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, 525 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”

An outdoor pool is featured with a modern design, surrounded by grey tile and lounge chairs. Clear blue water reflects the sky above. Urban buildings rise in the background, providing a cityscape view from the pool area.

4.9 out of 5 average rating, 96 reviews

The Executive's Escape (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.

4.96 out of 5 average rating, 213 reviews

A serene outdoor area features a curved pool surrounded by a wooden deck and lush greenery. Potted flowers add color to the scene, while a shaded umbrella provides seating comfort. Tall trees offer natural privacy, enhancing the tranquil ambiance of the space.

Guest suite in Bartlett

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.

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, 109 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.

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.

4.82 out of 5 average rating, 28 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.

4.98 out of 5 average rating, 92 reviews

An outdoor seating area features a cushioned sectional sofa and a wooden coffee table, overlooking a heated in-ground pool. Lounge chairs are positioned nearby, surrounded by trees, with a view of Lake Michigan in the background.

Guest suite in Gary

Beachfront- Lake Michigan- 2bd/2bath -Heated Pool

Lake Michigan - Beachfront w/heated in-ground Pool - Indiana Dunes National Park - Private Basement Guest Suite- 2 Bedroom/2 Bathrooms-Newly Renovated and Beautifully Decorated- Heated In ground Pool* Below Deck at Waters Edge has everything you need to have a comfy and relaxing stay with your family or friends. Hiking, Beaches, X-Country Skiing and so much more! Less than an hours drive to Chicago. *Heated Pool Open from Mid-May to Mid Oct. Pool closed until Mid-May 2024.

A spacious living area features large floor-to-ceiling windows that frame city views. A comfortable bed is positioned beside a stylish nightstand and lamp. A modern desk is arranged with office supplies, and a soft area rug adds warmth to the space.

4.9 out of 5 average rating, 99 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.

An indoor pool area is showcased, featuring sleek design elements and large windows allowing natural light to fill the space. Comfortable lounge chairs are positioned nearby, offering a serene view of the outdoors. Water flows elegantly along the pool’s edge, enhancing the tranquil atmosphere.

4.73 out of 5 average rating, 159 reviews

Sentral Studio Apt in South Loop Chicago

Experience a lifestyle where everything you need is right at your fingertips in the vibrant heart of Downtown Chicago. Explore the area effortlessly: ✔ Breathtaking views of Lake Michigan and the Chicago skyline ✔ Close to major business hubs and the Loop District ✔ Enjoy a walk along the scenic Lakefront Trail ✔ A lively array of world-class museums, gourmet restaurants, and iconic architecture ✔ Quick access to Millennium Park, the Art Institute of Chicago, and Grant Park

4.97 out of 5 average rating, 109 reviews

An above-ground pool is set amidst a lush green lawn, surrounded by trees. The deck area features steps leading up to the pool's edge, where colorful pool floats are visible. The peaceful outdoor space invites relaxation and enjoyment.

Yurt in Homewood

Glamping Yurt&RV-Game Room-Pool-Sauna-Hotub Court

Glamping Experience to the NEXT LEVEL! Opened April - Nov. Contact during off season. Mini Resort Includes: RV w/bathroom - 2 beds & sofa sleeper 20' Safari Yurt - 4 beds w/sofa sleeper Game Room w/bathroom 1 bed & sofa sleeper Gazebo w/2 twin beds Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court Breakfast included is 1 dozen fresh eggs!

An outdoor space features a white staircase leading to a second-level deck. Below, a lounge area includes a sectional couch and a grill, surrounded by lush greenery. Sunlight brightens the scene, highlighting a blend of natural and modern elements in the garden setting.

4.88 out of 5 average rating, 100 reviews

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

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!

Guesthouse in Merrillville

A private jacuzzi is situated under a shaded pergola, with warm ambient lights enhancing the serene atmosphere. A view of an outdoor dining area with a table and chairs is visible through a nearby opening, framed by lush greenery and a tranquil landscape.

