Holiday rentals with a pool in Near North Side, Chicago
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Near North Side, Chicago
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 Near North Side, Chicago rentals with a pool
House rentals with a pool
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 Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Home in Plainfield
4.89 out of 5 average rating, 27 reviewsPool* King beds* Grill & Patio* 30mi to Chicago
Home in Olympia Fields
4.58 out of 5 average rating, 31 reviewsLuxurious South Suburban Villa
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Home in Glenwood
4.84 out of 5 average rating, 37 reviewsSpacious Family Glenwood Estates Home w/ Hot Tub!
Apartment rentals with a pool
Apartment in Chicago
4.74 out of 5 average rating, 147 reviewsCentral Downtown Location-Modern 2BR Condo
Apartment in Lisle
4.95 out of 5 average rating, 44 reviewsPeaceful Condo in Lisle, Illinois
Apartment in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Apartment in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Apartment in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Apartment in Chicago
4.68 out of 5 average rating, 28 reviews1 bedroom in the heart of downtown Chicago.
Apartment in Evanston
4.94 out of 5 average rating, 71 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Apartment in Evanston
4.95 out of 5 average rating, 79 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Quick stats about holiday rentals with a pool in Near North Side, Chicago
Total rentals
720 properties
Wifi availability
720 properties include access to wifi
Rentals with dedicated workspaces
500 properties have a dedicated workspace
Pet-friendly rentals
470 properties allow pets
Family-friendly rentals
200 properties are a good fit for families
Total number of reviews
5.8K 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 pools Illinois
- Rentals with lake access Near North Side
- Rentals with a sauna Near North Side
- Rentals with a fireplace Near North Side
- Rentals with breakfast Near North Side
- Rentals with a cinema Near North Side
- Rentals with a hot tub Near North Side
- Apartment rentals Near North Side
- Family-friendly rentals Near North Side
- Rentals with a firepit Near North Side
- Rentals with an EV charger Near North Side
- Hotel rentals Near North Side
- Fitness-friendly rentals Near North Side
- Pet-friendly rentals Near North Side
- Family-friendly rentals Near North Side
- Waterfront rentals Near North Side
- Loft rentals Near North Side
- Flat rentals Near North Side
- Boutique hotel rentals Near North Side
- House rentals Near North Side
- Rentals with a washing machine and dryer Near North Side
- Townhouse rentals Near North Side
- Rentals with beach access Near North Side
- Rentals with outdoor seating Near North Side
- Monthly Rentals Near North Side
- Rentals with a patio Near North Side
- Rentals with pools Cook County
- 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