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Holiday rentals with lake access in South Side

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Top-rated rentals with lake access in South Side

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

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Home in Chicago

4.87 out of 5 average rating, 127 reviews

Soak Up Mid-Century Style in Wrigleyville and Boystown

This is an architecturally significant (3-bedroom 3.5-bathroom) home by noted Las Vegas architect Homer Rissman. We are located in the heart of East Lakeview, just half a block from Lake Michigan and Lincoln Park, and blocks away from Wrigley Field and Boystown. Smart TVs (with Netflix, Hulu, Amazon Prime) are located in the shared main level TV lounge, and also the lower level lounge. Entire home I like in-person check-in but full privacy is offered You will receive a link with detailed instructions within 24 hours of your check-in. If you have a U.S. mobile number, you will also receive a text message FULL DISCLOSURE: If you haven't used a lockbox (or don't know how to), self-check-in isn't for you. Your check-in should be in person. Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. You walk to Treasure Island (half block), Jewel Osco (2 minutes), Whole Foods (4 minutes), Lakeview Athletic Club (4 minutes), XSports Fitness (5 minutes), Walgreens (3 blocks), bars and restaurants aound the corner. Close to multiple buses on Lake Shore Drive. Grab a bus to downtown in 15 minutes You will have to climb one flight of stairs for all bedrooms Street parking is free on the east side of Broadway. The west side requires 383 permits. Please, read the signs.

Home in Whiting

4.84 out of 5 average rating, 146 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 favourite

Flat in Chicago

4.95 out of 5 average rating, 79 reviews

Loyola & Lake -3br/2bth close to the Lake & Loyola

Amazing lake views from 2 outdoor spaces! This spacious 3 bedroom, 2 bath unit has a large front balcony looking out to the lake and also a rear deck with lake views as well. The unit was recently renovated and has updated kitchen, bath & lots of entertaining space. In unit laundry and detergent included. Lots of books and games to keep you entertained! Walking distance to restaurants and bars. Starbucks is at the end of the block. Kayaks/paddle boards available for rent (May 1-Oct 15).

Guest favourite

Home in Westmont

4.93 out of 5 average rating, 30 reviews

Westmont,Il 4/3 on the Lake

We may take a refundable deposit. We must say this because our direct booking site is linked. A lovely place on the lake in summer we rent entire house. This is a home that is split into a duplex. One side we have 3 bedrooms 2 baths. The other side is 1 bedroom and 1 bath. Both sides have separate entrances and decks. Enjoy the beautiful view while staying. You have access to entire house and yard except garage with this listing. This listing is for renting both sides. They do not connect.

Guest favourite

Apartment in Chicago

4.99 out of 5 average rating, 145 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.

Guest favourite

Guest suite in Evanston

4.98 out of 5 average rating, 243 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!

Guest favourite

Flat in Chicago

4.92 out of 5 average rating, 182 reviews

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

Imagine a stone castle, medieval style; except this one has an 85" HDTV, Wifi, 16' long granite bar with full kitchen and appliances. The warm glow of recessed lighting and polished concrete floors of this basement unit create a comfortable atmosphere. Lots of space with over 2,000 square feet; fully rehabbed with all newly appointed features. A secure building with a private entrance, free parking. Perfect for large groups of up to 20 friends and family; located in East Lakeview.

Guest favourite

Apartment in Chicago

4.99 out of 5 average rating, 281 reviews

Cozy 3BR on Chicago's North Side & Free Parking

Enjoy this charming 3-bedroom condo with free on-site parking just three blocks from Lake Michigan. Convenient access to public transit, including the express bus to downtown (9 miles), Navy Pier, and Grant Park. The CTA Jarvis station is only three blocks away. Perfect for families, business travelers, and couples, this condo is also close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). A great home base to explore all that Chicago has to offer!

