Pet-friendly holiday rentals in South Side
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in South Side
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side pet-friendly home rentals
Pet-friendly house rentals
Home in Berwyn
4.91 out of 5 average rating, 249 reviewsPrivate apartment with retro vibe
Home in Forest Park
4.91 out of 5 average rating, 224 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Home in Chicago
4.95 out of 5 average rating, 130 reviewsChicago Riverhouse summer on our patio!
Home in Worth
4.88 out of 5 average rating, 105 reviewsThe Comfy King Ranch/ King Bed/Disney+ /Fast Wi-Fi
Home in Manteno
4.96 out of 5 average rating, 203 reviewsKing-size beds ! All the luxeries of home!
Home in Chicago
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
Home in Chicago
4.93 out of 5 average rating, 212 reviewsLuxe 6BR House *Trendy Logan Square *Garage Access
Home in Chicago
4.81 out of 5 average rating, 198 reviewsSpacious Luxury Townhouse - Old Town
Pet-friendly home rentals with a pool
Flat in Itasca
4.75 out of 5 average rating, 196 reviewsKing Bed at Chicago Northwest + PET Friendly
Flat in Chicago
4.87 out of 5 average rating, 111 reviewsLevel ◆ Two Bedroom Deluxe Corner Suite + Balcony
Flat in Chicago
4.86 out of 5 average rating, 192 reviewsSpectacular Corner 2BR Penthouse in the Loop | Roo
Flat in Chicago
4.92 out of 5 average rating, 36 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in Chicago
5.0 out of 5 average rating, 9 reviewsCozy studio near Michigan lake
Apartment in Portage
4.93 out of 5 average rating, 69 reviewsUnsalted Stay - Waterfront Condo
Flat in Chicago
4.91 out of 5 average rating, 11 reviewsDowntown Penthouse Lake Views #1|Gym, Parking+Pool
Flat in Rosemont
4.91 out of 5 average rating, 22 reviewsRelaxing Standard Room l Free Airport Shuttle
Private, pet-friendly home rentals
Flat in Chicago
4.9 out of 5 average rating, 343 reviewsSunny Logan Square Artists' home
Flat in Chicago
4.96 out of 5 average rating, 112 reviewsComfortable, modern apartment 20 Min from Downtown
Guest suite in Wood Dale
4.9 out of 5 average rating, 434 reviewsThe Deer Suite
Flat in Chicago
4.91 out of 5 average rating, 170 reviewsHandicap accessible apartment w/Level-2 EV Charger
Flat in Chicago
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 295 reviewsa SIMPLE place
Flat in Chicago
4.86 out of 5 average rating, 106 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Flat in Oak Park
4.92 out of 5 average rating, 106 reviewsLovely, spacious 2bd, 1bath home w/free parking
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Pet-friendly rentals Chicago
- Pet-friendly rentals Chicago
- Pet-friendly rentals Downtown Chicago
- Waterfront rentals South Side
- Rentals with outdoor seating South Side
- Flat rentals South Side
- Rentals with lake access South Side
- Rentals with a washing machine and dryer South Side
- Apartment rentals South Side
- Townhouse rentals South Side
- Family-friendly rentals South Side
- Rentals with an EV charger South Side
- Fitness-friendly rentals South Side
- Rentals with a fireplace South Side
- Rentals with breakfast South Side
- Rentals with a patio South Side
- Rentals with beach access South Side
- Family-friendly rentals South Side
- Rentals with a firepit South Side
- House rentals South Side
- Rentals with a hot tub South Side
- Private suite rentals South Side
- Monthly Rentals South Side
- Smoking-friendly rentals South Side
- Pet-friendly rentals Milwaukee
- Pet-friendly rentals Illinois
- Pet-friendly rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom