Holiday rentals with a pool in North Side
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in North 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 North Side rentals with a pool
House rentals with a pool
Home in Gary
4.93 out of 5 average rating, 126 reviewsBayless Dune Lodge at West Beach - Indiana Dunes!
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Plainfield
4.95 out of 5 average rating, 63 reviewsLarge Spanish style Home (w/heated pool)
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Home in Gary
4.82 out of 5 average rating, 213 reviewsOasis , Near Beach, Hard Rock and Dunes
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 147 reviewsCentral Downtown Location-Modern 2BR Condo
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Condo in Chicago
4.68 out of 5 average rating, 28 reviews1 bedroom in the heart of downtown Chicago.
Condo in Evanston
4.94 out of 5 average rating, 71 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Condo in Evanston
4.95 out of 5 average rating, 79 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Condo in Evanston
4.97 out of 5 average rating, 74 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Condo in Downers Grove
4.88 out of 5 average rating, 52 reviewsUpscale, Smoke and Pet Free, Washer Dryer, Balcony
Destinations to explore
- Downtown Chicago Holiday rentals
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- Lake Geneva Accommodation & holiday rentals
- Lake Michigan Beach Accommodation & holiday rentals
- Saugatuck Accommodation & holiday rentals
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- Rentals with pools United States
- Rentals with pools Chicago
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- Rentals with pools Milwaukee
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- Smoking-friendly rentals North Side
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- Kid-friendly rentals North Side
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- Yurt Rentals United States
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