Ontario may have travel restrictions in place due to COVID-19.

Find out moreOpens in new tab or window

Oakville Vacation Rentals

Search over 1 million properties and 550 airlines worldwide

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.

Vacation Rentals in Oakville

Staybridge Suites Oakville

Staybridge Suites Oakville

3 out of 5
2511 Wyecroft Rd, Oakville, ON
The price is CA $100 per night from Nov 27 to Nov 28

Situated in Oakville, this eco-friendly aparthotel is within a 15-minute walk of Bronte Creek Provincial Park and Oakville Art Society. Sovereign House and Bronte ...

4.3/5Excellent! (338 reviews)

"The studio suite was adequate for my needs in quarantine. Of course, I couldn’t access the breakfast or other amenities, so I can’t judge the entire experience under ordinary conditions. The room had a few issues of wear and tear that could be improved but was quite comfortable. The bathroom sink ..."…"

Reviewed on Oct. 20, 2020

Staybridge Suites Oakville
Modern Guesthouse Back to Ravine Trail in Oakville, 6 Beds up to 12 Guests

Modern Guesthouse Back to Ravine Trail in Oakville, 6 Beds up to 12 Guests

3161 Meadow Marsh Crescent, Oakville, ON

Situated in Oakville, this holiday home is 2.1 mi (3.4 km) from Joshua Creek Heritage Art Centre and 2.5 mi (4.1 km) from Sheridan College. Cameron's Brewing ...

5/5Exceptional! (4 reviews)
Comfortable space

"House had lots of space and comfort. Beds were great quality. Lots of bathrooms. Good access to shops & groceries. Only thing we missed was an outdoor space to relax or enjoy dinner on a warm evening or breakfast coffee. Would definitely stay again! Host was very helpful,."…"

Reviewed on Sep. 24, 2019

Modern Guesthouse Back to Ravine Trail in Oakville, 6 Beds up to 12 Guests
Luxurious Family Home Available-be Our Guest Now

Luxurious Family Home Available-be Our Guest Now

527 Taplow Crescent, Oakville, ON

Located in West Oakville, this romantic holiday home is within 2 miles (3 km) of Lake Ontario, Coronation Park and Kerr Village. Glen Abbey Golf Course and Canadian ...

3.7/5Good! (3 reviews)
Family home in Oakville

"We felt very much at home in this lovely little house. There was plenty of room for 2 parents and 3 teenagers. The kitchen was kindly stocked with all the basics and very well appointed. Hiten was a wonderful host and very easy to reach. Quiet neighbourhood close to Bronte and easy access to the ..."…"

Reviewed on Aug. 18, 2019

Luxurious Family Home Available-be Our Guest Now
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Oakville-31 Kaitting

Oakville-31 Kaitting

31 Kaitting Trail, Oakville, ON

Situated in Oakville, this holiday home is 2.4 mi (3.9 km) from Sheridan College and 2.8 mi (4.5 km) from Joshua Creek Heritage Art Centre. Canadian Golf Hall ...

Oakville-31 Kaitting
Lake - Marina - Restaurants - Shops - Huge Yard - Salt Pool - BBQ - Porch- Deck

Lake - Marina - Restaurants - Shops - Huge Yard - Salt Pool - BBQ - Porch- Deck

2314 Belyea St, Oakville, ON

Located in Bronte, this holiday home is within a 15-minute walk of Bronte Heritage Park and Lake Ontario. Sovereign House and Coronation Park are also within ...

Lake - Marina - Restaurants - Shops - Huge Yard - Salt Pool - BBQ - Porch- Deck
Life Suites Loft - CN Tower

Life Suites Loft - CN Tower

4 out of 5
20 John Street, Toronto, ON

Located in Toronto Entertainment District, this condo is steps away from The Path, PATH Underground Shopping Mall and TIFF Bell Lightbox. Princess of Wales Theatre ...

4/5Very Good! (1,062 reviews)
Best experience ever I love the view great owner very understanding kind and caring.

"This property has a great view close to everything you think of downtown ."…"

Reviewed on Aug. 31, 2020

Life Suites Loft - CN Tower
Staybridge Suites Hamilton Downtown

Staybridge Suites Hamilton Downtown

3 out of 5
20 Caroline St S, Hamilton, ON
The price is CA $142 per night from Nov 27 to Nov 28

Located in Central Hamilton, this aparthotel is within a 5-minute walk of Art Gallery of Hamilton, Hamilton City Hall and FirstOntario Centre. Hamilton Convention ...

4.4/5Wonderful! (732 reviews)

"Clean spacious suites and friendly staff. Its location downtown Hamilton has easy walkability to restaurants, coffee shops and a small nearby mall which also contains a supermarket which provides fresh seafood and poultry."…"

Reviewed on Sep. 21, 2020

Staybridge Suites Hamilton Downtown
Simply Comfort. DUNDURN LOFTS

Simply Comfort. DUNDURN LOFTS

3.5 out of 5
The price is CA $76 per night from Nov 25 to Nov 26

Located in Kirkendall North, this condo building is within 2 mi (3 km) of Cathedral Basilica of Christ the King, FirstOntario Centre, and Hamilton Convention ...

4.1/5Very Good! (13 reviews)

"Great location in leafy central neighbourhood near cafes and parks. I liked the industrial-loft decor of the suite, and it was very clean. The management company needs to be more on top of things - the first suite I stayed in did not have functioning wifi (which I needed, because I was there on a ..."…"

Reviewed on Oct. 5, 2020

Simply Comfort. DUNDURN LOFTS
Velvet Stays – CN Tower and Convention Center

Velvet Stays – CN Tower and Convention Center

3.5 out of 5
300 Front Street West, Toronto, ON

Located in Toronto Entertainment District, this aparthotel is within a 5-minute walk of The Path and PATH Underground Shopping Mall. CN Tower and Metro Toronto ...

4.1/5Very Good! (112 reviews)

"The apartment was very nice and clean, we had a great stay. Communication may be difficult at times but I was able to get a hold of someone eventually and they answered all my questions. The deposit was done through an etransfer and should be refunded within 24-48hrs, so we will see."…"

Reviewed on Oct. 5, 2020

Velvet Stays – CN Tower and Convention Center
Feel at Home While Away From Home

Feel at Home While Away From Home

Langholm court, 18, Brampton, ON
The price is CA $50 per night from Nov 25 to Nov 26

Situated in Brampton, this holiday home is 1.2 mi (1.9 km) from Historic Bovaird House and within 3 miles (5 km) of Rose Theatre and St. Paul's United Church. ...

Feel at Home While Away From Home
Avalon Suites Yorkville

Avalon Suites Yorkville

3.5 out of 5
155 Yorkville Avenue, Toronto, ON

Located in Yorkville, this aparthotel is within a 15-minute walk of Royal Ontario Museum and University of Toronto - St. George Campus. Casa Loma and Toronto ...

3.2/5 (12 reviews)

"Fantastic spot, and an even more beautiful space to sleep- I felt comfortable and right at home, loved the space and I will be returning again soon - highly recommend this incredible apartment"…"

Reviewed on Oct. 26, 2020

Avalon Suites Yorkville
White House Canada

White House Canada

3.5 out of 5
22 Estateview Cir, Brampton, ON
The price is CA $1,000 per night from Nov 25 to Nov 26

Situated in Brampton, this holiday home is within 6 miles (10 km) of Embassy Grand Convention Centre, Donald M. Gordon Chinguacousy Park and Pearson Convention ...

White House Canada
PlanURstay - Mississauga Downtown Square One

PlanURstay - Mississauga Downtown Square One

4 out of 5
3888 Duke of York Blvd, Mississauga, ON

Located in Downtown Mississauga, this condo is 4.2 mi (6.8 km) from Paramount Fine Foods Centre, and within 12 mi (20 km) of University of Toronto Mississauga ...

3.6/5Good! (5 reviews)
So special

"It was great and nice"…"

Reviewed on Mar. 17, 2020

PlanURstay - Mississauga Downtown Square One
Luxury Penthouse Suite

Luxury Penthouse Suite

4 out of 5
3880 Duke of York Boulevard, Mississauga, ON

Located in Downtown Mississauga, this condo is within a 5-minute walk of Mississauga Celebration Square, Mississauga Central Library and Art Gallery of Mississauga. ...

Luxury Penthouse Suite
Canada Suites on Bay

Canada Suites on Bay

3.5 out of 5
736 Bay Street, Toronto, ON
The price is CA $166 per night from Nov 29 to Nov 30

Located in Downtown Toronto, this aparthotel is within 1 mi (2 km) of Ryerson University, Royal Ontario Museum and Toronto Public Library. Hockey Hall of Fame ...

4.2/5Very Good! (224 reviews)

"The property is great for two couples or a family. It is centrally located in downtown Toronto with easy access too many sites. I found that the carpet in the hallway to be dirty, and could use a hull over. Michael the manager was always available and very friendly."…"

Reviewed on Jul. 25, 2020

Canada Suites on Bay
Simply Comfort. King St Apartments

Simply Comfort. King St Apartments

3 out of 5
235 King Street East, Hamilton, ON
The price is CA $67 per night from Nov 26 to Nov 27

Located in Central Hamilton, this apartment building is within a 15-minute walk of Theatre Aquarius and Hamilton Convention Centre. FirstOntario Centre and Mohawk ...

Simply Comfort. King St Apartments
Sonder - The Wellesley

Sonder - The Wellesley

3 out of 5
29 Wellesley Street East, Toronto, ON

Located in Downtown Toronto, this aparthotel is within a 15-minute walk of Downtown Yonge, University of Toronto - St. George Campus and Ryerson University. ...

4.2/5Very Good! (6 reviews)

"Everything was great, cleanliness, contactless check in, modern, location, ability to store luggage. The only problem was the front door of the building. It slams so loud. Ask to be at the back of the house. We were in 201 right at the front and the head of the bed is on the wall to the hallway which ..."…"

Reviewed on Aug. 15, 2020

Sonder - The Wellesley
Luxury Penthouse w Breathtaking CN Tower Views

Luxury Penthouse w Breathtaking CN Tower Views

Toronto, ON

Located in Toronto Entertainment District, this historic apartment building is within a 10-minute walk of The Path, Rogers Centre, and CN Tower. Metro Toronto ...

5/5Exceptional! (3 reviews)
Amazing stay!

"Kat's place was gorgeous, with breathtaking views in every room! I had such an amazing stay and definitely recommend booking here. 5 stars!"…"

Reviewed on Aug. 2, 2020

Luxury Penthouse w Breathtaking CN Tower Views
Simply Comfort Modern Hamilton Apartment

Simply Comfort Modern Hamilton Apartment

4 out of 5
115 Shoreview Pl, Hamilton, ON
The price is CA $100 per night from Dec 7 to Dec 8

Situated on the Strip, this apartment building is within 2 miles (3 km) of Lake Ontario, Wild Waterworks and Confederation Park. Saltfleet Arena Skating Rink ...

3.8/5Good! (6 reviews)
Great experience

"The actual stay was beyond amazing! The room was everything we wanted and more. On top of being extraordinary clean there were actual apartment necessities such as cleaning products both in kitchen and bathroom and utilities such as a washing machine in the room! The suite we were given looked out ..."…"

Reviewed on Jul. 15, 2020

Simply Comfort Modern Hamilton Apartment
Staybridge Suites Toronto Mississauga

Staybridge Suites Toronto Mississauga

3 out of 5
6791 Hurontario St, Mississauga, ON
The price is CA $104 per night from Nov 29 to Nov 30

Located in Gateway, this aparthotel is within 1 mi (2 km) of Apollo Convention Centre and Mississauga Convention Centre. Mississauga Grand Banquet and Convention ...

4.1/5Very Good! (170 reviews)

"Hotel is in a great location. Rooms are spacious and beds are comfy. Hotel is in dire need of updating- holes in walls, peeling wallpaper, missing drawer pulls on furniture. Even though it needs repair, it is clean and the staff is wonderful. Breakfast was good and there were some choices both hot ..."…"

Reviewed on Feb. 18, 2020

Staybridge Suites Toronto Mississauga
Don't see what you're looking for?
See all available properties in Oakville
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oakville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Oakville?
Yes, there are vacation rentals in Oakville close to Glen Abbey Golf Course, or you can go with a more secluded option if you’re looking for extra privacy while you relax. Visitors like the top-notch restaurants and theater scene in Oakville. Make sure you have time to check out the university setting and riverfront during your trip.
What's the top vacation rental that Oakville has to offer?
Modern Guesthouse Back to Ravine Trail in Oakville, 6 Beds up to 12 Guests: This highly rated vacation home rental in Oakville is equipped with a fireplace, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Another good choice for your trip to Oakville is Luxurious Family Home Available-be Our Guest Now.
How many vacation rentals are there in Oakville?
Expedia has 8 vacation rentals for your stay in Oakville.
What’s there to see and do in Oakville?
Cultural attractions include Oakville Centre for the Performing Arts and Glen Abbey Golf Course, whereas Coronation Park and Lake Ontario are a couple of picturesque spots to enjoy the outdoors. You’ll find favorite places to visit like FirstOntario Centre and High Park in the larger area.
What are vacation rentals like in Oakville?
Vacation rentals are privately owned accommodations you can reserve for a couple days or more in Oakville. Vacation rentals feature amenities like laundry facilities and kitchens so you’ll have all the conveniences of home. If you’re concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You’ll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for family gatherings.

Other types of properties in Oakville you may be interested in

Hilton Garden Inn Toronto/Oakville

Hilton Garden Inn Toronto/Oakville

3 out of 5
2774 South Sheridan Way, Oakville, ON
Free cancellationReserve now, pay when you stay
The price is CA $80 per night from Nov 27 to Nov 28
Hilton Garden Inn Toronto/Oakville
Sandman Hotel Oakville

Sandman Hotel Oakville

3 out of 5
3451 South Service Road West, Oakville, ON
Free cancellationReserve now, pay when you stay
The price is CA $72 per night from Nov 29 to Nov 30
Sandman Hotel Oakville
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.