Holiday Rentals in Oakville

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Oakville holiday rentals
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664 Holiday Rentals and Airbnb in Oakville

Best family friendly Oakville holiday rentals

Among the 664 accommodations in Oakville, here are the 3 best family friendly rentals

Luxury Oakville Home, Hot Tub, Fireplace, New Home - Oakville
10 1 review
Oakville
28/12 – 31/12
NZ$658/nighttotal: NZ$1974 (3 )

Luxury Oakville Home, Hot Tub, Fireplace, New Home

4 2
house , Milton
This luxurious property is situated in Oakville, just 24 kilometres from the Mississauga Convention Centre, 35 kilometres from BMO Field, and 37 kilometres from Budweiser Stage. The home has received excellent ratings for its location, cleanliness, and overall user experience.
This four-bedroom home is spacious and comfortable, with a floor area of 229 square metres and a guest capacity of 10. The property offers a range of amenities, including a private hot tub, outdoor dining area, fireplace, fully equipped kitchen, free Wi-Fi, washer and dryer, and a peaceful garden.
4br Luxury Close To Lake, 30 Mins Toronto/niagara - Oakville
9.1 13 reviews
Oakville
01/07 – 31/07
NZ$391/nighttotal: NZ$11730 (30 )

4br Luxury Close To Lake, 30 Mins Toronto/niagara

1 4
apartment , Toronto
This luxurious bungalow is located in a prestigious neighbourhood in the Greater Toronto Area, just a short drive from Lake Ontario and within easy reach of both Toronto and Niagara Falls, making it an ideal base for exploring the region. The spacious property boasts three bedrooms, three bathrooms, and a large recreation room with a wet bar, comfortably accommodating up to ten guests and offering plenty of space for family gatherings.
Two Bedroom Cozy Bsmt Home In Prime Location Including Parking & Laundry Room! - Oakville
9.0 8 reviews
Oakville
08/08 – 03/10
NZ$161/nighttotal: NZ$9016 (56 )

Two Bedroom Cozy Bsmt Home In Prime Location Including Parking & Laundry Room!

2 2
apartment , Toronto
This Mississauga basement flat, near the 403, 401 and QEW motorways, is conveniently located approximately 6 minutes from Ridgeway Plaza and 12 minutes from Clarkson GO station, offering easy access to Toronto Pearson International Airport (approximately 32km).
The self-contained two-bedroom property sleeps four, features a fully equipped kitchen, in-suite laundry, free parking, and a private entrance with 24/7 self check-in; nearby parks, pharmacies, and restaurants provide ample local amenities.

Best Oakville holiday rentals with parking

Luxury Modern Retreat With Sauna & Modern Amenities - Oakville
Oakville
10/07 – 15/07
NZ$1273/nighttotal: NZ$6365 (5 )

Luxury Modern Retreat With Sauna & Modern Amenities

4 2
house , Toronto
This Mississauga property, situated 19 kilometres from Toronto Pearson International Airport and 18 kilometres from the Mississauga Convention Centre, offers convenient access to major attractions.
The 250 square metre modern home boasts four bedrooms, four bathrooms, sleeps nineteen guests, and includes a fully equipped kitchen, sauna, garden, terrace, parking, and Wi-Fi.
Smart & Cute 1br Basement Apartment-milton - Oakville
9.4 12 reviews
Oakville
23/07 – 14/09
NZ$73/nighttotal: NZ$3869 (53 )

Smart & Cute 1br Basement Apartment-milton

1 2
apartment , Milton
This Milton basement flat is conveniently located 24km from Mississauga and 47km from Toronto's BMO Field and Budweiser Stage, offering easy access to major roads.
The self-contained apartment sleeps three, features a fully equipped kitchen, free Wi-Fi, private parking, and an electric vehicle charging point, plus a flat-screen TV.
Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville - Oakville
10 3 reviews
Oakville
28/12 – 31/12
NZ$440/nighttotal: NZ$1320 (3 )

Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville

2 2
house , Toronto
This modern bungalow is located in Oakville, a suburb of Toronto, situated around 40 kilometres from downtown attractions like BMO Field and Budweiser Stage. The property has received excellent ratings for location, cleanliness, and overall experience, making it a comfortable and convenient choice for travellers.
The two-bedroom, two-bathroom house can comfortably accommodate up to four guests. The fully equipped kitchen, private garden, free Wi-Fi, and parking make it easy to relax and enjoy your stay.
Contemporary, Quite Two Bedroom Home ! - Oakville
9.9 76 reviews
Oakville
06/07 – 12/07
NZ$398/nighttotal: NZ$2388 (6 )

Contemporary, Quite Two Bedroom Home !

2 2
apartment , Toronto
This two-bedroom flat is located in Mississauga, just 4 kilometres from Oakville and easily accessible via the 403 Highway and public transport. The property has received excellent ratings for its cleanliness, location, and overall experience.
The flat is ideal for families or groups of up to four people, offering a comfortable living space with a fully equipped kitchen, a spacious living area, and two modern bathrooms. Guests can enjoy a range of amenities including air conditioning, a washing machine and dryer, and a garden, making it a convenient and enjoyable base for exploring Toronto.

Frequently asked questions about holiday rentals in Oakville

  • What are the top family-friendly attractions in Oakville?

    The Oakville Public Library is a great place to take the kids, with lots of fun activities and events. The Oakville Museum also has a children's section with interactive exhibits. For outdoor fun, you can go to Coronation Park, which has a playground, splash pad, and plenty of green space.
  • What are the best Airbnb and holiday rentals in Oakville?

    Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are among the best Airbnb and holiday rentals in Oakville.

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

    The best time to book a vacation rental in Oakville depends on your preferences. If you want warm weather and outdoor activities, then July and August are popular months. For a quieter and more affordable experience, consider booking in the shoulder seasons, like spring or autumn.
  • 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 are the best budget-friendly activities in Oakville?

    Oakville has plenty of free or low-cost activities to enjoy. You can take a stroll along the waterfront, visit the Oakville Museum, or explore the many parks and green spaces. You can also check out the farmers market on Saturdays for fresh produce and local crafts.
  • What are the best holiday rentals with a pool in Oakville?

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

    For a taste of local cuisine, try the Oakville Fish Market, which serves fresh seafood. The Queen's Plate Restaurant is also a popular spot for traditional Canadian dishes. If you're looking for something a bit more casual, the Oakville Farmers Market has a variety of food vendors offering local produce and baked goods.
  • 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.

  • Are there pet-friendly attractions in Oakville?

    Yes, many of Oakville's parks and green spaces are pet-friendly. You can also take your furry friend for a walk along the waterfront or visit the Oakville Museum, which welcomes well-behaved dogs.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakville?

    The best holiday 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 benefits of choosing a vacation rental in Oakville?

    Vacation rentals offer more space and privacy than hotels, and they can be a great option for families or groups. They also often come with amenities like kitchens and laundry facilities, which can save you money on dining out and laundry costs.
  • What are the top sports attractions and facilities in Oakville?

    Oakville has a number of sports facilities, including the Oakville Soccer Club, the Oakville Tennis Club, and the Oakville Golf Club. You can also catch a hockey game at the Oakville Hawks, the town's junior hockey team.

