Smoking friendly vacation rentals in South Side

Find and book unique smoking friendly rentals on Airbnb

Top-rated smoking friendly rentals in South Side

Guests agree: these smoking friendly rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Lake Zurich

4.98 out of 5 average rating, 170 reviews

Take A Pebble Apartments (Studio 3)

Message me if you experiencing difficulties booking Greetings travelers! Come stay in my Studio Apartment located in downtown Lake Zurich, Illinois. A 2 minute walk to our lovely lake. Breakfast Place, Fast Food, Fine Italian/Pizza Restaurant & a few Bars all in our downtown area. Below your room is Offbeat Music & LP Records. Take a few records back home with you or better yet a Drum Set!!! Take A Pebble Properties L.L.C. was named after a song by the great band Emerson Lake & Palmer.

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 6 reviews

Entire Huge 1 BDRM Loft Unit

Newly Rehabbed, Renovated, 1 bedroom Loft style garden unit is available, Unit has a full kitchen with a separate dining room. Unit boasts a huge living room with 13 Ft ceilings, a huge bedroom with a walkin closet and a queen size bed along with a huge dresser. The bathroom has been renovated and the appliances are brand new. Corner Office space within living room along with other features. All Furniture is brand new as the unit has been completely redone for you Plenty of Restaurants around.

Superhost

Home in Chicago

4.89 out of 5 average rating, 36 reviews

Brand New Spacious Duplex

ZERO CLEANING FEE, NO EVENTS/NO PARTIES NO CHICAGO RESIDENTS This stylish place to stay is perfect for group trips. Minutes away from downtown Oak Park and downtown Chicago. Great open floor plans to accommodate groups of any size. Walking distance from public transportations. Plenty of parking near facility. Great backyard space with fire pit for nice summer nights. In unit laundry, bar, and projector in the lower level space for entertainment. Plenty of space for small to mid sized groups.

Guest favorite

Home in Chicago

4.95 out of 5 average rating, 130 reviews

Chicago Riverhouse summer on our patio!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. Amazing chef’s kitchen! 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Chill private patio with illuminating sofa

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 13 reviews

Luxury Villa 10 mins to Downtown

Welcome to the Windy City! La Villita is the gateway to Chicago's vibrant Mexican-American area. Super cozy , modern and centrally located in the heart of Chicago. Close to everything - 5 Star Dining and authentic shops making it easy to plan the perfect Chicago experiences. 15 Minutes to The Loop, Downtown, major event venues (Soldier Field, United Center, McCormick Place) University Of Illinois Chi, Medical District , Chinatown, Little Italy, and many restaurants and popular attractions.

Guest favorite

Home in Chicago

4.9 out of 5 average rating, 30 reviews

Cheerful 2 Bedroom Residential Home with Finished Basement, full kitchen and Dining Room. 2 Residential Parking passes per 24 hour stay!

This home offers you 2 Bedrooms, 2 full bathrooms, finished basement, full kitchen with microwave! Dining area and entertainment in a full finished basement with a restroom! This is your place to stay on quiet block, less than a half block to transportation. 1 Bus ride to Downtown Chicago and a short 15 minute ride to the Loop and Museum's. Centrally located, less than a minute drive to the Dan Ryan expressway. Clean, comfortable and spacious! Dining Room seats up to 7 people!

Guest favorite

Guest suite in Chicago

4.91 out of 5 average rating, 74 reviews

1 bed apartment + futon room bridgeport

Located at the geographic center of Chicago! Plenty of free street parking. Very safe and ~10 min walk to the 35th Orange line and 3 blocks from the Archer bus, both go directly downtown within minutes. Brand new lower level construction unit. Comfortable spacious rooms to relax in. Closet in both rooms for your use while here. The apartment has a separate entrance, bathroom, kitchen, dining space. Enjoy your own private space in Chicago with a back patio, grill, and laundry.

Guest favorite

Guest suite in Chicago

4.95 out of 5 average rating, 120 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

Superhost

Apartment in Chicago

4.82 out of 5 average rating, 88 reviews

McCormick Pl 420 friendly 1br/1ba parking/sleeps 4

• MESSAGE US for SPECIAL RATES • Minutes walk to McCormick Convention Center • 420 friendly unit. Smoking inside the unit allowed • Optional Parking space • State street location • Safe building monitored by our Security team • Queen size bedroom + Sofa bed for a comfortable stay for up to 4 guests • Dedicated fast Internet • 65" 4K Roku Smart HDTV(Roku and Netflix) • Fully equipped kitchen • Minutes to all touristic destinations • In-unit washer and dryer

Guest favorite

Apartment in Chicago

4.95 out of 5 average rating, 654 reviews

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 87 reviews

Cannabis Condo 4BR

Beautiful, spacious apartment is located 10 min from Beach. 10 mins to Hyde Park, (Tiger Woods) Golf Course. 10 mins from Obama Library (coming soon). 10 mins from Museum of Science and Industry. 20 mins from downtown/Soldiers Field (Bears Stadium), Northernly Island concerts, Field Museum, and Shedd Aquarium (beautiful drive down Lakeshore, Metra Electric Line train, or Bus). 15 min from Indiana casino. Ideal for summer time Chicago!

Guest favorite

Home in Chicago Ridge

4.88 out of 5 average rating, 57 reviews

Quiet cul-de-sac with huge fenced in backyard

3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.