
Holiday rentals 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

Winter Escape Tropical Dome! Animal Lovers Dream
Jungle Dome Farm Stay in Burlington! Be completely immersed in farm life and all that it entails while staying in our 500 square foot geodesic dome “glamping” greenhouse dwelling! Complete with a fish and turtle pond and filled to the brim with tropical plants! Designed as a tropical vacation getaway when you can’t get away to the tropics! Situated on a 5 acre animal farm where guests can experience farm life with goats, horses, highland cows, sheep, pigs and poultry. An Animal Lovers Dream!

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!

Executive Townhouse Oakville
This modern, fresh, open-concept home in the historic town of Oakville, Ontario, offers the perfect retreat for groups and families seeking comfort, relaxation and collaborative space. Situated between Toronto and Niagara Falls, this home provides convenient access to urban amenities and an array of outdoor attractions for sightseeing, exploration and adventure. Whether you're planning a short stay or a longer visit, its prime location in Ontario's largest town ensures a memorable experience.

The Stone Cottage in Vineland
Relax in this two bedroom three bathroom home that comes with a fully-equipped kitchen, dining room, laundry, and spacious living room with gas fireplace. Enjoy access to a beautifully landscaped backyard, with private deck overlooking acres of quiet farmland. The perfect modern day getaway, The Stone Cottage sports up-to-date amenities that combine with the peacefulness of country living, to create the ideal vacation retreat, within easy reach of everything the Niagara Region has to offer!

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.

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!

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.

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.

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 .

Stylish Oakville Condo to call home
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.
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
91 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

Apartment unit

Stunning Luxury Home

House in South Oakville - Close to Lake

Chic Luxury Townhome in The Heart of Oakville

Family-Ready 4BR | Close to Trails, Shops & More

Oakville Oasis

2026 FIFA |40 Mins to BMO Field |Oakville GO Train

Oakville Furnished Luxury 4 Bedrooms House
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £62 | £62 | £64 | £64 | £69 | £75 | £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 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 £7 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
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Pocono Mountains Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Pittsburgh Holiday rentals
- Erie Canal Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Rentals with beach access Oakville
- Rentals with a firepit Oakville
- Rentals with a fireplace Oakville
- Apartment rentals Oakville
- Rentals with lake access Oakville
- Rentals with a hot tub Oakville
- Rentals with outdoor seating Oakville
- Waterfront rentals Oakville
- Rentals with an EV charger Oakville
- Private suite rentals Oakville
- Fitness-friendly rentals Oakville
- Townhouse rentals Oakville
- Family-friendly rentals Oakville
- Rentals with a washing machine and dryer Oakville
- Rentals with breakfast Oakville
- Rentals with pools Oakville
- Pet-friendly rentals Oakville
- Rentals with a patio Oakville
- Flat rentals Oakville
- Cottage rentals Oakville
- House rentals Oakville
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- Port Credit
- 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
- Massey Hall
- Niagara Falls State Park
- Financial District
- Casa Loma
- Dufferin Grove Park
- Downsview Park
- Toronto City Hall
- Casino Niagara




