
Condo holiday rentals in Caledon
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Top-rated condo rentals in Caledon
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Popular amenities for Caledon condo rentals
Weekly condo rentals

Blue Mountain Getaway at North Creek Resort
We really enjoyed our stay. The bed was really comfortable! Everything we needed was provided including an early check in. Will be coming back for sure!

Beautifully Furnished New Condo at Friday Harbour
We had a great stay! The place was incredibly clean, and had everything we needed and more. We felt right at home, and communication with the host was excellent! Everything was easy to find. There was an awful snow storm over the weekend that we stayed, but the place was so cozy and clean, we were happy to stay in and binge watch some Netflix :) I can’t recommend Jennifer Nicole’s place enough!

South Wind - Modern Condo in Collingwood - Sleep 5
Beautiful place. Definitely will come back

Luxurious 2 bedroom condo
Beautiful place! Easy check in! Felt very safe and comfortable! Around more than enough food options to choose from! Very responsive host! Was always readily available to answer any question I had! Would most certainly stay again!

Mountainside Retreat - Ski in/out - Endless Coffee
This was our second time staying here. We loved it just as much the second time. Great location, clean and like a home away from home. The hosts were very friendly and had great communications with us. We will definitely be back!!

Resort Living with Amazing Water Views, Balcony
We really enjoyed our stay, the place was as described and matched the pictures. I'd definitely recommend this place. However, we'd appreciate if the instructions were a bit more clear about the parking, and if the hosts were more responsive, there was some delay in hearing back from them, so we had to figure out where the parking was located ourselves. this detail could be added in the instructions for more clarity.

Exceptional 2+1 ground floor condo @Friday Harbour
Shai was a great host. It is a beautiful location. We loved that there was a late check- out for 5 pm. I would definitely come back to stay.

Mountain Side One Bedroom
Connor was great to work with and highly responsive! He sent a very detailed listing of amenities in the area along with locally too like taxis, shuttle services, etc. The place was exactly as advertised. Would stay again!
Pet-friendly condo rentals

Bright MCM 2 Bedroom Walk Up with Private Deck/BBQ
My husband and I, along with our cat, were displaced due to the ice storm in our city. We had no power at home, and were struggling to find accommodation that would take a cat. Lisa was helpful, very responsive, and allowed us to check in early since we were between hotels. The place was amazing. Great location, clean, quiet, and had everything we needed - fully stocked kitchen, very comfortable living and dining room, and quiet/comfortable bedrooms. Our cat loved his stay too, and settled in quickly. The location was great, and was close to everything we needed.

Spring Sneak Away | Blue Mountain
Wonderful place, great host. Close to the slopes if you are going for that - we walked to Blue Mountain directly and only took 15-20 minutes. The shuttle is only for the winter season!! Don't make the same mistake we did and wait for a bus that doesn't show up - however, you can contact them directly to acquire a pick-up/drop off I believe. The place was amazing - excellent amenities, I've seen reviews complain about the couch but honestly if it's only one person sleeping on the couch and you don't unfold it into a futon we found it cozier than the bed. The tub is so deep that even tall people can get a good soak in it. Shower pressure and heat leaves something to be desired if your goal is HOT shower. 5/5 will be going back in any season

Beautiful suite in Downtown Toronto
My 7 year old daughter and I flew in to Toronto for Taylor Swift's ERAS concert. I can not say enough about the location. The Rogers Center is right across the street- we could watch the line up at our gate and then head over when there was no line. Amazing view of Rogers Center and CN tour. We walked everywhere the entire time- CN Tower, Ripley Aquarium, Convention Center for the Tayl-gate party and could easily rest at the condo in between activities. The condo was super clean. The bed was SO COMFY! Fully stocked kitchen. My mom came to visit us for a night from Windsor and Oron was extremely responsive to my request for parking. He got us set up right away. I would 100% stay here again for an event!

🔥Charming 1 BR Condo🔥 Steps To Square One!👌
The electric appliances namely toaster and percolator were downright dirty. The host did not add bin liners which we had to buy. But we loved the halal food places nearby.

Trendy & Cozy 1BD Condo in the Heart of Toronto
Ariana was a fantastic host—very responsive and accommodating. She quickly resolved issues and even arranged a late checkout. Highly recommended!

