Compare best Airbnb in Oakville from 100+ providers!

664 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Oakville vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Oakville

Top Vacation Rentals for Families in Oakville

Make family travel to Oakville seamless with spacious vacation rentals located just minutes from top city attractions.

Welcome To Your Comfort Retreat By The Lake - Oakville
10 1 review
Oakville
08/28 – 09/16
$609/nighttotal: $11571 (19 )

Welcome To Your Comfort Retreat By The Lake

4 4
apartment , Toronto
This spacious 3,230 square foot residence is situated in Burlington, offering convenient access to major attractions, located 25 miles from the Mississauga Convention Centre and 28 miles from Toronto's BMO Field and Budweiser Stage.
This pet-friendly rental features 4 bathrooms, accommodates up to 15 guests, and includes a private swimming pool, air conditioning, complimentary Wi-Fi, private parking, and a fully equipped kitchen for your stay.
Bright Oakville 3br Home |Family + Patio & Parking - Oakville
10 1 review
Oakville
07/01 – 07/05
$385/nighttotal: $1540 (4 )

Bright Oakville 3br Home |Family + Patio & Parking

1 3
house , Milton
This modern 3-bedroom house in Milton offers quick access to major highways and is a short drive to Oakville Trafalgar Hospital.
This pet-friendly, family-friendly rental accommodates up to 6 guests with 3 bedrooms, 2.5 bathrooms, a fully equipped kitchen, air conditioning, WiFi, a garden, and parking for 2 cars.
Comfortable Luxury Home In Oakville - Oakville
9.9 68 reviews
Oakville
08/26 – 09/06
$382/nighttotal: $4202 (11 )

Comfortable Luxury Home In Oakville

1 2
apartment , Milton
This spacious home is located in a premium area of Toronto, close to highways, grocery stores, bars, and other amenities. It has excellent user, location, and cleanliness ratings.
The apartment has four bedrooms and three bathrooms, accommodating up to nine guests. It features a fully equipped kitchen, air conditioning, a garden, a fitness center, parking, and high-speed internet, making it perfect for families or groups.
Cozy 2 Bedrooms Modern Basement Suite With Private Entrance, Kitchen And Parking - Oakville
9.1 16 reviews
Oakville
06/27 – 07/04
$212/nighttotal: $1484 (7 )

Cozy 2 Bedrooms Modern Basement Suite With Private Entrance, Kitchen And Parking

2 2
apartment , Toronto
This Mississauga basement suite, located approximately 11 miles from Toronto Pearson International Airport and 10 miles from the Mississauga Convention Centre, offers convenient access to major Toronto attractions.
This 850-square-foot, two-bedroom, one-bathroom rental comfortably sleeps nine guests and includes free Wi-Fi, private parking, a fully equipped kitchen with a dishwasher, air conditioning, and a flat-screen TV.

Best Oakville vacation rentals with parking

Modern Studio W-kitchen - Parking Near Appleby Go - 40 Min To Toronto - Oakville
Oakville
09/01 – 09/30
$88/nighttotal: $2552 (29 )

Modern Studio W-kitchen - Parking Near Appleby Go - 40 Min To Toronto

1 1
studio , Hamilton
This modern apartment in Burlington is conveniently located 19 miles from John C. Munro Hamilton International Airport and within driving distance of Toronto.
This studio apartment accommodates up to 3 guests and features a well-equipped kitchen, air conditioning, complimentary WiFi, and free private parking.
Luxury Oakville Home, Hot Tub, Fireplace, New Home - Oakville
10 1 review
Oakville
07/01 – 07/05
$684/nighttotal: $2736 (4 )

Luxury Oakville Home, Hot Tub, Fireplace, New Home

4 3
house , Milton
This luxurious Oakville house, a 15-mile drive from both the Mississauga Convention Center and Toronto Pearson International Airport, offers convenient access to major attractions.
This 2460-square-foot home boasts four bedrooms, three bathrooms, two living rooms, and accommodates up to 19 guests, featuring a fully equipped kitchen, Jacuzzi, spa, and private parking.
Modern 2-bed Basement Retreat! - Oakville
9.4 3 reviews
Oakville
08/26 – 09/06
$167/nighttotal: $1837 (11 )

Modern 2-bed Basement Retreat!

2 2
apartment , Toronto
This Erin Mills vacation rental is conveniently located within 1.8 miles of Woodhurst Heights Park, Erin Mills Twin Arenas, and the Oakville Entertainment Centre, with attractions like Putting Edge and iFLY Toronto Oakville within 3.1 miles.
This two-bedroom, two-bathroom house sleeps five, features a fully equipped kitchen with fridge and microwave, free WiFi, a smart TV, air conditioning, parking, and a smoke-free environment; nearby activities include parks and entertainment venues.
Cozy Modern Studio In Oakville | Free Parking - Oakville
9.5 151 reviews
Oakville
06/23 – 06/25
$98/nighttotal: $196 (2 )

Cozy Modern Studio In Oakville | Free Parking

1 2
apartment , Toronto
This Oakville basement apartment is conveniently located near Lake Ontario, Oakville Place Mall, and Downtown Oakville, offering easy access to public transit and walking trails.
The unit features a queen-size bed, in-unit laundry, a fully equipped kitchenette with microwave, fridge, and coffee maker, free Netflix, WiFi, and two parking spots; it sleeps two guests and is close to Bronte Harbour Park and the Oakville Museum.

