Family-friendly holiday rentals in Homewood
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Homewood
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 Homewood family-friendly rentals
Family-friendly home rentals with a hot tub
Home in West Town
4.85 out of 5 average rating, 305 reviewsLux Urban 3BR/3BA Duplex + Parking!
Loft in West Town
4.81 out of 5 average rating, 283 reviewsArtist Loft Duplex in a 1904 Former Factory
Home in Miller
4.55 out of 5 average rating, 127 reviewsSmart Home, Hot Tub, direct Beach/Nat’l Park access, luxury amenities
Home in Logan Square
4.9 out of 5 average rating, 86 reviewsLOFT606: Gigantic Sunlit Former Factory Home
Rental unit in Bronzeville
4.55 out of 5 average rating, 11 reviewsSpacious 2bdm unit 15min to Dwtn
Cottage in Valparaiso
4.93 out of 5 average rating, 396 reviewsThe Lake Escape -Cozy Lakefront Cottage Valparaiso
Home in Miller
4.53 out of 5 average rating, 154 reviewsSecluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Condo in Logan Square
4.98 out of 5 average rating, 255 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Family- and pet-friendly home rentals
Condo in West Town
4.89 out of 5 average rating, 257 reviews2 King Bed Condo Easy Downtown Free Street Parking
Rental unit in Roscoe Village
4.96 out of 5 average rating, 275 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Rental unit in Lincoln Park
4.81 out of 5 average rating, 138 reviewsThe Biddle House (#2)
Rental unit in Logan Square
4.9 out of 5 average rating, 376 reviewsSunny Logan Square Artists' home
Rental unit in Lincoln Park
4.87 out of 5 average rating, 175 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Home in Uptown
4.9 out of 5 average rating, 355 reviewsPrivate 3rd Floor Apartment
Guest suite in Logan Square
4.97 out of 5 average rating, 270 reviewsStylish Studio in Historic Logan Square
Guest suite in Portage Park
4.95 out of 5 average rating, 148 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
Family-friendly home rentals with a pool
Rental unit in The Loop
4.77 out of 5 average rating, 204 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Guest suite in Bridgeport
4.96 out of 5 average rating, 82 reviewsSweet Home Chicago-9min downtown/pool/free parking
Place to stay in Berwyn
Beat-Town Flex Stays
Rental unit in The Loop
4.63 out of 5 average rating, 56 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Rental unit in The Loop
4.73 out of 5 average rating, 40 reviewsThe Professional's Playground
Guest suite in Berwyn
4.67 out of 5 average rating, 42 reviewsMusic Hot Spot’s Main Level
Home in Cedar Lake
4.84 out of 5 average rating, 82 reviewsBeautiful Home Oasis
Home in Bridgeport
Sweet Home Chicago (house) - free parking, pool
Quick stats about holiday rentals that are family-friendly in Homewood
Total rentals
30 properties
Nightly prices starting at
$167 NZD before taxes and fees
Total number of reviews
730 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
30 properties include access to Wi-Fi
Destinations to explore
- Downtown Chicago Holiday rentals
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- Family-friendly rentals United States
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- Monthly Rentals Homewood
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