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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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Home in Brampton

4.9 out of 5 average rating, 79 reviews

💕NEW 3 Bedrm House, King & Queen BEDS, WIFI, Prkn

COME & Enjoy this beautiful, Renovated, clean, safe & comfortable 3bedroom house. Middle unit In the very highly sought after area of Brampton You’ll Enjoy the FAST WIFI, 1 KING bed, 2 QUEENs, SOFA BED, BIG COMFY COUCH+ NETFLIX etc, PARKING FOR 2, PRIVATE ENTRANCE & NO SHARED LIVING SPACES PLUS, You’ll be Located just walking distance to paths, parks, entertainment, restaurants, groceries, transit, stores and more! We also ensure a very detail deep clean 🧼 after every guest. Please Enjoy! 😊

Feb 11 – 18

G$25,074 GYD per night

Home in Mississauga

4.88 out of 5 average rating, 143 reviews

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.

Jul 10 – 17

G$18,515 GYD per night

Guest suite in Burlington

4.93 out of 5 average rating, 108 reviews

Burlington core close 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.

Oct 4 – 11

G$26,185 GYD per night

Home in Richmond Hill

4.87 out of 5 average rating, 126 reviews

Luxury 5 beds, 6 Baths custom home

Multi-million dollar custom home in Richvale Ontario. Over 5000sqf 5 bedrooms, 6 washrooms, bar, entertainment room, custom kitchen, 1 in-garage & 3 outdoor parking. Private backyard with deck from the main floor & a walk-out Juliette from primary bedroom. 3 smart TVs & internet included 2 sofa beds in addition to 5 Beds Pool/Snooker Table No parties/loud music allowed Closet in the basement is not accessible for guests Please bring your own personal items e.g. shampoo, body wash etc.

Apr 2 – 9

G$147,857 GYD per night

Apartment in Toronto

4.92 out of 5 average rating, 105 reviews

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. Not a shared space. Parking ✔️

Jul 12 – 19

G$33,387 GYD per night

Guest suite in Elora

4.99 out of 5 average rating, 317 reviews

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.

Jan 14 – 21

G$54,889 GYD per night

Bungalow in Toronto

4.93 out of 5 average rating, 102 reviews

Stylish Apartment! Steam sauna! Free Parking!

Check into this spacious and professionally decorated luxury apartment! You'll find comfort at every step with heated floors, a double steam sauna shower, fully stocked kitchen and 55" HD TV cable and Netflix. Lightning fast Bell internet (8gig) for streaming and work. Free Parking. 6 mins walk to the subway (Victoria Park). 15-20 mins by subway OR driving to the downtown core of Yonge and Bloor. 10mins drive to Scarborough Bluffer’s Park Beach and 7mins Drive to Woodbine Beach.

Apr 11 – 18

G$16,766 GYD per night

Guesthouse in Lincoln

4.99 out of 5 average rating, 107 reviews

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS MAY 2-12 MAY 14-22 MAY 25-31 JUNE 3-7 (4 nights/5 days) JUNE 9-18 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 station on-si

Jan 8 – 15

G$57,426 GYD per night

Apartment in Lincoln

4.97 out of 5 average rating, 126 reviews

Hygge Hus - Niagara Wine Country!Cozy Happy House

HYGGE HUS , “You don’t spell it, you feel it!” - Winnie-the-Pooh Just a short drive south of the GTA and 30 minutes to Niagara Falls. Experience an idyllic get away to one of Ontario’s top wine countries. This thoughtfully designed B&B boasts both new and vintage furnishings. Wine tours are available. Up to 4 people. You book the tastings at your wineries of choice. Local only (53 to choose from) Contact Janet when booking for price and availability.

Oct 10 – 17

G$25,761 GYD per night

Home in Hamilton

4.95 out of 5 average rating, 20 reviews

Hamilton Bay Getaway

Kick back and relax in our 2,000 sqft home, located downtown Hamilton. We are steps away from the Harbour West Go Station, whisking you to Toronto. Walking distance to the beautiful Bay Front Park with acres of trails, and playparks. James Street North is right on your doorstep and features award winning restaurants, shops, art galleries, festivals and malls. Your group will be close to everything when you stay at this centrally located place.

Dec 15 – 22

G$26,483 GYD per night

Guest suite in Brampton

4.92 out of 5 average rating, 95 reviews

A Lake House With Breathtaking View !

Scenic lakeside walkout basement apartment with breathtaking view! Bright, clean and spacious. Full kitchen, washer and dryer for your convenience. Free WiFi and one parking. Located at the most prestigious area in Brampton - Professor's Lake. Out side of my house is a trail around the whole lake for around 3 kilometers. Wonderful for runners or simply walk around the lake to enjoy the nature.