Frequently Asked Questions about vacation rentals in Oakville

  • What should a first-time visitor not miss in Oakville?

    For a first-time visitor, a stroll along the Oakville waterfront is a must. You'll find beautiful views of Lake Ontario, charming shops, and the iconic Oakville Harbour. And don't miss the Oakville Museum, which showcases the town's rich history.
  • What are the best Airbnb and vacation rentals in Oakville?

    Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are the most popular Airbnb and vacation rentals in Oakville among travelers.

  • Which neighborhood in Oakville should you consider for a vacation rental?

    The Old Oakville neighborhood is a great choice for a vacation rental. It's close to the waterfront, has plenty of restaurants and shops, and offers a charming, historic feel. The area around Bronte Creek Provincial Park is also lovely, with a more rural feel.
  • What are the most popular Airbnbs in Oakville?

    Among the Airbnbs in Oakville, Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are the most popular ones.

  • When is the best time to book a vacation rental in Oakville?

    The best time to book a vacation rental in Oakville is during the shoulder seasons, from April to May or September to October. You'll enjoy pleasant weather, fewer crowds, and potentially lower prices. Of course, if you're looking for summer fun, July and August are always popular.
  • What are the best vacation rentals with a pool in Oakville?

  • What events or festivals should visitors check out in and around Oakville?

    The Oakville Jazz Festival in July is a popular event, with live music and food vendors. The Oakville Fall Fair in September is another great option, with agricultural displays, competitions, and entertainment. And for something a little different, the Oakville Art Crawl, held in October, showcases local artists and their work.
  • What are the best rentals for families and kids in Oakville?

    The best rentals for families and kids in Oakville are Home Away From Home (Basement Apartment), Pathway Suites and Cozy & Beautiful Basement Apartment.

  • What are the best budget-friendly activities in Oakville?

    A walk along the Oakville waterfront is always free and offers beautiful scenery. You can also visit the Oakville Public Library, which offers free programs and events. And for a picnic lunch, head to Coronation Park, a large park with plenty of green space.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakville?

    The best vacation rentals or Airbnb with a jacuzzi in Oakville are Pathway Suites, Beautiful Cozy 1 Br Condo Steps To Sq1 and Beautiful City View 1br High Rise Sq1 Condo 5-.

  • What are the best restaurants with local dishes in Oakville?

    For a taste of local fare, check out The Oakville Grocery, which serves up fresh, seasonal dishes made with local ingredients. The Queen's Plate is another popular spot, known for its classic Canadian comfort food. And for a more casual dining experience, try The Oakville Brew House, which offers a wide selection of craft beers and pub fare.
  • What are the best walking or cycling routes in Oakville?

    The Waterfront Trail is a great option for walking or cycling, offering scenic views of Lake Ontario. The Oakville Creek Trail is another popular choice, winding through the town's natural areas. And for a more challenging ride, try the Bronte Creek Provincial Park trails, which offer a variety of terrain.
  • Are there pet-friendly attractions in Oakville?

    Yes, many attractions in Oakville are pet-friendly. Coronation Park is a great option for a walk with your furry friend, and the Oakville waterfront is also dog-friendly. Just be sure to keep your pet on a leash and clean up after them.
  • What are the benefits of choosing a vacation rental in Oakville?

    Vacation rentals often offer more space and privacy than hotels. They can also be a more affordable option, especially for families or groups. And you'll have the convenience of a kitchen, allowing you to prepare your own meals.
  • What are the top sports attractions and facilities in Oakville?

    Oakville is home to the Oakville Soccer Club, which offers programs for players of all ages. The Oakville Tennis Club has courts for both indoor and outdoor play. And the Oakville Golf Club offers a challenging 18-hole course.

Destinations nearby

Best Vacation Rentals with Balconies in Oakville

Elevate your stay in Oakville with a vacation rental featuring a private balcony and stunning city skyline views.