Destinations nearby

Best Oakville holiday rentals with a balcony

Luxary Villa With Pool, Sauna, Hot Tub Sleeps 12 - Oakville
Oakville
26/08 – 06/09
NZ$1270/nighttotal: NZ$13970 (11 )

Luxary Villa With Pool, Sauna, Hot Tub Sleeps 12

1 2
house , Toronto
This luxury villa in Oakville is situated approximately 35 kilometres from the Mississauga Convention Centre and Toronto Pearson International Airport, with major Toronto attractions such as BMO Field and Rogers Centre located within a 40-42 kilometre radius.
This spacious 279 square metre dwelling accommodates up to 27 guests, featuring one separate bedroom, four bathrooms, a fully equipped kitchen, air conditioning, a private swimming pool, sauna, hot tub, and direct terrace access, with complimentary WiFi and private parking including an electric vehicle charging station.
Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks - Oakville
Oakville
06/07 – 12/07
NZ$364/nighttotal: NZ$2184 (6 )

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

2 2
house , Toronto
This modern luxe residence is situated in Oakville, 26 kilometres from the Mississauga Convention Centre and 32-35 kilometres from Toronto landmarks such as BMO Field, Rogers Centre, and the CN Tower, with Toronto Pearson International Airport located 26 kilometres away.
This property offers free WiFi, private parking, air conditioning, a kitchen, and a balcony, accommodating up to seven guests with a check-out time of 11:00 AM.
*Cozy* 1 Bedroom Home Near Waterfront/trails - Oakville
Oakville
28/12 – 31/12
NZ$451/nighttotal: NZ$1353 (3 )

*Cozy* 1 Bedroom Home Near Waterfront/trails

1 2
apartment , Hamilton
This newly renovated one-bedroom flat is situated in Burlington, a short drive from the lakefront and Burlington Pier, offering convenient access to amenities.
This private suite accommodates two guests and features a fully equipped kitchen, high-speed WiFi, in-unit laundry, and two driveway parking spaces, with pets welcome.
The Oakville House - Oakville
Oakville
28/08 – 04/09
NZ$1482/nighttotal: NZ$10374 (7 )

The Oakville House

3 3
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.

Best Oakville holiday rentals with air conditioning

Luxurious Apartment With King Bed - Oakville
10 8 reviews
Oakville
10/08 – 15/08
NZ$350/nighttotal: NZ$1750 (5 )

Luxurious Apartment With King Bed

1 2
apartment , Toronto
This one-bedroom flat is located in a quiet, fashionable district of Toronto, a short walk from major attractions and entertainment venues.
This family-friendly apartment offers a fully equipped kitchen, air conditioning, Wi-Fi, and on-site parking, with a guest capacity of two.
Home Swap Opportunity!! Modern Home Quiet Area. - Oakville
Oakville
27/06 – 04/07
NZ$544/nighttotal: NZ$3808 (7 )

Home Swap Opportunity!! Modern Home Quiet Area.

3 2
apartment , Toronto
Accommodation for up to 4 guests. You will be based in Toronto.
Services and facilities: a kitchen, a garden and a washing machine. This apartment in Toronto also has air conditioning!
2 Bedroom $80/night Mississauga (30 Days Booking) - Oakville
9.6 105 reviews
Oakville
08/07 – 07/08
NZ$165/nighttotal: NZ$4950 (30 )

2 Bedroom $80/night Mississauga (30 Days Booking)

1 4
apartment , Toronto
This basement flat is located in a suburb of Toronto, a 35-minute drive or train ride from the city centre and a 25-minute drive from the airport. The property has received excellent ratings for cleanliness, location and user experience.
This self-contained apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. It includes modern amenities such as air conditioning, heating, a TV with Lodge, a fully equipped kitchen, free WiFi, and Netflix, as well as a shared parking space and a coin laundry.
Oakville Bright&airy 4-bdrm Home! Close To Highway 403&qew! - Oakville
Oakville
01/07 – 31/07
NZ$373/nighttotal: NZ$11190 (30 )

Oakville Bright&airy 4-bdrm Home! Close To Highway 403&qew!

4 4
apartment , Milton
This luxury townhome in Oakville offers tranquil pond views and is located approximately 5 kilometres from Benares Historic House and Oakville Museum, with convenient access to attractions such as Putting Edge and Glen Abbey Golf Course.
This spacious 232 square metre residence features four bedrooms, three and a half bathrooms, and accommodates up to eight guests, with amenities including air conditioning, internet, and private two-car garage parking.
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