Oakville Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oakville holiday rentals

Residence & Conference Centre - Oakville

Residence & Conference Centre - Oakville
1.5 star property
Oakville
8.0 out of 10, Very good, (402 reviews)
"Air conditioning was great, property is quiet overall."
Canada
Atur
The price is NZ$155
includes taxes & fees
10 June - 11 June
Residence & Conference Centre - Oakville

Residence & Conference Centre Toronto Downtown George Brown Polytechnic Campus Accommodation

Residence & Conference Centre Toronto Downtown George Brown Polytechnic Campus Accommodation
3.0 star property
Downtown Toronto
8.2 out of 10, Very good, (936 reviews)
"Beautiful , comfortable and convenient location"
United States
Starlena
The price is NZ$307
includes taxes & fees
5 July - 6 July
Residence & Conference Centre Toronto Downtown George Brown Polytechnic Campus Accommodation

Family-Friendly 3BR Downtown Toronto Stay. Steps from Top Attractions!

Family-Friendly 3BR Downtown Toronto Stay. Steps from Top Attractions!
Downtown Toronto
The price is NZ$1,143
includes taxes & fees
21 June - 22 June
Family-Friendly 3BR Downtown Toronto Stay. Steps from Top Attractions!

Peaceful Downtown 2BR Retreat with 2 Spacious Baths. Effortless City Access!

Peaceful Downtown 2BR Retreat with 2 Spacious Baths. Effortless City Access!
Downtown Toronto
The price is NZ$786
includes taxes & fees
4 July - 5 July
Peaceful Downtown 2BR Retreat with 2 Spacious Baths. Effortless City Access!

Yonge Street Downtown Toronto Condos

Yonge Street Downtown Toronto Condos
4.0 star property
Downtown Toronto
8.8 out of 10, Excellent, (270 reviews)
"Thank you for the great stay!"
Canada
Shawna
Yonge Street Downtown Toronto Condos

Peaceful Downtown Studio Retreat. Ideal for Solo Travelers!

Peaceful Downtown Studio Retreat. Ideal for Solo Travelers!
Downtown Toronto
The price is NZ$593
includes taxes & fees
15 June - 16 June
Peaceful Downtown Studio Retreat. Ideal for Solo Travelers!

Executive Hotel Cosmopolitan Toronto

Executive Hotel Cosmopolitan Toronto
4.0 star property
Downtown Toronto
8.4 out of 10, Very good, (2,492 reviews)
"Great hotel "
Canada
Kayode
The price is NZ$479
includes taxes & fees
14 June - 15 June
Executive Hotel Cosmopolitan Toronto

Maple Leaf Square

Maple Leaf Square
3.5 star property
Downtown Toronto
8.2 out of 10, Very good, (608 reviews)
"Great place to stay"
Canada
Roman
The price is NZ$383
includes taxes & fees
10 June - 11 June
Maple Leaf Square

York Suites Toronto

York Suites Toronto
3.0 star property
Downtown Toronto
7.0 out of 10, Good, (70 reviews)
"Clean property, amazing view, easy check in."
Canada
John
York Suites Toronto

The Summit - Downtown Toronto

The Summit - Downtown Toronto
2.0 star property
Downtown Toronto
10.0 out of 10, Exceptional, (2 reviews)
"Ideally located , excellent host, highly recommend"
Canada
Steven
The price is NZ$610
includes taxes & fees
10 June - 11 June
The Summit - Downtown Toronto

Teahouse Condos in Downtown Toronto

Teahouse Condos in Downtown Toronto
4.0 star property
Downtown Toronto
9.0 out of 10, Wonderful, (59 reviews)
"Excellent stay"
Canada
Kevin
Teahouse Condos in Downtown Toronto

Modern Downtown Apartments

Modern Downtown Apartments
4.0 star property
Downtown Toronto
8.2 out of 10, Very good, (569 reviews)
"Great location, across the street from Roger’s Centre, C.N. Tower and the aquarium. The value that you got for what you paid was fantastic!!! Spacious bedrooms with two bathrooms, great view and fully functioning kitchen! Definitely a place I would recommend for people that are attending events downtown :)"
Canada
Jaime
The price is NZ$482
includes taxes & fees
10 June - 11 June
Modern Downtown Apartments

