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.

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

Newly renovated, bright & clean ranch home

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.

Lakefront Paradise

Relax and have fun with the family and friends at this unique getaway! We are situated directly on the lakefront with private access to our pier where you can enjoy world class sunset views. Jump in and go swimming, roast s'mores over a campfire right next to the water, grill up some burgers on the spacious deck or get some rest in our luxurious suites in this newly renovated (June 2021) home.

Top-Rated- Modern Getaway

Experience the ultimate in comfort and style: This premier three-bedroom home is the perfect retreat, boasting a master bedroom with a plush king bed and two inviting bedrooms with queen beds. Each room is tastefully decorated, offering a cozy and welcoming atmosphere. Whether you're here for a weekend or a longer stay, this property promises a comfortable and inviting experience.

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 & Gameroom

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. We are so happy to have you in your home away from home.