Holiday Rentals in Oakville

664 available vacation rental offers

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Oakville holiday rentals
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Oakville holiday rentals: compare the best deals

Best family friendly Oakville holiday rentals

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

Feel At Home - Oakville
9.9 28 reviews
Oakville
08/26 – 09/06
HK$1341/nighttotal: HK$14751 (11 )

Feel At Home

2 2
apartment , Milton
This family-friendly, two-bedroom basement flat is situated in the Joshua Creek area of Oakville, approximately 6.4km from Oakville GO station, providing easy access to Toronto.
The 2-bedroom, 1-bathroom self-catering property sleeps up to 5 guests and features a well-equipped kitchen, high-speed Wi-Fi, driveway parking, and is close to Oakville Place shopping mall, Longo's and Metro supermarkets.
Immaculate House 5 Bdr 3.5 Bath - Oakville
9.9 24 reviews
Oakville
08/28 – 09/04
HK$2657/nighttotal: HK$18599 (7 )

Immaculate House 5 Bdr 3.5 Bath

1 9
apartment , Hamilton
This Hamilton family-friendly house, perfect for groups up to 11, offers four bedrooms and three bathrooms, along with amenities including internet, parking, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher.
The property boasts air conditioning and allows pets, but further details regarding its precise location within Hamilton, proximity to attractions such as Hamilton Gardens or the Waikato Museum, and the property's size and layout are needed.
Free Parking, Full Kitchen/bath, Wrkspc, Sep Ent - Oakville
10 11 reviews
Oakville
07/23 – 09/14
HK$745/nighttotal: HK$39485 (53 )

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

1 2
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.

Best Oakville holiday rentals with parking

Spacious Basement In Oakville - Oakville
9.0 2 reviews
Oakville
08/28 – 09/04
HK$1590/nighttotal: HK$11130 (7 )

Spacious Basement In Oakville

2 3
apartment , Toronto
This spacious Oakville basement flat, approximately 26-35 km from Toronto attractions such as the CN Tower and Rogers Centre, offers a peaceful alternative to the city centre.
The 79 square metre, two-bedroom property sleeps seven, includes a fully equipped kitchen with dishwasher, free Wi-Fi, private parking, and a washing machine; Toronto Pearson International Airport is 27 km away.
Luxury Basement Apartment In Oakville Monthly Stays Only - Oakville
9.5 23 reviews
Oakville
07/23 – 09/14
HK$935/nighttotal: HK$49555 (53 )

Luxury Basement Apartment In Oakville Monthly Stays Only

1 2
apartment , Milton
This luxury basement flat is located in Oakville, just 35 kilometres from both BMO Field and Budweiser Stage in Toronto, offering easy access to the city's attractions. It has received excellent ratings for location, cleanliness and user experience.
The self-catering flat, with a floor area of 11 square metres, can accommodate up to four guests. It offers a range of amenities, including a fully equipped kitchen, a washing machine, free Wi-Fi, a satellite flat-screen TV, a fireplace, a seating area, access to darts and tennis, a fitness room, and outdoor play equipment.
Private Home : Kitchen-bath-laundry-gym-parking - Oakville
9.8 35 reviews
Oakville
08/08 – 10/03
HK$567/nighttotal: HK$31752 (56 )

Private Home : Kitchen-bath-laundry-gym-parking

1 2
apartment , Toronto
This basement flat is conveniently located just 1.5 kilometres from Sheridan College and White Oaks Secondary School, offering easy access to Superstore, Walmart, Tim Hortons, and bus stations. It has received excellent ratings for user experience, location, and cleanliness.
The flat comfortably accommodates two guests and features a separate entrance for complete privacy. The self-catering flat includes a fully equipped kitchen, laundry facilities, a dedicated exercise space, and free parking on the driveway. Multilingual services in English, Chinese, and Cantonese are available.
Bromsgrove Hideaway - Oakville
10 1 review
Oakville
06/27 – 07/04
HK$1965/nighttotal: HK$13755 (7 )

Bromsgrove Hideaway

4 2
apartment , Toronto
This Clarkson-Lorne Park holiday home in Toronto is situated 1.4 km from Scooter's Roller Palace, within 5 km of Benares Historic House and Oakville Entertainment Centre, and a 15-minute walk from Clarkson Station.
This two-bedroom, two-bathroom property sleeps three guests and offers a fully equipped kitchen, free Wi-Fi, air conditioning, a terrace, garden, spa, fitness centre, and parking; nearby attractions include family-friendly activities and convenient public transport links.

Frequently asked questions about holiday rentals in Oakville

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

    You absolutely must visit the Oakville Museum, which showcases the town's history and art. For stunning views, take a stroll along the Oakville waterfront, where you can admire the lake and the beautiful gardens.
  • 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 neighbourhood is charming with historic houses and shops, and is a great choice for a vacation rental. It's close to the waterfront and many restaurants.
  • 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 top family-friendly attractions in Oakville?

    The Oakville Galleries is a great place to introduce kids to art, while the Oakville Public Library has fun events for families. For some outdoor fun, head to Coronation Park, which has a playground, splash pad, and a large green space.
  • What are the best vacation rentals with a pool in Oakville?

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

    The best time to book is during the shoulder seasons, from April to May or September to October, as the weather is still pleasant and the prices are lower.
  • What are the best rentals for families and kids in Oakville?

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

    The Oakville Jazz Festival in July is a highlight, featuring live music and food stalls. In August, the Oakville Waterfront Festival offers a variety of activities, from boat shows to live entertainment.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakville?

