Kid-friendly vacation rentals in West Side
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in West Side
Guests agree: these kid-friendly rentals 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 West Side kid-friendly rentals
Kid-friendly house rentals
Home in Chicago
4.95 out of 5 average rating, 171 reviewsParadise on the Park
Nov 13 – 20
Home in Chicago
4.97 out of 5 average rating, 318 reviewsCozy garden apartment historic Jackson Bvld.
Feb 25 – Mar 2
Home in Chicago
4.97 out of 5 average rating, 356 reviewsGreystone Haven in Logan Square
Oct 17 – 24
Home in Chicago
4.94 out of 5 average rating, 210 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
Feb 23 – Mar 2
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Jan 16 – 23
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Jun 25 – Jul 2
Home in Lake View
4.98 out of 5 average rating, 206 reviewsWrigleyville Southport Studio
Jan 1 – 8
Home in Chicago
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
Nov 24 – Dec 1
Kid-friendly apartment rentals
Apartment in Bridgeport
4.98 out of 5 average rating, 171 reviewsBridgeport Garden Apartment
Oct 16 – 23
Apartment in Little Italy
4.98 out of 5 average rating, 199 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Jan 20 – 27
Apartment in Forest Park
5.0 out of 5 average rating, 221 reviewsLike a Treehouse!
Sep 26 – Oct 3
Apartment in Oak Park
4.91 out of 5 average rating, 104 reviewsLovely, spacious 2bd, 1bath home w/free parking
Aug 27 – Sep 3
Apartment in Oak Park
4.85 out of 5 average rating, 531 reviewsLong stays welcome@warm&cute vintage 2BR
Sep 29 – Oct 6
Apartment in Chicago
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Sep 22 – 29
Apartment in Logan Square
4.96 out of 5 average rating, 220 reviewsSpacious apartment in Logan Square
Sep 7 – 14
Apartment in Chicago
4.96 out of 5 average rating, 163 reviews2BR Centrally Located in Cozy Hip Logan Square
Apr 17 – 24
Kid-friendly condo rentals
Condo in Chicago
4.87 out of 5 average rating, 107 reviewsSpacious Duplex in Great Location
Oct 13 – 20
Condo in Oak Park
4.88 out of 5 average rating, 164 reviewsAttractive Flat - Historic Oak Park
Dec 21 – 28
Condo in East Garfield Park
4.9 out of 5 average rating, 136 reviewsEast Garfield Park 2 Bedroom
Dec 25 – Jan 1
Condo in Chicago
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
Oct 25 – Nov 1
Condo in West Town
4.97 out of 5 average rating, 707 reviewsGreat location. Free parking.
Jul 28 – Aug 2
Condo in Lincoln Square
4.97 out of 5 average rating, 330 reviewsLincoln Square Gem!
Sep 28 – Oct 5
Condo in Chicago
4.97 out of 5 average rating, 101 reviewsStylish 3BR + Free Parking 10-15mins from Downtown
Sep 3 – 10
Condo in Chicago
4.91 out of 5 average rating, 233 reviewsModern/Spacious 2BR/2BA West Town
Apr 7 – 14
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Chicago Vacation rentals
- Kid-friendly rentals United States
- Kid-friendly rentals Chicago
- Kid-friendly rentals Chicago
- Kid-friendly rentals Downtown Chicago
- Kid-friendly rentals Milwaukee
- Kid-friendly rentals Illinois
- Family-friendly rentals West Side
- Rentals with a fire pit West Side
- Loft rentals West Side
- Smoking-friendly rentals West Side
- Fitness-friendly rentals West Side
- Waterfront rentals West Side
- Apartment rentals West Side
- Condo rentals West Side
- Rentals with breakfast West Side
- Rentals with a patio West Side
- Rentals with a fireplace West Side
- Guesthouse rentals West Side
- Hotel rentals West Side
- Rentals with a washer and dryer West Side
- Rentals with a hot tub West Side
- Rentals with pools West Side
- Rentals with a home theater West Side
- Rentals with an EV charger West Side
- Rentals with beach access West Side
- Rentals with lake access West Side
- Townhouse rentals West Side
- Private suite rentals West Side
- Pet-friendly rentals West Side
- Rentals with a sauna West Side
- Rentals with a balcony West Side
- Rentals with outdoor seating West Side
- Monthly Rentals West Side
- House rentals West Side
- Kid-friendly rentals Cook County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes