
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.

Sidarly Hills Cozy Yurt Getaway on 100 acre farm
Sleep under the stars on a 111 acre farm. This rustic experience allows you to live off-grid and among nature. There are a number of trails and outdoor areas to explore as well as a number of close-by amenities within a 5 minute drive including 2 ski resorts. If you really want to indulge, we are also just a 20min drive to the Thermëa spa by Nordik. Far enough away from the hustle and bustle but close enough to not require a long travel commitment, this place is a great way to relax and unwind.

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.

Cottage On Lake Ontario Niagara
OPEN TIMESLOTS JANUARY 28 (today) until FEBRUARY 1 FEBRUARY 2-5 (3 nights/4 days) 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. We are located along the south shore of Lake Ontario amongst the fruit belt of the Niagara. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include: Lake & orchard

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.

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.

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. A dog within minutes from the home. 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 apartment has the fastest wifi speed. The second floor back terrace has a lovely view with gorgeous sunsets. Parking ✅ Not a shared space.

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.

Private Studio Apartment in Brampton on Airport Rd
Relax in the safe, beautiful, estate neighbourhood of Castlemore in Brampton, ON. Enjoy a fully private studio apartment located centrally off Airport Road with access to Toronto Pearson Airport in 15-20 minutes, Highway 410 in 5 minutes, Highway 427 in 10 minutes, and Downtown Toronto in 35 mins. Within reach to a number of grocery stores and fast food restaurants. One guest maximum due to studio size.

Your Peaceful Santuary in Nature
Tranquil space to go walking through the 20 acres of forest with trails, lots of wildlife, and beautiful bright stars at night for stargazers. You can have a coffee in the morning on the patio set in front of the suite and have a drink on one of the hills in comfortable muskoka chairs up on a hill of the property and watch the sunset or sunrise if you are an early bird.
Popular amenities for smoke-friendly rentals in Caledon
Smoke-friendly flat rentals

Downtown Toronto: CN Tower View!

Wellesley Station 3-Min, Museums & Winter Shopping

Modern Luxe Living – Walk to Square One & Transit

Cozy & Stylish 1-Bedroom Condo

Cozy Two Bedroom Condo by SQ1

Urban Sanctuary

Independent Seniors

City Chic Home
Smoke-friendly house rentals

Villa CasaLuxe Designer Whole House on Subway Line

Cellar House - Entire Home in the Heart of NOTL

LongstayPromo: Erin Mills Best Area-airport&sq one

Yorkville | Exec Kitchen | Office | Spa bathrooms

kids paradise, extra storage, fenced, pet friendly

Weston Garden Cottage

7 bedroom getaway with pristine pool

Completely Renovated 1st Floor - 3 Bedroom Home
Smoke-friendly apartment rentals

2 Bedroom Condo near Univ of Waterloo & Laurier!

Upscale 1-bed condo near dining & nightlife

Downtown Fort York 1BR w Parking• Free Parking

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

Private Room & Washroom in high-rise near trainbus

Cozy Guest Bedroom + Shared Appt on Aquitaine Ave.

Luxury 2BDR modern private condo in Toronto

Lakeview, Skyview in Heart of Downtown,Fre parking
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 £7 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
- Blue Mountain Village
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Nike Square One Shopping Centre
- BMO Field
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Snow Valley Ski Resort
- Casa Loma
- Dufferin Grove Park
- Wasaga Beach Area
- Lakeridge Ski Resort




