Pet-friendly vacation 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.
Vacation 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 Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Jun 20 – 27
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Nov 19 – 26
Home in Chicago
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
Feb 26 – Mar 5
Home in Chicago
4.96 out of 5 average rating, 126 reviewsChicago Riverhouse summer on our patio!
Nov 14 – 21
Home in Chicago
4.83 out of 5 average rating, 138 reviewsHistoric Old Town, Fabulous 4 Bedroom Home
Jan 20 – 27
Home in Worth
4.87 out of 5 average rating, 102 reviewsThe Comfy King Ranch/ King Bed/Disney+ /Fast Wi-Fi
Jan 24 – 31
Home in Chicago
4.93 out of 5 average rating, 209 reviewsLuxe 6BR House *Trendy Logan Square *Garage Access
Dec 21 – 28
Home in Chicago
4.81 out of 5 average rating, 196 reviewsSpacious Luxury Townhouse - Old Town
Mar 10 – 17
Pet-friendly home rentals with a pool
Apartment in Chicago
4.78 out of 5 average rating, 156 reviewsBeautiful Corner 2 Bedroom in the Loop | Roof Deck
Feb 5 – 12
Apartment in Chicago
4.87 out of 5 average rating, 110 reviewsLevel ◆ Two Bedroom Deluxe Corner Suite + Balcony
Jun 17 – 24
Apartment in Itasca
4.77 out of 5 average rating, 181 reviewsKing Bed at Chicago Northwest + PET Friendly
Oct 25 – Nov 1
Apartment in Chicago
4.93 out of 5 average rating, 28 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Nov 13 – 20
Condo in Portage
4.94 out of 5 average rating, 67 reviewsUnsalted Stay - Waterfront Condo
Sep 28 – Oct 5
Apartment in Chicago
5.0 out of 5 average rating, 7 reviewsCozy studio near Michigan lake
Jul 9 – 16
Apartment in Rosemont
5.0 out of 5 average rating, 14 reviewsRelaxing Standard Room l Free Airport Shuttle
Jul 5 – 12
Campsite in Midlothian
4.99 out of 5 average rating, 76 reviewsWaverly Woods Outpost: Private Glampsite w Theater
Oct 16 – 23
Private, pet-friendly home rentals
Guest suite in Wood Dale
4.9 out of 5 average rating, 427 reviewsThe Deer Suite
Oct 17 – 24
Apartment in Chicago
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Dec 1 – 8
Apartment in Oak Lawn
4.95 out of 5 average rating, 123 reviewsCharming One Bedroom Apartment
Jul 11 – 18
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 293 reviewsa SIMPLE place
Apr 16 – 23
Apartment in Chicago
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
Oct 4 – 11
Apartment in Chicago
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apr 13 – 20
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Jul 16 – 23
Apartment in Chicago
4.89 out of 5 average rating, 176 reviewsHistoric Chicago neighborhood flat
Nov 10 – 17
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