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Holiday rentals with a pool in South Side
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in South Side
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side rentals with a pool
House rentals with a pool
![](https://a0.muscache.com/im/pictures/bd2b13fb-0a93-44fe-bf7f-71b1fe45b273.jpg?im_w=720)
Home in Plainfield
4.95 out of 5 average rating, 64 reviewsLarge Spanish style Home (w/heated pool)
![](https://a0.muscache.com/im/pictures/f83b9cbc-1499-406c-b48b-ffdf4075b8ec.jpg?im_w=720)
Home in Crown Point
5 out of 5 average rating, 34 reviewsLittle Pink House Downtown
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Home in Schaumburg
4.94 out of 5 average rating, 16 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
![](https://a0.muscache.com/im/pictures/miso/Hosting-707130735558417084/original/3ba3d9d7-2310-4628-a4b2-0d24c25576c6.jpeg?im_w=720)
Home in Cedar Lake
4.86 out of 5 average rating, 36 reviewsCheerful, Lake Home with amazing backyard!
![](https://a0.muscache.com/im/pictures/69d3bb7c-54f2-4454-ae3a-c4d38c5c61fe.jpg?im_w=720)
Home in Schaumburg
4.86 out of 5 average rating, 7 reviewsParadise 4BR w/ Pool & Games
![](https://a0.muscache.com/im/pictures/miso/Hosting-782525235032023073/original/c259bfd1-4e3a-4829-bd35-243c8b9b3f53.jpeg?im_w=720)
Home in Chicago
4.86 out of 5 average rating, 42 reviewsLuxury Cabin in Lakeview
![](https://a0.muscache.com/im/pictures/miso/Hosting-807719616224077441/original/cd959d50-37b2-474a-80cc-0136b51d909b.jpeg?im_w=720)
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
![](https://a0.muscache.com/im/pictures/hosting/Hosting-983449221511856312/original/2798be2f-5303-40c1-9ad5-61801e5cbee2.jpeg?im_w=720)
Home in Chicago Heights
4.33 out of 5 average rating, 3 reviewsOlympia field -matteson IL- homewood, park forest
Apartment rentals with a pool
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Apartment in Chicago
4.74 out of 5 average rating, 155 reviewsCentral Downtown Location-Modern 2BR Condo
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Apartment in Evanston
4.92 out of 5 average rating, 107 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
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Apartment in Portage
5 out of 5 average rating, 56 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
![](https://a0.muscache.com/im/pictures/530dbaeb-a4b5-4610-ab86-c8593cac89ae.jpg?im_w=720)
Apartment in Portage
4.92 out of 5 average rating, 26 reviewsSerenity on the Shores
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Apartment in Portage
4.91 out of 5 average rating, 78 reviewsUnsalted Stay - Waterfront Condo
![](https://a0.muscache.com/im/pictures/miso/Hosting-666950257559901732/original/c0078b72-7a30-43d5-84fd-8c7bcf711ea4.jpeg?im_w=720)
Apartment in Elk Grove Village
4.95 out of 5 average rating, 61 reviewsJust remodeled apartment close to airport and mall
![](https://a0.muscache.com/im/pictures/miso/Hosting-47113850/original/bab44d3c-5b9f-4ebc-bb5c-8f847af444e7.jpeg?im_w=720)
Apartment in Lombard
4.71 out of 5 average rating, 24 reviewsSmoke Free Community, Pet Free Unit, Washer Dryer
![](https://a0.muscache.com/im/pictures/3a6afd47-9f00-4a17-b390-b3961c529a06.jpg?im_w=720)
Apartment in Chicago
4.8 out of 5 average rating, 20 reviewsLovely condo studio
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