Holiday rentals in Oakville
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Top-rated holiday rentals in Oakville
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LUXURY CONDO, GREAT DECOR, WHEELCHAIR FRIENDLY!!!
NEW GORGEOUS LUXURY CONDO WHEELCHAIR ACCESIBLE. *** NEW BED in 2nd!*** PRIME BEDROOM has a queen size memory foam mattress & a desk. SECOND BEDROOM has a brand new bed with double mattress medium/firm and a working desk, now accessible to guests. 2 FULL BATHROOMS: The en-suite has has a step up shower and a Bidet. SECOND: Has a tub & shower, very spacious. *OPEN CONCEPT LIV. AREA. *OPEN BALCONY. TASTEFULLY FURNISHED, SOFT AND CLEAN COLORS HARDWOOD FLOORS THROUGHOUT EXTRA WIDE HALLS AND DOORS
Chic&Cozy LL 2Bed 2Bath-Kitchenette l *Near LAKE*
We are 1 BLOCK AWAY FROM THE LAKE. Luxurious and spacious 2 Bedrooms with ABOVE GRADE WINDOWS, Partially heated flooring in the basement, 2 bathroom, WIFI, Kitchenette &50” smart TV. Steps away from Bronte Harbor, Coronation Park, shopping, restaurants and GO station. 1hr drive to NIAGARA FALLS and 35mins drive to downtown Toronto. Suitable for all kinds of travelers. Solar heated pool can be accessed from 10am to 8pm (June to Sep). Pool may be shared with potential guests living in upper level.
Beautifully Upgraded One Bedroom and Den + Balcony
Charming 1-bedroom plus den condo located in a central area with easy walking access to major attractions. This well-appointed upgraded unit features a spacious living area, a versatile den perfect for an office or guest room, and modern amenities. Enjoy the convenience of nearby shops, dining, and entertainment options right at your doorstep. Ideal for those seeking both comfort and a vibrant urban lifestyle. Includes a dedicated underground parking spot and balcony. Fully upgraded and modern!
Condo Style Basement in Oakville (Walk Up)
Looking for a cozy and comfortable place to stay during your next vacation or business trip? This spacious and stylish Airbnb accommodates up to 6 guests! Our beautiful space features everything you need to feel right at home! This condo style basement apartment is located in Oakville, one of Ontario’s most desirable neighbourhoods. 2 bedrooms with walk in closets 2 full bathrooms Sofa-come bed Contemporary chef kitchen (including utensils ) TV with Disney Plus and Netflix Dryer and washers
South Oakville Apartment near Lake (Basement)
Situated just minutes from the Lake Ontario & Oakville Downtown, you’ll enjoy trendy restaurants, cafés, & boutique shops, all within a 5-minute drive Clean, safe and airy 1-Bedroom apartment in Prime South Oakville comes with 1 full-bathroom, full kitchen, laundry & free parking. 🚆 Excellent Transit & Travel Links Just off the QEW highway for trips to Toronto or Niagara Falls & Toronto Airpot. Nearby GO Train station offers 24-hour transit to downtown Toronto. T The price includes 13% HST
Bright, Spacious, Quiet 2 bedroom - Licensed
Quiet family neighborhood great for professionals, couples or family. Spacious and cozy home away from home. You control heat and cooling fan. Sound dampening so natural noises are minimized, not eliminated. 1 queen and 1 double bed. Two desks for computer work. Extra seating. Fast WiFi! Full kitchen. Bathroom with shower and bathtub. Close to highways, hospital, recreation centers, playgrounds, shopping, schools and college. All registered guests may be asked to provide ID upon request.
3Bd 2.5Bth House w/ Pool Table, Swing, Outdoor BBQ
Bring your friends and family to this family-friendly, centrally-located neighbourhood with lots of room for fun and find a home away from home during the travelling. Enjoy your stay in this licensed short-term accommodation for a modern, luxurious, and spacious three-bedroom and two-bathroom detached home with a huge backyard: watching a movie and cozying up by the fire, enjoying the company of friends and family seated around the dining table, or simply in between moving or renovations.
Modern Executive Townhome w/ Rooftop Hot Tub Oasis
Stylish contemporary townhome in Oakville! The perfect retreat for couples, families, and friends alike. Experience the rooftop terrace, complete with a Private Jacuzzi Hot Tub that provides the ultimate relaxation experience! It's the perfect spot to unwind after a long day of sightseeing or to enjoy an evening under the stars. You'll love the stunning and spacious living areas, fully equipped kitchen, and two comfortable bedrooms. Close to Three Major Highways in a Central Location!
Little Fort
Welcome to the Lil Fort! This cozy 1-bedroom condo offers an open concept living/dining area, and a secondary entrance via your private patio . Just steps from Fort York Park, the lakefront, and downtown dining/entertainment. Enjoy a comfy queen bed, 65” 4K TV, full kitchen, and relaxing bathroom. Skip the elevator—stay on the main floor and unwind in style! Keep it simple at this peaceful and centrally located place. Walking distance to entertainment district, shopping. Parks, and more!
Chic Luxury Townhome in The Heart of Oakville
Amazing, comfortable, stylish townhouse located in the vibrant area of Oakville. 3 Bdrms / 2.5 washrooms. This modern retreat boasts 3 spacious bedrooms and an office, a bright eat-in kitchen with all cooking essentials, and a cozy living area perfect for any couple or family. Enjoy the convenience of nearby shops, boutiques, parks, and restaurants. Whether you're visiting town or here for business or pleasure, our home offers a blend of comfort and relaxation for your stay in Oakville.
Guest Favorites Oakville Condo | Modern & Stylish
Welcome to your stylish home away from home in the heart of Oakville! This modern 1 bed, 1 bath condo at Dundas & Trafalgar offers comfort and convenience in a vibrant neighborhood. Enjoy a fully equipped kitchen, cozy living space, in-suite laundry, and a private balcony. Steps from shops, restaurants, parks, and transit, it’s perfect for solo travelers, couples, or business guests. Experience Oakville’s charm with easy access to Toronto and local attractions.
Charming House Near the Lake and Shopping Centre
Beautiful, detached bungalow with charming features 🌱 Enjoy a comfortable and convenient stay in this cozy, character-filled bungalow in the heart of prestigious South Oakville. Perfect for longer stays, this home offers a warm and inviting atmosphere with everything you need at your fingertips. Whether you’re here for work, family, or leisure, this bungalow provides a peaceful retreat with everything you need in top Location for an extended stay.
Popular amenities for Oakville holiday rentals
Stay near Oakville's top sights
Oakville Trafalgar Memorial Hospital Emergency Department
7 locals recommend
St Louis Bar and Grill
10 locals recommend
Bronte Creek Provincial Park
92 locals recommend
Sheridan College - Trafalgar Road Campus
10 locals recommend
Jack Darling Memorial Park
86 locals recommend
Cineplex Cinemas Winston Churchill
41 locals recommend
Other great holiday rentals in Oakville
Stunning Luxury Home
Spacious Urban Oasis:Stylish 2 Bed, 2 Bath Getaway
Oakville 2BR: Central, Comfy & Close to Everything
Bright & New Home, Great place
Oakville Oasis
Milton Home- a Family Oasis
Spacious & Luxury 4BR Home ~ Hamilton ~ Comfort
Panoramic Lake Views | Hot Tub | Beach Blvd Beauty
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $106 SGD | $106 SGD | $110 SGD | $110 SGD | $119 SGD | $129 SGD | $132 SGD | $133 SGD | $120 SGD | $116 SGD | $112 SGD | $118 SGD |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
Frequently Asked Questions
What are the best places to stay in Oakville?
Oakville has welcoming neighbourhoods such as Old Oakville, Bronte, and Kerr Village, each with a mix of historic charm and access to shops, waterfront areas, and parks. Many visitors enjoy stays that are close to the downtown core or along the lake for easy exploring.
What are the best things to do in Oakville with kids?
Families in Oakville often explore local parks, playgrounds, and the waterfront trails. The Oakville Museum at Erchless Estate and indoor play centres are frequently suggested for educational fun and interactive experiences.
What are some of the best things to do in Oakville?
Explore the trails and gardens at Lakeside Park, stroll vibrant Kerr Village, and visit the Oakville Museum at Erchless Estate for local history. Waterfront activities and the lively arts scene are often recommended by visitors.
How is the weather in Oakville?
Oakville experiences cold winters around 20–33°F (-7–1°C) and warm summers near 65–81°F (18–27°C), with spring and autumn bringing mild temperatures. Rainfall is spread throughout the year; packing layers and a rain jacket is suggested.
