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Vacation rentals with lake access in South Side

Find and book unique lake access rentals on Airbnb

Top-rated lake access rentals in South Side

Guests agree: these lake access rentals are highly rated for location, cleanliness, and more.

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Rental unit in Chicago

4.84 out of 5 average rating, 176 reviews

The Lakefront Lookout (2BR)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, Navy Pier, Riverwalk, Soldier Field, The Field Museum, Oak Street Beach, and more. Additionally, guests are merely blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Home in Whiting

4.85 out of 5 average rating, 142 reviews

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

Guest suite in Gary

4.96 out of 5 average rating, 338 reviews

Miller Mermaid Suite-100 yds from the beach!

100 yds from the beach, the cozy MERMAID SWEET awaits you and is well suited for a young family or 2-3 adult friends. This artsy basement open studio space includes a private entrance, kitchenette, unique art & a cozy reading/sleeping nook! Enjoy beautiful sunsets from the upstairs deck or use the sun room on rainy days. BBQ on the grill. Visit local restaurants, shops & galleries. Hike wooded trails & swim by sandy, dune-grass beaches. . House-trained dogs welcome! Sorry no cats (allergies)

Rental unit in Chicago

4.9 out of 5 average rating, 189 reviews

Spacious Vintage 3 BR in Chicago's NorthCenter!

Location, location, location! Vintage 3BR second floor Apartment only 10 Blocks from Wrigley Field & 2 miles from Lake Michigan. Bus stop in front, CTA Brownline train to loop a 5 minute walk, bus/CTA from OHare airport 1 block away. Washing machine and dryer in apartment. Neighborhood setting. Walk to restaurants, local breweries, Old Town School of Folk Music & theaters, ballgames, concerts, Trader Joe's, banks, boutiques . Divy bikes, CVS & Starbucks across the street. Garage option.

Condo in Chicago

4.92 out of 5 average rating, 218 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed,TV, dining table, & partial kitchenette. Dogs only. Parking free on street or one spot for a fee.

Guest suite in Carol Stream

4.94 out of 5 average rating, 288 reviews

Cozy Lakefront Retreat: Hot Tub & Bar/Pool Table

Very large guest suite with 3 separate areas. Just like your own apartment. Great for friends traveling together! ENTRANCE IS THRU THE MAIN PART OF THE HOUSE. This is just for the basement apartment but you have complete privacy down there. Fenced-in yard, hot tub, large patio, bbq, firepit, enjoy fishing or sitting watching the beautiful sunsets. Stocked lake, walking path, 3 parks! Check out the pictures to see all our home has to offer! (Full kitchen & laundry room are shared space)

Condo in Chicago

4.99 out of 5 average rating, 132 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

HAVE IT ALL @ W3A Boys Town/Wrigley Field/East -Newly renovated/brand new in safe centrally located East Lakeview. -10 min walk from Wrigley Field, Boys town, beaches, super markets restaurants with late night dining. 5 min walk to the Metro Sheridan Red Line (straight shot downtown), 1 free enclosed parking plus free permitted street passes. -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish furnishings & in unit washer and dryer.

Cottage in Gary

4.96 out of 5 average rating, 149 reviews

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is perfect for a romantic getaway. A newly renovated cottage with new kitchen, modern appliances and new bathroom all in a bright airy home. It is located in Indiana Dunes National Park/Miller Beach. Only 1.5 blocks to the beach, you can hike trails nearby and come back to relax in a unique, comfortable setting with ambiance and charm. It's perfect for summer/holidays. Wifi, onsite parking and self check in, allow you to enjoy our wonderful home in privacy and peace.

Guest suite in Evanston

4.97 out of 5 average rating, 235 reviews

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 guest suite w/private kitchen, 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!

Condo in Chicago

4.88 out of 5 average rating, 105 reviews

Downtown Park #11 - Mich Ave PH | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

Rental unit in Chicago

4.78 out of 5 average rating, 281 reviews

Superb 2BR Old Town APT, PRIME LOCATION!(+Parking)

BOOK with US with CONFIDENCE! 15% OFF monthly stays!! Cozy apartment right in the center of Old Town and right by all the action on Wells st, you are able to walk to some of the hottest and most popular attractions. This open-floor apartment offers two bedrooms, a spacious living room, and a brand new kitchen! You will love your stay here! 5 minute walk (0.4 miles) to Clark/Division Red-line stop (CTA L) which will take you to all downtown attractions in minutes!

Rental unit in Chicago

4.96 out of 5 average rating, 284 reviews

Cozy loft in Chicago's Uptown

Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

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Popular amenities for South Side lake access rentals

Free parking on premises

Air conditioning

Lake access house rentals

Home in Chicago

5 out of 5 average rating, 6 reviews

Gold Coast Pristine 4BR/4.5BA Home | Free Parking.

Home in Chicago

5 out of 5 average rating, 11 reviews

Amazing historic campus mansion!

Home in Chicago

4.9 out of 5 average rating, 48 reviews

CasaNova Modern City Living

Home in Downers Grove

4.96 out of 5 average rating, 24 reviews

Lakefront Getaway Home! Lots of Fun! Win.Discount$

Home in Chicago

4.81 out of 5 average rating, 36 reviews

Exec Lux home wth 3 Level,6 Bdrms/3bth & 2 Kitchen

Home in Skokie

4.88 out of 5 average rating, 84 reviews

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

Home in Gary

4.95 out of 5 average rating, 80 reviews

Steps from the beach and a mile from National Park

Home in Chicago

4.96 out of 5 average rating, 26 reviews

Private Downtown Retreat with Rooftop Oasis

Lake access apartment rentals

Rental unit in Chicago

4.94 out of 5 average rating, 99 reviews

3bdrm/2bth in restored brownstone in Bronzeville

Rental unit in Chicago

4.93 out of 5 average rating, 30 reviews

NEW Garden Unit Close to Downtown

Rental unit in Chicago

4.99 out of 5 average rating, 114 reviews

KING bed FREE P-Spot EV EZZY Accessible NO stairs

Rental unit in Highland Park

4.93 out of 5 average rating, 149 reviews

Lovely studio near the beach! (and heated floors!)

Rental unit in Chicago

4.95 out of 5 average rating, 98 reviews

420 at Cheltenham 4BR

Rental unit in Chicago

5 out of 5 average rating, 24 reviews

Old Town Tranquility (+parking)

Rental unit in Chicago

4.93 out of 5 average rating, 146 reviews

Executive Apartment on Lake Michigan with parking

Rental unit in Whiting

4.84 out of 5 average rating, 142 reviews

NEW! |Studio Apartment Whiting IN, United States#2

Lake access cottage rentals

Cottage in Gary

4.95 out of 5 average rating, 61 reviews

SYLVIA's CHARMING & RELAXING COTTAGE

Cottage in Cedar Lake

4.91 out of 5 average rating, 32 reviews

Cedar Sunset On the Lake

Cottage in Cedar Lake

4.97 out of 5 average rating, 30 reviews

Quant Cottage with private dock and boathouse

Cottage in Gary

4.82 out of 5 average rating, 181 reviews

Midcentury Cottage 3bd IN Dunes Natl Park, Lake MI

Cottage in Gary

4.91 out of 5 average rating, 77 reviews

Luxury Cottage nestled in nature, close to beach

Cottage in Cedar Lake

5 out of 5 average rating, 49 reviews

Cedar Sunrise- 1 BR Lake Home

Cottage in Gary

4.83 out of 5 average rating, 12 reviews

Miller Beach Early Mid-Century Lake Cottage

Destinations to explore