Vacation rentals with a pool in Downtown Chicago

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Top-rated rentals with a pool in Downtown Chicago

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Guest favorite

Rental unit in Chicago

4.9 out of 5 average rating, 496 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”

Superhost

Rental unit in Chicago

4.8 out of 5 average rating, 61 reviews

Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!

Welcome to Your Charming Oasis! Step into this delightful 3-BR, 1-BA retreat in a friendly neighborhood with views of a picturesque public park. Just moments from Logan Square's top restaurants and bars, this stylish gem is perfect for families and friends. Highlights: ✔ 3 Comfortable Bedrooms ✔ Fully Equipped Kitchen ✔ Fenced Backyard – BBQ, Fire pit, Games, & Movie Projector! ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Public Park (Playground, Field, & More) ✔ Street Parking 🌟 Discover More Below!

Guest favorite

Rental unit in Chicago

4.97 out of 5 average rating, 30 reviews

The Downtown Oasis (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 favorite

Rental unit in Chicago

4.97 out of 5 average rating, 95 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

Condo in Evanston

4.96 out of 5 average rating, 101 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

Guest favorite

Home in Schaumburg

4.96 out of 5 average rating, 25 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

Freshly updated house with in-ground POOL! Minutes to Woodfield mall and restaurants in Schaumburg. One of the only houses with private pool in the area. LOCATION: 35 min to downtown Chicago, 20 min to O'Hare airport, 20 min to Rosemont convention area MASTER BEDROOM extra large for primary guest(s). Unpack and stay awhile with a large walk in closet. Luxurious attached master bathroom with double sink and large walk in shower with bench. Pool is open from May until the end of September.

Superhost

Rental unit in Chicago

4.84 out of 5 average rating, 31 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 favorite

Home in Bloomingdale

4.94 out of 5 average rating, 35 reviews

Whole House with a Hot Tub!

Welcome to our spacious 4-bedroom home! Enjoy lounging in the airy living area or cooking in the fully equipped kitchen. With a master bedroom featuring a king bed and en-suite, a second bedroom with a king bed, a third with a queen, and an office space for the fourth bedroom, so there's plenty of room. Plus, unwind with a game of pool on the basement's pool table. High-speed internet keeps you connected. Book now for a spa session at our HotTub! Pool closing starting October 21st!

Superhost

Serviced apartment in Chicago

4.87 out of 5 average rating, 143 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.

Superhost

Rental unit in Chicago

4.86 out of 5 average rating, 63 reviews

Unbelievable!Gold Coast’s Finest Stay|The Jersey

Struggling to find accommodations that offer both luxury and a prime location in the heart of Chicago? Our 1133ft² stylish apartment is located in Chicago’s most prestigious neighborhood, just steps from Michigan Avenue and the city’s best dining, shopping, and attractions. It features modern design, private balconies with skyline views, and premium amenities like a rooftop pool, health club, and meditation lounges. ★ Guests rave about our unbeatable location!

Guest favorite

Rental unit in Chicago

4.98 out of 5 average rating, 40 reviews

53 Floor MagMile Penthouse Views, Balcony, Pool

This Penthouse level unit is a magnificent unique rental in Chicago. Towering 50+ Floors above the city, this Penthouse gives you the ultimate in city living. It's all about the views and the location. The city unfolds before you with Lake Michigan as a backdrop; nowhere in Chicago can you stay with views like these. Bordered by the elegance and glamour of North Michigan Avenue to the east and the artsy sophistication of the River North District to the west.

Guest favorite

Rental unit in Chicago

4.93 out of 5 average rating, 72 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!