Vacation rentals with a pool in Chicago

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”

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!

The Professional's Playground (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.

Andersonville Luxury Pool Escape

Welcome to the only chic, two-story pool house just steps from the heart of Andersonville. Enjoy a full kitchen, queen bed, spa-style bath, washer/dryer, and high-speed Wi-Fi. Outside, unwind in your private heated pool and spa in a tranquil, secure setting shared with the owner. Perfectly located near vibrant shops, dining, and a pleasant walk to the beach, this stylish retreat blends comfort, privacy, and convenience for the ideal city escape. The pool and spa are heated heated through 12/31.

Luxury Designer Penthouse West |Pool| Gold Coast

NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center of nightlife, restaurants, and shopping. Sitting 38 stories in the sky, your 3 bedroom/2 bathroom penthouse offers some of the best views in all of Chicago. The highly secure building includes elevator, rooftop pool, full gym, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

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.

Spectacular 2BR Penthouse in the Loop | Roof Deck

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 Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed. The building has a pool and an amazing outdoor rooftop terrace with 360 degree views of the skyline and lake. This is the best location in the city!

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.

Sentral Studio Apt in South Loop Chicago

Indoor/Outdoor Resort-Style Pool • Grilling Station • Four-Story Indoor Garden • Fitness Center • Demonstration Kitchen • Pet Friendly w/ Amenities • Co-Working Space w/ High-Speed WiFi • Across from Grant Park • Steps to South Loop Dining & Nightlife • Breathtaking Views of Lake Michigan & the City Skyline Sentral Michigan Ave offers upscale comfort in the heart of Chicago’s South Loop, blending premium amenities with unmatched access to parks, culture, and entertainment.

Spacious 3-Bedroom Urban Getaway

Welcome to your spacious urban getaway in Chicago’s Printer’s Row! - Modern 3-bedroom, 3-bathroom unit with floor-to-ceiling windows - Bright, open-concept living space with sleek furnishings - Fully equipped kitchen with stainless steel appliances - Rooftop pool and panoramic skyline views - Access to fitness center and lounge areas - Steps from cafes, restaurants, and iconic parks Managed by TheDreamRentals

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.

"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.