Family-friendly holiday rentals in South Side
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in South Side
Guests agree: These family-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 family-friendly rentals
Family-friendly home rentals with a hot tub
Condo in Chicago
4.98 out of 5 average rating, 237 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Home in Chicago
4.85 out of 5 average rating, 293 reviewsLux Urban 3BR/3BA Duplex + Parking!
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Condo in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Home in Miller Beach
4.52 out of 5 average rating, 151 reviewsSecluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Loft in Chicago
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Home in Miller Beach
4.67 out of 5 average rating, 89 reviewsDunes Nat’l Park, HotTub, Sauna, Firepit, Foosball
Home in Miller Beach
4.54 out of 5 average rating, 124 reviewsSmart Home, Hot Tub, direct Beach/Nat’l Park access, luxury amenities
Family- and pet-friendly home rentals
Home in Forest Park
4.9 out of 5 average rating, 227 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Condo in Evanston
4.76 out of 5 average rating, 573 reviewsSpacious Evanston Unit - Walk to Northwestern U
Guest suite in Wood Dale
4.9 out of 5 average rating, 437 reviewsThe Deer Suite
Guest suite in Chicago
4.97 out of 5 average rating, 242 reviewsStylish Studio in Historic Logan Square
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 299 reviewsa SIMPLE place
Apartment in Chicago
4.83 out of 5 average rating, 485 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Chicago
4.76 out of 5 average rating, 302 reviewsITALIAN garden apt/kids friendly/great location!!
Apartment in Chicago
4.86 out of 5 average rating, 329 reviewsThe Avondale Garden Unit
Family-friendly home rentals with a pool
Apartment in Chicago
4.77 out of 5 average rating, 207 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Apartment in Chicago
4.83 out of 5 average rating, 29 reviewsThe Professional's Playground
Guest suite in Berwyn
4.75 out of 5 average rating, 32 reviewsMusic Hot Spot’s Main Level
Home in Cedar Lake
4.85 out of 5 average rating, 74 reviewsBeautiful Home Oasis
Guest suite in Chicago
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Apartment in Chicago
4.77 out of 5 average rating, 191 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Apartment in Chicago
5.0 out of 5 average rating, 8 reviewsThe Playwright's Palace
Apartment in Chicago
4.6 out of 5 average rating, 52 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
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
- Condo rentals South Side
- Rentals with a washing machine and dryer South Side
- Private suite rentals South Side
- Rentals with breakfast South Side
- Waterfront rentals South Side
- Apartment rentals South Side
- Rentals with lake access South Side
- Rentals with outdoor seating South Side
- Fitness-friendly rentals South Side
- Rentals with a fireplace South Side
- Townhouse rentals South Side
- Rentals with a hot tub South Side
- Pet-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with a fire pit South Side
- House rentals South Side
- Kid-friendly rentals South Side
- Rentals with beach access South Side
- Monthly Rentals South Side
- Rentals with pools South Side
- Rentals with a patio South Side
- Smoking-friendly rentals South Side
- Family-friendly rentals Illinois
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- Yurt Rentals United States
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- 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
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- Holiday Apartments Australia
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- Big Cottages Australia
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
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- Beach Cabins United States
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