Vacation rentals with a pool in West Loop, Chicago

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Top-rated rentals with a pool in West Loop, Chicago

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Guest favourite

Rental unit in Uptown

4.89 out of 5 average rating, 485 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 favourite

Rental unit in Near South Side

4.87 out of 5 average rating, 187 reviews

Skyline Serenity: Sauna, Hot Tub, Peloton, Views

**Second Unit Available (2B | 2B)** http://airbnb.com/h/wentyone382907 Discover the ultimate urban getaway at Skyline Serenity in Chicago's vibrant South Loop! This luxurious apartment offers a private sauna, hot tub, a Peloton bike, and panoramic skyline views. Enjoy top-notch amenities, including high-speed Wi-Fi, a fully equipped kitchen, and family-friendly comforts, perfect for both relaxed and active travelers. Across from McCormick Place and Wintrust with easy access to transportation

Superhost

Rental unit in The Loop

4.82 out of 5 average rating, 208 reviews

Spectacular Corner 2BR Penthouse in the Loop | Roo

This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, 13 foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of downtown Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed, ideal for families, business travelers, or couples traveling together. The building has a pool and an amazing outdoor rooftop terrace with 360 degree vi

Guest favourite

Rental unit in Near South Side

4.91 out of 5 average rating, 69 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.

Guest favourite

Rental unit in West Loop

5 out of 5 average rating, 17 reviews

Skyline Oasis: City & Lake Views

Welcome to our breathtaking one bedroom penthouse-like corner apartment! With stunning city, lake, and river views, this high-floor oasis offers an unforgettable stay. Stylish and luxurious designer furniture, spacious balcony, full kitchen stainless steel appliances, work area, fast wifi, immaculate cleanliness, rain shower, king-size bed, TVs, fan, AC. Building amenities: pool, jacuzzi, fitness room, plus more. Cleanliness is our top priority, ensuring an immaculate space for your stay. Enjoy!

Guest favourite

Rental unit in Logan Square

4.97 out of 5 average rating, 89 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 West Loop

5 out of 5 average rating, 3 reviews

Million Dollar Views! Luxury Downtown Skyhouse!

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 (regular sized cars only).

Superhost

Rental unit in East Rogers Park

4.83 out of 5 average rating, 23 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 favourite

Rental unit in Near North Side

4.94 out of 5 average rating, 68 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.

Superhost

Serviced apartment in Old Town

4.86 out of 5 average rating, 136 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 executive suite is the whole package with all the comforts of home and thoroughly cleaned to the highest standards. The cleanliness of our suites have rightfully earned us the GBAC STAR™ facility accreditation. A separate additional destination amenity fee totaling $19.96 will be added daily. The fee is a separate charge that will be collected at check in.

Guest favourite

Rental unit in Logan Square

4.93 out of 5 average rating, 57 reviews

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

New for July 2024! 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!

Guest favourite

Rental unit in The Loop

4.94 out of 5 average rating, 51 reviews

Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central location near Grant Park, Art Institute, & more! -1 Free parking pass -FAST WIFI -En-suite Laundry -The Lake & Park are only 2 blocks away -KING beds -Private Rooftop Deck w/ stunning views -Amenity Floor (Gym, Pool, Lounge, Doggy Park) -1 block from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums