Family-friendly vacation 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.
Vacation 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, 233 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Apr 29 – May 6
Home in West Town
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Sep 24 – Oct 1
Condo in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Apr 6 – 13
Home in Miller Beach
4.54 out of 5 average rating, 123 reviewsSmart Home, Hot Tub, direct Beach/Nat’l Park access, luxury amenities
Apr 1 – 8
Loft in Chicago
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Oct 12 – 19
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jul 5 – 12
Home in Miller Beach
4.54 out of 5 average rating, 150 reviewsSecluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Apr 19 – 26
Condo in Chicago
4.46 out of 5 average rating, 79 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
Sep 25 – Oct 2
Family- and pet-friendly home rentals
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Feb 10 – 17
Apartment in Irving Park
4.76 out of 5 average rating, 298 reviewsITALIAN garden apt/kids friendly/great location!!
Oct 25 – Nov 1
Apartment in Chicago
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
Mar 3 – 10
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Jun 25 – Jul 2
Condo in Chicago
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
Sep 13 – 20
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 294 reviewsa SIMPLE place
Jan 6 – 13
Apartment in Wicker Park
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Oct 15 – 22
Apartment in Chicago
4.9 out of 5 average rating, 154 reviewsSpacious unique artist's home in Pilsen
Sep 13 – 20
Family-friendly home rentals with a pool
Apartment in Chicago
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Feb 12 – 19
Apartment in Chicago
4.8 out of 5 average rating, 25 reviewsThe Professional's Playground
Nov 17 – 24
Apartment in The Loop
5.0 out of 5 average rating, 8 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Jan 3 – 10
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
Dec 6 – 13
Guest suite in Chicago
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Nov 23 – 30
Apartment in Chicago
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Sep 11 – 18
Apartment in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Mar 11 – 18
Apartment in Chicago
New place to stayThe Playwright's Palace
Jan 12 – 19
Destinations to explore
- Downtown Chicago Vacation rentals
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- Rentals with beach access South Side
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