Vacation rentals with a pool in Tinley Park

4.9 out of 5 average rating, 529 reviews

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.

Apartment in Uptown

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”

4.94 out of 5 average rating, 78 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

Unique Spanish style Home (w/inground pool)

Experience a mix of old and new at this recently renovated Spanish style villa. Casa Dra’eh – less than an hour from Chicago! Staying for business or leisure, this stylish retreat offers the perfect blend of sophistication and comfort. Relax on the private rooftop balcony overlooking the backyard , featuring a pool and veranda ideal for dining. Cook in the chef’s kitchen or unwind in modern Spanish decor. With Chicago just a short drive away, enjoy the best of both worlds. Book your stay today!

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.

Apartment in Logan Square

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, 114 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.

Guest suite in Saint Charles

A spacious bedroom features a queen bed dressed in crisp white linens, accompanied by decorative pillows. Soft lighting is provided by a bedside lamp, while an accent rug adds warmth to the wood floor. A built-in shelf displays various decorative items.

5 out of 5 average rating, 293 reviews

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed with mattress topper, studio area includes Smart TV, water station, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

4.97 out of 5 average rating, 117 reviews

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

4.95 out of 5 average rating, 203 reviews

A private cottage is surrounded by lush greenery and features a wooden deck adorned with several blue planters. Steps lead up to the entrance, which is framed by large windows allowing natural light to fill the interior.

Guesthouse in Valparaiso

Private Cottage in Gated Nudist Community

We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is mandatory. Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area . The cottage is sanitized after every rental.

Apartment in Near North Side

A spacious bedroom features large floor-to-ceiling windows, allowing natural light to fill the room. A large bed with neutral bedding is complemented by a contemporary desk and chair setup, which is arranged near a wood-framed lamp. A subtle area rug lies beneath the bed.

4.9 out of 5 average rating, 101 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.

4.89 out of 5 average rating, 783 reviews

An aerial view captures the Pool Barn alongside a spacious swimming pool surrounded by multiple loungers. Lush greenery and tall trees frame the scene, creating a serene outdoor environment. A camper is parked nearby, complementing the recreational setting of the backyard.

Guesthouse in Porter

'Pool Barn' w/Games & Hot Tub near Indiana Dunes

The Pool Barn offers a great location & unique experience. 1 hour from Chicago & less than 10 minutes from large sand beaches & hiking trails of Indiana Dunes National Park & Indiana Dunes State Park. pool, hot tub, grill, firepit, playground, & we are on hike/bike trail. Inside is ping pong, air hockey, darts, popashot, foosball, board games, large smart tv, 6 beds, couch, & full kitchen. *pool table is currently broken due to guests attempting attempting to move it*

4.93 out of 5 average rating, 138 reviews

A serene pool area features a heated in-ground pool surrounded by lush greenery. Lounge chairs with red umbrellas provide shaded seating. Colorful flowers and tropical plants enhance the peaceful outdoor setting, creating an inviting place for relaxation.

Home in Miller

Bayless Dune Lodge at West Beach - Indiana Dunes!

Bayless Dune Lodge at West Beach is a gorgeous, Lodge-themed home in Miller Beach, Indiana, a scenic community surrounded by the Indiana Dunes National Park! A short walk to one of the finest white sand beaches on Lake Michigan, the Lodge sits on nearly half an acre of land nestled into the "Bayless Dunes Nature Preserve." The property boasts a heated, in-ground swimming pool, pool-side lounge area, two outdoor dining areas, two spa-quality bathrooms and more!

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!

Apartment in Logan Square

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, 104 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!

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Popular amenities for Tinley Park rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 11 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 stars6 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.

4.98 out of 5 average rating, 44 reviews

A private heated pool is surrounded by a spacious wooden deck, furnished with lounge chairs and shaded umbrellas. A dining area with multiple tables sits nearby, covered by a clear blue sky and lush green trees, creating an inviting outdoor relaxation space.

Home in Chesterton

Pool House near the Indiana Dunes

DanaRating, 5 stars3 weeks ago

This was a wonderful Airbnb. It was very clean and the decor was lovely. It was a short drive to Indiana Dunes State Park and restaurants in the area. Very convenient. We really enjoyed the heated pool and the dog friendly atmosphere. My dog loved the yard. Would 100% stay again if in the area.

Superhost

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

5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars1 month 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!

4.92 out of 5 average rating, 52 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

AmyRating, 5 stars3 days ago

Really great place to stay, super responsive host! The pool was pretty great and so was the hot tub! Great location too, lots of stores, restaurants around, and parks like the Busse Woods (it’s huge and lots of walking paths)!

Superhost

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 Miller

4.83 out of 5 average rating, 36 reviews

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

Superhost

A cozy loft area features exposed brick walls and wooden beams. A compact sleeping space includes a spacious bed covered in neutral bedding. Two white chairs and a small side table are positioned for seating, with a window allowing natural light to enter.

Home in Lincoln Park

4.88 out of 5 average rating, 56 reviews

Luxury Loft with Private Pool and Movie Theater

RyanRating, 5 stars1 week ago

Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!

4.93 out of 5 average rating, 28 reviews

A spacious backyard is illuminated by soft evening light, showcasing a lush green lawn framed by well-maintained gardens. Multiple seating areas are visible, including a hammock, lounge chairs, and patio furniture. A large tree offers shade, while a pool is partially seen beyond the greenery.

Home in Schaumburg

Schaumburg Oasis:Private Pool & Enchanted Garden

AshleaRating, 5 stars1 day ago

Beautiful Airbnb. Had everything we needed and more. Appreciated the special touches. Host tried to think of everything a guest might need. The beds were VERY comfortable, all of them. The place was clean and the backyard is amazing. We had a great time with family and spent a lot of time in the backyard. Would stay again.

5 out of 5 average rating, 54 reviews

Home in Crown Point

Little Pink House Downtown

ErikaRating, 5 stars8 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.

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Condo rentals with a pool

4.92 out of 5 average rating, 63 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,

ChidoRating, 5 stars3 months ago

I really loved the place—it was cozy, soundproof, and felt just like home. It had a warm, inviting atmosphere and a great sense of comfort. Plus, the neighborhood felt very safe, which made our stay even better.

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, 98 reviews

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

PhillipRating, 5 stars1 month ago

Great Stay - Nice unit and facility. Michelle was very responsive and helpful during my stay. Would stay in one of her properties again when I’m back in town.

4.95 out of 5 average rating, 108 reviews

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

EricaRating, 5 stars2 days ago

We loved our stay especially the appreciating the air conditioner, the large bedrooms, coffee maker, having separate bathrooms, and the outdoor pool was great. Very friendly building. Great location -- thank you so much!!

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 The Loop

4.42 out of 5 average rating, 12 reviews

voco: Balcony & City View

AmitRating, 5 stars3 weeks ago

gorgeous views and very nice condominium. great balcony and very safe. The elevators were super fast. Even though the actual location is different than the one mentioned in listing, it still wasn't disappointing. There is enough space for a small family or a couple.

A cozy living area is highlighted by a wood-burning fireplace, where a warm fire flickers. A sleek coffee table sits in front of a comfortable sectional sofa, complemented by a textured area rug. Two glasses of wine rest atop the table, adding a touch of relaxation.

Condo in Lombard

4.84 out of 5 average rating, 56 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

LelandRating, 5 stars5 months ago

Briana was responsive before, during and immediately after our stay, always seeking to ensure our comfort and satisfaction. We would have no reservations about staying with them again if they have an opening during a future visit to the area.

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 Magnificent Mile

4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars25 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 stars3 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.