Holiday houses in Oakville
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Oakville
Guests agree: these stays are highly rated for location, cleanliness and more.
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
Family-Ready 4BR | Close to Trails, Shops & More
Welcome to your home away from home in Oakville! This stylish 4-bedroom, 4-bathroom retreat is perfect for families, professionals, or long-term guests. Enjoy soaring ceilings, hardwood floors, and a fully equipped chef’s kitchen — ideal for cooking and entertaining. Located in a family-friendly neighborhood just minutes from highways (403/407), parks, shopping, and dining. Whether it’s a weekend getaway, family trip, or extended stay, this home offers comfort, convenience, and a warm welcome.
Cottage On Lake Ontario Niagara
OPEN TIMESLOTS JUNE 22 (today 1 night/2 days) JUNE 24 (1 night JUNE 27-JULY 6 JULY 8-18 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
Debonair Home near Downtown Oakville
Discover our delightful 2-bedroom basement apartment featuring a private entrance, ideally situated near downtown Oakville. Tucked away on a tranquil, tree-lined street, this inviting haven seamlessly combines comfort with convenience. Steps from the following (walking times): - Forster Park (splash pad, playground, basketball ball and tennis court) - 4 min - Kerr Street Village - 8 min - Food Basics - 15 min - Shopper's Drug Mark - 16 min - Downtown Oakville and Waterfront Trail - 20 min
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!
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!
Maia's cozy Bronte cottage by the Lake
Take it easy at this unique and tranquil getaway. Cute and cozy, secluded 3 bedroom bungalow on quiet private street in the heart of Bronte Village. 6 minute walking distance to the lake and all amenities including restaurants, cafe's, parks, and incredible walking trails. Convenient highway access to the QEW, 407 and GO train station nearby. Enjoy the local golf courses, heritage parks with easy access to Toronto, Niagara Falls and Pearson Airport from this centralized location.
Spacious Urban Oasis:Stylish 2 Bed, 2 Bath Getaway
Welcome to our spacious and stylish property. This is a spacious (>900 sq ft) and modern 2-bedroom, 2-bathroom condo, perfectly nestled in the picturesque town of Oakville, Ontario. Ideal for families, couples, or small groups, this condo promises a comfortable and unforgettable stay. Don't miss the opportunity to experience the best of Oakville and Toronto from the comfort of this stylish condo. Book your stay and create lasting memories! We look forward to hosting you.
Luxury-5 BR-King Bed-2 Car-Pond View-403/407/QEW
Welcome to our exquisite Oakville retreat, where luxury meets comfort in every detail. This stunning 5-bedroom home is tailored to provide an unforgettable stay: ✨ Stylish 5BR luxury escape in Oakville 🛏️ Sleeps 10+ | King, Queens, Bunk & Crib ⚡ Blazing 1 Gbps Wi-Fi + 2 WFH desks 📺 70" & 50" Smart TVs for ultimate downtime 🚗 Free 2-car parking 🛍️ 5 mins to 403/407/QEW, Walmart, Longo’s, Starbucks 🚉 10 mins to Oakville GO ✨Perfect for families, groups & business trips
Summertime! 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.
Cozy Modern Studio in Oakville | Free Parking
Welcome to your perfect retreat - an oasis for 1-2 guests seeking ultimate comfort. Enjoy seamless connectivity with WiFi, Netflix, and a luxurious Queen bed. Experience the essence of home in our inviting, modern basement studio. With a full kitchenette, in-unit laundry, and lots of storage. This modern unit is ideally situated in a serene, safe neighborhood in Oakville, steps from public transit, close to various amenities like restaurants, malls and trails
Waterfront Hillside Villa
Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.
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
93 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
Feel at home
Luxurious Upper Oakville Condo
Cottage Style House with Hot Tub
Oakville 2BR: Central, Comfy & Close to Everything
Entire basement apartment with separate entrance
New Studio Unit with Full kitchen in Oakville
Luxurious Prince Mansion
Modern Private Suite | Oakville | Parking
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $153 NZD | $153 NZD | $159 NZD | $150 NZD | $162 NZD | $176 NZD | $180 NZD | $181 NZD | $164 NZD | $159 NZD | $153 NZD | $160 NZD |
| 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 $17 NZD 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 and kid-friendly amenities
Pet-friendly accommodation
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
Wi-Fi availability
850 of Oakville holiday rentals include Wi-Fi 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!
Destinations to explore
- Pittsburgh Holiday rentals
- Columbus Holiday rentals
- Cleveland Holiday rentals
- Detroit Holiday rentals
- Niagara Falls Holiday rentals
- Mississauga Holiday rentals
- Buffalo Holiday rentals
- Brampton Holiday rentals
- London Holiday rentals
- Niagara Falls Holiday rentals
- Rochester Holiday rentals
- Prince Edward Holiday rentals
- Rentals with a hot tub Oakville
- House rentals Oakville
- Rentals with outdoor seating Oakville
- Rentals with beach access Oakville
- Apartment rentals Oakville
- Cottage rentals Oakville
- Rentals with a fire pit Oakville
- Rentals with a patio Oakville
- Fitness-friendly rentals Oakville
- Townhouse rentals Oakville
- Private suite rentals Oakville
- Rentals with a fireplace Oakville
- Rentals with lake access Oakville
- Rentals with pools Oakville
- Condo rentals Oakville
- Rentals with a washing machine and dryer Oakville
- Family-friendly rentals Oakville
- Rentals with an EV charger Oakville
- Rentals with breakfast Oakville
- Pet-friendly rentals Oakville
- Waterfront rentals Oakville
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Union Station
- BMO Field
- The Danforth Music Hall
- Downsview Park
- Harbourfront Centre
- Toronto Eaton Centre
- Niagara Falls State Park
- Exhibition Place
- Toronto Zoo
- Scarborough Town Center
- Nike Square One Shopping Centre
- Trinity Bellwoods Park
- Niagara Falls
- Massey Hall
- Enercare Centre
- Casa Loma
- Yorkdale Shopping Centre
- Wilfrid Laurier University
- York University