Luxury 4br Oakville Townhome + 3 Free Parking - Oakville
Oakville
09/01 – 02/28
$149/nighttotal: $26820 (180 )

Luxury 4br Oakville Townhome + 3 Free Parking

4 4
apartment , Hamilton
This 1,890 sq ft, 4-bedroom townhouse in Oakville is a short drive from Downtown Oakville, offering proximity to its boutiques, dining, and Lakeshore, as well as Glen Abbey Golf Course and the Oakville Museum.
This residence accommodates up to 8 guests with 4 bathrooms, features a full kitchen with a fridge, microwave, and dishwasher, offers air conditioning, a terrace/balcony, and parking, with high-speed WiFi and an in-unit washer/dryer for convenience.
3bed Bright Oakville Townhome With Balcony, Office - Oakville
9.0 2 reviews
Oakville
07/10 – 07/15
$271/nighttotal: $1355 (5 )

3bed Bright Oakville Townhome With Balcony, Office

3 2
house , Toronto
This Oakville townhome is located 16 miles from Toronto Pearson International Airport and the Mississauga Convention Centre, offering a suburban base with convenient access to Toronto landmarks such as BMO Field, Budweiser Stage, and Exhibition Place, all within a 20-mile radius.
This non-smoking accommodation accommodates up to 11 guests with 2 bathrooms, featuring complimentary private parking, free WiFi, a fully equipped kitchen, and a private balcony for relaxation.
South Oakville Bliss Haven Monthly Stays Only - Oakville
8.5 2 reviews
Oakville
09/01 – 09/30
$308/nighttotal: $8932 (29 )

South Oakville Bliss Haven Monthly Stays Only

5 1
house , Toronto
South Oakville Bliss Haven, located in Oakville, Ontario, offers a peaceful retreat about 20 miles west of Toronto Pearson International Airport and within easy driving distance of attractions like the Budweiser Stage and Exhibition Place.
This five-bedroom, three-bathroom house rental sleeps 19 guests, boasts 140 square feet of living space, and includes amenities such as a fully equipped kitchen, private balcony with barbecue, free Wi-Fi, and free parking.
Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville - Oakville
8.8 17 reviews
Oakville
07/01 – 07/31
$193/nighttotal: $5790 (30 )

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville

3 4
apartment , Milton
This 3-bedroom townhome in Oakville is conveniently located just 17 miles from both the Mississauga Convention Center and Toronto Pearson International Airport, offering easy access to both city attractions and the peaceful ambiance of Oakville. The apartment consistently receives high ratings for its cleanliness, location, and overall experience.
The spacious 1850 square foot townhome comfortably accommodates up to 6 guests. Enjoy modern amenities like a fully equipped kitchen, a private terrace, and free high-speed internet, making this a perfect choice for families or groups looking for a comfortable and convenient stay.

Best Oakville vacation rentals with air conditioning

Cozy Spacious 2 Bedrooms - Oakville
9.8 38 reviews
Oakville
07/06 – 07/12
$133/nighttotal: $798 (6 )

Cozy Spacious 2 Bedrooms

1 2
apartment , Milton
This Oakville vacation rental boasts excellent location ratings, near Toronto Pearson International Airport and a 20-minute drive from Square One Shopping Centre, Celebration Square, and the Hershey Centre.
This two-bedroom, one-bathroom home sleeps five guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, a garden, parking, and excellent user ratings.
Clean Modern One Br Condo | Full Kitchen, Laundry - Oakville
Oakville
06/27 – 07/04
$140/nighttotal: $980 (7 )

Clean Modern One Br Condo | Full Kitchen, Laundry

1 1
apartment , Toronto
This conveniently located condo is situated in a quiet neighborhood near Ridgeway Plaza, offering easy access to Highways 403 and 407, the Oakville border, and a 30-minute drive to Toronto.
This furnished studio apartment accommodates two guests with a queen bed, a Smart TV, fast WiFi, a dedicated workspace, in-suite laundry, and free parking.
Oakville Oasis: Modern 4br Townhouse With Chic Amenities! - Oakville
Oakville
08/04 – 08/12
$425/nighttotal: $3400 (8 )

Oakville Oasis: Modern 4br Townhouse With Chic Amenities!

4 3
apartment , Milton
This Oakville vacation home, near Memorial Park, Joshua Creek Heritage Art Centre, and Sheridan College (all within 3 miles), offers easy access to Oakville and Milton attractions.
This four-bedroom, three-bathroom house sleeps eight guests and includes a fully equipped kitchen, in-unit laundry, and is close to Glen Abbey Golf Course and the Canadian Golf Hall of Fame (within 6 miles).
Private One Bedroom Suite.   B And B On Main Floor - Oakville
9.7 41 reviews
Oakville
07/06 – 07/27
$71/nighttotal: $1491 (21 )

Private One Bedroom Suite. B And B On Main Floor

1 1
house , Milton
This home is located in Oakville, just a short drive from Milton and close to major highways, shopping, grocery stores, and the Oakville Hospital. The house has excellent user, location, and cleanliness ratings, making it a great choice for travelers. This one-bedroom home comfortably sleeps one guest and features a private back yard entrance, a full kitchen in the basement, and a private en-suite bathroom. Amenities include free wifi, Netflix, a comfortable couch, a coffee table, and a 50-inch TV.
©2026 cozycozy.com