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
Apartment in Chicago
4.98 out of 5 average rating, 235 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Apartment in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Home in Miller Beach
4.54 out of 5 average rating, 150 reviewsSecluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Flat in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Loft in Chicago
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Home in Miller Beach
4.54 out of 5 average rating, 123 reviewsSmart Home, Hot Tub, direct Beach/Nat’l Park access, luxury amenities
Home in Miller Beach
4.61 out of 5 average rating, 59 reviewsBeach Compound w/ hot tub, sauna, firepit, v-ball
Family- and pet-friendly home rentals
Flat in Chicago
4.89 out of 5 average rating, 341 reviewsSunny Logan Square Artists' home
Flat in Irving Park
4.86 out of 5 average rating, 325 reviewsThe Avondale Garden Unit
Guest suite in Wood Dale
4.9 out of 5 average rating, 430 reviewsThe Deer Suite
Flat in Chicago
4.76 out of 5 average rating, 299 reviewsITALIAN garden apt/kids friendly/great location!!
Flat in Chicago
4.88 out of 5 average rating, 160 reviewsBright, Gorgeous Apt Private Parking available
Apartment in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 295 reviewsa SIMPLE place
Flat in Chicago
4.9 out of 5 average rating, 154 reviewsSpacious unique artist's home in Pilsen
Family-friendly home rentals with a pool
Flat in The Loop
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Flat in Chicago
5.0 out of 5 average rating, 9 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Flat in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Guest suite in Berwyn
4.75 out of 5 average rating, 32 reviewsMusic Hot Spot’s Main Level
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Flat in Chicago
4.77 out of 5 average rating, 205 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Flat in Chicago
5.0 out of 5 average rating, 4 reviewsThe Playwright's Palace
Flat in Chicago
4.61 out of 5 average rating, 49 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
- Rentals with outdoor seating South Side
- Waterfront rentals South Side
- Rentals with lake access South Side
- Rentals with breakfast South Side
- Flat rentals South Side
- Rentals with a washing machine and dryer South Side
- Private suite rentals South Side
- Apartment rentals South Side
- Rentals with a hot tub South Side
- Rentals with a fireplace South Side
- Rentals with an EV charger South Side
- Rentals with a firepit South Side
- Pet-friendly rentals South Side
- Fitness-friendly rentals South Side
- House rentals South Side
- Monthly Rentals South Side
- Smoking-friendly rentals South Side
- Rentals with beach access South Side
- Rentals with a patio South Side
- Townhouse rentals South Side
- Family-friendly rentals South Side
- Family-friendly rentals Illinois
- Family-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