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 4 best family friendly rentals

Cozy 2 Bedroom Basement Apart - Oakville
10 4 reviews
Oakville
01/08 – 30/09
94 €/nighttotal: 5640 € (60 )

Cozy 2 Bedroom Basement Apart

1 4
apartment , Toronto
This two-bedroom Toronto apartment, perfect for group trips of up to four guests, is situated in an unspecified area of the city; further details regarding proximity to specific Toronto landmarks such as the CN Tower or the Royal Ontario Museum are needed.
The 1-bathroom flat features a fully equipped kitchen including a fridge, freezer, and dishwasher, air conditioning, parking, and internet access; additional information on the property's size, interior design, and nearby activities is required for a complete description.
Luxury Modern Retreat: W/ Sauna & Modern Amenities - Oakville
10 2 reviews
Oakville
01/07 – 31/07
364 €/nighttotal: 10920 € (30 )

Luxury Modern Retreat: W/ Sauna & Modern Amenities

4 3
apartment , Toronto
This Mississauga Erin Mills holiday home, near Lake Ontario and The Riverwood Conservancy, offers easy access to Toronto, approximately 24 kilometres from the city centre.
This spacious 224 square metre property boasts a four-bedroom, four-bathroom layout sleeping up to ten guests, complete with a fully equipped kitchen, garden, parking, and air conditioning; nearby attractions include Benares Historic House and Playdium.
Designer 4br Basement Suite – Oakville - Oakville
Oakville
01/09 – 28/02
118 €/nighttotal: 21240 € (180 )

Designer 4br Basement Suite – Oakville

1 4
apartment , Milton
This four-bedroom, two-bathroom flat in Oakville offers ample space for up to eight guests, featuring two full kitchens, a private gym, and keyless entry, with on-site parking and fast internet ideal for families or groups visiting Milton. Situated in a family-friendly neighbourhood, this property is conveniently located approximately 1.5 kilometers from the Milton Sports Centre and 3 kilometers from the historic Milton Town Hall, with easy access to local parks and shopping areas.
Apartment Unit - Oakville
9.6 75 reviews
Oakville
28/12 – 31/12
103 €/nighttotal: 309 € (3 )

Apartment Unit

1 2
apartment , Milton
This one-bedroom apartment is situated in a peaceful neighbourhood in Milton, just a 10-minute drive from Lake Ontario and 25-30 minutes from the airport. The apartment has consistently received excellent reviews for its cleanliness, location and overall experience.
This comfortable flat can accommodate up to four guests and features a fully equipped kitchen, a dedicated workspace, a smart TV, and a private outdoor area with a barbecue. Guests also have access to free parking, an EV charging outlet, and a washing machine and dryer.

Best Oakville holiday rentals with parking

Luxury Retreat In Burlington - Oakville
8.0 1 review
Oakville
01/07 – 31/07
146 €/nighttotal: 4380 € (30 )

Luxury Retreat In Burlington

1 4
apartment , Hamilton
This Burlington house, a short drive from Hamilton, offers a tranquil escape for families seeking a base to explore both towns.
The three-bedroom, three-bathroom property boasts a spacious open-plan living, dining, and kitchen area (equipped with fridge, freezer, microwave, and dishwasher), comfortably accommodating up to five guests and including air conditioning.
Serene High-celling Retreat In Upsacle And Safe Neighbourhood - Oakville
Oakville
01/08 – 31/10
68 €/nighttotal: 6188 € (91 )

Serene High-celling Retreat In Upsacle And Safe Neighbourhood

2 3
apartment , Toronto
This Glen Abbey holiday home in Oakville, Ontario, is situated within 2km of Saw-Whet Golf Course and Bronte Creek Provincial Park, and 3km from the Oakville Art Society.
The two-bedroom, one-bathroom property sleeps four guests and offers free Wi-Fi, a fully equipped kitchen including a dishwasher, in-home laundry facilities, and air conditioning.
Apartment ∙ 2 Bedrooms ∙ 4 Guests - Oakville
Oakville
28/12 – 31/12
160 €/nighttotal: 480 € (3 )

Apartment ∙ 2 Bedrooms ∙ 4 Guests

2 2
apartment , Milton
This two-bedroom flat in Halton offers convenient access to Oakville and Mississauga (both 32 kilometres away) and is 56 to 79 kilometres from downtown Toronto, with a GO station 630 metres from the property.
This modern apartment for four guests features a fully equipped kitchen with a dishwasher and microwave, air conditioning, a swimming pool, a jacuzzi, and private parking, providing a comfortable base for exploring the Greater Toronto Area.
Basement Studio In Mississauga - Oakville
10 8 reviews
Oakville
27/06 – 04/07
123 €/nighttotal: 861 € (7 )

Basement Studio In Mississauga

1 1
apartment , Toronto
This private basement studio is located in Clarkson, a short 1.2 kilometre drive from the lake and within easy reach of entertainment venues such as iFLY, Cineplex, and Dave & Buster's.
This self-contained apartment offers accommodation for two guests with one bedroom and one bathroom, featuring essential amenities including internet, a kitchen, air conditioning, and dedicated parking.

Frequently asked questions about holiday rentals in Oakville

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

    Oakville has a lot to offer, but you shouldn't miss the waterfront. Take a stroll along the Oakville Harbour, admire the beautiful sailboats, and enjoy the views of Lake Ontario. For a taste of history, visit the Oakville Museum, which showcases the town's past, and don't forget to check out the charming shops and restaurants in the historic downtown core.
  • 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.