Guest favourite

Apartment in Chicago

4.98 out of 5 average rating, 256 reviews

Near Lake Michigan & Wrigley Field

Available 2B/2B condo with 2 King Size Beds. One block from the Aragon Ballroom and Riviera with great views of Uptown and two blocks from Lake Michigan. It’s also a perfect place to stay if your in town for a Cubs game. You can see the stadium from the rooftop deck. Walking distance to everything you need, 2 train stations, groceries, gym, restaurants/ bars. The perfect place to come and go as you please with easy key code entry.

Flat in Chicago

4.92 out of 5 average rating, 154 reviews

Executive Apartment on Lake Michigan with parking

Stay in a furnished 2nd-floor apartment in a walk-in building with its own beach on Lake Michigan. Watch the waves from your living room or sit out on the terrace. -Free Wifi, -Onsite Parking with EV charging station -Steps away from parks, minutes away from universities, shopping, and restaurants -Less than 25 min drive to Wrigley Field, Downtown Chicago, Soldier Field, and museums.

Guest favourite

Flat in Skokie

4.97 out of 5 average rating, 132 reviews

Charming Apt.Fully Equipped Prk.Inc 12 min 2 Lake

Newly renovated, 2-bedroom apartment. New appliances. Relaxing atmosphere. Walking distance to shopping, restaurants, grocery, train station, etc. Nice and quiet neighborhood. Central air & heating, washer & dryer, iron & ironing board, shampoo, conditioner, body wash, hair dryer, coffee maker, toaster, large fridge. All kitchen utensils available for use.

Guest favourite

Home in Chicago

4.93 out of 5 average rating, 153 reviews

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

Sophisticated Roscoe & Halsted duplex w garden. Sleeps 6 - 3 beds in 3 bedrooms + 2.5 baths. Steps from bars & restaurants, 2 blocks from Wrigley Field & Lake Michigan. Perfect for sports enthusiasts, enjoy Boystown, get-aways. In addition to central heat and air conditioning, ceiling fans with remote control in each bedroom.

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Popular amenities for lake access rentals in South Side

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Air conditioning

Lake access house rentals

Home in Des Plaines

4.86 out of 5 average rating, 35 reviews

House in the Park- 5 Min from O'Hare.

Guest favourite

Home in Chicago

4.9 out of 5 average rating, 138 reviews

Spacious Two Story Luxurious Home w/Outdoor Deck!

Guest favourite

Home in Chicago

4.9 out of 5 average rating, 48 reviews

CasaNova Modern City Living

Home in Chicago

4.8 out of 5 average rating, 5 reviews

The Lytle House Loft

Home in Barrington

4.83 out of 5 average rating, 23 reviews

Cozy 3 bedroom river cottage w/ indoor fireplace

Home in Chicago

4.81 out of 5 average rating, 37 reviews

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

Home in Miller Beach

4.81 out of 5 average rating, 58 reviews

Indiana Dunes Park Getaway w/Firepit, Near Beach

Guest favourite

Home in Downers Grove

4.97 out of 5 average rating, 30 reviews

Lakefront Getaway Home! Amazing View! Hot tub! Ski

Apartment rentals with lake access

Flat in Chicago

4.82 out of 5 average rating, 282 reviews

Archways at the Lincoln Park Zoo 2bed/2ba

Guest favourite

Flat in Chicago

4.97 out of 5 average rating, 227 reviews

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

Flat in Chicago

4.83 out of 5 average rating, 163 reviews

The Posh Apt. Mins to Downtown & Hyde Park

Guest favourite

Flat in Chicago

4.98 out of 5 average rating, 352 reviews

Lincoln Pk-parking-wifi-King bd-crib-kid friendly

Flat in Evanston

4.82 out of 5 average rating, 171 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Guest favourite

Flat in Chicago

4.93 out of 5 average rating, 426 reviews

Andersonville Living

Guest favourite

Flat in Chicago

4.86 out of 5 average rating, 155 reviews

Midcentury Modern Lakeview 2 Bedroom Apartment

Guest favourite

Flat in Chicago

4.86 out of 5 average rating, 119 reviews

minimal lakefront apartment

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