4.92 out of 5 average rating, 108 reviews

Romantic Getaway Guesthouse/ Jacuzzi/Sauna/Pool

Romantic Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse/in-law suite offers ultimate relaxation with a private entrance, spa-like jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

4.95 out of 5 average rating, 106 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Urban-Luxe experience at the Bliss of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view of downtown Evanston. Resort-like amenities with fitness center, outdoor pool, free parking in indoor GAR, biz ctr, and much more. 2 bedrooms, 2 full baths, 2 roll-out beds welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown.

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Popular amenities for South Side rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 10 reviews

A spacious living room is featured with a cream-colored sectional couch facing a mounted flat-screen TV. Natural light pours in through large windows adorned with blinds. A stone accent wall adds texture, complemented by two decorative pieces and a ceiling fan.

Home in Munster

Munster hide away

ChristopherRating, 5 stars5 months ago

Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

5 out of 5 average rating, 3 reviews

A sunny backyard features a round in-ground pool surrounded by lush green grass and vibrant flower pots. The house showcases a two-story design with a balcony and large windows, providing views of the serene outdoor space and nearby landscaping.

Home in Des Plaines

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars2 weeks ago

Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!

4.94 out of 5 average rating, 50 reviews

A spacious basement game area features a classic pool table with a vibrant green felt surface, complemented by cues and an arranged set of colored balls. Nearby, a seating area with leather couches and an arcade machine is visible along the wooden-paneled wall.

Home in Bloomingdale

Now Open: Heated Pool with Entire House

TaraRating, 5 stars3 weeks ago

Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.

4.83 out of 5 average rating, 36 reviews

An above-ground pool is visible in the backyard, surrounded by greenery. Colorful floating loungers are placed in the water. A spacious deck with seating overlooks the pool area, while a grassy lawn provides additional space for outdoor activities.

Home in Gary

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars6 months ago

This home was super cozy for my big family. Everything was clean, comfortable, and the way it is set up makes you feel right at home. This home had everything we needed. TV’s, kitchen items, recommendations, and even fun family games and activities to do. Every time I visit the area I’ll be checking to see if it’s available. 10/10

4.92 out of 5 average rating, 24 reviews

A vibrant backyard is depicted, featuring a lush green lawn with a variety of plants and flowers. A stone pathway leads towards a fire pit area surrounded by seating. Sunlight filters through trees, creating a warm and inviting atmosphere, complemented by colorful garden decor.

Home in Schaumburg

Schaumburg Oasis:Private Pool & Enchanted Garden

BrandonRating, 5 stars1 week ago

Marzena was an awesome host, she responded super quickly and helped with anything we needed. the pictures do not do the backyard justice, it is so beautiful and fun. I will definitely stay again.

5 out of 5 average rating, 54 reviews

Home in Crown Point

Little Pink House Downtown

ErikaRating, 5 stars7 months ago

The Little Pink House greatly exceeded our expectations. Suzanna was a wonderful host who went above and beyond to make sure our stay went smoothly. We were in town for a wedding and had an infant with us and the provided amenities made it feel like home. We would absolutely love to stay again if we get the chance.

4.94 out of 5 average rating, 77 reviews

A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. An island with bar seating is positioned in the foreground, while a spacious archway leads to an elegantly designed hallway featuring artwork and natural light.

Home in Plainfield

Beautiful Spanish style Home (w/inground pool)

BethanyRating, 5 stars1 month ago

Stayed here the night before my wedding with my siblings who stayed the night of the wedding. We hosted our getting ready portion here for the morning of the wedding and Olinka and Daniel were gracious enough to allow us to stay in their beautiful home. Made for gorgeous pictures and a comfortable stay both nights. Thank you!!

A spacious living area is highlighted by two navy blue sofas and a modern coffee table, with a wood piano situated against the wall. Large windows allow natural light to flow in, illuminating the soft carpeting and neutral wall colors.

