
Condo vacation rentals in Oakville
Find and book unique condos on Airbnb
Quick stats about condo rentals in Oakville

Total vacation rentals
Explore 40 vacation rentals in Oakville

Nightly prices starting at
Oakville vacation rentals start at $42 CAD per night before taxes and fees

Verified guest reviews
Over 970 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
40 of Oakville vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oakville rentals

4.8 Average rating
Oakville stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated condo rentals in Oakville
Guests agree: these condos 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
4.87 out of 5 average rating, 124 reviews
Entire Condo - 20min from Toronto Airport
This cozy one bedroom, 500 sq. ft., condo is located in the desirable Churchill Meadows area. It’s conveniently located across the street from Erin Mills Mall and within walking distance to all major amenities. You’ll find highway access to be a breeze; HWY 403 is only 1 minute away and the 401 under 10 minutes. Toronto Pearson Airport is a 15 minute drive, and you’ll find yourself downtown Toronto within 25 minutes. My place is perfect for business travelers, solo adventurers and couples.
4.91 out of 5 average rating, 139 reviews
Luxurious Condo Apartment 1BR-1BA-1Den, w. parking
"Thanks for stopping by! A lovely space to unwind and relax. Indulge in the comfort and tranquility of this contemporary space. Amazing location! Whether your visit is for business or pleasure - this is a perfect space with all the comforts of home. Enjoy great views and morning sun on the 90 SF balcony. Walking distance to restaurants, shopping and parks. Close access to Airport, hwy410, 401, 407 & Mount pleasant GO Station. Come and see why Brampton is rated one of the best cities in Canada."
4.89 out of 5 average rating, 114 reviews
Stylish 1BR Condo by Square One
Welcome to this modern, sophisticated, and fully furnished 1-bedroom apartment located in the heart of Mississauga’s Square One district. Features 65” living room TV, bedroom TV, full kitchen with cookware and basics, washer/dryer, and fast Wi-Fi. Enjoy building amenities like a gym, secure fob access, parking, grocery store on-site, and close proximity to restaurants and LCBO. Just 15 minutes to Pearson Airport and 25 minutes to downtown Toronto attractions. Perfect for a couple & small groups.
4.98 out of 5 average rating, 54 reviews
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!
4.91 out of 5 average rating, 56 reviews
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
4.8 out of 5 average rating, 66 reviews
Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1
Welcome to this exquisite 2-bedroom 2 bathroom condo, a blend of modern sophistication and breathtaking views. Nestled in the heart of downtown Mississauga this private-corner unit is everything you’re looking for. Everything in this unit is brand new. Cleanliness and providing a 5 star stay is our priority. All necessities are provided to make you feel at home. Amenities are available to all guests including a gym, pool, hot-tub, sauna, yoga room, music room, game room and much more.
4.9 out of 5 average rating, 169 reviews
King Bed, Queen Bed, Free Parking, Gym, WiFi
Well Equipped Luxury Suite Centrally Located is Perfect For Couples or Families. Quiet Neighborhood and Brand New Finishes Await You at This Urban Oasis! This Pristine Space Has an Open-Concept Kitchen/Living/Dining to Maximize Flow and Usage, and Stimulates the Creative Mind. Step Out onto the Balcony to Enjoy the Outdoor Space, You Will Be Amazed at the Peace and Quiet! Wake Up and Get Cooking in a Fully Equipped Suite! 1 Parking and Free WiFi Included. Don't Wait, Book Today
4.91 out of 5 average rating, 46 reviews
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!
4.59 out of 5 average rating, 17 reviews
Luxury 2 Bedroom Condo + Den in Oakville
Enjoy a stylish experience at this centrally located place in Oakville by Dundas and Trafalgar Rd This modern contemporary suite has all what you need for short or long stays with high attention to small details , elegantly furnished for your utmost comfort! The suite features two spacious bedrooms and two full bathrooms with an extra den that can be used as your workplace or office Enjoy a huge corner balcony with an amazing view of Dundas St and the city!
5.0 out of 5 average rating, 21 reviews
Gallery Suite
The Gallery Suite near Locke St. and McMaster is ideal for business or leisure stays. This bright, open-concept suite with a separate bedroom features unique artwork by Guelph artist Ryan Price. Located above a quiet RMT clinic, you'll enjoy a peaceful and private stay. Walking distance to trendy shops and cafes. Free parking is included for your convenience. Book now to experience a blend of comfort, art, and convenience!
4.95 out of 5 average rating, 198 reviews
Cozy Condo-Apartment/Suite in Brampton
Welcome to our beautiful, Pristine & Spacious 1-queen Bed, well decorated Condo Studio-Apartment/Suite in Brampton west, the apartment is a minute walk to Mount Pleasant Go Station which connects you to anywhere in Greater Toronto Area, and some few steps to shops, parks. Close access to Airport, Hwy 410, 401, 407 & Mount pleasant village. Providing the experience to see the nice beauty of Mount pleasant /Brampton west.
4.89 out of 5 average rating, 258 reviewsPopular amenities for Oakville condo rentals
Weekly condo rentals

