Photo by Scott Schweiger

Oakville Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • 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

Apartment in Grand Center

White House at Grand Central
4.0 star property
8.6 out of 10, Excellent, (125)
"Very clean and very friendly people "
United States
Mary
The price is NZ$240
includes taxes & fees
6 Jan - 7 Jan 2026
White House at Grand Central
8.6 out of 10, Excellent, (4)
"The property was very clean and the host was very helpful! It fit my needs quite well."
United States
Hunter S.
The price is NZ$263
includes taxes & fees
20 Jan - 21 Jan 2026
1 bed duplex near downtown Belleville next to heart garden and long story coffee

Apartment in Marine Villa

Stylish South City King 1BR Apt
2.0 star property
10.0 out of 10, Exceptional, (9)
"Great location, great accommodations, great host."
United States
Scott W.
The price is NZ$306
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish South City King 1BR Apt
9.6 out of 10, Exceptional, (50)
"We enjoyed a comfortable stay at this location. Everything was as described. We would not hesitate to stay here again. "
United States
Genna L.
The price is NZ$348
includes taxes & fees
29 Dec - 30 Dec
Stylish South City 2BR w/ Garage & Blazing Wi-fi
10.0 out of 10, Exceptional, (4)
"We had a nice stay in the area, and we were looking for a reasonably priced lodging for the whole family. There are a couple inflatable mattresses included in case additional beds are required. The full kitchen was appreciated, as was the comfortable couch. Solid proximity to other businesses and towns. The property is a little tricky to spot from afar off the side of the road, but it's easy to see once you're near it (Google maps is helpful). Overall, a good stay & I would stay here again!"
United States
Zach L.
The price is NZ$167
includes taxes & fees
5 Jan - 6 Jan 2026
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Apartment in Soulard

Top of Geyer apartment
9.8 out of 10, Exceptional, (43)
"Convenient location "
United States
julie s.
The price is NZ$323
includes taxes & fees
29 Dec - 30 Dec
Top of Geyer apartment
9.6 out of 10, Exceptional, (59)
"Enjoyed the vibe of the neighborhood "
United States
Brett
The price is NZ$327
includes taxes & fees
19 Jan - 20 Jan 2026
Cozy Soulard 2BR w/ Free Parking

Apartment in Mount Pleasant

Pet-Friendly 1BR Apartment
8.6 out of 10, Excellent, (10)
"I really enjoyed my stay and the host was very nice and prompt with my questions and concerns however, I would've love to have not had mold in the bathroom on the window ledge and a little more safety regarding the doors. In all the place was very comfortable and yes I would stay here again."
United States
Miltha J.
The price is NZ$266
includes taxes & fees
28 Jan - 29 Jan 2026
Pet-Friendly 1BR Apartment
9.8 out of 10, Exceptional, (18)
"It was a great place to stay for the night. Comfortable and close to the stadium. "
United States
Bryan D.
The price is NZ$344
includes taxes & fees
19 Jan - 20 Jan 2026
Spacious & Centrally Located Apt (Sleeps 8)

Apartment in Princeton Heights

Chic Minimalist Gem w/ Fenced Backyard + W/D
9.6 out of 10, Exceptional, (9)
"Nice location."
United States
Holly R.
Chic Minimalist Gem w/ Fenced Backyard + W/D
10.0 out of 10, Exceptional, (2)
"Host was very welcoming and the house had everything we needed!"
United States
Sullivan F.
The price is NZ$223
includes taxes & fees
29 Dec - 30 Dec
Gorgeous Spacious Full Apartment Close to Everything in St. Louis
9.8 out of 10, Exceptional, (53)
"Easy check-in, great communication with owner, nice area that is close to restaurants, bars, very clean."
United States
Vickie L.
The price is NZ$344
includes taxes & fees
20 Jan - 21 Jan 2026
Classic Soulard 2BD King Master & Private Deck
9.4 out of 10, Exceptional, (13)
"Great place for a short get away"
United States
andytrower U.
The price is NZ$330
includes taxes & fees
30 Dec - 31 Dec
Adorable small house - quiet & safe - 2 BR 1 Bath

Apartment in The Gate

Classy Midtown 3BR, King Master
10.0 out of 10, Exceptional, (61)
"Very charming and comfortable accommodations in a safe and beautiful part of town, convenient to many attractions."
United States
Robin L.
The price is NZ$352
includes taxes & fees
4 Jan - 5 Jan 2026
Classy Midtown 3BR, King Master
7.6 out of 10, Good, (11)
"Great stay...needs some minor upgrades. Smart tv, dishwasher and more silverware"
United States
Daniel S.
The price is NZ$262
includes taxes & fees
26 Jan - 27 Jan 2026
Work-Ready 1BR | Fast Wi-Fi & Laundry – Steps to Tower Grove Park (65)
9.8 out of 10, Exceptional, (139)
"Great little place and location was close to our event."
United States
RL T.
The price is NZ$283
includes taxes & fees
7 Jan - 8 Jan 2026
Centrally located in the Tower Grove East neighborhood!
9.6 out of 10, Exceptional, (17)
"It was a great place to stay for our needs we had our little dog with us as was there for weekend, it had a nice fenced back yard we could let her just go out didn't have to have her on leash. Was very nice inside clean well kept, beds were surprising comfortable. The host stayed in contact and answered a lot questions before we arrived which put me a ease for our trip. High recommand this place if needing to stay in the area. "
United States
Terry
The price is NZ$440
includes taxes & fees
4 Jan - 5 Jan 2026
Cute town house with fenced backyard
9.8 out of 10, Exceptional, (160)
"Very clean, check in was easy, great neighborhood with lots of food close. "
United States
Laura H.
The price is NZ$246
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
8.6 out of 10, Excellent, (4)
"One of the nicer places I’ve stayed at. Parking is weird on the driveway, but street parking is abundant. "
United States
Paul
The price is NZ$266
includes taxes & fees
1 Jan - 2 Jan 2026
Ground-Floor Forest Park Studio | Parking, Washer/Dryer & Fast Wi-Fi
7.0 out of 10, Good, (4)
"Amazing property and access was easy. Would highly recommend."
United States
Armhad
The price is NZ$262
includes taxes & fees
19 Jan - 20 Jan 2026
1BR Apartment – Washer/Dryer, Fenced Backyard, Free Parking, Near Arch
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

Everything you need to know about Oakville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakville holiday rentals we have selected for you start as low as NZ$240 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakville rentals

At Expedia, we put the best Oakville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Oakville?

Yes, there are holiday rentals close to the most popular sights in Oakville, or you can select a more secluded option if you're looking for a relaxing stay. Oakville is known for its football matches and jazz scene. Make sure you have time to check out the restaurants while you're in the area.

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

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: This holiday home rental outside of Oakville is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Oakville?

Meramec River and Mississippi River are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find popular places such as Busch Stadium and St. Louis Union Station.

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 offer extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a small group gathering.