
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.

Bed of Roses Airbnb. Hot tub! 45 mins N of Toronto
*Requests typically replied to within 15 mins during the day.* Private bright 2 bedroom basement (sleeps 4 & no shared areas), 45 minutes N of Toronto. We live in a safe neighbourhood, in a home which backs onto a forest. Walking distance to a train station and a very large mall. You will have two private bedrooms, your OWN bathroom and full kitchen, 3 fireplaces, internet & HOT TUB! Separate entrance. No parties. No instant booking. We screen our guests as we live upstairs with our kids.

Cottage On Lake Ontario Niagara
OPEN TIMESLOTS APRIL 6-12 APRIL 13-20 APRIL 23-25 APRIL 26-MAY 3 MAY 5-8 Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include: beautiful lake views and orchards.

Private 1-br Apartment: Your Secluded Getaway!
Welcome to our modern, fully-equipped unit that features a spacious backyard. Whether you are traveling for business or pleasure, our unit is the perfect base. The location provides convenient access to everything, just 10 minutes from downtown Toronto and the airport, 5 minutes from Lakeshore Blvd, Port Credit, and the GO stn, and steps away from public transportation. Additionally, you will find a plethora of local restaurants, shops, a scenic walking trail, and beautiful parks in the area.

Burlington core.Walk to to lakefront and downtown
Large bright lower level walkout 3 bedroom in quiet residential neighborhood within walking distance to downtown and lake. Plenty of greenspace and deck and parking. Brand new kitchen fully stocked including oil spices tea coffee. Separate entrance with self-check in. Own free laundry facilities. Close to beach, promenade, festivals, trails, restaurants, shopping and more. 45 mins to Niagara Falls and Toronto. Wi-Fi, freezer, cable, Netflix included. 3 piece bathroom and unlimited towels.

Spacious & Vibrant upstairs apartment
There are several shops and restaurants on St. Clair Ave W. Plenty of transit options north of you on the St. Clair line or the bus line on Dufferin. Dog parks are close by. The actual space is perfect. Opposite of the open concept apartment, this spacious one bedroom had a separate eat-in kitchen, separate living room, and bedroom. The second floor back terrace has a lovely view with gorgeous sunsets. ✅Parking for 2 vehicles. ✅Extra Queen sized bed & air mattress available during FIFA.

JJ’s small town country retreat
Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

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.

Karger Gallery Suite
Located within Elora's downtown core, the Karger Suite is only a few short steps to the many fine restaurants and the Elora Mill. Enjoy the views and vibes of being in the heart of Ontario's most beautiful village. The private suite overlooks pine trees, century-old stone walls, angled rooftops and the charming village of Elora. Enjoy a glass of wine on your private 1500 sq. ft. third floor patio, keeping warm and cozy beside the fire-table. Day or night the views are enchanting.

Quirky Fun Mimico Hideaway near the lake
Relax and unwind in this private, charming unit with its own entrance and a backyard that feels like a world of its own. Nestled in the heart of Mimico—Toronto’s lush west-end neighbourhood just steps from the shores of Lake Ontario. The space is comfortable, eclectic, and inviting, with a safe, functional layout and an easygoing vibe. Perfectly located for concert-goers, sports fans, downtown explorers, and nature lovers alike. The train to Exhibition (at BMO Field) is only one stop.

Gorgeous Downtown Condo
Gorgeous high-ceiling condo in downtown Toronto, located in the vibrant old fort york neighborhood. Spacious and bright unit with 2 bedrooms, 2 bathrooms, and 2 balconies. Equipped for remote work with 2 desks. A step away from the city best-known attractions: Lakefront, CN Tower, Rogers Center, Aquarium, shops, bars, restaurants and nightclubs Easy access to commodities (5 min walk from Starbucks, LCBO, Lowblaws, CityAirport and TTC) Underground parking spot is included.

Experience Country Living at Firefly Ridge
Your private living space is comfortable and bright, with lots of picturesque windows and high ceilings. There is a walkout to a private area where you can relax, and unwind, enjoying the sounds of nature and some farm animals, such as horses, minis, donkeys, goats, chickens, cats, 2 Australian cattle dogs and even some piggies. We love our animals and we welcome yours as we are a pet friendly farm. PLEASE NOTE DOGS MUST BE ON A LEASH WHILE ON THE PROPERTY.

Entire cozy place in the middle of all
This private basement apartment features 9’2” ceilings with a separate, private entrance. includes a laundry room and a fully furnished living room with a sleeper sofa. Comfortable space with a TV and various complimentary streaming applications. Located in one of the best areas of Vaughan, the apartment is close to major attractions and amenities including Vaughan Mills, Hillcrest Mall, GO Transit, Canada’s Wonderland, numerous parks, cafés, restaurants.
Popular amenities for smoke-friendly rentals in Caledon
Smoke-friendly flat rentals

Luxurious Private Suite by the Lake

Wellesley Station 3-Min, Museums & Winter Shopping

2+2 Condo Heart of Downtown + FREE parking

Cozy little apartment in Wasaga Beach.

Cozy Two Bedroom Condo by SQ1

Urban Sanctuary

Independent Seniors

Urban Gem, 3 Mins to Wellesley Station, Balcony
Smoke-friendly house rentals

Villa CasaLuxe Designer Whole House on Subway Line

Peaceful country getaway

Niagara's Hidden GEM: Mainfloor

Cellar House - Entire Home in the Heart of NOTL

LongstayPromo: Erin Mills Best Area-airport&sq one

Weston Garden Cottage (park & walk to UP train)

7 bedroom getaway with pristine pool

Farm House Oasis: Hot Tub, Pool, Horses, sleeps 12
Smoke-friendly apartment rentals

Carnival • Colourful mosaic room

Upscale 1-bed condo near dining & nightlife

Stunning 2BR Condo + Gym + Parking + CN Tower View

Friday Harbour Ground Floor w/ Large Terrance

Private Room & Washroom in high-rise near trainbus

Cozy Guest Bedroom + Shared Appt on Aquitaine Ave.

Four-Season Escape at Friday Harbour. Top Floor

Luxury 2BDR modern private condo in Toronto
Quick stats about holiday rentals that are smoking-friendly in Caledon

Total holiday rentals
Explore 20 holiday rentals in Caledon

Nightly prices starting at
Caledon holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 370 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Wifi availability
20 of Caledon holiday rentals include wifi access

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

4.8 Average rating
Caledon stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Caledon’s top spots include SilverCity Brampton Cinemas, Landmark Cinemas 7 Bolton and Uptown Theatre
Destinations to explore
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Blue Mountain Village
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Distillery District
- Harbourfront Centre
- Nike Square One Shopping Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Snow Valley Ski Resort
- Massey Hall
- Financial District
- Wilfrid Laurier University
- Casa Loma
- Downsview Park
- Dufferin Grove Park
- Lakeridge Ski Resort




