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Oakville vacation rentals
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Best Vacation rentals and Airbnb offers in Oakville

Browse Vacation Rentals in the Historic District of Oakville

Stay in downtown Oakville to keep top attractions within walking distance. Browse our central vacation rentals and find your perfect base.

Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks - Oakville
10 2 reviews

Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks

house, Toronto
This Oakville home offers a convenient base, located 16 miles from the Mississauga Convention Center and within 20-22 miles of Toronto landmarks including BMO Field, Rogers Centre, and the CN Tower.
This house accommodates up to 7 guests and features 2 bathrooms, air conditioning, internet, a full kitchen, a balcony, and free private parking.
Modern Luxe Home | 2br | Balcony | Parking - Oakville
10 9 reviews

Modern Luxe Home | 2br | Balcony | Parking

apartment, Toronto
This recently renovated two-bedroom condo in Oakville offers convenient access to Toronto, located just 15 miles away, and is a short 20-mile drive to Niagara Falls, with shopping, dining, and transit within walking distance.
This pet-friendly residence accommodates up to four guests and features a fully equipped kitchen, in-unit laundry, high-speed Wi-Fi, air conditioning, a private balcony, and dedicated workspaces.
Modern And Comfortable Basement Suite - Oakville
9.9 39 reviews

Modern And Comfortable Basement Suite

apartment, Toronto
This two-bedroom, one-bathroom private basement suite in Toronto offers a secluded stay with its own entrance and laundry facilities, conveniently located near shopping centers and diverse dining options.
This independent apartment accommodates up to four guests with air conditioning, internet, and parking, providing a comfortable base for exploring the city.
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 condo offers a quiet residential district experience, providing a peaceful retreat with convenient access to local amenities. The 6-bedroom, 3-bathroom residence accommodates up to 6 guests and features air conditioning and a kitchen for a comfortable family stay.

Best Oakville vacation rentals with air conditioning

Escarpment Views - Luxury 1br Condo - Resort-style Amenities In North Burlington - Oakville
8.0 1 review

Escarpment Views - Luxury 1br Condo - Resort-style Amenities In North Burlington

apartment, Hamilton
This one-bedroom condo in Burlington offers escarpment views, located 20 miles from Hamilton International Airport, 21 miles from Mississauga Convention Center, and 28 miles from BMO Field.
This luxurious apartment features a spacious living room, a modern kitchen with a refrigerator, microwave, and dishwasher, air conditioning, free WiFi, and a sauna, accommodating up to three guests.
Lovely 2-bedroom Basement Unit With Free Parking - Oakville
9.3 117 reviews

Lovely 2-bedroom Basement Unit With Free Parking

apartment, Milton
This Milton apartment rental is conveniently located 4.3 miles from the Oakville GO station, providing easy access to Toronto and Niagara Falls, and just 0.6 miles from a bus stop.
This two-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen (fridge, freezer, microwave), air conditioning, a garden, parking, and excellent security with external cameras; nearby attractions include the Milton Historical Society Museum (distance unspecified).
Beautiful Pond View Town - Oakville
No reviews

Beautiful Pond View Town

apartment, Milton
This Milton house rental boasts a convenient location near Highways 401, 403, and 407, placing it within easy reach of Costco, Walmart, Square One Shopping Centre, and Coronation Park.
The 4-bedroom, 3-bathroom home sleeps 8 guests, features a fully equipped kitchen with stainless steel appliances, a garden, and air conditioning, making it ideal for families or groups visiting the Milton area.
Charming Oakville Getaway - Oakville
10 1 review

Charming Oakville Getaway

apartment, Milton
This Oakville condo is located 14 miles from the Mississauga Convention Centre and 20 miles from BMO Field, Budweiser Stage, and Exhibition Place.
This spacious 5-bedroom, 4-bathroom condo accommodates up to 17 guests and includes air conditioning, Wi-Fi, a balcony, a terrace, and private parking.

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.

Popular destinations

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.

Modern Luxury Designer Home The Poshest Neighbourhood In Canada - Oakville
No reviews

Modern Luxury Designer Home The Poshest Neighbourhood In Canada

apartment, Toronto
This 4-bedroom, 3-bathroom designer rental house in West Oakville offers proximity to Lake Ontario, located just a short drive from Square One Shopping Centre and Toronto Premium Outlets.
This fully furnished luxury estate accommodates up to 8 guests and features a private backyard with a pool and BBQ, a home cinema projector, and 5 free parking spaces, with kayaking, boating, cycling, and hiking opportunities nearby.
The Oakville House - Oakville
No reviews

The Oakville House

apartment, Milton
This Oakville House offers a 3-bedroom rental in Oakville, 15 miles from the Mississauga Convention Center and 22 miles from BMO Field.
This spacious 2500 sq ft apartment accommodates up to 11 guests with air conditioning, a full kitchen including a dishwasher, three bathrooms, a private terrace, and onsite parking.
Spacious 2 Bedrooms 2 Bathrooms With Cozy Charm Plus 1 Parking - Oakville
No reviews

Spacious 2 Bedrooms 2 Bathrooms With Cozy Charm Plus 1 Parking

apartment, Milton
This Mississauga apartment, located approximately 15 miles from the Mississauga Convention Centre and 25 miles from Toronto attractions such as BMO Field and Exhibition Place, offers convenient access to major landmarks. This one-bedroom, one-bathroom rental unit features 90 square feet of space, a balcony, free parking, Wi-Fi, and in-unit laundry.
Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville - Oakville
No reviews

Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville

house, Toronto
Accommodation. Your accommodation will be based in Toronto.
Services and facilities: a kitchen, a fridge and a dish washer. This house in Toronto also has a terrace!

