Pet-friendly holiday rentals in South Side
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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
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Popular amenities for South Side pet-friendly home rentals
Pet-friendly house rentals
Home in Chicago
4.84 out of 5 average rating, 155 reviewsHistoric Old Town, Fabulous 4 Bedroom Home
Home in Oak Park
4.88 out of 5 average rating, 104 reviewsUrban Chic 3beds w/2bath + free parking & W/D
Home in Chicago
4.91 out of 5 average rating, 112 reviewsBoHo House - A Chic, 1903 Chicago Workers Cottage
Home in Naperville
4.84 out of 5 average rating, 105 reviewsDog Friendly Cozy North Naperville 3 BED/2 BA Home
Home in Chicago
4.95 out of 5 average rating, 138 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Home in Chicago
4.99 out of 5 average rating, 109 reviewsAndersonville/ Cozy 3b 3b House / 99 walk score
Home in Chicago
4.82 out of 5 average rating, 218 reviewsSpacious Luxury Townhouse - Old Town
Home in Chicago
4.84 out of 5 average rating, 136 reviewsBucktown Home W/ Free Garage Parking for 2 Cars!
Pet-friendly home rentals with a pool
Rental unit in Chicago
4.85 out of 5 average rating, 33 reviewsDowntown Penthouse Lake Views #1|Gym, Parking+Pool
Home in Munster
5 out of 5 average rating, 7 reviewsMunster hide away
Rental unit in Chicago
4.98 out of 5 average rating, 60 reviewsLuxe Ranch & Spa, Euro Opulence, a 4-Season Oasis
Rental unit in Itasca
4.74 out of 5 average rating, 270 reviewsKing Bed at Chicago Northwest + PET Friendly
Rental unit in Rosemont
4.96 out of 5 average rating, 116 reviewsRelaxing Standard Room l Free Airport Shuttle
Rental unit in Chicago
4.8 out of 5 average rating, 61 reviewsCozy Family 3BR Oasis: Park, Private Yard, & BBQ!
Rental unit in Chicago
5 out of 5 average rating, 10 reviewsLuxury Designer Penthouse West |Pool| Gold Coast
Serviced apartment in Chicago
4.87 out of 5 average rating, 142 reviewsLevel ◆ Two Bedroom Deluxe Corner Suite + Balcony
Private, pet-friendly home rentals
Rental unit in Chicago
4.96 out of 5 average rating, 274 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Apartment in Chicago
4.95 out of 5 average rating, 117 reviewsEntire 3Bed/2Bath Condo Near McCormick & Metro
Rental unit in Chicago
4.87 out of 5 average rating, 175 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Apartment in Chicago
4.9 out of 5 average rating, 101 reviewsConvenient & Spacious 3BR Condo w/Free Parking
Townhouse in Chicago
4.82 out of 5 average rating, 167 reviews⭐️Cozy Garden Unit by Downtown & Blue Line Stop⭐️
Guest suite in Chicago
4.95 out of 5 average rating, 147 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
Apartment in Chicago
4.93 out of 5 average rating, 215 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Rental unit in Chicago
4.98 out of 5 average rating, 114 reviewsElegant Suite in Gold Coast
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Saugatuck 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
- Rentals with a fireplace South Side
- Family-friendly rentals South Side
- Flat rentals South Side
- Rentals with breakfast South Side
- Bed and breakfasts South Side
- Private suite rentals South Side
- Rentals with a washing machine and dryer South Side
- Rentals with beach access South Side
- Rentals with pools South Side
- Waterfront rentals South Side
- Rentals with a hot tub South Side
- Townhouse rentals South Side
- House rentals South Side
- Rentals with a patio South Side
- Apartment rentals South Side
- Rentals with outdoor seating South Side
- Rentals with lake access South Side
- Monthly Rentals South Side
- Rentals with a firepit South Side
- Fitness-friendly rentals South Side
- Family-friendly rentals South Side
- Smoking-friendly rentals South Side
- Rentals with an EV charger 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