
Family-friendly holiday rentals in West Side
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in West 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 West Side family-friendly rentals
Family-friendly home rentals with a hot tub

Lux Urban 3BR/3BA Duplex + Parking!

Super Paradise Chicago

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Spacious 2bdm unit 15min to Dwtn

Bright and Beautiful Penthouse - Close to the lake
Family- and pet-friendly home rentals

2 King Beds /Easy Downtown / Free Str Parking-Read

Sunny Logan Square Artists' home

Historic Old Town, Fabulous 4 Bedroom Home

Private 3rd Floor Apartment

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Quirky Bucktown Loft w/ Parking No Parties

The Deer Suite

Modern Luxury In Old Town - Sleeps 4
Family-friendly home rentals with a pool

Music Hot Spot’s Main Level

Beat-Town Flex Stays

Stylish Corner 2 Bedroom in the Heart of Chicago |

Luxury Corner 2 Bedroom in the Loop | Roof Deck
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Rentals with a home theatre West Side
- Rentals with lake access West Side
- Apartment rentals West Side
- Rentals with a fire pit West Side
- Rentals with breakfast West Side
- Waterfront rentals West Side
- Rentals with an EV charger West Side
- Rentals with a sauna West Side
- Hotel rentals West Side
- Rentals with a fireplace West Side
- Rentals with a patio West Side
- Rentals with an accessible height bed West Side
- Rentals with pools West Side
- Rentals with a hot tub West Side
- Private suite rentals West Side
- House rentals West Side
- Pet-friendly rentals West Side
- Smoking-friendly rentals West Side
- Townhouse rentals West Side
- Rentals with a washing machine and dryer West Side
- Kid-friendly rentals West Side
- Rentals with beach access West Side
- Loft rentals West Side
- Condo rentals West Side
- Rentals with outdoor seating West Side
- Rentals with a balcony West Side
- Fitness-friendly rentals West Side
- Family-friendly rentals Cook County
- Family-friendly rentals Illinois
- Family-friendly rentals United States
- 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
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Garfield Park Conservatory
- Washington Park Zoo
- Wicker Park
- Illinois Beach State Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do West Side
- Entertainment West Side
- Food and drink West Side
- Things to do Chicago
- Food and drink Chicago
- Sightseeing Chicago
- Nature and outdoors Chicago
- Tours Chicago
- Art and culture Chicago
- Things to do Cook County
- Tours Cook County
- Food and drink Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Things to do Illinois
- Art and culture Illinois
- Tours Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Sports activities Illinois
- Nature and outdoors Illinois
- Things to do United States
- Food and drink United States
- Sports activities United States
- Nature and outdoors United States
- Sightseeing United States
- Entertainment United States
- Tours United States
- Wellness United States
- Art and culture United States