
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

Peaceful 2BR Condo EV Charger: FIFA World Cup
Experience refined urban living in this stylish 2-bedroom condo in Oakville. Located in a fully automated building with seamless app-based access, this 3rd-floor unit offers comfort and convenience. Step into a bright open-concept living space with floor-to-ceiling windows, a fully equipped kitchen, and two bedrooms; each with a queen bed and private ensuite. Enjoy access to premium building amenities, including a modern gym and EV charging station; perfect for both short and extended stays.

Sun-Soaked Modern Townhome | Modern and Stylish
Welcome to our spacious and inviting retreat! Nestled in a prime location in Oakville, this entire house offers a perfect blend of comfort and convenience. Unwind in the ample living spaces, and relish the privacy of having the entire house to yourself. With nearby attractions and a tranquil atmosphere, our Airbnb is your ideal home away from home. Explore the city by day which is 30 min drive, and return to the spacious serenity of your temporary abode by night. Your perfect getaway awaits

Opulent Chic Town Home in the Heart of Oakville
Welcome to your chic getaway in the heart of Oakville! This opulent townhome is perfect for families, business travelers and friends. Relax in the spacious living room, cook your favorites or unwind on the patio. Fast Food & Grocery stores a short walk away & easy access to highways 403, 401 & 407. -McDonalds, Subway, Tim Hortons, Popeyes: 5 mins walk -Superstore, Walmart, LCBO: 5 mins drive -GO Station: 12 mins drive -Toronto Premium Outlet: 15 mins drive Your perfect stay awaits!

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!

Oakville 2BR: Central, Comfy & Close to Everything
Enjoy the convenience of a central Oakville location perfect for families. You’ll be close to everything, including the Waltmar Superstore, Shoppers, Oakville Place, and Toronto Premium Outlets. With easy access to three major highways, public transportation, and the train station, getting around is a breeze. Plus, the nearby hospital offers extra peace of mind. This modern 2-bedroom space is thoughtfully designed for comfort, making it the ideal home base for your Oakville visit.

Serene Stays - Oakville (3 Bed, 2 Bath, 1 Parking)
Welcome to Serene Stays - Oakville, where you'll find comfort, style, and convenience all come together! This is a newly built, spacious condo suite, where you can completely relax with access to the entire suite - boasting 2 bedrooms, 2 bathrooms, living room, dining room, full kitchen, private outdoor patio, and laundry room. You will also have access to the condo's shared gym and yoga room on the lower level. This suite has 1 parking space and is perfect for families or groups!

Cozy Basement Apartment in Oakville
Welcome to Your Cozy Oakville Basement Apartment! Newly built, this 2 bedroom apartment holds a open-concept living room that flows into the fully-equipped kitchen, offering a cozy space to relax along with backyard area. Guests have private access through a separate entrance and independent working area. Pond facing, located in a quite neighborhood in close proximity to restaurants and grocery stores. 10-15 mins from Oakville GO Station. 25-30 mins from YYZ Airport .

Cottage On Lake Ontario Niagara
OPEN TIMESLOTS JUNE 17 (1 night/2 days) JUNE 21-JULY 6 Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include orchards and the Lake

Springtime! Steam shower+breakfast+rooftop hottub
Nestled in a picturesque escarpment community overlooking the historic town of Dundas, The Hayloft is a charming getaway for anyone looking for an escape and a breath of fresh air. Relax in the steam shower inside or the hot tub on the fully private rooftop deck overlooking gardens. Take a nap on the lounge chairs. Visit with the chickens, make friends with the fish or the frogs. Unwind at night with a movie in bed, with breakfast (surcharge) in the morning.
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
88 locals recommend
Cineplex Cinemas Winston Churchill
41 locals recommend
Other great holiday rentals in Oakville

Modern Retro Oak guest suite

Beautifully Upgraded One Bedroom and Den + Balcony

Bright & Spacious 3Br/2Bth Suite Private Entrance

HotTub Retreat • Sleeps 12 • Cinema•FIFA•5 parking

New Studio Unit with Full kitchen in Oakville

Modern 2 BDR + 2WSH Condo W/Parking in Oakville

Modern Private Suite | Oakville | Parking

Luxurious Ravine 3 BR Town Home
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £66 | £66 | £68 | £64 | £70 | £76 | £77 | £78 | £70 | £68 | £66 | £69 |
| 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 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.
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.
Quick stats about holiday rentals in Oakville

Total holiday rentals
Explore 860 holiday rentals in Oakville

Nightly prices starting at
Oakville holiday rentals start at £7 per night before taxes and fees

Verified guest reviews
Over 18,540 verified reviews to help you choose

Family-friendly holiday rentals
400 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 200 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
550 properties have a dedicated workspace

Wifi availability
850 of Oakville holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Oakville rentals

4.8 Average rating
Oakville stays are highly rated by guests – averaging 4.8 out of 5!
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- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Harbourfront Centre
- Nike Square One Shopping Centre
- Toronto Eaton Centre
- Niagara Falls State Park
- Downsview Park
- Exhibition Place
- Toronto Zoo
- Trinity Bellwoods Park
- Niagara Falls
- Casa Loma
- Massey Hall
- Wilfrid Laurier University
- Scarborough Town Center
- York University
- Casino Niagara
- Fallsview Indoor Waterpark





