
Holiday rentals in South Side
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Top-rated holiday rentals in South Side
Guests agree: these stays are highly rated for location, cleanliness and more.

Home in Carol Stream
4.57 out of 5 average rating, 23 reviewsAmazing Summer Pool Awaits You!
Vacation, Staycation or Business, you will love your stay at this beautiful paradise with heated pool and tri-level entertainment deck equipped with grill and outside seating and gazebo! Semi-secluded backyard, walking distance to bike path, playground, skate park, walking trails, restaurants and even the gym! Relax on the magnificent deck while watching the sunset This home is pet free and smoke free. Pool is available May-Sept. WiFi is available throughout and Smart TV in the family room.

Flat in Chicago
4.94 out of 5 average rating, 162 reviewsSun drenched 2 bedroom 1 bath with Kitchen & W/D
Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Home in Chicago
4.91 out of 5 average rating, 174 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Say "WOW" in this top floor, IMMACULATE SPACIOUS with cozy FIREPLACE + ROOFTOP overlooking skyline! Open 2-story layout w/7 bed options, 3 bathrooms, private rooftop with skyline. Luxury flooring, soaring high ceilings, fully-stocked kitchen + huge island, keyless entry, 2 HD TVs, & outdoor grill. Perfect for SPECIAL OCCASIONS! Next to all Wrigley bars & restaurants. Train to Downtown <12 mins. Private parking for rent. As a "GUEST FAVORITE" we boast >1220 5-star reviews across listings!

Home in Oak Park
5 out of 5 average rating, 9 reviewsDowntown Oak Park LUXE Home | 3 Bedrooms, 2 Baths
Enjoy the comfort & luxury of this large, cozy and stylish 3-bedroom property located in Oak Park's historic district. Just a few steps from iconic sites like the Frank Lloyd Wright Studio and the Ernest Hemingway Birthplace Museum, this contemporary oasis is within walking distance of Oak Park’s vibrant downtown and public transit. This special home is brand new and meticulously clean! it is close to everything, making it easy to plan your visit. Party is not allowed in the house.

Home in Homewood
4.91 out of 5 average rating, 121 reviewsPeaceful & Private Hot Tub Vacation Home Getaway
A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

Home in Chicago
5 out of 5 average rating, 9 reviewsAlluring Avondale Abode
Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Flat in Chicago
4.91 out of 5 average rating, 11 reviews2-level PH w/ 2 Luxe Suites Combined; Spa Access
The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Home in Schaumburg
4.96 out of 5 average rating, 51 reviewsParadise in Schaumburg Low Cleaning Fee, 3 BR, 4Bd
Welcome to this inviting 3-bedroom, 1.5-bathroom home in a very safe and quiet neighborhood. Enjoy the tranquility while being close to all shopping, restaurants, and entertainment options. The spacious interior includes a bright living area and a functional kitchen. Additionally, an indoor park nearby offers a great place for year-round recreation. This home combines comfort, convenience, and a prime location, perfect for families and individuals alike.

Home in Crete
4.92 out of 5 average rating, 26 reviewsCozy Cabin in Crete With Hot Tub
Tucked away on two acres is our stunning, updated cabin with a modern feel! The property is peaceful and offers guests a private, relaxing stay. Private hot tub on the front porch with string lights and jets. Pets stay free! 4 minutes up the road is downtown Crete, which includes a delicious coffee shop, brewery, ice cream shop, and restaurants. *Only registered guests allowed on the property at anytime*

Guest house in Oak Park
4.96 out of 5 average rating, 103 reviewsO'Malley Oasis!
Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!

Flat in Chicago
4.96 out of 5 average rating, 278 reviewsSpacious 1BR apartment in a central location
Private 1BR in Avondale neighborhood of Chicago. Right off the Expressway, it's 20 mins from O'Hare, 20 mins from Downtown (both by Blue Line) 20 mins from Wrigley Field (bus). Comfortable and spacious attic apartment in a residential area. Lots of street parking.

Home in Whiting
5 out of 5 average rating, 14 reviewsTop location Historical downtown
Top Location! Next to the Whiting Historical downtown, home to many festivals, where there are many restaurants and micro-breweries. Short walk to Whiting Lakefront Park and Whihala Beach. Home is in a quiet neighborhood and ready to accommodate your next stay.
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Other great holiday rentals in South Side

Home in Chicago
4.94 out of 5 average rating, 34 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking

Home in Schaumburg
4.8 out of 5 average rating, 80 reviewsSpacious 5 Bedroom 1 Level Renovated Modern House

Flat in Chicago
4.95 out of 5 average rating, 39 reviewsElegant 4Bedroom with Free Parking in Albany Park

Flat in Chicago
4.81 out of 5 average rating, 16 reviewsCity Gem: Stylish 3BR for Urban Explorers

Home in Lockport
5 out of 5 average rating, 20 reviewsCozy 4 Bed Ranch w Fenced Yard *Netflix

Home in Lombard
5 out of 5 average rating, 21 reviewsSpacious Home in Chicago Suburbs

Flat in Merrillville
4.82 out of 5 average rating, 83 reviewsLovely 2 Bed Room Apartment, all to yourself

Home in Chicago
5 out of 5 average rating, 17 reviewsComfy Home Away From Home
Destinations to explore
- Downtown Chicago Holiday rentals
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- Pet-friendly rentals South Side
- Rentals with a hot tub South Side
- Smoking-friendly rentals South Side
- Rentals with pools South Side
- Rentals with an EV charger South Side
- Rentals with a patio South Side
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