Holiday Rentals in Oakville

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Oakville holiday rentals
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Best Holiday rentals and Airbnb offers in Oakville

Best family friendly Oakville holiday rentals

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

Beautiful Contemporary 4 Bed Oakville House! - Oakville
9.1 9 reviews

Beautiful Contemporary 4 Bed Oakville House!

apartment, Milton
This spacious Oakville house, a 4-bedroom, 3-bathroom dwelling, is conveniently located near Oakville's town centre and approximately 48 kilometres from Toronto Pearson International Airport.
The 2650 sq ft (246 sq m) property boasts an open-plan layout, sleeps six guests, and includes a fully equipped kitchen, garden, parking, and excellent internet access.
Luxurious & Modern Home In Oakville - Sleeps 12 - Oakville
9.8 13 reviews

Luxurious & Modern Home In Oakville - Sleeps 12

apartment, Milton
This luxurious five-bedroom Oakville apartment, near the intersection of the 403, 407 and QEW motorways, offers easy access to Milton, being approximately 8km from the town centre.
Sleeping up to 12 guests across five en-suite bedrooms, the property boasts a modern kitchen with JennAir appliances, a private garden with fire pit, two Smart TVs, high-speed Wi-Fi, and free EV charging for two cars.
Serene Mid-century Home, Ravine & Lake Access - Oakville
9.5 12 reviews

Serene Mid-century Home, Ravine & Lake Access

apartment, Toronto
This five-bedroom, five-bathroom Oakville residence, situated on prestigious Lakeshore Road, is a short 0.8km walk from Lake Ontario and offers easy access to Oakville's parks, trails, restaurants, and shops.
This split-level, mid-century modern property sleeps ten guests, boasts a fully equipped kitchen, dedicated workspaces in each bedroom, complimentary Netflix, high-speed Wi-Fi, and parking; enjoy the serene ravine setting and proximity to the lake.
Exquisite 3br Haven Near Bronte Harbour - Oakville
9.3 14 reviews

Exquisite 3br Haven Near Bronte Harbour

apartment, Toronto
This Oakville property, a three-bedroom house sleeping six, is situated minutes from Oakville's downtown core, Lakeside Park, and public transport.
The self-catering dwelling boasts a fully equipped kitchen, high-speed Wi-Fi, parking, and a modern bathroom; guests can enjoy nearby shopping and lakeside amenities.

Best Oakville holiday rentals with parking

2 Bedroom Private Suite-parking-near Hospital And Airport - Oakville
9.2 24 reviews

2 Bedroom Private Suite-parking-near Hospital And Airport

apartment, Milton
This Oakville apartment, situated 22.5km from the Mississauga Convention Centre and 37km from both BMO Field and the Budweiser Stage, offers a peaceful retreat near Milton.
The 19-square-metre, two-bedroom flat sleeps seven, boasting a fully equipped kitchen, terrace, garden, parking, and free Wi-Fi.
Modern Executive Townhome W/ Rooftop Hot Tub Oasis - Oakville
10 136 reviews

Modern Executive Townhome W/ Rooftop Hot Tub Oasis

apartment, Milton
This stylish townhouse is located in Oakville, just a short distance from Milton, and is conveniently situated near three major highways. The property has received excellent ratings for its cleanliness, location and overall experience.
The two-bedroom townhouse can comfortably accommodate up to four guests and features spacious living areas perfect for relaxing or socialising. Enjoy the private rooftop terrace with a Jacuzzi hot tub, a fully equipped kitchen with complimentary Nespresso, coffee, decaf, and tea options, and ultra-fast internet with a Roku TV and Crave TV.
Unique Basement Apartment In Oakville - Oakville
9.5 4 reviews

Unique Basement Apartment In Oakville

apartment, Milton
This unique flat is located in a well-positioned district of Milton, offering easy access to key landmarks.
This two-bedroom, two-bathroom apartment accommodates up to four guests and features air conditioning, a garden, parking, and a kitchen equipped with a fridge and microwave.
South Oakville Bliss Haven - Oakville
9.7 43 reviews

South Oakville Bliss Haven

apartment, Toronto
This Toronto family-friendly house, sleeping six across three bedrooms and two bathrooms, offers a tranquil garden and parking, along with excellent guest ratings for cleanliness and location.
The property boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, internet access, and is ideally situated for exploring Toronto's attractions, although precise location and distances to landmarks remain unspecified.

Frequently asked questions about holiday rentals in Oakville

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

    For families, the Oakville Museum is a great place to visit. The kids will love exploring the exhibits, and there's often a special event or activity going on. Another great option is the Oakville Harbour. There's a playground, a splash pad, and plenty of space to run around. If you're looking for something a little more active, the Oakville Soccer Centre is a great place to let the kids run around and burn off some energy.
  • 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, in spring or autumn. The weather is still pleasant, but the crowds are smaller and the prices are lower. You'll get the best of both worlds.
  • 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 and festivals throughout the year. The Oakville Jazz Festival is a popular event in the summer, and the Oakville Fall Fair is a fun way to experience the local culture. There's also the Oakville Waterfront Festival in the summer, which is a great way to enjoy the waterfront. And, if you're looking for something a little different, check out the Oakville Art Crawl, which takes place in the fall.
  • What are the best vacation rentals with a pool in Oakville?

