Vacation rentals with a pool in South Side

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Top-rated rentals with a pool in South Side

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Guest favorite

Rental unit in Chicago

4.89 out of 5 average rating, 495 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”

Superhost

Rental unit in Chicago

4.83 out of 5 average rating, 54 reviews

Highrise Hideout (2BD/2BA)

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, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Guest favorite

Yurt in Homewood

4.97 out of 5 average rating, 101 reviews

Glamping Yurt&RV;Game Room;Pool;Sauna;Hotub Courts

Glamping Experience to the next level now open all year. Spring/Summer & Fall/Winter Mini Resort Includes: RV - Spring/Summer 20' Safari Yurt - Spring/Summer 30' Event Yurt w/beds all year Outdoor wooden Barrel-Sauna 27' above ground swimming pool 6-7 Person outdoor hot-tub Gazebo twin beds, TV Game Room w/bathroom, pool/air hockey table Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court Spring/Summer May - Oct sleeps 14 Fall/Winter - Nov - Apr sleeps 8-10

Guest favorite

Rental unit in Chicago

4.97 out of 5 average rating, 93 reviews

Fun & cozy getaway w/POOL/game room/FREE parking

Enjoy our Pool & Play Getaway in hot Logan Square! Thoughtful upscale touches throughout. Conveniently located on a tree-lined Chicago Cul-de-Sac, just a 5 min walk to the L Blue Line. Relax in our extended outdoor living space, spend an afternoon lounging in the pool, al fresco grilling & dining on the deck or toast smores over the firepit in the yard. We're steps from all the hot restaurants and nightlife, including Chicago's #1 farmer's market. Free permit street parking for our guests.

Superhost

Rental unit in Chicago

4.83 out of 5 average rating, 29 reviews

Cozy studio near Michigan lake

Welcome to your cozy urban retreat by the shores of Lake Michigan! Nestled in the lively neighborhood near Loyola Park, this charming studio apartment offers a delightful blend of modern comfort and vibrant city living. The decor is welcoming and will create a pleasant atmosphere. Kitchen provides everything you need to prepare meals! Enjoy the sandy shores of Lake Michigan. Our convenient location offers access to public transportation, grocery stores, a variety of dining options!

Guest favorite

Rental unit in Chicago

4.85 out of 5 average rating, 33 reviews

Downtown Penthouse Lake Views #1|Gym, Parking+Pool

Feel at Home, Unwind, and Enjoy the amenities you deserve at our 2-Story Penthouse with Million $ Views. Guests love staying with us because: -Central location near Grant Park, Soldier Field, Art Institute, & Museums! -1 Free parking pass -FAST WIFI -En-suite Laundry -The Lake & Park are 2 blocks away -2 KING beds -Private Rooftop Deck w/ stunning views -Amenity Floor (Gym, Pool, Lounge, Doggy Park) -1 block from Red "L" subway This is rated the top 5 Airbnbs in Chicago.

Guest favorite

Rental unit in Chicago

5 out of 5 average rating, 9 reviews

Lux Skyhouse West Loop w/Parking

Stunning, Floor to Ceiling Panoramic Skyline Views from this Spacious 3-Bedroom, 2.5 Bath Apartment in the Sky! Located in Chicago's most exciting neighborhoods: Downtown/West Loop/Fulton Market District, this High-End Apt is on Restaurant Row (all of Chicago's best restaurants and bars, such as Girl & The Goat, Au Cheval, Sawada Coffee, etc.) and just steps from the Tourist/Business Attractions (near Willis Tower). Walk to Whole Foods. Garage Parking included!

Guest favorite

Rental unit in Chicago

4.93 out of 5 average rating, 70 reviews

Luxe Suite + Spa House! Key West Vibes 4-Seasons

New for July 2024! This Luxe 1BR + Den suite added an expanded deck & supersized the patio leading to the spa house. It's an indoor & outdoor oasis with lush landscape year round! Amenities: -Uber-fast Wifi streaming, -Hot-tub house - 75" hi-def 4k tv movie nights on the oversized plush sectional - Comfy queen bed with 15" hybrid mattress - The touristy 606 Trail access 100ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Superhost

Rental unit in Chicago

4.73 out of 5 average rating, 15 reviews

Cloud9|@Lincoln Park | Floor 18 View |The Pine

Welcome to The Pine! Guests must pass screening with ID. A $1000 USD security deposit on major credit cards is required as per House Rules. Spanning 1,100ft²/102m², this apartment is located steps from Lincoln Park, one of the best neighborhoods in Chicago. It's within an easy five-minute walk from sophisticated shopping experiences and the best restaurants and bars. You can find more about the neighborhood at the end of the photo gallery.

Guest favorite

Guesthouse in Merrillville

4.9 out of 5 average rating, 63 reviews

Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

Romantic Getaway for Couples This stylish and beautifully designed private guesthouse/in-law suite with a private entrance is the perfect escape for couples seeking relaxation. Indulge in the comfort of your own private jacuzzi, sauna, pool, and gym, or unwind by the cozy, indoor fireplace. Our thoughtfully designed space offers a home-away-from-home feeling with luxury touches and VIP accommodations that make every moment special.

Guest favorite

Home in Bensenville

5 out of 5 average rating, 15 reviews

New! Arcade+Sauna+Slots+Karaoke+more by O’Hare

Welcome to Bensenville Hidden Haven: Your Ideal Chicago Getaway! Conveniently near O'Hare Airport and minutes from River Forest and White Pines Golf Clubs, our retreat offers relaxation and fun. Enjoy the indoor heated pool, sauna, steam shower, arcade room, massage chairs, slot machines, and karaoke. Located in a peaceful neighborhood with a large park nearby, it's perfect for the whole family. We look forward to welcoming you!

Guest favorite

Condo in Oak Lawn

5 out of 5 average rating, 7 reviews

1flr Spacious-3Bedrooms/2 Bath w Garage Parking

Very Comfortable, 1st flr- Big Condo. Great Location. King size, Queen, 2twin beds, 1.5 bath. 3 T.Vs, Wifi. Garage parking. Midway Airport, Metra Train, easy access to Expressways I90/94 to downtown 20mins, Toll Road I-294. Walk to Walgreens, Jewel, Target, Andy’s Custard, Portillo's Rest., Amazon Fresh, Christ/Children’s, OSF Hospital. No pets, No smoking. If guests can't verify Identity I will decline reservation.