Kitchen - Oakville
10 12 reviews

Large 2bdrm Bsmt Apt, Furnished, Laundry, Kitchen

B&B, Toronto
This two-bedroom basement flat is located in the peaceful Clearview neighbourhood of Oakville, a 48-kilometre drive from Toronto city centre and a 35-kilometre drive from Toronto Pearson International Airport. The self-contained flat boasts a private entrance, kitchen, bathroom, and laundry facilities, providing a comfortable base for a family of four, with a private garden, patio, and a gas BBQ grill.
Serene Oakville Retreat - Modern 2-bedroom Apartment - Oakville
No reviews

Serene Oakville Retreat - Modern 2-bedroom Apartment

apartment, Milton
This two-bedroom flat is situated in Halton, offering convenient access to Oakville (32 kilometres), Mississauga (32 kilometres), and Toronto (56-77 kilometres), with a GO Station a mere 7-minute drive away.
This family-friendly apartment, accommodating up to four guests, boasts a fully equipped kitchen, air conditioning, a jacuzzi, and private parking, and is located within a 15-minute drive of Oakville Place, Toronto Premium Outlet, and Erin Mills Town Centre.
Feel At Home - Oakville
9.8 35 reviews

Feel At Home

apartment, Milton
This family-friendly, two-bedroom basement flat is situated in the Joshua Creek area of Oakville, approximately 6.4km from Oakville GO station, providing easy access to Toronto.
The 2-bedroom, 1-bathroom self-catering property sleeps up to 5 guests and features a well-equipped kitchen, high-speed Wi-Fi, driveway parking, and is close to Oakville Place shopping mall, Longo's and Metro supermarkets.

Frequently asked questions about short term rentals in Oakville

  • What kind of weather can travelers expect in Oakville?

    Oakville has a humid continental climate, so you can expect warm summers and cold winters. The best time to visit is during the spring or fall, when the weather is mild and pleasant. Summer can get quite hot and humid, while winter can be very cold and snowy.
  • 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.

  • Are there any famous stadiums or sports arenas in Oakville?

    Oakville doesn't have any major stadiums or arenas. However, you can find several smaller sports facilities, including the Oakville Soccer Club and the Oakville Tennis Club.
  • What are the best short term rentals with a pool in Oakville?

  • What notable natural landmarks are near Oakville?

    Oakville is surrounded by some beautiful natural landmarks! The most notable is the Niagara Escarpment, a UNESCO World Biosphere Reserve. You can also visit the nearby Bronte Creek Provincial Park, a lovely natural area with trails and historic buildings.
  • 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 part of Oakville is ideal for finding lodging?

    The best place to stay in Oakville is probably the downtown area, near the waterfront. You'll find plenty of hotels, restaurants, and shops within walking distance. If you're looking for something more budget-friendly, you could consider staying in the north end of town, near the Oakville GO Station.
  • What are the best short term rentals for families and kids in Oakville?

Popular destinations

Browse Holiday Lets with a Jacuzzi in Oakville

Coming back to a hot tub after a day in Oakville changes the whole feel of a stay. Every option here features one.

Spacious House With Pond View And Jacuuzi - Oakville
10 1 review

Spacious House With Pond View And Jacuuzi

apartment, Toronto
This four-bedroom, three-bathroom flat is located in Joshua Creek, Oakville, offering convenient access to major motorways (403, 407, QEW) and a brief drive to local amenities, approximately 25 kilometres west of downtown Toronto.
This spacious accommodation accommodates up to ten guests, featuring a gourmet kitchen with stainless steel KitchenAid appliances, a private patio with a hot Jacuzzi and BBQ, a laundry room with an LG washer and dryer, and parking for four vehicles, including a two-car garage.
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.
Modern Executive Townhome W/ Rooftop Hot Tub Oasis - Oakville
10 140 reviews

Modern Executive Townhome W/ Rooftop Hot Tub Oasis

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.
The Serenity Home Pool/yoga/game Room By The Lake - Oakville
9.8 46 reviews

The Serenity Home Pool/yoga/game Room By The Lake

apartment, Toronto
This apartment is located in Mississauga, just 5 kilometres from Lake Ontario and 30 kilometres from Toronto city centre, offering a peaceful retreat with easy access to the city's attractions. The apartment has consistently received excellent ratings for its cleanliness, location, and overall user experience.
This comfortable dwelling features four bedrooms and four bathrooms, comfortably accommodating up to eight guests. Amenities include a swimming pool, a fitness centre, a garden, parking, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay for families and groups.

Best Oakville luxury short term rentals

Modern Walk-out Lower Level Unit W/separate Den - Oakville
9.9 24 reviews

Modern Walk-out Lower Level Unit W/separate Den

apartment, Milton
This Oakville flat, a walk-out lower level, is situated approximately 56 kilometres from downtown Toronto and 48 kilometres from Pearson Airport, offering convenient access to major hubs.
This self-contained unit features a private entrance with electronic locks, a fully equipped kitchen with a fridge and microwave, in-unit laundry, driveway parking for one vehicle, a workspace den, air conditioning, heating, and high-speed Wi-Fi with a Smart TV, accommodating up to two guests.

Our Favourite Holiday Lets with Free Parking in Oakville

Driving to Oakville? Each short-term let here includes a car park, making the city centre simple from arrival.

Luxury Apartment Living In An Elite Neighborhood - Oakville
10 17 reviews

Luxury Apartment Living In An Elite Neighborhood

apartment, Toronto
Welcoming Homestay With Relaxing Private Room - Oakville
8.4 22 reviews

Welcoming Homestay With Relaxing Private Room

B&B, Toronto
4 Bed & 4 Bath Mansion Near Lake / Pool /Sleeps 10 - Oakville
10 1 review

4 Bed & 4 Bath Mansion Near Lake / Pool /Sleeps 10

apartment, Toronto
Cozy Spacious 2 Bedrooms - Oakville
9.8 49 reviews

Cozy Spacious 2 Bedrooms

apartment, Milton
©2026 cozycozy.com