
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.

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.

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.

Romantic Spa/Sauna Cabin Getaway
This unique 'off grid style' is a tiny cabin surrounded by nature & panaramic views. Hosted on the lands of WÄRME Wellness- A SPOT TO RETREAT, relax & endure much needed downtime : by yourself, a couple/ two family members/friends who are looking for spa quality time 'away from it all.' Inside - enjoy the benefits of sauna/spa culture w/ an authentic large wood powered sauna. Bathrooms are located adjacent to cabin. Yoga studio available for rent. Ask about our ‘elevated romance package.’

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 apartment has the fastest wifi speed. The second floor back terrace has a lovely view with gorgeous sunsets. Parking for 2 vehicles ✅ Not a shared space.

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.

Cottage On Lake Ontario Niagara
OPEN TIMESLOTS MARCH 23-26 (3 nights/4 days) MARCH 27-APRIL 20 APRIL 23-30 MAY 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: Lake & orchards.

Beautiful Spacious In-LawApartment Ready For You
Our home is in the country side but not limited to grocery,parks..etc.. The 401 & 403 exits are 10 mins away. Guelph University and downtown Guelph is also10 to 15 mins away. Its a shared home we live here also have 2 small dogs in case anyone allergic.They will not be in your space if that's going to be a concern. It's a separate entrance and room for a vehicle for parking. The laundry is not shared but I'm willing to accommodate if necessary. The apartment is an in-law sweet.
Popular amenities for Caledon smoking friendly rentals
Smoking friendly apartment rentals

Luxurious Private Suite by the Lake

Wellesley Station 3-Min, Museums & Winter Shopping

Cozy Two Bedroom Condo by SQ1

Urban Sanctuary

1 bed+den luxry private condo appt near train-airp

Independent Seniors

Urban Gem, 3 Mins to Wellesley Station, Balcony

City Chic Home
Smoking 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

Weston Garden Cottage (park & walk to UP train)

7 bedroom getaway with pristine pool

Snow valley ski (12km)Scandinavian therapy retreat

Shanty Bay Escape
Smoking friendly condo 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

Cozy Guest Bedroom + Shared Appt on Aquitaine Ave.

Four-Season Escape at Friday Harbour. Top Floor

Luxury 2BDR modern private condo in Toronto

Lakeview, Skyview in Heart of Downtown,Fre parking
Quick stats about vacation rentals that are smoking-friendly in Caledon

Total vacation rentals
Explore 20 vacation rentals in Caledon

Nightly prices starting at
Caledon vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 370 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Wi-Fi availability
20 of Caledon vacation rentals include wi-fi 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
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Blue Mountain Village
- Metro Toronto Convention Centre
- BMO Field
- Distillery District
- The Danforth Music Hall
- Nike Square One Shopping Centre
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Snow Valley Ski Resort
- Massey Hall
- Financial District
- Casa Loma
- Wilfrid Laurier University
- Dufferin Grove Park
- Lakeridge Ski Resort
- Downsview Park




