
Vacation rentals with beach access in South Side
Find and book unique beach access rentals on Airbnb
Top-rated beach access rentals in South Side
Guests agree: these beach access rentals are highly rated for location, cleanliness, and more.

Hidden Gem:Artsy Speakeasy in Historic Bronzeville
Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TV, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles), Navy Pier, Obama Library, Millennium Park, Beach (1 mile), Museum, & Sports arenas.

Cozy 2BD Lake Apt Near Downtown, McCormick & More
Enjoy your getaway in this cozy solar powered and eco-sustainable garden apartment 5 minutes walking to Lake Michigan where you can access beaches, bike paths, prairies, parks & more! We are less that 8 min away from downtown, the University of Chicago, Soldier Field, the Field Museum and more. Our home is located in the historic Oakland neighborhood, central to so much of what Chicago has to offer. We love welcoming guests to our garden apartment where making your stay relaxing is our pleasure

The Spa of Downtown Whiting
so close to Chicago but so far away. NEWLY REMODELED AND COMPLETELY FURNISHED. There's so much to enjoy in this incredible converted 2 flat, now a single unit. WE COMPLETELY RIPPED ON AND REDID THE ENTIRE INTERIOR. 1ST Flr-spa w/ 2 person jacuzzi, shower, continuous hot water, family room, kitchen 2nd flr, sitting room w/ TV and surround sound, 2 bedrooms, w/ bathroom and bath/shower. -FRONT BALCONY, -SPEAKERS THROUGHOUT -BLOCKS FROM THE BEACH & WOLFE LAKE -PERFECT LOCATION FOR PIEROGIFEST

Cozy 2 bdrm near McCormick Place & Wintrust Arena
Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled between Hyde Park and South Loop, where you will find plenty of restaurants, theaters, and nightlife. Only minutes away from McCormick Place, 10-15 min drive from downtown and 3-12 miles from all the sports arenas and airports. You can bike or walk to the nearest grocery store, park, gym, and beach. The nearest bus and/or train is 2-3 blocks away for your convenience as well.

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.

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.

Spacious 2 Bedroom in the heart of Lakeview!
Come enjoy this warm and spacious 2br/1ba vintage apartment in the heart of Lakeview! 10 Minute walk to Wrigley Field and steps away from many dining and shopping options. Fully stocked kitchen, dining room (seats six), decorative fireplace, TV w/ Fire Stick, two bedrooms with queen beds, office space for working remote, and large private deck with gas grill. Very close to Lake Shore Drive, short walk to the Belmont L, and easy access to many buses. Two night minimum stay.

Blue Brick Apartment in Bridgeport - Park for Free
• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)

Cannabis Condo 4BR
Beautiful, spacious apartment is located 10 min from Beach. 10 mins to Hyde Park, (Tiger Woods) Golf Course. 10 mins from Obama Library (coming soon). 10 mins from Museum of Science and Industry. 20 mins from downtown/Soldiers Field (Bears Stadium), Northernly Island concerts, Field Museum, and Shedd Aquarium (beautiful drive down Lakeshore, Metra Electric Line train, or Bus). 15 min from Indiana casino. Ideal for Summer time Chi or Winter snow Chicago!

3bdrm/2bthrm brownstone 10 mins to Obama Center
Newly restored Brownstone in historic Bronzeville neighborhood near ecerything (5 mins to Oakwood Beach, 8 mins to McCormic Place Ctr., White Sox pk, & Museum of Science and Industry, 10 mins to Obama Center, Soldiers Field, & U of C, 11 mins to Art Institute, & 12 mins to Millennium park) Built in 1868, this 3br/2ba apartment has antique furniture and finishes with contemporary touches, smart tech & security, in lakefront neighborhood

Elegant Suite in Gold Coast
Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

Stylish 2BR Andersonville — Walk to Lake & Cafés
Steps to Chicago’s lakefront, cozy cafes, and Andersonville’s best shops. This bright 2BR blends vintage charm with fast Wi-Fi, plush bedding, and a fully stocked kitchen—ideal for couples, remote workers, and weekend explorers. Stroll tree-lined streets, explore the nearby lakefront, or curl up indoors as the seasons change. Enjoy Superhost hospitality for an effortless stay. We’d love to host your next Chicago escape.
Popular amenities for South Side beach access rentals
Apartment rentals with beach access

The Lakefront Lookout (Rooftop Deck • Gym)

The Loyola Garden Flat: Huge 2BR Near Lake

Convenient Location Near Loyola/Northwestern

Guest Favorite Escape Next to the Beach

Andersonville 2 bed with modern kitchen + bath

Andersonville Garden Living

*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

Beautiful Hollywood-Ridge Suite in Edgewater
House rentals with beach access

3BD | 2 Ensuites | Sleeps 8| Near Sox & McCormick

B42: Spacious w/ Modern Art/Decor Mins to DWTN

CasaNova Modern City Living

Historic Old Town, Fabulous 4 Bedroom Home

Cheryl's on Sheffield! 3 bedroom in Lincoln Park.

Private Downtown Retreat with Rooftop Oasis

Spacious 3 Level Home with 5 BDR/3 BA & 2 Kitchens

Stylish Duplex • King Suite • 12 min to Downtown
Condo rentals with beach access

Studio flat in the heart of Chicago's Gold Coast

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

South Shore Dr Retreat

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

The ModernFarmhouse Chicago-Near Downtown Chicago

Spacious Beauty 3BR 3Bath Duplex w/ Roof-Top Deck

Pets OK | Walk Score 95 | Desk | 1,750ft² |W/D

FreeParking/Laundry/BigSpace!/FamilyFun!/GameRoom!
Destinations to explore
- Chicago Vacation rentals
- Platteville Vacation rentals
- Indianapolis Vacation rentals
- Downtown Chicago Vacation rentals
- Columbus Vacation rentals
- Louisville Vacation rentals
- Detroit Vacation rentals
- Southern Indiana Vacation rentals
- St. Louis Vacation rentals
- Cincinnati Vacation rentals
- Milwaukee Vacation rentals
- Wisconsin River Vacation rentals
- Rentals with breakfast South Side
- Condo rentals South Side
- Rentals with a hot tub South Side
- Rentals with lake access South Side
- Rentals with pools South Side
- Rentals with a washer and dryer South Side
- Family-friendly rentals South Side
- House rentals South Side
- Waterfront rentals South Side
- Fitness-friendly rentals South Side
- Rentals with a fire pit South Side
- Pet-friendly rentals South Side
- Smoking-friendly rentals South Side
- Private suite rentals South Side
- Rentals with a patio South Side
- Bed and breakfasts South Side
- Rentals with outdoor seating South Side
- Apartment rentals South Side
- Rentals with a fireplace South Side
- Rentals with an EV charger South Side
- Townhouse rentals South Side
- Rentals with beach access Chicago
- Rentals with beach access Cook County
- Rentals with beach access Illinois
- Rentals with beach access United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Soldier Field
- 875 North Michigan Avenue
- The Field Museum
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Union Park
- University of Chicago
- Lincoln Park Zoo
- Chicago River Walk
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Washington Park Zoo
- Loyola University Chicago
- Indiana Dunes State Park
- Oak Street Beach
- Illinois Beach State Park





