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Near South Side Vacation Homes and Villas with Pools

Find Luxury Places to Stay Near Near South Side with a Swimming Pool. Find pool in Near South Side, Chicago.

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Only stays with pool access are shown on this page

13 stays

a living room with a green couch and a table at Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop in Chicago

From US $427

Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop Pool available

8.5 (81 Reviews) Apartment

Apartments • Private parking • Outdoor swimming pool

Chicago Loop • In Near South Side · 2.8km to center

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a pool at a hotel with people in the water at The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile in Chicago

From US $449

The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile Pool available

9.2 (59 Reviews) Apartment

Apartments • Private parking • Outdoor swimming pool

Chicago Near North Side • In Near South Side · 4.4km to center

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a living room with a couch and a table at Fulbrix Bright Designer Apartments with West Loop Views in Chicago

From US $468

Fulbrix Bright Designer Apartments with West Loop Views Pool available

9.5 (50 Reviews) Apartment

Apartments • Private parking • Outdoor swimming pool

Chicago Near West Side • In Near South Side · 4.5km to center

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a living room with a blue couch and a kitchen at Aurelien Spacious Apartments in the Heart of Gold Coast in Chicago

From US $446

Aurelien Spacious Apartments in the Heart of Gold Coast Pool available

8.9 (58 Reviews) Apartment

Apartments • Private parking • Outdoor swimming pool

Chicago Near North Side • In Near South Side · 4.5km to center

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a living room with a view of the ocean at Lux Apts with Lake Views and Top Amenities in Chicago

From US $564

Lux Apts with Lake Views and Top Amenities Pool available

9.9 (26 Reviews) Apartment

Apartments • Private parking • Indoor swimming pool

Chicago Loop • In Near South Side · 1.4km to center

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a living room with a couch and two chairs at K2 Sky High Apartments with Stunning Chicago Views in West Loop in Chicago

From US $418

K2 Sky High Apartments with Stunning Chicago Views in West Loop Pool available

9.5 (24 Reviews) Apartment

Apartments • Private parking • Outdoor swimming pool

Chicago West Town • In Near South Side · 4.1km to center

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a bedroom with a bed and a large window at Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop in Chicago

From US $348

Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop Pool available

8.4 (51 Reviews) Apartment

Apartments • Private parking • Indoor swimming pool

Chicago Loop • In Near South Side · 3.4km to center

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a bedroom with a large bed and large windows at Premier Penthouses and Apartment with Captivating Views of Millennium Park in Chicago

From US $651

Premier Penthouses and Apartment with Captivating Views of Millennium Park Pool available

9.4 (8 Reviews) Apartment

Apartments • Private parking • Indoor swimming pool

Chicago Loop • In Near South Side · 3.1km to center

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a living room with a couch and chairs and windows at Jeffjack Heated Pool Penthouse in Chicago's West Loop in Chicago

From US $482

Jeffjack Heated Pool Penthouse in Chicago's West Loop Pool available

8.0 (9 Reviews) Apartment

The entire place is yours • 1000 m² size • Private parking

Chicago Near West Side • In Near South Side · 3.0km to center

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a white bed with white sheets and pillows at South Loop Rooftop With In and Out Parking 3 in Chicago

From US $226

South Loop Rooftop With In and Out Parking 3 Pool available

9.2 (5 Reviews) Apartment

The entire place is yours • 82 m² size • Swimming pool

Chicago Loop • In Near South Side · 2.1km to center

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a living room with a couch and a table at South Loop Rooftop With In and Out Parking 2 in Chicago

From US $153

South Loop Rooftop With In and Out Parking 2 Pool available

9.7 (3 Reviews) Apartment

The entire place is yours • 82 m² size • Swimming pool

Chicago Loop • In Near South Side · 2.1km to center

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a living room with a black couch and a kitchen at Sophisticated 3BR Suite - New Modern and Luxurious in Chicago

From US $219

Sophisticated 3BR Suite - New Modern and Luxurious Pool available

7.7 (7 Reviews) Apartment

The entire place is yours • 139 m² size • Outdoor swimming pool

Chicago Near West Side • In Near South Side · 4.5km to center

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a white bathroom with a sink and a mirror at South Loop Rooftop With In & Out Parking 1 in Chicago

From US $146

South Loop Rooftop With In & Out Parking 1 Pool available

8.5 (4 Reviews) Apartment

The entire place is yours • 82 m² size • Swimming pool

Chicago Loop • In Near South Side · 2.1km to center

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See More Vacation Rentals with Pools in Near South Side

About Near South Side Vacation Rentals with Pools on NearbyHoliday

Looking for pool in Near South Side? Compare top options in Chicago.

Find Near South Side Rentals, Hotels, and Resorts with Swimming Pools.

Discover 13 places to stay, including hotel waterparks, vacation homes, resorts, private villas, and condos in Near South Side that feature indoor, outdoor, or private pools.

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Frequently Asked Questions About Vacation Rentals With Pools in Near South Side

There are a lot of vacation rentals with pools in Near South Side. If you plan on staying in the Near South Side area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals with Pools in Near South Side:

We have many family-friendly luxury rentals in Near South Side. The top family-friendly holiday rentals in Near South Side are:

See all family-friendly luxury rentals in Near South Side on NearbyHoliday

Many vacation rentals with pools on NearbyHoliday have a heated pool. These are some popular rentals in Near South Side that you may consider:

See all stays with pools in Near South Side on NearbyHoliday