Vacation rentals with a pool in West Side
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in West Side
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for West Side rentals with a pool
House rentals with a pool
Home in Plainfield
4.95 out of 5 average rating, 62 reviewsSpanish style Home (w/heated pool)
Sep 26 – Oct 3
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Jul 7 – 14
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Jan 13 – 20
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul 23 – 30
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Jan 24 – 31
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Aug 13 – 20
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Aug 18 – 25
Home in Gary
4.82 out of 5 average rating, 213 reviewsOasis , Near Beach, Hard Rock and Dunes
May 7 – 14
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 146 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 7 – 14
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Sep 16 – 23
Condo in Downers Grove
4.88 out of 5 average rating, 52 reviewsUpscale, Smoke and Pet Free, Washer Dryer, Balcony
Oct 20 – 27
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Sep 16 – 23
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul 23 – 30
Condo in Evanston
4.94 out of 5 average rating, 71 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Nov 18 – 25
Condo in Evanston
4.97 out of 5 average rating, 73 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Oct 21 – 28
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Oct 12 – 19
Destinations to explore
- Downtown Chicago Vacation rentals
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