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

    Take a walk or bike ride along the waterfront trail, which offers stunning views of Lake Ontario. You can also visit the Oakville Public Library, which has free events and exhibitions.
  • What are the best restaurants with local dishes in Oakville?

    Try the fish and chips at The Captain's Boil, or enjoy a classic Canadian meal at The Keg Steakhouse + Bar. For something a bit more unique, check out the menu at The Oakville Bistro, which features modern Canadian cuisine.
  • What are the best walking or cycling routes in Oakville?

    The Waterfront Trail is a popular choice for walking and cycling, offering scenic views of Lake Ontario. For a more challenging ride, try the Oakville Creek Trail, which winds its way through the Oakville Creek.
  • Are there pet-friendly attractions in Oakville?

    Yes, many parks in Oakville are dog-friendly, including Coronation Park and Bronte Creek Provincial Park. You can also find dog-friendly patios at some restaurants.
  • What are the benefits of choosing a vacation rental in Oakville?

    Vacation rentals offer more space and privacy compared to hotels. They often come with amenities like kitchens and laundry facilities, making them ideal for families or longer stays.
  • What are the top sports attractions and facilities in Oakville?

    The Oakville Soccer Club offers various programs for all ages. The Oakville Golf Club is a popular destination for golfers, and the Oakville Tennis Club has courts for both casual and competitive players.

Destinations nearby

Best Oakville holiday rentals with a balcony

Stylish 3br 2.5 Bath Townhouse With Patio And Parking - Oakville
Oakville
07/01 – 07/31
HK$3233/nighttotal: HK$96990 (30 )

Stylish 3br 2.5 Bath Townhouse With Patio And Parking

3 2
house , Toronto
This townhouse is situated in Streetsville, approximately 16 kilometres from the Mississauga Convention Centre and 19 kilometres from Toronto Pearson International Airport.
This property offers 125 square metres of living space with three bedrooms and two bathrooms, accommodating up to nine guests with amenities including a dishwasher, microwave oven, fridge, air conditioning, a terrace, balcony, and free private parking.
Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks - Oakville
Oakville
08/28 – 09/04
HK$1851/nighttotal: HK$12957 (7 )

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

2 3
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.
Charming Oakville Getaway - Oakville
Oakville
09/01 – 09/30
HK$1452/nighttotal: HK$42108 (29 )

Charming Oakville Getaway

5 4
apartment , Milton
This five-bedroom, four-bathroom serviced apartment in Oakville offers convenient access to Milton, situated 23 kilometres from the Mississauga Convention Centre and 33 kilometres from Toronto's BMO Field, Budweiser Stage, and Exhibition Place.
The spacious accommodation provides a fully equipped kitchen, air conditioning, a terrace, balcony, free Wi-Fi, and private parking, with a guest capacity of 17.
Luxurious House With Pond View And Jacuzzi - Oakville
Oakville
07/08 – 08/07
HK$2413/nighttotal: HK$72390 (30 )

Luxurious House With Pond View And Jacuzzi

4 4
apartment , Milton
This Oakville holiday home, an 11-minute (17.7km) drive from Lake Ontario and a 13-minute (20.9km) drive from Square One Shopping Centre, offers convenient access to Oakville's attractions.
Sleeping eight guests, the property boasts four bedrooms, four bathrooms, a fully equipped kitchen including a dishwasher and lobster pot, a jacuzzi, and covered parking; nearby activities include Putting Edge mini golf and Glen Abbey Golf Course.

Best Oakville holiday rentals with air conditioning

Luxury 3 Bed Urban Townhome In North Oakville - Oakville
9.9 27 reviews
Oakville
08/28 – 09/04
HK$2348/nighttotal: HK$16436 (7 )

Luxury 3 Bed Urban Townhome In North Oakville

1 3
house , Milton
This three-bedroom Oakville townhouse, near the 401 and 403 motorways, offers easy access to Milton, being a short drive from Oakville GO station and within a 2.4km walk of Superstore and Walmart.
The 3-storey property sleeps six, boasting a fully equipped kitchen with dishwasher, air conditioning, a garden, and is ideally suited for families or groups exploring the local area, with parks, restaurants, and Trafalgar Memorial Hospital nearby.
Luxury Oakville Home, Hot Tub, Fireplace, New Home - Oakville
10 1 review
Oakville
12/28 – 12/31
HK$2996/nighttotal: HK$8988 (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.
Luxury 5br Oakville Home | King Suite & Balcony - Oakville
Oakville
08/28 – 09/04
HK$4930/nighttotal: HK$34510 (7 )

Luxury 5br Oakville Home | King Suite & Balcony

1 9
apartment , Milton
This luxury Oakville residence, a spacious maisonette, is located in a quiet, upscale neighbourhood minutes from the M407, offering convenient access to Milton.
This property features 5 bedrooms accommodating up to 10 guests, a chef's kitchen, open-plan living areas, a private garden, and a dedicated workspace with WiFi, perfect for professionals and families visiting Milton.
Serene Retreat - Cozy + Private! - Oakville
9.3 8 reviews
Oakville
08/01 – 09/30
HK$947/nighttotal: HK$56820 (60 )

Serene Retreat - Cozy + Private!

1 4
apartment , Toronto
This Toronto apartment, located on Grand Oak, offers a private lower-level unit with parking, ideal for exploring the city's attractions; the precise distance to landmarks requires further clarification.
The two-bedroom, one-bathroom flat sleeps five guests and features a fully equipped kitchen, air conditioning, and exclusive outdoor access.
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