Vacation Rentals in Oakville

871 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Oakville vacation rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

871 Vacation rentals and Airbnb in Oakville

Best family friendly Oakville vacation rentals

Among the 871 accommodations in Oakville, here are the 4 best family friendly rentals

Spacious House With Pond View And Jacuuzi - Oakville
10 1 review

Spacious House With Pond View And Jacuuzi

apartment, Toronto
This four-bedroom, three-bathroom flat is located in Joshua Creek, Oakville, offering convenient access to major motorways (403, 407, QEW) and a brief drive to local amenities, approximately 25 kilometres west of downtown Toronto.
This spacious accommodation accommodates up to ten guests, featuring a gourmet kitchen with stainless steel KitchenAid appliances, a private patio with a hot Jacuzzi and BBQ, a laundry room with an LG washer and dryer, and parking for four vehicles, including a two-car garage.
South Oakville Apartment Near Lake (Basement) - Oakville
9.6 20 reviews

South Oakville Apartment Near Lake (Basement)

apartment, Toronto
This Oakville basement flat, a 15-minute walk from Lake Ontario and near the QEW and Trafalgar GO Station, offers easy access to both Toronto (30-minute drive) and downtown Oakville.
The self-contained one-bedroom suite, sleeping two, features a fully equipped kitchen, private laundry, high-speed Wi-Fi, a 55-inch Smart TV, dedicated parking, and was newly furnished in 2025.
Luxury Stay, Cozy & Bright, Nature's Art - Oakville
9.9 42 reviews

Luxury Stay, Cozy & Bright, Nature's Art

apartment, Toronto
This five-bedroom, three-bathroom Oakville apartment, a short drive from Toronto, offers easy access to local amenities; precise distances to Toronto landmarks are not specified.
Sleeping up to twelve guests, this spacious property boasts a fully equipped kitchen, air conditioning, parking, and excellent internet access; bird feeders outside provide a tranquil setting.
Designer 4br Basement Aymond Suites Oakville - Oakville
No reviews

Designer 4br Basement Aymond Suites Oakville

apartment, Milton
This Oakville flat is located 22.5 kilometres from Toronto Pearson International Airport and 20.9 kilometres from the Mississauga Convention Centre, offering convenient access for travellers.
This spacious 177 square metre apartment accommodates up to 17 guests with one bedroom and two bathrooms, featuring a fully equipped kitchen, kitchenette, in-unit washing machine, complimentary WiFi, air conditioning, and access to an on-site fitness room and an electric vehicle charging station, with nearby hiking trails for outdoor pursuits.

Best Oakville holiday rentals with parking

South Oakville Bliss Haven Monthly Stays Only - Oakville
8.5 2 reviews

South Oakville Bliss Haven Monthly Stays Only

house, Toronto
This five-bedroom house, ideal for large groups, is situated in South Oakville, approximately 32-37 kilometres from Toronto attractions including the Mississauga Convention Centre, BMO Field, Budweiser Stage, and Exhibition Place.
The 13-square-metre property boasts three bathrooms, a fully equipped kitchen, private parking, Wi-Fi, and a balcony with barbecue facilities, comfortably accommodating up to 19 guests.
Tranquil Haven Retreat - Oakville
9.5 16 reviews

Tranquil Haven Retreat

apartment, Toronto
This Toronto property, ideal for families, sleeps up to 10 and offers three bedrooms, one bathroom, and a fully equipped kitchen including a dishwasher; precise location within Toronto is unspecified.
The self-catering house boasts a garden, air conditioning, internet access, and pets are welcome; a private swimming pool is available at an extra cost.
Stylish New 2br Suite W/ Parking - Oakville
9.8 20 reviews

Stylish New 2br Suite W/ Parking

apartment, Milton
This modern two-bedroom apartment in Oakville offers convenient access to Milton via the nearby highway and GO Train station, reducing travel time to the town centre.
The 2-bedroom flat sleeps four guests comfortably, boasting a fully equipped kitchen, in-unit laundry, high-speed internet, and free on-site parking; self check-in is available 24/7.
Lovely 2 Bedroom Condo - Oakville
No reviews

Lovely 2 Bedroom Condo

apartment, Toronto
This apartment is located in Oakville, a town just west of Toronto, a 10-minute walk from the bustling downtown area with its many restaurants. You can easily reach Toronto by car or public transport, making this a convenient base for exploring the city. This two-bedroom flat offers ample space for four guests and includes two bathrooms. The apartment is equipped with modern amenities such as a fully equipped kitchen, comfortable furniture, laundry facilities, and a swimming pool, fitness centre, and parking.

Frequently asked questions about holiday rentals in Oakville

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

    For a vacation rental, I'd recommend the Old Oakville neighbourhood. It's charming, with lots of Victorian architecture and a great selection of restaurants and shops. It's also within walking distance of the waterfront and the Oakville Museum.
  • 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.

  • 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, like spring or autumn. You'll avoid the crowds and the prices are usually lower.
  • 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.

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

    Oakville has a lot of great events throughout the year. In the summer, there's the Oakville Jazz Festival, which is always a big hit. And in the fall, there's the Oakville Fall Fair, which is a great place to experience local culture. If you're looking for something a bit different, you could check out the Bronte Creek Provincial Park, they have a lot of events throughout the year.
  • What are the best vacation rentals with a pool in Oakville?

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

    If you're looking for local dishes, I'd recommend checking out The Oakville Chop House. They're known for their steaks and their Canadian-inspired menu. Another great option is The Stone House, they have a great selection of local seafood.
  • 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 walking or cycling routes in Oakville?

