Fitness-friendly vacation rentals in South Side

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Top-rated fitness-friendly rentals in South Side

Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Rental unit in Chicago

4.9 out of 5 average rating, 496 reviews

Whole Flat in Private Club. Walk to L, Dining & Shows

Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

Guest favorite

Rental unit in Chicago

4.97 out of 5 average rating, 146 reviews

Urban Cottage:Near Transit/20min MagMile & Wrigley

Inside a Classic Chicago brick building with high ceilings and plenty of light -centrally located for all your sightseeing needs! A well-equipped kitchen with quartz countertops and stainless steel appliances-this apartment is perfect for families and friends looking for easy access to downtown without sacrificing a neighborhood vibe. Irving Park is referred to as the "country in the city" with green spaces & tree lined streets. Plenty of restaurants & cafes nearby, we'd love to host you here!

Guest favorite

Guest suite in Chicago

4.92 out of 5 average rating, 83 reviews

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

Guest favorite

Rental unit in Chicago

4.91 out of 5 average rating, 102 reviews

Ground-Level Speakeasy: 1BR-1.5BA Near Everything!

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 TVs, 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 to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Guest favorite

Home in Chicago

4.96 out of 5 average rating, 152 reviews

Chicago River House with private patio!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and illuminating seats

Guest favorite

Condo in Chicago

4.96 out of 5 average rating, 142 reviews

Stylish 3BR + Free Parking 10-15mins from Downtown

This apartment is located in Historical Humboldt Park, a residential area that is an easy 10-15mins drive to Downtown, Medical District, Wicker Park, West Town, Logan Square, and Ukranian Village. Due to the proximity, we host guests visiting for tourism, fests,concerts, sport events , work conferences, weddings, birthdays, and visiting family. There are grocery stores closeby. There’s street parking and a gated private parking available. Location wise, you are close enough to everything.

Superhost

Condo in Chicago

4.88 out of 5 average rating, 179 reviews

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

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

Guest favorite

Guest suite in Chicago

4.85 out of 5 average rating, 241 reviews

Wrigleyville/Boystown/Entire Private Floor!

1000 sq ft-entire private floor & door access. The perfect Wrigleyville/Boystown/Lake location. Zip to downtown Chicago in minutes via cab or public transportation options. Our friendly neighborhood is packed with fun bars, fabulous restaurants, unique boutiques & great music venues. Enjoy pool, ping pong and pinball and our 65" 4K flat screen TV or a seat at the bar. A Queen bed, 2 single beds in the main room, steam shower and bathroom. We have a mini fridge, microwave, coffee and home gym.

Guest favorite

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.

Guest favorite

Rental unit in Chicago

4.93 out of 5 average rating, 75 reviews

50th Floor Mag Mile Studio

This Downtown Chicago unit is towering 50 stories above the city, with floor to ceiling windows in the living areas. This unit gives you the ultimate in Luxury urban living. It's all about the views and location. The city unfolds before you with amazing sunsets; nowhere in Chicago can you stay with views like these. The building provides the very best in amenities. A state of the art fitness center, Outdoor pool, Outdoor kitchens, business center, are available to our guests.

Guest favorite

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!

Guest favorite

Condo in Chicago

4.87 out of 5 average rating, 143 reviews

McCormick 2B/2Ba for up to 8 guests w Opt Parking

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • City Skyline view • 2 shifts Security officers in the building • 2 Queen size beds + Sofa bed + queen sized air mattress for 4 extra guests • Comfortable stay for up to 8 guests at a time • Access to the Gym • Fast Internet • 4K smart HDTV(Netflix) • Fully equipped & stocked kitchen with Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day