Vacation rentals with a pool in Cook County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cook County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

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 Chicago

4.9 out of 5 average rating, 536 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

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

4.94 out of 5 average rating, 80 reviews

Relaxing 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!

Guest favorite

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.

Apartment in Chicago

4.89 out of 5 average rating, 101 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.

Top guest favorite

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

4.96 out of 5 average rating, 217 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.

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.

Apartment in Chicago

4.97 out of 5 average rating, 119 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 favorite

A spacious living area features a large sectional sofa set around a modern coffee table with a textured surface. Natural light floods in through large windows, illuminating a neutral color palette. Decorative plants and stylish furniture pieces enhance the contemporary design.

Apartment in Chicago

4.88 out of 5 average rating, 58 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

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

4.98 out of 5 average rating, 99 reviews

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.

Superhost

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.

Apartment in Chicago

4.72 out of 5 average rating, 162 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

Guest favorite

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 Gary

4.94 out of 5 average rating, 142 reviews

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!

Top guest favorite

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

4.97 out of 5 average rating, 113 reviews

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!

Guest favorite

An inviting above-ground pool is surrounded by a wooden deck and protective railing. A ladder leads into the water, and a large white inflatable float is positioned nearby. The area is complemented by green grass and trees in the background, creating a tranquil outdoor setting.

Guesthouse in Merrillville

4.91 out of 5 average rating, 117 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.

Guest favorite

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.

Apartment in Chicago

4.9 out of 5 average rating, 106 reviews

50th Floor Mag Mile Studio

The Penthouses at Grand Plaza PH#12: Towering 50 stories above Downtown Chicago, this luxury unit features floor-to-ceiling windows and breathtaking skyline views. Enjoy sunsets, unmatched location, and true urban living. Walk Score of 100 with a grocery store in the building. Amenities include a fitness center, outdoor pool, kitchens, and business center. The city is at your feet—experience Chicago in style.