Romantic Oasis with Stunning Views & Amenities
4.99 out of 5 average rating, 91 reviews
Stunning Toronto view! Guest Favourite w/ parking!
4.9 out of 5 average rating, 82 reviews
The Calm House | 5 mins Walk to Square One Mall
4.83 out of 5 average rating, 40 reviews
Elegant 2BR Sky Condo for 9 - Terrace - Lake Views
4.91 out of 5 average rating, 56 reviews
Square One Suite by Canterra Stays · Parking
5.0 out of 5 average rating, 10 reviews
Mississauga Square One Condo
4.83 out of 5 average rating, 78 reviews
Luxury New Condo In Oakville W/Free Parking & WiFi
4.79 out of 5 average rating, 19 reviews
Stylish Downtown - Condo Sleeps 8 - YYZ Airport
4.89 out of 5 average rating, 62 reviewsPet-friendly condo rentals

Beautiful Penthouse with Breathtaking View
4.86 out of 5 average rating, 219 reviews
Fort York- Lake View Studio Condo + Indoor Parking
4.98 out of 5 average rating, 111 reviews
Stylish Apartment in Toronto - Long term available
4.88 out of 5 average rating, 129 reviews
Expansive Suite & Stunning Lake Views
4.85 out of 5 average rating, 108 reviews
Cozy Condo • Free Parking• Steps from the CN Tower
4.98 out of 5 average rating, 102 reviews
Bright & Cozy Condo w/ Private Balcony - Ent. Dist
4.89 out of 5 average rating, 134 reviews
Stylish Yorkville Studio: Near U of T & ROM
4.85 out of 5 average rating, 246 reviews
Modern 1BR Toronto Downtown Condo, King size bed
4.95 out of 5 average rating, 117 reviewsCondo rentals with a pool

Luxury 2BR Condo w/ Skyline Views & Balcony
4.94 out of 5 average rating, 172 reviews
The Penty: Luxurious Penthouse with Pool, Hot Tub
4.99 out of 5 average rating, 167 reviews
Stylish Downtown Toronto Condo + Free Parking
4.98 out of 5 average rating, 225 reviews
Lakeside Condo /Pool/ Walking Trail/Parking/CNE
4.95 out of 5 average rating, 163 reviews
Luxury Condo with lake view and Free Parking
4.86 out of 5 average rating, 160 reviews
Yorkville Luxury Suite | Pool, Sauna & Gym Toronto
4.98 out of 5 average rating, 103 reviews
Lakeside Condo Studio In Downtown Toronto
4.89 out of 5 average rating, 481 reviews
Apartment in Fort York BMO field walking distance
4.9 out of 5 average rating, 117 reviewsWhen is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $125 CAD | $127 CAD | $127 CAD | $136 CAD | $140 CAD | $147 CAD | $154 CAD | $160 CAD | $150 CAD | $139 CAD | $133 CAD | $136 CAD |
| 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 |
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- CN Tower
- Rogers Centre
- Scotiabank Arena
- University of Toronto
- Union Station
- Downsview Park
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Harbourfront Centre
- Niagara Falls
- Toronto Eaton Centre
- Niagara Falls State Park
- Scarborough Town Center
- Nike Square One Shopping Centre
- Toronto Zoo
- Exhibition Place
- Elora Gorge
- Yorkdale Shopping Centre
- Casa Loma
- Sheppard–Yonge Station
- Trinity Bellwoods Park
- York University
- The International Centre
- Enercare Centre





