Kid-friendly holiday rentals in South Side
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in South Side
Guests agree: these family-friendly rentals 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 family-friendly rentals
Kid-friendly house rentals
Home in Whiting
4.8 out of 5 average rating, 231 reviewsWhiting Getaway
Home in West Loop
4.98 out of 5 average rating, 320 reviewsCozy garden apartment historic Jackson Bvld.
Home in Forest Park
4.91 out of 5 average rating, 225 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Home in Berwyn
4.91 out of 5 average rating, 258 reviewsPrivate apartment with retro vibe
Home in Chicago
4.97 out of 5 average rating, 362 reviewsTop Floor Escape | Modern Amenities | Lush Garden
Home in Chicago
4.95 out of 5 average rating, 178 reviewsParadise on the Park
Home in Joliet
4.83 out of 5 average rating, 163 reviewsCozy Private Cottage in the Cathedral District
Home in Chicago
4.93 out of 5 average rating, 220 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
Family-friendly apartment rentals
Flat in Woodlawn
4.83 out of 5 average rating, 155 reviewsUniversity Retreat
Flat in Cicero
4.98 out of 5 average rating, 210 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Flat in Chicago
4.89 out of 5 average rating, 249 reviewsModern
Flat in Chicago
4.89 out of 5 average rating, 302 reviewsVintage Bridgeport Apartment
Flat in West Loop
4.87 out of 5 average rating, 220 reviewsGarden Apartment in the Historic Heart of the City
Flat in Chicago
4.84 out of 5 average rating, 177 reviewsThe Cottage
Flat in Chicago
4.96 out of 5 average rating, 102 reviewsCute, Clean, Cozy Apartment in Pilsen
Flat in Chicago
4.82 out of 5 average rating, 146 reviewsThe Posh Apt. Mins to Downtown & Hyde Park
Family-friendly apartment rentals
Apartment in Chicago
4.9 out of 5 average rating, 102 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Apartment in Chicago
4.86 out of 5 average rating, 340 reviewsNear McCormick Place and Minutes from Downtown!
Apartment in Lincoln Square
4.97 out of 5 average rating, 337 reviewsLincoln Square Gem!
Apartment in Chicago
4.97 out of 5 average rating, 716 reviewsGreat location. Free parking.
Apartment in Chicago
4.97 out of 5 average rating, 108 reviewsStylish 3BR + Free Parking 10-15mins from Downtown
Apartment in Chicago
4.87 out of 5 average rating, 138 reviewsThe En Bronze ~ 7mins To Dining & Downtown Chicago
Apartment in Chicago
4.96 out of 5 average rating, 129 reviewsPrivate hot tub - King bed suite - Free parking
Apartment in Chicago
4.82 out of 5 average rating, 126 reviews-CHICAGO STUDIO IN JEFFERSON PARK O'HARE ROSEMONT-
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
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Family-friendly rentals Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with breakfast South Side
- Apartment rentals South Side
- Rentals with lake access South Side
- Rentals with a fireplace South Side
- Flat rentals South Side
- Rentals with a washing machine and dryer South Side
- Waterfront rentals South Side
- Private suite rentals South Side
- Rentals with outdoor seating South Side
- Rentals with pools South Side
- Family-friendly rentals South Side
- Rentals with a hot tub South Side
- Rentals with an EV charger South Side
- Rentals with a patio South Side
- Rentals with a firepit South Side
- Monthly Rentals South Side
- Fitness-friendly rentals South Side
- Rentals with beach access South Side
- Pet-friendly rentals South Side
- House rentals South Side
- Smoking-friendly rentals South Side
- Townhouse rentals South Side
- Family-friendly rentals Milwaukee
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- Family-friendly rentals Cook County
- Yurt Rentals United States
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- 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
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- Mansion Rentals United States
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- Holiday Bungalows United Kingdom
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- 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
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