Family-friendly holiday rentals in South Side

Quiet and Cozy 2 bedroom condo

Welcome to your tranquil retreat! This thoughtfully designed two-bedroom 1 bath condo blends modern amenities with a welcoming atmosphere, making it an ideal getaway. The living area features contemporary décor and comfortable seating. The kitchen is equipped with stainless steel appliances & granite countertops. Conveniently located near shopping, restaurants & coffee shops O’Hare & Midway airports are approximately a 25 minute drive and Downtown Chicago is approximately a 20 minute drive!

4BR/2BA + Fenced Backyard + Garage + Near MDW

Unwind in style at our stunning Burbank home! With its modern, ultra-cool vibe and sensational light fixtures this house is the perfect retreat after a day of adventures. Conveniently located near Midway Airport✈️ and public transportation 🚍 and just a short Uber ride to downtown Chicago 🌆 you'll enjoy the perfect blend of convenience, comfort, and cool + enjoy free garage and driveway parking for added convenience. 🚗 Come experience the best of Burbank – book now for an unforgettable stay!

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house.

A guest suite centrally located, but so quiet

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my private guest suite w/kitchenette, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

Homewood Oasis

Welcome to our Homewood Oasis, where relaxation meets family fun! As former residents of this charming town, we know the importance of a comfortable and enjoyable stay when coming back to visit. Our Airbnb is more than just a place to sleep; it's a carefully curated space designed for families like yours. As hosts who've experienced the need for a home away from home, we've put our heart into making this space welcoming and enjoyable for you. We look forward to hosting you!

Pool, 30 mins to CHI, 3 Kings, Outdoor Space, BBQ

Discover the Farmhouse on Main! Where character meets comfort. Soak up the sun by the in-ground pool with loungers, or enjoy a firepit for cozy nights. Fire up the BBQ grill or sip drinks at the granite bar. Inside, relax in the cozy seating areas, gather around the large dining table, and enjoy the spacious, fully equipped kitchen. ★ 5 minutes to downtown Plainfield ★ 20 minute drive to Naperville ★ Just a 30 minute drive into Chicago Come enjoy Plainfield with us!

4BR/1.5BA+Fenced Backyard +Near MDW+One Level

Come experience this beautiful home in Burbank, a sweet spot for family living in a quiet suburban neighborhood just minutes from Chicago and Midway Airport. This inviting home blends comfort and modern finishes with a warm, welcoming feel throughout. Designed for families, it offers spacious living areas perfect for relaxing, entertaining, and everyday life. Close to parks, shopping, dining, and major highways for an easy commute into the city

Cozy Guesthouse near NU - next to Lee Street Beach

Welcome to our cozy and comfortable guesthouse nestled on a quiet and beautiful neighborhood in Southeast Evanston. We are 2 blocks from Lee street beach and 10 minutes walking distance to the Main Street El train (purple line) and Metra stop. We are a 10 minute walk to downtown Evanston and Northwestern University. We are 10 miles from downtown Chicago.

Stylish Coachhouse in lovely Oak Park!

Enjoy the privacy and artistry of your very own coachhouse. The interior is a personalized mix of artistic, industrial and farmhouse. Cool colors, personalized details and local art included. You have your own washer, dryer, complete kitchen, and private patio space. Walk the lovely neighborhood, to the L train, or even to a local brewery.