Oct 12 – 19

G$24,288 GYD per night

Guest suite in Orangeville

4.97 out of 5 average rating, 139 reviews

Your very own 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.

Jul 4 – 11

G$17,387 GYD per night

Vacation rentals for every style

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Popular amenities for Caledon smoking friendly rentals

Free parking on premises

Air conditioning

Smoking friendly apartment rentals

Apartment in Mississauga

5.0 out of 5 average rating, 17 reviews

Luxury Condo 20 minutes from Downtown Toronto

Jul 10 – 17

G$32,204 GYD per night

Apartment in Toronto

5.0 out of 5 average rating, 9 reviews

Spacious 2BR 1BA, Instaworthy Views, free parking

Jun 4 – 11

G$32,589 GYD per night

Apartment in Burlington

4.92 out of 5 average rating, 59 reviews

Burlington ON -pets, private apt, walkout backyard

Jul 19 – 26

G$16,798 GYD per night

Condo in Toronto

4.85 out of 5 average rating, 20 reviews

Literally steps to CN Tower & Huge Private Terrace

Jul 13 – 20

G$54,706 GYD per night

Apartment in Toronto

4.89 out of 5 average rating, 36 reviews

Free Parking|Entire 2Br+Balcony|Downtown|Skyline

Aug 26 – Sep 2

G$88,633 GYD per night

Apartment in Toronto

5.0 out of 5 average rating, 5 reviews

Entire Unique Toronto Apartment - 3 Bedrooms

Aug 17 – 24

G$82,775 GYD per night

Apartment in Toronto

Dupont Home, Two Bedroom

Sep 7 – 14

G$35,769 GYD per night

Apartment in Cedar Valley

Luxury 1B Condo in Downtown

Nov 2 – 9

G$60,980 GYD per night

Smoking friendly house rentals

Home in North York

4.85 out of 5 average rating, 168 reviews

Spacious house, 8 minutes away from airport

Apr 3 – 10

G$143,454 GYD per night

Home in Badjeros

5.0 out of 5 average rating, 30 reviews

JJ’s small town country retreat

Jan 27 – Feb 3

G$66,982 GYD per night

Home in Hamilton

4.94 out of 5 average rating, 54 reviews

Steel Town's Stone House

Aug 12 – 19

G$21,351 GYD per night

Home in Bright

4.98 out of 5 average rating, 45 reviews

Country Oasis Accessible B&B-main level 2300 sq ft

Jul 12 – 19

G$65,567 GYD per night

Home in Toronto

5.0 out of 5 average rating, 26 reviews

Cozy Apartment - 20min Downtown w/ Patio

Apr 8 – 15

G$33,476 GYD per night

Home in Mississauga

5.0 out of 5 average rating, 10 reviews

Completely Renovated 1st Floor 3 Bedroom Home

Aug 10 – 17

G$39,201 GYD per night

Home in Lincoln

5.0 out of 5 average rating, 14 reviews

Heart of Wine Country

Apr 17 – 24

G$65,644 GYD per night

Home in Newmarket

4.92 out of 5 average rating, 13 reviews

Chic & Spacious Home off Yonge St With Everything

Mar 3 – 10

G$166,797 GYD per night

Smoking friendly condo rentals

Condo in Toronto

4.88 out of 5 average rating, 161 reviews

1Bedrm Condo|❤️ of Dt-Union Stn, Scotiabank Arena

May 11 – 18

G$45,885 GYD per night

Condo in Mississauga

4.84 out of 5 average rating, 61 reviews

Mississauga Sq 1 Building Condo with Balcony

May 1 – 8

G$21,369 GYD per night

Condo in Mississauga

4.96 out of 5 average rating, 28 reviews

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

Jan 14 – 21

G$49,882 GYD per night

Condo in Toronto

4.92 out of 5 average rating, 76 reviews

THE LOFT + Parking - Near Gladstone hotel

Sep 23 – 30

G$62,843 GYD per night

Condo in Toronto

4.66 out of 5 average rating, 232 reviews

Awesome 1 + 1 Condo @ A+ Location - Free Parking!

Jan 4 – 11

G$48,190 GYD per night

Condo in Toronto

4.89 out of 5 average rating, 53 reviews

Gorgeous Downtown Condo

Jun 8 – 15

G$66,669 GYD per night

Condo in Toronto

4.9 out of 5 average rating, 31 reviews

Modern 1B Condo Downtown Toronto w/ Priv. Terrace!

Oct 16 – 23

G$51,644 GYD per night

Condo in Toronto

4.82 out of 5 average rating, 22 reviews

Lovely apartment w/ amazing view

Jul 17 – 24

G$62,907 GYD per night

Quick stats about vacation rentals that are smoking-friendly in Caledon

Total rentals
30 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
430 reviews

Destinations to explore