Vacation rentals with a pool in South Side

Find and book unique homes with a pool on Airbnb

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, 494 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

4.96 out of 5 average rating, 27 reviews

The Downtown Oasis (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

Guesthouse in Merrillville

4.9 out of 5 average rating, 63 reviews

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

This Stylish, Beautiful Private Guesthouse/ In- Law Suite with private entrance is the perfect getaway for couples. Enjoy this spacious townhouse with your own private jacuzzi, sauna, pool and gym. Relax by the indoor huge fireplace. This Airbnb is designed to give you your own home feeling with the extra vip accommodations for a total relaxation experience. If you enjoy your privacy and like to relax in luxury, then feel free to book with us. Your vacation home away from home is waiting.

Guest favorite

Guest suite in Bartlett

4.96 out of 5 average rating, 207 reviews

Cozy & Spacious Suite in Quiet Neighborhood

This 950 sq. ft. guest suite is in a quiet, upscale neighborhood, less than 1/2 mile from Bartlett Hills Golf Club and a mile from Metra Train Station. 50 min. train ride to downtown Chicago. 10 min. walk to downtown Bartlett. A private entrance makes check-in easy and convenient, while offering privacy during your stay. Full kitchen, accessible bathroom, WIFI, and cable provided. Washer/Dryer available upon request. Pool is for registered guests only. Owners on site to assist if needed.

Guest favorite

Rental unit in Chicago

4.97 out of 5 average rating, 92 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

4.82 out of 5 average rating, 28 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

Guest suite in Homewood

4.97 out of 5 average rating, 72 reviews

Cozy Fun Game Room Suite & Hot Tub w/Yurt add on

Cozy intimate family/friendly fun space that includes: Large outdoor heated Jacuzzi opened year round 27' above ground heated pool (seasonally) until Oct. Pool table Air hockey table Arcade machine with 12 games Life Size Connect 4 Board games Basketball machine Indoor Electric fire place Queen size bed Queen Sofa pull out sleeper Gazebo with two twin beds (seasonal) Fresh Eggs with chickens Spring/Summer/Fall Gas Grill-propane included Romantic Robe for 2 (ask to include)

Guest favorite

Home in West Chicago

5 out of 5 average rating, 11 reviews

Cozy & Specious Private Basement Apartment

Nice and clean place to stay in West Chicago and call it your home during your personal or business trip. You'll enjoy the accessibility to all nearby restaurants, grocery stores and shopping mall. Close to major highways. You’ve your own private entrance & space. No SHARING!! Why Share if you can have your own private space for a reasonable rate. It is our priority to create an experience for you that is cozy, comfortable, and relaxing! Hope to see you soon!

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!

Superhost

Rental unit in Rosemont

5 out of 5 average rating, 3 reviews

Near Chicago OHare Airport | Free Breakfast

Welcome to our Residence Inn Chicago O'hare Hotel, located near the Chicago OHare Airport, winner of the 2021 Trip Advisor Travelers Choice Hotel. Guests can enjoy complimentary shuttle service to and from the airport. Start your day with our complimentary hot breakfast buffet served daily or a quick workout in the fitness center. Attractions are near the Residence Inn Chicago OHare and we are also within walking distance of corporate headquarters.

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

Home in Bensenville

5 out of 5 average rating, 14 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!