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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
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Home in Chicago
4.99 out of 5 average rating, 101 reviewsHuge Sunlit Gem, Free Parking, No Cleaning Fee
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Home in Bolingbrook
4.93 out of 5 average rating, 107 reviewsThe Sunshine Spot
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Home in Chicago
4.81 out of 5 average rating, 205 reviewsSpacious Luxury Townhouse - Old Town
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Home in Chicago
4.96 out of 5 average rating, 141 reviewsChicago Riverhouse with private fenced in patio!
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Home in Markham
4.89 out of 5 average rating, 124 reviewsThe Jewell, Clean, comfortable 3 bed/2bath Home.
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Home in Worth
4.88 out of 5 average rating, 113 reviewsThe Comfy King Ranch/ King Bed/Disney+ /Fast Wi-Fi
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Home in Chicago
4.83 out of 5 average rating, 132 reviewsBucktown Home W/ Free Garage Parking for 2 Cars!
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Home in Maywood
4.84 out of 5 average rating, 117 reviewsFull Home, Drive Way Parking!
Pet-friendly home rentals with a pool
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Rental unit in Chicago
4.83 out of 5 average rating, 204 reviewsSpectacular Corner 2BR Penthouse in the Loop | Roo
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Rental unit in Itasca
4.74 out of 5 average rating, 228 reviewsKing Bed at Chicago Northwest + PET Friendly
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Rental unit in Rosemont
4.93 out of 5 average rating, 68 reviewsRelaxing Standard Room l Free Airport Shuttle
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Campsite in Midlothian
4.99 out of 5 average rating, 78 reviewsWaverly Woods Outpost: Private Glampsite w Theater
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Rental unit in Chicago
4.82 out of 5 average rating, 17 reviewsCozy studio near Michigan lake
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Rental unit in Chicago
4.96 out of 5 average rating, 50 reviewsCozy 2 Bed Apt in Wicker Park East w/ Free Parking
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Rental unit in Chicago
4.82 out of 5 average rating, 22 reviewsDowntown Penthouse Lake Views #1|Gym, Parking+Pool
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Home in Schaumburg
4.92 out of 5 average rating, 13 reviewsParadise 4BR w/ Pool & Games
Private, pet-friendly home rentals
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Condo in Chicago
4.96 out of 5 average rating, 188 reviewsUpdated Designer Duplex In Fulton Market W/parking
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Rental unit in Chicago
4.92 out of 5 average rating, 24 reviewsBeverly Cottage Loft
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Guest suite in Chicago
4.89 out of 5 average rating, 80 reviewsPRIVATE 2-bedroom 1.5 bath w/ living room
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Rental unit in Chicago
4.94 out of 5 average rating, 36 reviewsTravel To Chicago New City
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Rental unit in Chicago
4.82 out of 5 average rating, 11 reviewsChic & Cozy, New Build 2beds, 15mins from The Bean
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Serviced apartment in Chicago
4.9 out of 5 average rating, 30 reviewsLovely Two bedroom apartment +free street parking
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Condo in Chicago
5 out of 5 average rating, 20 reviewsUniversity of Chicago Condo-Upgraded and Spacious
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Condo in Chicago
4.98 out of 5 average rating, 40 reviewsChic & Comfy • Close to Wrigley
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
- Schaumburg Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Pet-friendly rentals Chicago
- Pet-friendly rentals Chicago
- Pet-friendly rentals Downtown Chicago
- Kid-friendly rentals South Side
- Fitness-friendly rentals South Side
- Apartment rentals South Side
- Condo rentals South Side
- Rentals with beach access South Side
- Rentals with outdoor seating South Side
- Waterfront rentals South Side
- Rentals with lake access South Side
- Rentals with a fireplace South Side
- Family-friendly rentals South Side
- House rentals South Side
- Rentals with a hot tub South Side
- Rentals with a fire pit South Side
- Rentals with pools South Side
- Rentals with a washing machine and dryer South Side
- Rentals with breakfast South Side
- Rentals with an EV charger South Side
- Rentals with a patio South Side
- Monthly Rentals South Side
- Private suite rentals South Side
- Smoking-friendly rentals South Side
- Townhouse rentals South Side
- Bed and breakfasts South Side
- Pet-friendly rentals Milwaukee
- Pet-friendly rentals Illinois
- Pet-friendly rentals Cook County
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- Farm Cottages United Kingdom
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- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
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- 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
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