Vacation rentals with a pool in Chicago River
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chicago River
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 Chicago River rentals with a pool
House rentals with a pool
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Aug 17 – 24
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Jul 7 – 14
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul 23 – 30
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
Nov 12 – 19
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Feb 2 – 9
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Jul 29 – Aug 5
Home in Tinley Park
4.8 out of 5 average rating, 5 reviewsPerfect safe stay
Jan 21 – 28
Home in Lisle
Welcoming, cozy, and a fur baby paradise.
Sep 27 – Oct 4
Condo rentals with a pool
Condo in Chicago
4.75 out of 5 average rating, 145 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 21 – 28
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Oct 26 – Nov 2
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Jan 10 – 17
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul 21 – 28
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Nov 3 – 10
Condo in Evanston
4.94 out of 5 average rating, 71 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Jul 24 – 31
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 Evanston
4.95 out of 5 average rating, 79 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Dec 19 – 26
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- Chicago Vacation rentals
- Rentals with pools United States
- Rentals with pools Chicago
- Rentals with pools Downtown Chicago
- Rentals with pools Milwaukee
- Family-friendly rentals Chicago River
- Rentals with a hot tub Chicago River
- Rentals with a patio Chicago River
- Rentals with lake access Chicago River
- Monthly Rentals Chicago River
- Rentals with beach access Chicago River
- Pet-friendly rentals Chicago River
- Condo rentals Chicago River
- Rentals with a washer and dryer Chicago River
- Fitness-friendly rentals Chicago River
- Rentals with outdoor seating Chicago River
- Hotel rentals Chicago River
- Rentals with an EV charger Chicago River
- Apartment rentals Chicago River
- Rentals with a fireplace Chicago River
- Boutique hotel rentals Chicago River
- Kid-friendly rentals Chicago River
- Rentals with a sauna Chicago River
- Rentals with a fire pit Chicago River
- Rentals with pools Illinois
- Rentals with pools Cook County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes