Vacation rentals with a pool in South Side

An indoor mosaic-tiled pool is surrounded by a spacious, elegantly arched ceiling. Soft lighting reflects off the water, enhancing the serene atmosphere. Wooden lounge chairs are placed along the poolside, providing a comfortable area to relax.

4.9 out of 5 average rating, 519 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”

4.86 out of 5 average rating, 7 reviews

Home in Carol Stream

Spacious 4 Bed/3.5 Bath Sleeps 8+

Just 30 minutes from downtown Chicago! You will love this gorgeous 4-bedroom home perfect for a vacation, staycation or business travel! Walking distance to the playground & walking trails, restaurants and even the local gym! Home has free parking, 3.5 baths, fully finished basement equipped with work-out room! May-Sept you can enjoy the deck, gazebo, outdoor gas grill & heated 27’ pool! Home is pet free and smoke free. Wi-Fi to enjoy your programs on the Smart TV inthrough your personal apps

4.75 out of 5 average rating, 48 reviews

A panoramic view of downtown Chicago showcases a skyline filled with modern high-rise buildings. Expansive green spaces and Millennium Park are visible in the foreground, with a large, metallic outdoor concert venue prominently featured. The image captures a clear blue sky and vibrant city life.

Condo in Chicago

2BD Central Downtown Location! Spacious & Cozy

Explore Chicago from its heart & stay at the best downtown location, right by the Magnificent Mile, Chicago River, and walk to all main tourist attractions - Museums, Millenium Park, Navy Pier and more. Building offers 24/7 security onsite, indoor pool, gym, and outdoor patio with grills. Apartment unit comfortably accommodates 4 guests via 2 bedrooms with queen beds & memory foam mattresses, kitchen is equipment with everything needed. Great deal for visiting with family or a business trip!

Top guest favorite

An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.

4.97 out of 5 average rating, 104 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.

4.96 out of 5 average rating, 113 reviews

Condo in Evanston

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Sky Terrace and resort-like amenities are just steps from Northwestern University, Loyola, and Kellogg and minutes from Chicago. Harmony of Evanston features granite countertops in the kitchens, 9 ft ceilings, and designer plank flooring. Enjoy luxury amenities such as a fully equipped fitness center, BBQ and picnic area and beautiful landscaping. In the warmer months, Guests can enjoy the Clark Street Beach & Lighthouse

4.96 out of 5 average rating, 27 reviews

An inviting backyard scene features a sparkling in-ground pool surrounded by lounge chairs and shaded by greenery. The house's exterior showcases large glass doors that open onto the patio area, providing a seamless connection between indoor and outdoor spaces.

Home in Schaumburg

Schaumburg Woodfield Pool House 4bedroom 2.5bath

Freshly updated house with in-ground POOL! Minutes to Woodfield mall and restaurants in Schaumburg. One of the only houses with private pool in the area. LOCATION: 35 min to downtown Chicago, 20 min to O'Hare airport, 20 min to Rosemont convention area MASTER BEDROOM extra large for primary guest(s). Unpack and stay awhile with a large walk in closet. Luxurious attached master bathroom with double sink and large walk in shower with bench. Pool is open from May until the end of September.

A modern living area features a cozy seating arrangement with large windows showcasing panoramic views of the Chicago skyline. The stylish bedroom is adorned with elegant decor, while a luxurious bathroom displays sleek fixtures and essential amenities for comfort.

4.88 out of 5 average rating, 200 reviews

Stunning Panoramic Chicago Views & Free Parking

Indulge in the epitome of luxury at our exceptional property with a host of amenities: 24-hour door attendant, heated parking, hot tub, modern workout and rec room, and stunning Chicago views. Situated in a secure, scenic South Loop neighborhood, our upscale abode grants swift access/steps to McCormick Place and Wintrust Arena. Discover the best of Chicago from this ideal spot, with easy public transport and airport commutes. Your remarkable experience begins in this lavish urban retreat!

An outdoor heated pool features clear blue water, surrounded by a spacious deck. Lounge chairs line the poolside, with a high-rise building visible in the background. Trees provide a touch of greenery, enhancing the inviting atmosphere.

4.86 out of 5 average rating, 147 reviews

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

You won’t need to trade luxury for location when staying with Level in Chicago’s historic Old Town neighborhood, your suite is the whole package with all the comforts of home and thoroughly cleaned to the highest standards. A separate fee totaling $22.32 per night will be added upon arrival. This fee is separate from Airbnb and will be collected at check in. This would include a pet fee of $20 per night per pet as well as a parking charge of 68.30 per night should you choose to utilize.

An indoor heated pool area features large glass windows, allowing ample natural light and views of the city. The pool is surrounded by tiled flooring and lounge chairs, with a hot tub located nearby. The space is well-designed for relaxation and enjoyment.

4.85 out of 5 average rating, 89 reviews

Quiet but in the Heart of City walk Everywhere

Exhausted from ENDLESS SCROLLING through subpar options? Sick of SETTLING FOR LESS than perfect? Our spacious 1100 sq ft penthouse is your answer, with an UNBEATABLE CENTRAL LOCATION. Revel in our OPEN LAYOUT and STUNNING VIEWS from floor-to-ceiling windows. 500 guests RAVE about our PRIME SPOT. Trust Cloud9, Chicago's FIRST AIRBNB LUX PROVIDER, for an unforgettable stay. Enjoy the PERFECT BLEND of comfort and convenience. Don't miss out – this UNIQUE 2-BED PENTHOUSE books up fast!

The exterior of a charming cottage is showcased, featuring a sleek dark grey facade. A series of stairs lead up to the entrance, flanked by a decorative black railing. Lush greenery surrounds the base, enhancing the inviting appeal of the home.

4.83 out of 5 average rating, 24 reviews

Modern unit in Bridgeport-Chicago

Make sometiny and family-friendly place 15 minutes from Downtown Chicago and 3 blocks away from the Bridgeport Art Center and the Chicago River. 5 min to the White Sox Stadium or 10 minutes ,you can enjoy the plunge pool (June - September 9:30am/9:30pm ) We’re pets friendly, there is a $100 dollar fee. NO PARTIES ARE ALLOWED!! All guests must provide dentification at the time of booking & arrival, & will be the only ones allowed on the property. We have security cameras outside.

An aerial view captures a landscaped amenity yard featuring an indoor hot tub house and multiple lounge seating areas. A mix of patio furniture in shades of blue is arranged over green grass. The outdoor space is surrounded by trees and includes access to the rear deck.

4.92 out of 5 average rating, 12 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

A rooftop pool area is surrounded by lounge chairs with vibrant orange cushions. The pool's clear water reflects the colors of a sunset, while city buildings rise majestically in the background, showcasing a blend of urban architecture against a dusk sky.