
Family-friendly vacation 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.
Vacation 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 Coach house near Lincoln Square!

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

Master qtr close to nature & easy urban facilities

Secluded Modern Retreat Near Beach - "Sandlot"

Unique Dome Retreat by Indiana Dunes w/ Lake View

The Spa of Downtown Whiting

The Lake Escape -Cozy Lakefront Cottage Valparaiso

Belmont Pleasures - hot tub / arcade gaming room
Family- and pet-friendly home rentals

Cozy Lakeview Studio with Private Access

Lovely, spacious 2bd, 1bath home w/free parking

Manteno Luxury Comfy Cozy home with- 2 king beds!

1920s fully updated unique open artist loft space

Less is more! Pet friendly Tiny Home near Chicago!

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Charming Homewood Away from Home

Great location. Free parking.
Family-friendly home rentals with a pool

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

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

Private Cottage in Gated Nudist Community

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Stunning 3BR Penthouse in the Loop | Roof Deck

5-Star Gold Coast Experience in a Luxe 2BR Retreat

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

The Executive's Escape (2BD / 2BA)
Quick stats about vacation rentals that are family-friendly in Homewood
Total rentals
30 properties
Nightly prices starting at
€ 112 before taxes and fees
Total number of reviews
1K reviews
Pet-friendly rentals
10 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 Vacation rentals
- Downtown Chicago Vacation rentals
- Indianapolis Vacation rentals
- St. Louis Vacation rentals
- Detroit Vacation rentals
- Columbus Vacation rentals
- Louisville Vacation rentals
- Platteville Vacation rentals
- Cincinnati Vacation rentals
- Southern Indiana Vacation rentals
- Milwaukee Vacation rentals
- Traverse City Vacation rentals
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606
- Olympia Fields Country Club
- DuSable Museum of African American History