Family-friendly vacation 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.
Vacation 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
Condo in Chicago
4.98 out of 5 average rating, 234 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Jan 7 – 14
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Nov 18 – 25
Apartment in The Loop
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Jan 16 – 23
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Apr 5 – 12
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jul 5 – 12
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Aug 6 – 13
Condo in Bronzeville
4.46 out of 5 average rating, 79 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
Sep 27 – Oct 4
Family- and pet-friendly home rentals
Apartment in Chicago
4.84 out of 5 average rating, 480 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Oct 17 – 24
Apartment in Forest Park
4.92 out of 5 average rating, 112 reviewsVillage Cottage - Forest Park Studio Pets 72142F
May 9 – 16
Apartment in Roscoe Village
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Dec 2 – 9
Guest suite in Logan Square
4.97 out of 5 average rating, 239 reviewsStylish Studio in Historic Logan Square
Sep 21 – 28
Condo in West Town
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
Oct 30 – Nov 6
Apartment in Chicago
4.76 out of 5 average rating, 299 reviewsITALIAN garden apt/kids friendly/great location!!
Feb 20 – 27
Apartment in Irving Park
4.86 out of 5 average rating, 325 reviewsThe Avondale Garden Unit
Jul 1 – 8
Guest suite in Wood Dale
4.9 out of 5 average rating, 430 reviewsThe Deer Suite
Nov 14 – 21
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 |
Oct 30 – Nov 6
Apartment in Chicago
5.0 out of 5 average rating, 9 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Jan 8 – 15
Guest suite in Berwyn
4.75 out of 5 average rating, 32 reviewsMusic Hot Spot’s Main Level
Mar 20 – 27
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Nov 11 – 18
Apartment in Chicago
4.76 out of 5 average rating, 204 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Nov 17 – 24
Apartment in The Loop
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Mar 25 – Apr 1
Place to stay in Berwyn
Beat-Town Flex Stays
May 23 – 30
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
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Family-friendly rentals Chicago
- Family-friendly rentals Downtown Chicago
- Family-friendly rentals Illinois
- Rentals with beach access West Side
- Rentals with a fireplace West Side
- Waterfront rentals West Side
- Loft rentals West Side
- Monthly Rentals West Side
- Rentals with lake access West Side
- Rentals with a balcony West Side
- Rentals with a hot tub West Side
- Townhouse rentals West Side
- Guesthouse rentals West Side
- Rentals with breakfast West Side
- Rentals with an EV charger West Side
- Rentals with a sauna West Side
- Kid-friendly rentals West Side
- Rentals with a home theater West Side
- Hotel rentals West Side
- Rentals with outdoor seating West Side
- Rentals with pools West Side
- Rentals with a washer and dryer West Side
- Condo rentals West Side
- House rentals West Side
- Rentals with a patio West Side
- Pet-friendly rentals West Side
- Smoking-friendly rentals West Side
- Apartment rentals West Side
- Rentals with a fire pit West Side
- Private suite rentals West Side
- Fitness-friendly rentals West Side
- Family-friendly rentals Cook County
- 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