1BR Lower Boutique Suite • Sleeps 4 • WiFi+Parking

1BR Lower Boutique Suite • Sleeps 4 • WiFi+Parking
Downtown Toronto
The price is NZ$726
includes taxes & fees
22 June - 23 June
1BR Lower Boutique Suite • Sleeps 4 • WiFi+Parking

Vintage Roost at Fleming Farms

Vintage Roost at Fleming Farms
Beamsville
10.0 out of 10, Exceptional, (23 reviews)
"Joshua was an excellent host. The space was beautiful and location was great! Made some excellent winery suggestions and communication was amazing. Would highly recommend and will stay again for sure!"
Canada
Erica
The price is NZ$534
includes taxes & fees
11 June - 12 June
Vintage Roost at Fleming Farms

The McCaul | Lower Level Suite near FIFA 2026

The McCaul | Lower Level Suite near FIFA 2026
Downtown Toronto
10.0 out of 10, Exceptional, (1 review)
"My husband & I have just spent a very enjoyable 4 nights at one of the McCaul apartments & will certainly stay again. It was in an a great location very close to shops, cafes, restaurants & places of interest.Everything was top grade & beautifully designed with great style. It was very clean & well stocked with everything you could want. Also, Shameza & her team were very accommodating & helpful, nothing was too much trouble. We would most definitely recommend it to other guests!"
United States
NORMA P.
The McCaul | Lower Level Suite near FIFA 2026

Elegant Downtown Apartments

Elegant Downtown Apartments
4.0 star property
Downtown Toronto
8.0 out of 10, Very good, (656 reviews)
"Good place!"
Canada
Matthew
Elegant Downtown Apartments

Beautiful Condos In the Heart of Downtown

Beautiful Condos In the Heart of Downtown
3.5 star property
Downtown Toronto
9.0 out of 10, Wonderful, (375 reviews)
"Clean and great location"
Canada
Prince
The price is NZ$398
includes taxes & fees
10 June - 11 June
Beautiful Condos In the Heart of Downtown

Fort York Suites Toronto

Fort York Suites Toronto
3.5 star property
Old Toronto
8.2 out of 10, Very good, (379 reviews)
"Great location"
Canada
Brandon
Fort York Suites Toronto

Atlantis at Waterpark City Condos in DT

Atlantis at Waterpark City Condos in DT
4.0 star property
Old Toronto
9.0 out of 10, Wonderful, (13 reviews)
"Room was clean and very well located"
Canada
Sébastien
Atlantis at Waterpark City Condos in DT

Oak House Residence

Oak House Residence
3.0 star property
Downtown Toronto
8.8 out of 10, Excellent, (42 reviews)
"Super convenient location, very fair price, and the rooms were nice and clean."
Canada
Sarah
The price is NZ$294
includes taxes & fees
11 June - 12 June
Oak House Residence
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Oakville Hotel Reviews

Find out more about Oakville

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oakville holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oakville. 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 Oakville. 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 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 holiday 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 Oakville short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Oakville?

Yes, there are holiday rentals in Oakville close to Glen Abbey Golf Course, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and theatre scene in Oakville. Make sure you have time to check out the university setting and riverfront during your trip.

What are some of the best holiday rentals that Oakville has to offer?

4 Bedroom Bungalow In Lakeview Mississauga With 2 Parkings: This holiday home rental outside of Oakville offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Oakville?

Expedia has 60 holiday rentals for your stay in Oakville.

What’s there to see and do in Oakville?

Cultural attractions include Glen Abbey Golf Course and Oakville Museum, whereas Lake Ontario and Gairloch Gardens are a couple of picturesque spots to enjoy the outdoors. Kerr Village and Bronte Creek Provincial Park are other places to visit while you're in town.

What are holiday rentals like in Oakville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakville. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.