
Vacation rentals in Oakville
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Top-rated vacation 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

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

Sun-kissed 3BR family home in a quiet neighborhood
♡ The fastest internet w/ 1Gb download speed ♡ Fully Equipped Kitchen ♡ minutes drive to Sheridan college, Walmart, Oakville Place, lakeshore ♡ 7 min. drive to Trafalgar GO Station, 20 min. to Toronto premium outlets 25 min. to Pearson airport 30 min. to Toronto downtown ♡ Walking distance to convenient store, trails, food, bus stop, library. ♡ Free Parking ( 2 Spots) ♡ Automated Check in & Check Out ♡ Flexible Check in Check out - Message for Details ♡ A/C ♡ Laundry ❤ Book today!

Inn The Orchard, Valley View, Modern Container
Enjoy the sounds of nature when you stay in this unique place. Our newly renovated "Valley View, Container Home" in beautiful Niagara at Inn The Orchard, has been designed with all luxuries of home but created guaranteeing a relaxing atmosphere and simplicity that you'll never forget. We love creating spaces allowing you to escape the city and be surrounded by nature while remaining in the heart of Niagara's Wine Country! Enjoy this unique spot surrounded by fruit orchards on the valley edge.

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.

Spacious and Comfy 2 BR Suite
Discover tranquility in our 2-bedroom legal basement apartment, nestled in Milton’s quiet and peaceful neighborhood. Enjoy an open-concept living room with 8.5 ft ceiling, and 2 roomy bedrooms; perfect for couples or families to relax in this comfortable, private, retreat. Easy access to Oakville, Burlington, Mississauga, and Toronto Pearson Airport, and minutes away from Toronto Premium Outlets, Mattamy Cycling Centre, and scenic trails, makes this location ideal for both work and play.

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!

Luxury Guest Suite
Welcome to our cozy basement apartment! This modern Airbnb is located in a peaceful residential neighborhood 40 min drive from Toronto downtown and an hour from Niagara Falls. The well-lit space features a comfortable queen-sized bed, ample storage in the spacious closet, and a beautifully designed interior with natural light flooding through large windows. Note: We have 2 single folding matresses available to place on the floor in the living room. Extra linen and pillows are provided.

Large Luxury Villa with Swim Spa! Near downtown!
Forget your worries in this spacious, serene and unique house! Large backyard with a Swim Spa to enjoy! Backyard filled with fire places! 6 Bedroom, 7 beds, 4 full baths, 4 offices, 3 family rooms, 9 TV, equipped kitchen, patio, board games, BBQ grill, fire place, Tesla charger. Quiet yet central from downtown Oakville, highways, groceries, shopping, bars, restaurants, cafe's and much more! Always professionally cleaned. For elderly guests a bedroom and full bath is on ground floor.

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

Winter Escape Tropical Dome! Animal Lovers Dream
Jungle Dome on a farm in Burlington! Enjoy a tropical stay in our 500 square foot geodesic dome “glamping” greenhouse dwelling! Sleeps 4. Complete with a fish and turtle pond and filled to the brim with tropical plants! Designed to be a tropical vacation getaway when you can’t get away to the tropics! Situated on a 5 acre animal farm where guests can feed and interact with goats, horses, highland cows, sheep, pigs and poultry. An Animal Lovers Dream!
Popular amenities for Oakville vacation rentals
Stay near Oakville's top sights
Oakville Trafalgar Memorial Hospital Emergency Department
6 locals recommend
St Louis Bar and Grill
10 locals recommend
Bronte Creek Provincial Park
91 locals recommend
Sheridan College - Trafalgar Road Campus
10 locals recommend
Jack Darling Memorial Park
86 locals recommend
Cineplex Cinemas Winston Churchill
40 locals recommend
Other great vacation rentals in Oakville

Feel at home

Charming spacious townhome in Prime Oakville

Beautifully Upgraded One Bedroom and Den + Balcony

Oakville Oasis - Free Parking and WiFi

Chic Luxury Townhome in The Heart of Oakville

1 BR Boutique Charm, Urban Calm!

Spacious Basement in Oakville

Luxury Urban Town home
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ305 | ﺩ.ﺇ305 | ﺩ.ﺇ316 | ﺩ.ﺇ316 | ﺩ.ﺇ342 | ﺩ.ﺇ371 | ﺩ.ﺇ378 | ﺩ.ﺇ382 | ﺩ.ﺇ345 | ﺩ.ﺇ342 | ﺩ.ﺇ342 | ﺩ.ﺇ331 |
| 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 vacation rentals in Oakville

Total vacation rentals
Explore 870 vacation rentals in Oakville

Nightly prices starting at
Oakville vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 18,900 verified reviews to help you choose

Family-friendly vacation rentals
430 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 200 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
560 properties have a dedicated workspace

Wi-Fi availability
860 of Oakville vacation rentals include wi-fi 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
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- Clifton Hill
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- BMO Field
- Toronto Zoo
- CF Toronto Eaton Centre
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Niagara Falls State Park
- Casa Loma
- Whistle Bear Golf Club
- Dufferin Grove Park
- Legends on the Niagara Golf Course
- Toronto City Hall
- Casino Niagara




