Holiday rentals with a pool in Chicago River

Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool

Feel at Home, Unwind, and Enjoy the amenities you deserve at our 3bed 2-Story Penthouse. Most homes don’t provide professional service along with “local vibes.” 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 + 1 Queen bed ✅Private Rooftop Deck w/ stunning views ✅Amenity Floor (Gym, Pool, Lounge, Doggy Park) ✅1 block from Red "L" subway

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!

High Rise Unit w/ Parking, Gym, Pool & Game Room

Welcome to your spacious urban getaway in the heart of Chicago’s Printer’s Row neighborhood! This modern 3-bedroom, 3-bathroom unit is located in a stunning high-rise building, offering sweeping city views and access to premium amenities—perfect for families, business travelers, or groups looking to explore the best of downtown. Whether you're here for work or play, this retreat offers the perfect blend of style, comfort, and location. Book your stay today and experience Chicago like a local!

2BD Central Downtown Location! Spacious & Cozy

Explore Chicago from its heart & stay at the best downtown location, right by the Magnificent Mile, Chicago River, and walk to all main tourist attractions - Museums, Millenium Park, Navy Pier and more. Building offers 24/7 security onsite, indoor pool, gym, and outdoor patio with grills. Apartment unit comfortably accommodates 4 guests via 2 bedrooms with queen beds & memory foam mattresses, kitchen is equipment with everything needed. Great deal for visiting with family or a business trip!

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.

Level ◆ Brand New Luxe One Bedroom

Suite at Level Grand River North is the personal sanctuary that you’ve been looking for! Your modern suite is more than luxurious and spacious; they are meticulously cleaned with the highest standards for your peace of mind. A separate fee totaling $22.32 per night will be added upon arrival. This fee is separate from Airbnb and will be collected at check in. This would include a pet fee of $20 per night per pet as well as a parking charge of $68.30 per night should you choose to utilize.

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.

Sentral 1 Bedroom 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

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!