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

    For a vibrant atmosphere, choose a vacation rental in the Old Oakville neighbourhood. It's close to the harbour, has plenty of restaurants and cafes, and is within walking distance of many attractions. If you prefer a quieter stay, consider Bronte Creek, a residential area with parks and trails, and easy access to the lakefront.
  • 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?

    Oakville has plenty for families. The Oakville Museum is a great place to learn about the town's history, and the Oakville Galleries is a fun spot for art lovers of all ages. For some outdoor fun, head to Coronation Park, which has a playground, splash pad, and a scenic walking trail.
  • What are the best holiday rentals with a pool in Oakville?

  • 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. The weather is still pleasant, the crowds are smaller, and the prices are often lower.
  • 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 events or festivals should visitors check out in and around Oakville?

    Oakville has a lively events calendar. The Oakville Jazz Festival in July brings world-class musicians to town, and the Oakville Fall Fair in September is a great family event with live music, food, and entertainment. For a unique experience, visit the Bronte Creek Provincial Park during their annual Renaissance Festival in August.
  • 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 budget-friendly activities in Oakville?

    You can enjoy Oakville without breaking the bank. Take a walk or cycle along the waterfront trail, visit the free Oakville Museum, or explore the many parks and green spaces. For a picnic lunch, grab some fresh produce from the Oakville Farmers' Market.
  • What are the best restaurants with local dishes in Oakville?

    Oakville boasts a diverse culinary scene. For a taste of local seafood, try the fresh oysters at The Fish House. If you're craving a delicious burger, head to The Oakville Grill. For a more casual dining experience, enjoy the classic Canadian dishes at The Old Mill.
  • What are the best walking or cycling routes in Oakville?

    Oakville offers beautiful walking and cycling routes. The Waterfront Trail is a popular choice, offering stunning views of Lake Ontario. The Bronte Creek Provincial Park has several scenic trails for all levels, and the Oakville Trafalgar Trail is a great option for a longer ride.
  • Are there pet-friendly attractions in Oakville?

    Oakville is a dog-friendly town. Many parks, like Coronation Park and Bronte Creek Provincial Park, welcome well-behaved dogs on leash. The waterfront trail is also a great option for a walk with your furry friend.
  • What are the benefits of choosing a vacation rental in Oakville?

    Vacation rentals offer more space and privacy than hotels. They often come with amenities like kitchens and laundry facilities, making them ideal for families or longer stays. You can also find rentals in different locations, allowing you to choose the neighbourhood that best suits your needs.

Destinations nearby

Best Oakville holiday rentals with a balcony

Modern Townhouse Rooftop Vibes - Oakville
Oakville
01/09 – 30/09
120 €/nighttotal: 3480 € (29 )

Modern Townhouse Rooftop Vibes

1 1
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.
*Cozy* 1 Bedroom Home Near Waterfront/trails - Oakville
Oakville
28/12 – 31/12
227 €/nighttotal: 681 € (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.
Stylish 3br 2.5 Bath Townhouse With Patio And Parking - Oakville
Oakville
01/07 – 31/07
354 €/nighttotal: 10620 € (30 )

Stylish 3br 2.5 Bath Townhouse With Patio And Parking

3 4
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.
Luxary Villa With Pool, Sauna, Hot Tub Sleeps 12 - Oakville
Oakville
28/12 – 31/12
738 €/nighttotal: 2214 € (3 )

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.

Best Oakville holiday rentals with air conditioning

Luxury Oakville Home, Hot Tub, Fireplace, New Home - Oakville
10 1 review
Oakville
05/07 – 12/07
549 €/nighttotal: 3843 € (7 )

Luxury Oakville Home, Hot Tub, Fireplace, New Home

4 10
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.
Chic&cozy Ll 2bed 2bath-kitchenette L *Near Lake* - Oakville
9.3 16 reviews
Oakville
25/06 – 28/06
211 €/nighttotal: 633 € (3 )

Chic&cozy Ll 2bed 2bath-kitchenette L *Near Lake*

2 4
house , Oakville
This two-bedroom apartment is situated in the Bronte neighbourhood of Oakville, just a short walk from Lake Ontario and the bustling Bronte Harbour. It has received excellent ratings for location, cleanliness, and overall experience.
This modern apartment is perfect for a family or group of up to five people, offering a comfortable and convenient stay. You'll enjoy a fully equipped kitchen, two bathrooms, and a private outdoor space, as well as access to a swimming pool and jacuzzi.
Luxury 5br Oakville Home | King Suite & Balcony - Oakville
Oakville
28/08 – 04/09
544 €/nighttotal: 3808 € (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.
One Bedroom And One Washroom - Oakville
Oakville
01/07 – 31/07
59 €/nighttotal: 1770 € (30 )

One Bedroom And One Washroom

1 2
apartment , Milton
This Oakville flat is situated on a quiet street opposite a park, with banks, grocery stores, restaurants, Bronte Creek Provincial Park, and the Oakville Museum all within a 3-5 kilometre drive.
This one-bedroom flat for two guests offers complimentary WiFi, air conditioning, and on-site driveway parking, with the option of house-made Indian vegetarian or non-vegetarian meals for breakfast and dinner.
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