Top Vacation Rentals for Families in Oakville

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

@Oakville South- 2 Bed And 1 Bath - Oakville
No reviews

@Oakville South- 2 Bed And 1 Bath

apartment, Toronto
This private suite is located in the prestigious South Oakville neighborhood, just a short distance from Downtown Oakville's waterfront, fine dining, and luxury boutiques.
This 2-bedroom, 1-bathroom apartment accommodates up to 3 guests and offers a hotel-caliber experience with a private garden, air conditioning, and a full kitchen with a dishwasher.
Luxury Modern Retreat: W/ Sauna & Modern Amenities - Oakville
10 2 reviews

Luxury Modern Retreat: W/ Sauna & Modern Amenities

apartment, Toronto
This spacious Erin Mills, Mississauga vacation rental is a short drive from Toronto, offering easy access to Lake Ontario and attractions like the Benares Historic House and Bradley Museum.
This 2,600-square-foot home features a four-bedroom, four-bathroom layout, comfortably accommodating up to ten guests and including amenities such as a fully equipped kitchen, high-speed internet, and a private garden with parking.
Spacious House With Pond View And Jacuuzi - Oakville
10 1 review

Spacious House With Pond View And Jacuuzi

apartment, Toronto
This newly furnished 4-bedroom townhome is located in the peaceful Joshua Creek neighborhood of Oakville, offering convenient access to major highways (403, 407, QEW) and proximity to grocery stores, restaurants, walking trails, and parks.
This pet-friendly, family-friendly townhouse accommodates up to 10 guests and features 4 bedrooms, 3 bathrooms, a modern gourmet kitchen with stainless steel KitchenAid appliances, a private patio with a hot Jacuzzi and BBQ grill, and ample parking including a 2-car garage.
Oakville Hottub Family Retreat - Oakville
9.8 21 reviews

Oakville Hottub Family Retreat

apartment, Toronto
This 5-bedroom, 2-bathroom house is located in a quiet Oakville neighborhood, offering easy access to parks, shops, and public transit for convenient trips to downtown Toronto, approximately 20 miles away.
This spacious residence accommodates up to 12 guests with a fully equipped kitchen, in-unit laundry, a private deck with a hot tub, and high-speed Wi-Fi, all within 1 mile of grocery stores, parks, and restaurants.

Best Oakville vacation rentals with parking

Live In Lux - Oakville
10 17 reviews

Live In Lux

apartment, Milton
Spacious Private Suite | King Bed - Oakville
9.8 43 reviews

Spacious Private Suite | King Bed

apartment, Milton
Cozy Basement Apartment In Oakville - Oakville
9.7 121 reviews

Cozy Basement Apartment In Oakville

apartment, Milton
5 Bedroom Beautiful Home - Oakville
No reviews

5 Bedroom Beautiful Home

apartment, Milton

Compare Luxury Vacation Rentals in Oakville

Experience the best of the city in a luxury vacation rental in Oakville, where high-end design meets a prime location.

Stunning Unit In Heart Of Joshua Creek, Oakville - Oakville
9.2 10 reviews

Stunning Unit In Heart Of Joshua Creek, Oakville

apartment, Toronto

Our Favorite Pet-Friendly Vacation Rentals in Oakville

Experience a pet-friendly stay in Oakville with vacation rentals located steps away from city dog parks and walking trails.

Stylish 2br Condo | Gym | Free Parking - Oakville
10 1 review

Stylish 2br Condo | Gym | Free Parking

apartment, Hamilton
Bungalow-3 Car Parking-big Backyard-bbq-ping Pong - Oakville
9.8 60 reviews

Bungalow-3 Car Parking-big Backyard-bbq-ping Pong

apartment, Hamilton
*Family Haven* Renovated 3br  Backyard  Parking - Oakville
No reviews

*Family Haven* Renovated 3br Backyard Parking

apartment, Hamilton
Hidden Gem Close To Everything-shopping & Lake - Oakville
7.2 5 reviews

Hidden Gem Close To Everything-shopping & Lake

apartment, Toronto

Explore Vacation Rentals with a Pool in Oakville

An Oakville vacation rental with a pool ensures a refreshing swim in the heart of the city is always an option.

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
Modern Cozy Bungalow - Oakville
10 1 review

Modern Cozy Bungalow

apartment, Toronto
Pool Retreat In Oakville - Oakville
9.5 130 reviews

Pool Retreat In Oakville

apartment, Toronto
Modern Luxury Designer Home In Oakville - Oakville
No reviews

Modern Luxury Designer Home In Oakville

apartment, Toronto

Search Vacation Rentals with Jacuzzi in Oakville

Coming home to a private hot tub after a day of urban exploration completely transforms your Oakville experience.

Whole House New Luxury Kitchen5 Bedrooms 5 Baths - Oakville
10 1 review

Whole House New Luxury Kitchen5 Bedrooms 5 Baths

house, Milton
Luxurious House With Pond View And Jacuzzi - Oakville
9.6 22 reviews

Luxurious House With Pond View And Jacuzzi

apartment, Milton
Luxurious House With Pond View And Jacuzzi - Oakville
No reviews

Luxurious House With Pond View And Jacuzzi

apartment, Milton
Luxury Modern Retreat With Sauna & Modern Amenities - Oakville
10 1 review

Luxury Modern Retreat With Sauna & Modern Amenities

house, Toronto
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