Vacation rentals with a pool in West Loop, Chicago
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in West Loop, Chicago
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 Loop, Chicago rentals with a pool
House rentals with a pool
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Home in Lisle
5.0 out of 5 average rating, 3 reviewsWelcoming, cozy, and a fur baby paradise.
Home in Niles
5.0 out of 5 average rating, 12 reviewsLuxury Modern House Epic Master Bath & Pool Table
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Home in Lisle
Cozy Lisle Home w/ Fenced Backyard: Pets Welcome!
Home in Skokie
Skokie town home
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 148 reviewsCentral Downtown Location-Modern 2BR Condo
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Condo in Chicago
4.68 out of 5 average rating, 28 reviews1 bedroom in the heart of downtown Chicago.
Condo in Chicago
4.76 out of 5 average rating, 17 reviewsLovely condo studio
Condo in Evanston
4.95 out of 5 average rating, 79 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Condo in Evanston
4.94 out of 5 average rating, 71 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Condo in Evanston
4.97 out of 5 average rating, 74 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Quick stats about vacation rentals with a pool in West Loop, Chicago
Total rentals
250 properties
Wifi availability
250 properties include access to wifi
Rentals with dedicated workspaces
180 properties have a dedicated workspace
Pet-friendly rentals
210 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
770 reviews
Destinations to explore
- Rentals with pools United States
- Rentals with pools Chicago
- Rentals with pools Chicago
- Rentals with pools Downtown Chicago
- Rentals with pools Milwaukee
- Rentals with a fireplace West Loop
- Family-friendly rentals West Loop
- Rentals with a patio West Loop
- Fitness-friendly rentals West Loop
- Condo rentals West Loop
- Kid-friendly rentals West Loop
- Rentals with an EV charger West Loop
- Rentals with a sauna West Loop
- Pet-friendly rentals West Loop
- Rentals with outdoor seating West Loop
- Rentals with a washer and dryer West Loop
- Monthly Rentals West Loop
- Rentals with a hot tub West Loop
- Apartment rentals West Loop
- Rentals with a fire pit West Loop
- 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