Home in Glenwood

4.81 out of 5 average rating, 59 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

TiffanyRating, 5 stars4 weeks ago

I really enjoyed my stay. The owner was very helpful and quick to respond when I needed help. I definitely will keep this Airbnb in mind!

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Condo rentals with a pool

4.92 out of 5 average rating, 62 reviews

A modern living area features a blue sofa accented by colorful pillows. A flat-screen TV is positioned on a white media console. A round coffee table sits on a textured area rug, with plants adding a touch of greenery. The open kitchen is visible, showcasing light wood cabinetry.

Condo in Downers Grove

Upscale, Washer Dryer, Smoke Free, Pet Free,

NormaRating, 5 stars5 months ago

My husband and I stayed here over the holidays. The apartment was pretty well appointed, clean and is in a good location- centrally located for our purposes of being near family and close enough to the expressway to get to the city.

An outdoor pool area is shown, featuring a clear blue pool surrounded by lounge chairs. Trees provide a touch of greenery, while a modern glass structure offers shaded seating. Sunshine reflects off the water, creating a bright and inviting atmosphere.

4.96 out of 5 average rating, 97 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

AaronRating, 5 stars2 weeks ago

I would highly recommend Michelle's listing! The listing is spacious and perfect for a couple or small family (we had our <1 year old). Michelle is communicative, all the instructions are clear, and the location is convenient.

A serene bedroom is illuminated by soft purple lighting. A spacious bed with a polka dot blanket is centered in the room. Floor-to-ceiling glass doors reveal a view of a vibrant city skyline at night, with city lights twinkling in the background.

Condo in Chicago

4.33 out of 5 average rating, 9 reviews

voco: Balcony & City View

BrookeRating, 5 stars2 weeks ago

Our stay here worked out perfectly. The host was nice, and the location was centrally located to great shopping and restaurants. Very private and safe. The view at night was beautiful.

An outdoor pool area features a clear, blue body of water surrounded by lounge chairs. Lush greenery is placed in large planters along the perimeter, with a backdrop of modern high-rise buildings and a cloudy sky.

Condo in Chicago

4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars24 months ago

Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.

Condo in Elk Grove Village

The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.

4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars2 months ago

I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

An outdoor swimming pool is surrounded by lounge chairs, offering a relaxing space. Trees are strategically placed around the area, and large glass walls provide views to the inside. Sunlight reflects off the water, enhancing the serene setting.

4.91 out of 5 average rating, 124 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

NinaRating, 5 stars2 months ago

We had a great stay at Michelle’s “Heart of Evanston.” I loved the indoor garage parking option with easy in and out. If you have a large vehicle /SUV, maneuvering in and out of the spot may be challenging depending if the spot over is occupied. We have a mid-size SUV and had no issues. The room was easily accessed from the garage and we had no issues getting in. The place was clean and well organized. I loved that it smelled clean and also had a faint hint of bleach in the bathroom. It was a little warm in the bedrooms at night but we used the air conditioning to bring the temperature down. Town is very walkable and we enjoyed the local restaurants (Taco Diablo, Bat 17, Bennison’s bakery). We found the town to be very quiet - almost too quiet for what we expected but after our visit to Northwestern found out it was spring break for the students. Michelle was available for any questions and always replied promptly. We had a great stay and would stay again!

A cozy living area features a sectional sofa adorned with pillows and a throw pillow inscribed with 'Enjoy.' A round coffee table holds decorative items, while framed art showcases serene designs on the wall. A small dining area is visible in the background.

Condo in Lombard

4.91 out of 5 average rating, 46 reviews

Pond View, Washer Dryer, Non Smoking Community

AsgharRating, 5 stars6 months ago

Place was neat and very clean, enjoyed our stay, location was great as it was near all the malls and restaurants in Lombard and Oakbrook.