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, 234 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Mar 18 – 25
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Nov 14 – 21
Apartment in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Nov 17 – 24
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Mar 21 – 28
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 23 – 30
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Jun 13 – 20
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jul 5 – 12
Apartment in The Loop
5.0 out of 5 average rating, 3 reviewsThe Playwright's Palace
Oct 31 – Nov 7
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
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 294 reviewsa SIMPLE place
Feb 19 – 26
Apartment in Chicago
4.84 out of 5 average rating, 480 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Oct 23 – 30
Apartment in Irving Park
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
Jan 12 – 19
Apartment in Chicago
4.76 out of 5 average rating, 299 reviewsITALIAN garden apt/kids friendly/great location!!
Mar 18 – 25
Guest suite in Wood Dale
4.9 out of 5 average rating, 430 reviewsThe Deer Suite
Jul 16 – 23
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Dec 18 – 25
Apartment in Lincoln Park
4.89 out of 5 average rating, 145 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Jan 5 – 12
Family-friendly home rentals with a pool
Apartment in The Loop
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Nov 26 – Dec 3
Apartment in Chicago
5.0 out of 5 average rating, 8 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Apr 12 – 19
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
Aug 8 – 15
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Dec 18 – 25
Apartment in Chicago
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Dec 14 – 21
Apartment in The Loop
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Mar 11 – 18
Place to stay in Berwyn
Beat-Town Flex Stays
Mar 4 – 11
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
G$8,359 GYD before taxes and fees
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