
Smoking friendly vacation rentals in Caledon
Find and book unique smoking friendly rentals on Airbnb
Top-rated smoking friendly rentals in Caledon
Guests agree: these smoking friendly rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Caledon smoking friendly rentals
Smoking friendly apartment rentals

The Vintage Whinery at the Falls!
This was such a unique Air BnB and one of the most charming we have ever stayed at! The decor was early 20th century Parisian and offered beautiful spots indoors for cute pictures! I had no idea it was a local famous AirBnB! I booked it based on price and proximity to the Falls! Not even a 1mile directly from the front door to Maid of the Mist. It was so convenient to park on the street for free (observe her guidance for street parking!) There were several tasty restaurants near by all walkable and easy to get on the main road to go to Wegmans or Walmart. And if you’re a runner make sure to bring your running shoes. Trails easily accessible from her front porch! Shelia herself was very sweet! We saw her on the way out due to us arriving late and needing to let ourselves in. Enjoy her collage artworks too which are throughout! Her artistic abilities create the most beautiful Air BnB!

Chic 2BR Gateway | Family Suite | Close to Falls
Excellent accommodation. The Shah was always in touch and resolved various issues in a timely manner, and also allowed us to check in ahead of schedule. There was a missing kettle in the apartment. Overall, I liked everything. Thanks

Urban Sanctuary
Wonderful home, comfy bed, love to stay there.

Cozy Two Bedroom Condo by SQ1
Great place, location, and view!

Welcome to Hub Central
This was a lovely air bnb with an incredibly comfortable bee! It’s a beautiful, spacious space and very comfortable. We cannot recommend it enough!

Downtown Gem by the Subway
we had a great time, the apartment was adorable

Spacious 2BR 1BA, Instaworthy Views, free parking
Alex is a great host. We had a enjoyable stay there.

Pat's Country Home
I had a great time here. I went to celebrate New Year's at Niagara with my hubby and to be honest Pat’s place is one of the best I have found at Airbnb. Beautiful, peaceful, clean, and felt like home. We went for a little walk at Niagara on the lake and found a very cute restaurant. Everything was perfect. Cannot wait to go back in summer.
Smoking friendly house rentals

2 living rms | 3 TVs | Foosball | Family fun!
This was our home away from home through renovations and cannot be more thankful for Helena and Matt allowing us to use their home. We had two extensions and the team was more than accommodating - communication was quick and easy! Thank you so much again for opening your home to us! Happy Holidays!

Luxury Home - 20min to Downtown w/ Outdoor Patio
Ana was an exceptional host. She was very friendly and helpful, made our stay feel very welcomed. She provided great helpful tips which made getting around and planning that much easier. Check in and check out was very easy and she was very flexible and accommodating. Holly the host dog was exceptionally friendly and cuddly which made the stay that much warmer and more welcoming. I would highly recommend this Airbnb for your next stay.

Cellar House - Entire Home in the Heart of NOTL
Eric’s home is what you see in the pictures and more! Great home with all the furnishing you would need for your stay. Well equipped kitchen, entertainment, washroom filled with towels and they included slippers for the hot tub. Eric is a great host. Quick and responsive. Gives amazing recommendations for wine tours and restaurants so definitely ask when booking! We can’t wait to come back to Eric’s lovely Airbnb!

Office | Chef Kitchen | 2 Fireplaces | 4 floors
Our family of 6 really enjoyed Esther’s place. The location is fantastic, walking distance to restaurants, shops, museums, subway. The rooms are spacious, the kitchen well appointed, and living areas very comfortable. We will stay here again when we come back to Toronto!

kids paradise, extra storage, fenced, pet friendly
We loved staying here! There was SO much space, it felt very homey and cozy. The backyard was beautiful! This is an amazing home to stay in with tons and tons of room.

Private 1-br Apartment: Your Secluded Getaway!
very helpful, place is very clean. very responsive. i will stay here every chance i get

Shanty Bay Escape
I had a fantastic stay at Ped’s place! The accommodation was clean, cozy, and exactly as described. The location was peaceful, making it a perfect getaway. Ped was an excellent host—quick to respond and very helpful throughout our stay. Everything was well-prepared, and I felt truly welcomed. I would highly recommend this place to anyone looking for a comfortable and relaxing stay. I’d love to come back in the future!

Serene country retreat - your home away from home!
We booked this home for 1 night as a group because we were attending a wedding in the area. The home was large with plenty of sleeping space and bathrooms which was great. The bedding and pillows were extremely comfortable. Overall we had a great stay. Ameet also was very responsive after our stay when one of our group realized they had forgotten some items and worked with them to find a way to get the items shipped back to them. Thank you Ameet!
Smoking friendly condo rentals

2 Bedroom Condo close to both Universities!
Amazing space

Stunning 2BR Condo + Gym + Parking + CN Tower View
Very nice place with an amazing views within the apartment. The location was walkable 10/10 would recommend. However, I think the instructions for parking could be better.

Amazing Large 2Bed Condo in Downtown Sqr 1
Was so relaxing and the view was amazing host was super nice and my kids enjoyed the pool!

Friday Harbour Ground Floor w/ Large Terrance
The host replied back to my inquiries extremely quickly and with kindness. The location was also amazing and the room was very clean. We were there to celebrate a birthday and the host had prepared an assortment of decorations for us, including banners and balloons.

Riverside Pad
Stuart was super quick to respond which made the process really smooth. The location is great, just steps from interesting local restaurants and pubs.

Luxury 2BDR modern private condo in Toronto
I had an absolutely wonderful stay! The place was spotless—super clean and well-maintained—and the views were just breathtaking. It was the perfect spot to relax and take in the surroundings. What really made the stay great! was the host. They were incredibly kind, helpful, and responsive throughout the entire experience. From the moment I booked, communication was clear and timely. They went above and beyond to accommodate my schedule, including helping me with an early check-in, which made my travel day so much smoother. Every little detail felt thoughtfully handled, and it genuinely felt like they cared about making sure I had the best experience possible. I would absolutely stay here again and highly recommend it to anyone looking for a peaceful, scenic getaway with a top-notch host.

Awesome 1 + 1 Condo @ A+ Location - Free Parking!
Great condo. Nicely located. The condo is surrounded by an alleyway, making it easier to get keys and garage FOB. The condo is also quiet at night. If you are a coffee drinker there are three types of coffee making devices. Office setup with large monitors were in the alcove ( I think Toronto condo developers call this a +1) . Loved the views from the balcony.

Studio for 2 in Downtown Toronto
Stayed for a week and absolutely loved it. Lovely pool, big tv that was great for movies and close to the best parts of Toronto. Will definitely stay here again in the future.
Quick stats about vacation rentals that are smoking-friendly in Caledon
Total rentals
30 properties
Total number of reviews
480 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- Blue Mountain Village
- Budweiser Stage
- Port Credit
- Horseshoe Resort
- University of Toronto
- The Danforth Music Hall
- Metro Toronto Convention Centre
- Exhibition Place
- CF Toronto Eaton Centre
- Toronto Zoo
- TPC Toronto at Osprey Valley
- Royal Woodbine Golf Club
- Snow Valley Ski Resort
- Whistle Bear Golf Club
- Massey Hall
- Harbourfront Centre
- Yonge-Dundas Square
- Osler Bluff Ski Club
- Trinity Bellwoods Park
- Royal Ontario Museum
- Royal Alexandra Theatre