
Condo holiday rentals in Caledon
Find and book unique condos on Airbnb
Top-rated condo rentals in Caledon
Guests agree: These condos are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
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
My boyfriend and I just stayed at Hosting Blue’s place this last weekend, and we hope it won’t be our last time there! Hosting Blue had very clear and thorough instructions on everything imaginable which made it a very easy and peaceful stay! The place looks exactly like the photos, furnished comfortably and is in a convenient location near Blue Mountain, with parking included (which is the best!!!) Our favourite part of the place was the kitchen, fully equipped with everything we needed, where we were able to cook all of our meals instead of having to eat out. This while watching the Deal or No Deal Roku channel with a glass of wine, we were in heaven!! Thank you again for a wonderful weekend!

Luxurious 2 bedroom condo
First of all, Stefano was very responsive, helpful and kind. Whatever we needed and had questions on he was very quick to reply! The condo itself was clean, homey, and the kitchen was very well equipped. Down to the details even the toilet paper in the washrooms were folded, towels set ready for us on the beds. The tv was loaded with all kinds of entertainment and it was easy to navigate! Side note, the coffee selections Stefano provided are really good. Location wise, parking is right in front of the condo. Surrounding area was very convenient with multiple food locations, gas stations and grocery stores nearby! The falls itself was only a five minute drive along with the other attractions like the casino, olg stage, clifton hill, and many more. We’re definitely recommending this unit and host and are planning to book with Stefano again in the future!!

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
Apartment was even beyond our expectations. It was the most amazing place we have ever rented on New Year holidays. There were 6 people and the place was big and comfortable enough for everybody. Moreover, the apartment was extremely clean and had everything in it to live for short or long terms without any issues. The apartment is located in Friday Harbour which is the perfect place to live in. There are lots of shops, restaurants, a beautiful marina, pool , beach club nearby. We also went for skiing to Horseshoe resort, which took us approx 30 minutes to get there. Shai is a wonderful host, he was in touch during the entire period of our stay in his apartment. He left us a bottle of wine and chocolates as a present, it was so cute. Thank you so much for your attention and care. We will definitely rent your apartment again.

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.

Lovely Toronto entire Condo!Renovated!Amazing view
Very convenient neighborhood and very nice living area

Winter Retreat | Blue Mountain
We were delighted and surprised about how well equipped was the studio. Jacinda delivered plenty of staff that made our stay as a home. I cannot ignore that the pre instructions and communication made our travel easy and more comfortable

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!👌
Great place to stay and excellent location. Place was clean, instructions were clear and Omar was always very helpful and responsive to our questions. Highly recommended!

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.
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 is an awesome host!! Very quick with responding to our questions. We had probably too many. All were questions about dinner recommendations or activities in the area. He was very very helpful. His place is well maintained and clean with awesome views. Definitely recommend. We will definitely be in touch for our next visit. Great location to catch a BlueJays game!!!! Thanks.

Stylish Downtown Toronto Condo with Free Parking
stayed here a few times, always a pleasure. host is so nice and place is just as pictured.

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)
Clean, very conveniently located, and always quick communication before and during the trip from Bri and Mike! Great set up for our family (2 adults and 2 kids). Would definitely stay here again if returning to Toronto.

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!

Bohemian Luxury at Friday Harbour Resort Simcoe
A very restful and relaxing weekend!
Quick stats about condo rentals in Caledon
Total rentals
20 properties
Nightly prices starting at
$78 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
Destinations to explore
- Niagara Falls Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- London Holiday rentals
- Brampton Holiday rentals
- Niagara Falls Holiday rentals
- Buffalo Holiday rentals
- Niagara-on-the-Lake Holiday rentals
- Pocono Mountains Holiday rentals
- Mississauga Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Rentals with pools Caledon
- Bungalow rentals Caledon
- Townhouse rentals Caledon
- Family-friendly rentals Caledon
- Rentals with a patio Caledon
- Rentals with outdoor seating Caledon
- Smoking-friendly rentals Caledon
- Pet-friendly rentals Caledon
- Fitness-friendly rentals Caledon
- Rentals with a washing machine and dryer Caledon
- Apartment rentals Caledon
- Waterfront rentals Caledon
- Bed and breakfasts Caledon
- House rentals Caledon
- Kid-friendly rentals Caledon
- Guesthouse rentals Caledon
- Rentals with an EV charger Caledon
- Rentals with a fireplace Caledon
- Rentals with a fire pit Caledon
- Rentals with a hot tub Caledon
- Rentals with breakfast Caledon
- Private suite rentals Caledon
- Rentals with lake access Caledon
- Condo rentals Regional Municipality of Peel
- Condo rentals Ontario
- Condo rentals Canada
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Rogers Centre
- Scotiabank Arena
- CN Tower
- Blue Mountain Village
- Budweiser Stage
- Port Credit
- Horseshoe Resort
- University of Toronto
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Exhibition Place
- CF Toronto Eaton Centre
- Snow Valley Ski Resort
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Royal Woodbine Golf Club
- Massey Hall
- Whistle Bear Golf Club
- Harbourfront Centre
- Yonge-Dundas Square
- Osler Bluff Ski Club
- Trinity Bellwoods Park
- Royal Ontario Museum
- Royal Alexandra Theatre