Holiday rentals in South Side

2-Story 3BR Hyde Park | Theater+Arcade | UChicago

Relax with family and friends this summer in our spacious 2-level home, equipped with central air! The lower level is your private fun zone—featuring a 120" projector for movies, a retro arcade game, ping pong, board games, a bedroom and bath, plus a NEW sectional for movie nights. Upstairs, you'll find two more bedrooms, a full bathroom, an outdoor patio, and a fully stocked kitchen with an air fryer, Keurig, and complimentary coffee. Everything you need for a fun, comfortable stay together.

University of Chicago Condo-Upgraded and Spacious

Beautiful, spacious, 1 bedrm, 2 bathrm condo near the University of Chicago. Open floorplan, hardwd floors, stainless appliances, 2 Smart TVs in bedrm & living rm, in-unit laundry, and private parking space. Features a cozy reading nook and large outdoor patio. On a quiet treelined street - minutes from Hyde Park and waking distance to Lake Michigan, Jackson Park Golf Course, the 222,000sq ft Regal Mile Film Studios, and upcoming Obama Presidential Library. Your stylish home away from home!

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

2BR Brownstone 7-min to Events, Downtown, & Beach

Welcome to The Garden Oasis! Stay here if you want to live like a local in a historic Chicago Brownstone just minutes from the heart of the city. Thoughtfully designed with modern touches, a cozy living space, and plenty of natural light, it's the perfect place to relax after exploring. Walk to the beach, lakefront trail, and local eateries, or take a quick ride downtown to visit Chicago’s top attractions. Experience the best of the city from your own private retreat!

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Classic Den @ U Chicago

Our homey space includes full bath, kitchenette, living area and super comfy Queen bed. Direct access to unit from the exterior rear door makes coming and going easy. Located on University Ave. just a minutes walk to U. Chicago campus, easy access to public transportation taking you downtown in just over half an hour. *Note*This is in the basement of our home. Interior stair door locks from basement side to ensure guest privacy. You will hear us upstairs at times.

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.

Cozy In the Middle of Everything

Enjoy a stylish experience at this centrally-located place. About a mile from the University of Chicago. 10 Minutes to Downtown Chicago. 3 Blocks from the beach, walking, and bike trails. Near grocery stores and beloved Bronzeville Eateries. Right off Lake Shore Drive with access to all Chicago Expressways. This is the perfect spot to relax while you enjoy all that the City of Chicago has to offer.

The Sweet!

Privacy and comfort without the hefty price tag. This sweet basement suite is perfect for the solo traveler or couple needing space to relax and recharge. It's located in the wonderfully diverse and convenient neighborhood of Bridgeport (in between Pilsen and Chinatown) on a friendly and peaceful street. Some of the best restaurants and bars are within just a few blocks!