Mountainside Studio w/Kitchen - Beside Blue
Just as described and pictures. A quiet unit at the back on the building, which is as nice. Check in and accessibility was easy. Just as pictured and you can’t beat the price! Uber was under $7 to the mountain, we did not look at free shuttle but know it was available. Hot tub was great, pool looks like it would be too in the summer months. Extra toilet paper would be appreciated, but we did bring back up so was not a problem. Ottoman/coffee table could use an upgrade, something easier to clean. Overall great experience, would book again. Dave and his team were on the ball and in communication often. Appreciated the instructions for check in/ check out. He had the unit ready 3+ hours before planned check in which was amazing! Lots of extra linens and pillows were available. Fireplace was a nice touch. Wifi was easy to access and worked well. Did not use the jacuzzi tub, but definitely a nice added feature to have. Deck out front and on the side we’re more spacious than expected.

Luxury 1 Bedroom Condo in Downtown Toronto
Great place - super convenient for downtown Toronto. I came for a business trip but it would also work great for leisure, entertainment etc. Roman was very accommodating and communicative, particularly given my flight got in late. Would recommend.

Upscale Condo in the Clouds at CN Tower
Super clean and well-equipped 60th floor condo with an absolutely spectacular view overlooking the CN Tower, the lake, and the entire west side of Toronto. 5 stars for sure!
Condo rentals with a pool

FH Aquarius Bldg: Modern 2BR/2B Condo
Beautiful unit with fully equipped kitchen & everything you need to feel right at home. Beds are comfortable, we were 2 people but it would fit 4 comfortably. Would definitely be back.

Perfect Comfort 2 Bed ~ BBQ ~ Parking ~ Resort
Franco and his team are lovely to deal with. They are extremely communicative and in a timely manner. The apartment is exactly “like” the pictures shown, warm, cozy and overall a very welcoming home. In addition, to having such a wonderful place to stay in, they have thought of every kitchen tool you may need during your stay, it’s great to have access to all these accessories. Thank you for the great stay, I would definitely recommend your place to anyone staying in the area.

Prime location • Amazing views • FREE parking
Radmir was an excellent host. Great getaway it was peaceful. It was private. It was convenient so many restaurants around everybody so nice everybody so pleasant the environment was clean. It felt like a home away from home. Great experience for my first time in Toronto Canada.

Stylish Downtown Toronto Condo with Free Parking
Honestly, this was the best AirBnB I have stayed at. Super clean, beautifully decorated, well equipped, super soft sheets on an extremely comfortable bed - there is not anything I would say I wished were different. The location is a bit on the outskirts, but I really enjoyed the walk to get further into the action. There was no issues with noise/neighbors. Loved it and will definitely try to book again if I’m headed to Toronto.

Large 1 Bedroom Condo Near Horseshoe
We enjoyed our stay. Tim was responsive, provided clear instructions. The unit was clean and nice. We also liked the pool and the sauna located at the recreational building in the complex. Overall, good experience.

Wasaga Beach/WaterFront BeachHouse/ BBQ/AC/parking
We had a wonderful and pleasant stay! The host was very responsive and made sure we had everything we needed. The place was clean, comfortable, and welcoming. We’re already planning to come back again. Highly recommend!

Luxury Downtown Condo For 6 (Near CN Tower)
I really enjoyed our stay here. The unit was exactly how it was described and shown in the pictures. Check in and out went very smoothly. The location was the best of all. The Rogers centre is pretty much right across the street if attending another Roger centre event, I will definitely Stay here again.

Private Backyard/Shuttle/Pool/10min walk 2 village
Elyse’s place is lovely! It looks just like the pictures. It was cozy and comfortable during a huge snowstorm. The kitchen is very well quipped. Neighborhood is very pretty and security was visible. Snow was cleared very quickly. Nice proximity to both Blue Mountain and Collingwood. Elyse is a welcoming and very responsive host. Would definitely stay again!
Quick stats about condo rentals in Caledon
Total rentals
20 properties
Nightly prices starting at
$78Â AUD before taxes and fees
Total number of reviews
230 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Blue Mountain Village
- Budweiser Stage
- Distillery District
- Port Credit
- Horseshoe Resort
- The Danforth Music Hall
- Metro Toronto Convention Centre
- Exhibition Place
- Toronto Zoo
- CF Toronto Eaton Centre
- TPC Toronto at Osprey Valley
- Massey Hall
- Royal Woodbine Golf Club
- Harbourfront Centre
- Whistle Bear Golf Club
- Snow Valley Ski Resort
- Yonge-Dundas Square
- Trinity Bellwoods Park
- Osler Bluff Ski Club
- Casa Loma