Family-friendly vacation rentals in Woodlawn, Chicago
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Woodlawn, Chicago
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 Woodlawn, Chicago family-friendly rentals
Family-friendly home rentals with a hot tub
Condo 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, 293 reviewsLux Urban 3BR/3BA Duplex + Parking!
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Home in Miller Beach
4.67 out of 5 average rating, 89 reviewsDunes Nat’l Park, HotTub, Sauna, Firepit, Foosball
Condo in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
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, 150 reviewsSecluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
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
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Chicago
4.9 out of 5 average rating, 343 reviewsSunny Logan Square Artists' home
Guest suite in Wood Dale
4.9 out of 5 average rating, 434 reviewsThe Deer Suite
Apartment in Irving Park
4.86 out of 5 average rating, 326 reviewsThe Avondale Garden Unit
Apartment in Chicago
4.83 out of 5 average rating, 482 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Chicago
4.76 out of 5 average rating, 300 reviewsITALIAN garden apt/kids friendly/great location!!
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 295 reviewsa SIMPLE place
Home in Forest Park
4.91 out of 5 average rating, 224 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Family-friendly home rentals with a pool
Apartment in Chicago
4.78 out of 5 average rating, 189 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Apartment in Chicago
4.87 out of 5 average rating, 159 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in Chicago
4.81 out of 5 average rating, 27 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
Apartment in Chicago
4.77 out of 5 average rating, 205 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Apartment in Chicago
4.62 out of 5 average rating, 50 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Apartment in Chicago
5.0 out of 5 average rating, 4 reviewsThe Playwright's Palace
Quick stats about vacation rentals that are family-friendly in Woodlawn, Chicago
Total rentals
100 properties
Wifi availability
100 properties include access to wifi
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
3.6K reviews
Nightly prices starting at
$40 before taxes and fees
Destinations to explore
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