Vacation rentals with a pool in North Side

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Top-rated rentals with a pool in North Side

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Guest favorite

Apartment in Chicago

4.9 out of 5 average rating, 548 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”

Top guest favorite

Apartment in Chicago

4.97 out of 5 average rating, 31 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 favorite

Apartment in Chicago

4.9 out of 5 average rating, 106 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.

Superhost

Apartment in Chicago

4.85 out of 5 average rating, 20 reviews

Luxury Designer Penthouse NW | 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!

Top guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 84 reviews

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

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Central location near Grant Park, Art Institute, The Bean, Soldier Field, & 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

Top guest favorite

Apartment in Chicago

4.98 out of 5 average rating, 131 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

Apartment in Chicago

4.64 out of 5 average rating, 28 reviews

Level ◆ Brand New Luxe Studio

Suite at Level Grand River North are 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. We are proud to announce that the cleanliness of our suites have secured Level the GBAC STAR™ facility accreditation. A separate additional destination amenity fee totaling $22.30 will be added daily. The fee is a separate charge that will be collected at check in.

Superhost

Apartment in Chicago

4.82 out of 5 average rating, 274 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 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!

Superhost

Apartment in Lombard

4.82 out of 5 average rating, 50 reviews

Balcony, Pond View, Washer Dryer, Non Smoking

Welcome to our cozy retreat! Fully furnished for affordability and convenience, our prime location near Downers Grove, Wheaton, Oakbrook, and Downtown Chicago ensures the perfect base for your stay. Enjoy free parking, washer-dryer, dishwasher, and amenities like linens, dishes, cookware, cable, wireless internet, queen-size beds, smart TV, and Hulu access. Little touches make guests feel truly at home, creating a delightful and memorable stay, whether for business or leisure.

Guest favorite

Home in Chicago

4.84 out of 5 average rating, 64 reviews

Luxury Loft with Private Pool and Movie Theater

Have fun with the whole family at this stylish home in Lakeview. Near to Fullerton Beach, Lincoln Park Zoo, Diversey Harbor, Wrigley Field, restaurants and nightlife. Perfect for families, travel teams, bachelor and bachelorette groups. Or stay in and enjoy the luxury loft with private access to the pool (open in the summer months) and hot tub and fire pit (open in the winter months) between 8am and 10pm. One compact car parking spot in secure garage included with listing.

Superhost

Apartment in Chicago

4.59 out of 5 average rating, 107 reviews

Sentral 1BR Premium 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.

Superhost

Apartment in Chicago

4.7 out of 5 average rating, 44 reviews

Level Studio | Fulton Market

Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern studio, one, two, and three-bedroom luxury furnished apartments. 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.