
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.

Beachfront- Lake Michigan-Hot Tub-Heated Pool
Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

Cozy barn loft on organic vegetable farm
Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

MiniGolfHouse-Chicago Close Beach & Indoor Fun!
🌆 30min drive to downtown Chicago ⭐️ Near Horseshoe Casino, Lake Michigan, Whihala Beach, Whoa Zone ⛳️ Heated basement with mini golf, arcade games and big TV 🐶 Pet fee: $150 (Must let us know BEFORE BOOKING if bringing a pet) ⭐️ Close To: Wolf Lake, Indiana Dunes, HardRock 🏠 cots, air mattress, futon sofa in basement 🍼 pack & play, high chair avail ❤️ Guests love: -short drive into Chicago -comfortable beds -indoor mini golf -nearby shops & food -heated bidet toilet seats

'Pool Barn Camper' w/Hot Tub near Indiana Dunes
Heated pool open until mid October! Hot tub open all year! Fully equipped RV sleeps 5, has bathroom w/shower, stove, microwave, TV, heat & A/C, & running water all year. Located on the bike trail & only minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hike in the Indiana Dunes National Park along the Little Calumet River & the historic Bailley homestead, only 1 block from the RV. Enjoy our large pool, hot tub, grill, campfire, & playground too. Schedule your visit today!

Boulderstrewn: Historic Homewood home
Charming and historic Sears Catalog House on 2/3 acre wooded lot. Less than 10 minute walk to shops and restaurants in downtown Homewood to Metra rail (and Amtrak) station with express service to Hyde Park and University of Chicago (less than a half hour) and Chicago's 3 magnificent downtown waterfront stations (~40 minutes). Fire pit in yard can be used to enjoy summer nights. No cable, but several digital antenna channels available as well as Netflix, XBox and DVDs.

Glamping Yurt&RV Gaming Room Pool/Hotub/Court more
GLAMPING FUN! April - mid Nov RV w/bathroom - 2 beds 20' Safari Yurt - 4 beds Gaming Room w/bathroom queen & sofa sleeper Gazebo w/2 twin beds (seasonal) Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs (seasonal) mini golf 3-n-1 Court; Event Yurt add on $180 up to 15 additional non/overnight guest Contact me for Fall/Winter Glamping no more than 10. RV and Safari Yurt not included in Winter. Event Yurt is. It's heated!

Warm and comfortable inviting Suburban home !
160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

Plant MOOD FREE Wi-fi, parking, washer & dryer!
LATE CHECK-IN guest are welcome!!!! PLEASE READ MY FULL AIRBNB LISTING PRIOR TO BOOKINGS!!!! This special place is close to everything, making it easy to plan your visit. • I80, 294, 94 highways/tolls, etc. • Chicago • Shopping galore • A fun array of restaurants AND A LOT OF FREE PARKING!!! I’m extremely close to MUNSTER, HIGHLAND, SCHERERVILLE, DYER and many more Indiana locations! I’m extremely close to LYNWOOD, LANSING, CALUMET CITY, and many more!

The Hideaway-Single R&R or Couple's Only Retreat
Welcome to your cozy cottage ESCAPE, a modern sanctuary 30 minutes from Chicago. This secluded private, detached cottage on a 3-acre property features a NEW SAUNA with Bluetooth & light therapy, a king-size bed, and a full kitchen. Enjoy your own yard, fire pit, and covered parking. A perfect blend of comfort and convenience. Jacuzzi will be installed in 4-6 weeks :-) Single, or couples only. No charging port for vehicles, 2 stations w/in 2 miles.

IT'S THE WRIGHT PLACE
Private guest house newly remodeled. One bedroom queen bed, bath w/shower, full kitchen stocked, including microwave and Keurig coffee maker pods included, family room TV, and WIFI. No matter if you are in town for work, sport competition, family or just vacationing we offer all the comforts of home. Air Mattress available upon request. Please treat as your own home, follow all house rules. No party or gatherings. This is a no smoking home.

Less is more! Pet friendly Tiny Home near Chicago!
Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome

Charming Unique 2 Bdrm Apartment in Victorian Home
My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.
Popular amenities for Homewood family-friendly rentals
Family-friendly home rentals with a hot tub

Romantic Spa Getaway -Private Jacuzzi, Sauna, Pool

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

Secluded Modern Retreat Near Beach - "Sandlot"

The Studio at the Dunes

The Spa of Downtown Whiting

The Lake Escape -Cozy Lakefront Cottage Valparaiso

Belmont Pleasures - hot tub / arcade gaming room

Private hot tub - King bed suite - Free parking
Family- and pet-friendly home rentals

Ultra Modern Beverly Suite

Modern Peaceful Home | Firepit | Steps to Downtown

Manteno Luxury Comfy Cozy home with- 2 king beds!

1920s fully updated unique open artist loft space

Home in Forest Park Upstairs.

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Quiet cul-de-sac with huge fenced in backyard

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

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

Private Cottage in Gated Nudist Community

Beautiful home with Beach views in Beachwalk

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

Stunning 3BR Penthouse in the Loop | Roof Deck

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

The Executive's Escape (2BD / 2BA)

Bayless Dune Lodge at West Beach - Indiana Dunes!
Quick stats about holiday 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 Holiday rentals
- Downtown Chicago Holiday rentals
- Indianapolis Holiday rentals
- St. Louis Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Platteville Holiday rentals
- Cincinnati Holiday rentals
- Southern Indiana Holiday rentals
- Milwaukee Holiday rentals
- Traverse City Holiday 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