Kid-friendly holiday rentals in Illinois

Jackson Ready Properties

Bring the whole family to this great place with lots of room for fun. Enjoy the patio or deck and cozy up to the outdoor firepit. Socialize with family and friends inside with two large living areas featuring plenty of seating and pool, foosball or wet bar to keep guests entertained. Three large bedrooms that sleep 6 comfortably as well as a sofa sleeper for kids or tag-along adults! Located within walking distance to the Owner's Club or a short cruise down the hill to the Marina.

DunPuttin Place

Nestled on a secluded hillside that overlooks miles of Galena Territory's wildlife preserve, DunPuttin Place offers its guests total privacy, yet the convenience of being only minutes from the area's many popular amenities. DunPuttin Place is not just another carbon copy resort rental. It is a unique private home that has many features seldom found in vacation rentals. It has been tastefully designed and decorated to comfortably accommodate up to 12 guests of all ages.

1BR Apartment - Walk to Shops - Downtown OAK PARK

Your family will be close to everything when you stay at this centrally-located place. - 4 min drive to the train - 2 min drive to grocery stores & shopping - 20 min drive to Downtown Chicago Enjoy the historic neighborhood and see Frank Lloyd architecture nearby. ➢ Everything is sanitized/washed/cleaned after every guest ➢ Fast, Dedicated Wifi ➢ 2 Smart TVs (Living Room, Bedroom) ➢ Fully equipped + stocked kitchen / bathroom ➢ Pack 'n Play

InstaWorthy! Modern Gem, Perfect Family Getaway-Pe

Have fun with the whole family at this stylish place! - Minutes away from Woodfield Mall, Legoland Waterworks Indoor Water Park, Golf, Outdoors, and more! - Private Driveway - Blazing Fast 1GB internet speed - 60 4K Smart TV w/ Roku Live TV - Pack n Play, High Chair, Stroller - Stocked Kitchen with Coffee and Waffle Bar! - Outdoor Patio Area w/ games - Working Desk Area. - Firepit, Corn Hole, Pool Table - King Size Bed in Main

Bright family-friendly Lincoln Square 2-bed 1-bath

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

Clean & bright ranch home. 5 Min to downtown

Traveling with family or on business relax in this two bedroom ranch home in a quiet neighborhood centrally located in Rockford Illinois. Just minutes from several gardens, river path, restaurants, golfing, and downtown attractions. Fully equipped kitchen with new appliances. High speed internet and Roku TV ready for your streaming services. Both bedrooms have work desks. Many starter essentials.

Stewart house

Nestled in the heart of Central Illinois, this house is conveniently located 3 miles from State Farm Corp, 8 miles from Rivian and 5 miles from the ISU/IWU. campuses. Quick access to Highways 55/74/39. So whether you are coming for work or pleasure, you can relax with your family at this peaceful retreat.

#1 Old Lake House at Cypress Resort & Marine

Set atop a hill overlooking Petite Lake, this 1900's Lake House is ideal for anyone looking to enjoy a get away! Relax on 480ft of beach, swim, boat, ski & fish or take in the changing seasons. A great old lake resort for family fun. Looking for more cottages? All are listed under my profile.

Happy at the Heights: 3+BRs/3BA

Have fun with the whole family at this stylish place. This home has a bedroom and a bathroom on every level. It is spacious and serene. Fully fenced yard for your furry friends! We are so happy to have you in your home away from home.