When is the best time to visit Oakville?
Late spring through early autumn is often recommended for mild weather and accessible outdoor activities. Summer brings warmer temperatures, frequent community events, and lively waterfront gatherings.
What are the best places to visit in Oakville?
The Oakville Museum at Erchless Estate, Lakeside Park, and Bronte Harbour are frequently suggested for history, green spaces, and scenic lake views. Kerr Village is known for local shops and arts venues around the downtown area.
What are some hiking trails in Oakville?
Oakville has several scenic walking and hiking trails, including the Bronte Creek Trail, Sixteen Mile Creek Trail, and paths through Lakeside Park. These trails wind through forests, meadows, and along the waterfront.
What are some family activities we can do in Oakville?
Families often explore Oakville's parks, splash pads, and interactive exhibits at the local museum. Seasonal festivals, community markets, and family-friendly waterfront events are popular throughout the year.
What are some of the best day trip ideas from Oakville?
Around Oakville, you can discover vibrant nearby cities, nature reserves, and regional art galleries for a full day of exploring. The Niagara region and Royal Botanical Gardens are often recommended for unique landscapes and cultural experiences.
Are there any pet friendly accommodations available in Oakville?
Many Oakville stays welcome pets, especially in neighbourhoods near parks and waterfront trails like Bronte and Old Oakville. Check for listings with amenities suited for pets and easy access to outdoor spaces.
What are some local tips for visiting Oakville?
Exploring Oakville’s waterfront trails early in the morning lets you enjoy quieter scenery. Support local businesses in Kerr Village, and many community events are held throughout the year—check local calendars for festive happenings.
What is Oakville known for?
Oakville is known for its extensive waterfront, green parks, and its lively arts and cultural community. The downtown area blends historic architecture, local shops, and galleries with a relaxed, welcoming atmosphere.
What are the best hidden gems to explore in Oakville?
Visitors often mention Gairloch Gardens for its art gallery and landscaped grounds, and hidden paths along Sixteen Mile Creek Trail. Smaller independent cafés and boutique shops in Kerr Village add to the distinct local character.
What are the best foods to try in Oakville?
Oakville’s dining scene features locally sourced seafood, seasonal Canadian ingredients, and diverse global cuisines. Bakery treats, fresh lake fish, and handcrafted coffees are often enjoyed by visitors exploring downtown and Kerr Village.
What should I bring for a trip to Oakville?
Pack layers for changing weather, including a rain jacket and comfortable walking shoes for exploring trails. A reusable water bottle and sunscreen are useful for outdoor activities, especially during spring and summer.
What is the nightlife in Oakville like?
Oakville’s nightlife centers around local pubs, cozy wine bars, and live music venues in downtown and Kerr Village. Many visitors enjoy relaxed evenings with art spaces, cafes, and performances creating a welcoming community feel.
What are the most popular events or festivals in Oakville?
Oakville has a variety of community festivals throughout the year, such as summer celebrations focused on food, arts, and live music. Cultural events often take place around Labor Day weekend, drawing visitors to explore local traditions and performances.
Are there family friendly vacation rentals in Oakville?
Oakville has many family friendly rentals in neighbourhoods near parks, playgrounds, and the waterfront. Look for stays in Bronte, Old Oakville, or around Kerr Village for convenient access to family activities.
Quick stats about holiday rentals in Oakville
Total holiday rentals
Explore 890 holiday rentals in Oakville
Nightly prices starting at
Oakville holiday rentals start at $13 SGD per night before taxes and fees
Verified guest reviews
Over 19,610 verified reviews to help you choose
Family-friendly holiday rentals
450 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 210 rentals that welcome pets
Holiday rentals with a pool
50 properties feature pools
Rentals with dedicated workspaces
570 properties have a dedicated workspace
Wifi availability
880 of Oakville holiday rentals include wifi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Oakville rentals
4.7 Average rating
Oakville stays receive an average rating of 4.7 out of 5 from guests
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- BMO Field
- Distillery District
- The Danforth Music Hall
- Nike Square One Shopping Centre
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Niagara Falls State Park
- Massey Hall
- Financial District
- Casa Loma
- Wilfrid Laurier University
- Dufferin Grove Park
- Downsview Park
- York University
- Toronto City Hall