Vacation 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.
Vacation 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 Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul 23 – 30
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
Aug 17 – 24
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Feb 2 – 9
Home in Tinley Park
4.8 out of 5 average rating, 5 reviewsPerfect safe stay
Jan 21 – 28
Home in Lisle
Cozy Lisle Home w/ Fenced Backyard: Pets Welcome!
Jul 26 – Aug 2
Home in Riverwoods
Riverwoods Nature Retreat
May 5 – 12
Home in Munster
Munster hide away
Oct 28 – Nov 4
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 146 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 21 – 28
Condo in Lisle
4.95 out of 5 average rating, 42 reviewsPeaceful Condo in Lisle, Illinois
Jan 28 – Feb 4
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
Oct 2 – 9
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Nov 3 – 10
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul 21 – 28
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
4.94 out of 5 average rating, 71 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Jul 24 – 31
Quick stats about vacation 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
- Apartment rentals Near North Side
- Rentals with a patio Near North Side
- Fitness-friendly rentals Near North Side
- Hotel rentals Near North Side
- Rentals with a hot tub Near North Side
- Kid-friendly rentals Near North Side
- House rentals Near North Side
- Rentals with lake access Near North Side
- Rentals with an EV charger Near North Side
- Boutique hotel rentals Near North Side
- Rentals with outdoor seating Near North Side
- Family-friendly rentals Near North Side
- Rentals with a home theater Near North Side
- Condo rentals Near North Side
- Townhouse rentals Near North Side
- Rentals with beach access Near North Side
- Monthly Rentals Near North Side
- Rentals with a sauna Near North Side
- Rentals with a washer and dryer Near North Side
- Rentals with a fireplace Near North Side
- Pet-friendly rentals Near North Side
- Beachfront rentals Near North Side
- Loft rentals Near North Side
- Waterfront rentals Near North Side
- Rentals with breakfast Near North Side
- Rentals with a fire pit 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