
Smoking friendly holiday rentals in Caledon
Find and book unique smoke-friendly rentals on Airbnb
Top-rated smoke-friendly rentals in Caledon
Guests agree: these smoking-friendly rentals 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 smoke-friendly rentals in Caledon
Smoke-friendly flat rentals

Luxurious Private Suite by the Lake
I had an amazing stay. This is definitely the BEST Airbnb I’ve ever stayed at. Everything was organized and I felt right at home. Personal hygiene essentials were made available as well along with some snacks in the kitchen. I look forward to coming back for another stay.

Unique Apt in Trendy West End
It suited my needs perfectly

Cozy & Stylish 1-Bedroom Condo
Dada's place is a very good location. it was worth it

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

Cozy Two Bedroom Condo by SQ1
Our stay at Jibran's was exactly what we needed. A quiet, comfortable space that was private and well equipped with amenities. The hosts were very responsive and accommodating, we felt right at home during the check in process. The location itself was amazing with beautiful views of the city and literally across the street from Square One. Wish we could have stayed longer and will definitely be back!

Independent Seniors
Andre was very caring and went above and beyond that of a host.

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

Private Studio Apartment in Brampton on Airport Rd
This booking exceeded my expectations, extremely clean and comfy. Umar was very easy to reach and communicate with. I will stay here again.
Smoke-friendly house rentals

2 living rms | 3 TVs | Foosball | Family fun!
It's a very quiet neighborhood and a great location in Burlington. It's very close to the downtown area with lots of restaurants and walkable activities. Matt and Helena were very communicative and proactive regarding weekly landscaping, pool maintenance, and garbage pickup. The house was spotless upon arrival and was as described. The upstairs bedroom was warmer than the rest of the house, so depending on outside temperatures, it may be a nonusable space for some. Overall, the house met our needs and allowed us to be comfortable during our stay. Thank you!

Cellar House - Entire Home in the Heart of NOTL
Eric's house was wonderful! Very clean and a convenient location in the town where we could walk everywhere. Our whole family enjoyed relaxing at the house, especially in the spacious backyard. Eric was a great host - very responsive to any questions we had, gave very clear check in instructions, and even gave recommendations on local places for us to check out. We would love to come back to NOTL and stay there again!

Office | Chef Kitchen | 2 Fireplaces | 4 floors
Esther’s place was one of the most fantastic Airbnb’s I’ve ever stayed in! I felt right at home and in fact would love to make this my full-time home. It’s just gorgeous and has every possible feature one could look for in a home, is super conveniently located, and yet still somehow quiet and peaceful, despite being in the city. Do not hesitate to book this place!

Weston Garden Cottage
This was a quiet, peaceful, safe, clean place to stay. The host was very responsive and helpful and kind! Check in and check out were easy as could be. And it was located close enough to make a quick commute to most attractions. When I come back to the GTA I will likely try to stay here again.

Farm House Resort Stay Pool Hot Tub
The stay was amazing with family ! There was always lots to do lots of room for everyone ..pool and hot tub were wonderful it was nice to have both as an option ! Communication was on key Amanda answered right away there was no waiting on her that was nice ! If you forgot something behind it was available ( shampoo, spices, ect ) . Overall stay was amazing we are hoping to go back same time next year if available !

Private 1-br Apartment: Your Secluded Getaway!
Super cute and comfortable little spot. Had lots of amenities that were in the home not only for humans but also for my two dogs. They loved the foldable floor bed, they were fighting over it. The bed was very comfortable and kitchen was very clean and organized. The neighborhood was very calm and well taken care of. So many nice coffee and food spots nearby, also the lakefront trails were awesome!!

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!

Completely Renovated 1st Floor - 3 Bedroom Home
Luca’s home is well placed in a peaceful and accessible area in Mississauga. Large family of 5. There was a room for everyone. The boys had their own beds in a shared room. Check-in was flexible and quite simple. his instructions were also super easy. Very thoughtful and response, Luca was always available and eager to help. He showed when needed. Happy to return.
Smoke-friendly apartment rentals

2 Bedroom Condo close to both Universities!
Amazing space

Stunning 2BR Condo + Gym + Parking + CN Tower View
The place was easy to find & clear instructions were provided. Henry is very responsive & communicative. I would highly recommend staying here.

Friday Harbour Ground Floor w/ Large Terrance
We had amazing time! Tiana goes above and beyond. The outside patio was so nice and relaxing. Recommend to everyone. Thank you!

Riverside Pad
Loved staying here, Stuart was amazingly helpful and answered all questions quickly and kindly. Highly recommend staying here

Mississauga Sq 1 Building Condo with Balcony
Thank you so much for letting me staying at this amazing Airbnb. The unit was very clean and organized, location was perfect, it was in square one, the building has all the amenities you could ever imagine, the host is always available for anything you need, always assisting, very respectful and kind. I honestly loved the whole experience and would highly recommend this place to anyone. Thank you !!!!

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!
Perfect location, felt like home also during my travel. Easy communication and fast responses from the host! Appartment had all the amenities needed and I had a very comfortable stay! Highly recommended!

Studio for 2 in Downtown Toronto
Very amazing trip all thanks to this location! Easy for me to walk around and also meet with my partner who flew into Billy Bishop. The gym was better than expected and we loved the pool as well. Overall a 10/10 experience.
Quick stats about holiday 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
Destinations to explore
- Niagara Falls Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Brampton Holiday rentals
- London 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
- Apartment rentals Caledon
- Townhouse rentals Caledon
- Fitness-friendly rentals Caledon
- Rentals with a washing machine and dryer Caledon
- Rentals with lake access Caledon
- House rentals Caledon
- Rentals with a fireplace Caledon
- Rentals with a patio Caledon
- Rentals with a firepit Caledon
- Flat rentals Caledon
- Waterfront rentals Caledon
- Rentals with an EV charger Caledon
- Rentals with a hot tub Caledon
- Pet-friendly rentals Caledon
- Family-friendly rentals Caledon
- Rentals with breakfast Caledon
- Bed and breakfasts Caledon
- Rentals with outdoor seating Caledon
- Private suite rentals Caledon
- Family-friendly rentals Caledon
- Guest house rentals Caledon
- Bungalow rentals Caledon
- Smoking-friendly rentals Regional Municipality of Peel
- Smoking-friendly rentals Ontario
- Smoking-friendly 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
- University of Toronto
- Budweiser Stage
- Blue Mountain Village
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Exhibition Place
- The Danforth Music Hall
- Harbourfront Centre
- CF Toronto Eaton Centre
- Massey Hall
- BMO Field
- Trinity Bellwoods Park
- Whistle Bear Golf Club
- Casa Loma
- Royal Woodbine Golf Club
- Dufferin Grove Park
- Royal Ontario Museum
- Royal Botanical Gardens