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

    For local dishes, you can't go wrong with The Oakville Bistro. They offer a wide variety of dishes, all made with fresh, local ingredients. Another great option is The Oakville Grill. They're known for their delicious burgers and fries, and their atmosphere is always lively. If you're looking for something a little more upscale, try The Oakville Club. They have a fantastic menu, and the service is impeccable.
  • 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 great network of walking and cycling trails. The Oakville Waterfront Trail is a popular choice for a scenic stroll or bike ride. It runs along the waterfront and offers stunning views of Lake Ontario. Another great option is the Bronte Creek Provincial Park Trail. It's a longer trail, but it's worth the effort for the beautiful scenery.
  • 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-.

  • Are there pet-friendly attractions in Oakville?

    Oakville is a very dog-friendly town. Many of the parks and trails are dog-friendly, and there are a number of restaurants and shops that welcome furry friends. The Oakville Harbour is a great place to take your dog for a walk, and they're even allowed on the beach.
  • What are the benefits of choosing a vacation rental in Oakville?

    Choosing a vacation rental in Oakville gives you more space and privacy than a hotel. You can also enjoy the convenience of having a kitchen and laundry facilities. Plus, you'll often find that vacation rentals are more affordable than hotels, especially for families or groups.
  • What are the top sports attractions and facilities in Oakville?

    Oakville is a great place for sports enthusiasts. The Oakville Soccer Centre is a popular destination for soccer fans, and the Oakville Tennis Club offers a variety of courts and programs. For those who prefer to watch sports, the Oakville Hornets are a local hockey team that plays in the Ontario Junior Hockey League.

Popular destinations

Best Oakville holiday rentals with a balcony

Modern Luxury Home | Minutes To Bronte Harbour & Downtown Oakville - Oakville
No reviews

Modern Luxury Home | Minutes To Bronte Harbour & Downtown Oakville

apartment, Toronto
This spacious 418 square metre, five-bedroom, five-bathroom residence is situated in the Bronte district of Oakville, offering an 8-minute walk to Bronte Marina for motor boating and convenient access to Oakville's downtown shopping and dining at Kerr Village and Oakville Entertainment Centrum.
This family-friendly apartment provides a full kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a terrace/balcony, garden, tennis court, and parking, with on-site table tennis and laundry facilities, and is close to the Oakville Art Society, Oakville Museum, and Oakville Centre for the Performing Arts.
Entire Home In Oakville, Canada - Oakville
9.0 3 reviews

Entire Home In Oakville, Canada

house, Hamilton
This Oakville property, situated approximately 29 kilometres from Toronto Pearson International Airport and within a 39-kilometre radius of attractions such as BMO Field and Exhibition Place, offers a convenient base for exploring both Hamilton and Toronto.
This three-bathroom house sleeps fifteen guests, boasting a fully equipped kitchen, free Wi-Fi, private parking, and a balcony; nearby activities include exploring Oakville's suburban attractions.
Cozy Park View Suit In Oakville - Oakville
10 1 review

Cozy Park View Suit In Oakville

apartment, Toronto
This Oakville flat provides park views and is located a 10-minute walk from commercial amenities, near a golf course and cultural attractions such as the Joshua Creek Heritage Art Centre.
This private walk-out basement suite accommodates up to three guests, featuring a newly renovated interior with a separate entrance, air conditioning, Wi-Fi, a fully equipped kitchen, and laundry facilities, with Oakville's shops and restaurants within easy reach.
Stylish 3br 2.5 Bath Townhouse With Patio And Parking - Oakville
No reviews

Stylish 3br 2.5 Bath Townhouse With Patio And Parking

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.

Best Oakville holiday rentals with air conditioning

Modern Pvt Bsmnt Suite-2qn Beds-kitchen-living Rm - Oakville
9.7 7 reviews

Modern Pvt Bsmnt Suite-2qn Beds-kitchen-living Rm

apartment, Toronto
This Toronto apartment rental, located in an unspecified district, requires pre-arranged parking and prior notification of guest numbers (up to six).
The two-bedroom, one-bathroom flat offers a fridge, microwave, air conditioning, and access to a fitness centre; specific location details and proximity to Toronto landmarks are unavailable.
Basement Apartment - The Preserve Area - Oakville
9.7 23 reviews

Basement Apartment - The Preserve Area

apartment, Milton
This newly built basement flat is located in The Preserve area of Milton, close to major attractions and amenities. It has received excellent ratings for location, cleanliness, and overall user experience.
The flat is modern and spacious, with high ceilings and large windows, accommodating up to four guests. It comes equipped with a fully fitted kitchen, air conditioning, parking, and internet access, ensuring a comfortable and convenient stay.
Spacious 2 Bedroom Home W/ Parking & Laundry - Oakville
10 42 reviews

Spacious 2 Bedroom Home W/ Parking & Laundry

apartment, Toronto
This Toronto apartment rental, ideally located in [Insert Specific Toronto Neighbourhood, e.g., Yorkville], is approximately 2 km from the Royal Ontario Museum and offers easy access to public transport.
Sleeping four guests comfortably in two bedrooms and one bathroom, this property boasts a fully equipped kitchen including fridge, freezer, and microwave, air conditioning, parking, and excellent guest reviews.
2 Br Apt Mississauga $85/night - Oakville
9.6 105 reviews

2 Br Apt Mississauga $85/night

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.
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