    Oakville has a lot of great walking and cycling routes. The Waterfront Trail is a popular option, it stretches for kilometers along the lake. You could also try the Oakville Creek Trail, it's a bit more off the beaten path, but it's really scenic.
  • 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 Luxurious1 Br Condo In Downtown Mississauga .

  • Are there pet-friendly attractions in Oakville?

    Yes, Oakville is quite pet-friendly. You can bring your dog to Coronation Park, they have a designated off-leash area. And most of the restaurants along the waterfront have outdoor patios where you can enjoy a meal with your furry friend.
  • What are the benefits of choosing a vacation rental in Oakville?

    Vacation rentals offer a lot of benefits, like more space and privacy compared to a hotel. You can also often find rentals with amenities like a kitchen and laundry facilities, which can be very convenient. And of course, you'll have the chance to experience local life in a more authentic way.

Popular destinations

Best Oakville holiday rentals with a balcony

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville - Oakville
No reviews

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville

apartment, Milton
This 3-bedroom townhouse is located in Oakville, just 27 kilometres from Mississauga Convention Centre and Toronto Pearson International Airport, and 37 kilometres from BMO Field and Budweiser Stage. The property enjoys excellent location and cleanliness ratings, with guests consistently praising its comfort and convenience.
The townhouse offers 172 square metres of space, comfortably accommodating up to 6 guests. A fully equipped kitchen, private terrace, air conditioning, free Wi-Fi, satellite TV, and parking are all provided for your enjoyment.
Modern Luxury Home Near Bronte Harbour & Oakville Downtown - Oakville
No reviews

Modern Luxury Home Near Bronte Harbour & Oakville Downtown

house, Toronto
This spacious five-bedroom detached house is situated in Oakville, offering a peaceful setting 37 kilometres from the Mississauga Convention Centre and 42 kilometres from BMO Field, with the marina a mere 720 metres walk away.
The property boasts 19 square metres of floor area, accommodates up to 27 guests, and features a fully equipped kitchen, a fireplace, an indoor play area, a balcony, a garden, private parking, and free WiFi.
The Oakville House - Oakville
No reviews

The Oakville House

apartment, Milton
This spacious three-bedroom flat is located in Oakville, 24 kilometres from the Mississauga Convention Centre and 24 kilometres from Toronto Pearson International Airport, offering city views from its patio.
The 232 square metre residence accommodates up to 11 guests with air conditioning, a kitchen equipped with a fridge and dishwasher, a terrace with garden views, and private parking, with proximity to the Budweiser Stage, Exhibition Place, Rogers Centre, and CN Tower within a 38 kilometre radius.
Modern Townhouse Rooftop Vibes - Oakville
1.0 1 review

Modern Townhouse Rooftop Vibes

house, Milton
This Milton house, sleeping seven guests, offers one bedroom and three bathrooms within an 111 square metre space and includes free private parking; its precise location within Milton requires further clarification to determine proximity to local landmarks.
The property boasts a fully equipped kitchen, free Wi-Fi, a terrace/balcony, air conditioning, and an outdoor fireplace, perfect for relaxing evenings.

Best Oakville holiday rentals with air conditioning

South Oakville Bliss Haven: Spacious 3 Bedroom Home With Kitchen And Terrace - Oakville
No reviews

South Oakville Bliss Haven: Spacious 3 Bedroom Home With Kitchen And Terrace

apartment, Toronto
This West Oakville flat is located approximately 32 kilometres from Toronto Pearson International Airport and 36 kilometres from BMO Field, offering a residential setting with straightforward access to city attractions.
This spacious accommodation, ideal for up to 10 guests, features five bedrooms, three bathrooms, two kitchens, air conditioning, free Wi-Fi, and is situated near family-friendly activities and a local mini-market.
Executive Townhouse Oakville - Oakville
10 20 reviews

Executive Townhouse Oakville

apartment, Milton
This three-bedroom, three-bathroom house is conveniently located near the junction of Dundas Street and Trafalgar Road in Milton, offering easy access to the 403, QEW, 407 and 401 highways, approximately 48-72 km from Toronto and 130 km from Niagara Falls.
The property sleeps six guests and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, air conditioning, parking, internet access, and is pet-friendly, making it ideal for family or group trips exploring Milton and its surroundings.
Free Parking, Full Kitchen/bath, Wrkspc, Sep Ent - Oakville
9.8 12 reviews

Free Parking, Full Kitchen/bath, Wrkspc, Sep Ent

apartment, Toronto
This basement flat is located in a convenient area of Toronto, less than 1 kilometre from a grocery store, pharmacy, bakery, and restaurants, and just an hour's drive from Niagara Falls. The apartment is ideal for couples or solo travellers seeking a comfortable and affordable base for exploring the city.
The property offers a well-equipped kitchen with a fridge and microwave, a dedicated workspace for remote working, a comfortable living area with a TV, books, and games, and a bedroom with a queen-size bed. Guests can also enjoy the convenience of a washing machine and dryer, air conditioning, and free Wi-Fi.
Spacious Brand New Townhome - Oakville
9.7 29 reviews

Spacious Brand New Townhome

apartment, Toronto
This newly constructed townhome is located in Oakville, a residential community situated approximately 35 kilometres west of downtown Toronto, offering a peaceful alternative to city centre living.
This unfurnished residence accommodates up to eight guests with four bedrooms and three bathrooms, featuring air conditioning, parking, and a kitchen, making it suitable for professionals working in the Greater Toronto Area.
©2026 cozycozy.com