
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

Private Cottage in Gated Nudist Community

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Pet Fndly

Master qtr close to nature & easy urban facilities

Secluded Modern Retreat Near Beach - "Sandlot"

The Spa of Downtown Whiting

The Lake Escape -Cozy Lakefront Cottage Valparaiso

Belmont Pleasures - hot tub / arcade gaming room

Luxe 3BR, 2BA + Hot Tub
Family- and pet-friendly home rentals

South Shore Studio Apartment {National Park}

Chicago River House -BBQ Oasis now open!

Retro Modern Bungalow | free parking | fire pit

Horizon - 4 BRs, 2 BA Game Room & Gym

Quiet cul-de-sac with huge fenced in backyard

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Escape to relax in peace

Miller Mermaid Suite-100 yds from the beach!
Family-friendly home rentals with a pool

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Comfortable 3BR Home-Prime Video, WiFi, Parking

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Munster hide away

Forest Park Oasis - Dog Friendly - Parks - the "L"

Penthouse Near Fulton: Skyline, Spacious

Whole Flat in Private Club. Walk to L, Dining & Shows

Beautiful Spanish style Home (w/inground pool)
Quick stats about holiday rentals that are family-friendly in Homewood
Total rentals
30 properties
Nightly prices starting at
£97 before taxes and fees
Total number of reviews
970 reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Platteville Holiday rentals
- St. Louis Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Southern Indiana Holiday rentals
- Cincinnati Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Chicago Cultural Center
- Deep River Waterpark