Vacation 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.
0 of 0 items showing
1 of 3 pages
Vacation 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
Guest favorite
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Guest favorite
Home in Chicago
5 out of 5 average rating, 6 reviewsLuxury Condo Downtown Chicago
Guest favorite
Home in Chicago
4.86 out of 5 average rating, 29 reviews2Bed+2Bath PentHouse in South Loop
Guest favorite
Home in Bloomingdale
4.94 out of 5 average rating, 35 reviewsWhole House with a Hot Tub!
Superhost
Home in Schaumburg
4.82 out of 5 average rating, 11 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Home in Chicago
New place to stayCity Close, Country Calm
Guest favorite
Home in Carol Stream
4.86 out of 5 average rating, 7 reviewsSpacious 4 Bed/3.5 Bath Sleeps 8+
Condo rentals with a pool
Condo in Downers Grove
4.92 out of 5 average rating, 59 reviewsUpscale, Washer Dryer, Smoke Free, Pet Free,
Guest favorite
Condo in Evanston
4.95 out of 5 average rating, 84 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Condo in Chicago
4.69 out of 5 average rating, 39 reviews2BD Central Downtown Location! Spacious & Cozy
Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 94 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Condo in Lombard
4.83 out of 5 average rating, 53 reviewsSmoke & Pet Free, Washer Dryer, Fireplace, Balcony
Guest favorite
Condo in Evanston
4.91 out of 5 average rating, 117 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Chicago
4.8 out of 5 average rating, 25 reviewsLovely condo studio
Condo in Lombard
4.91 out of 5 average rating, 44 reviewsPond View, Washer Dryer, Non Smoking Community
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Evanston Vacation rentals
- Saugatuck Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Bend Vacation rentals
- South Side Vacation rentals
- Schaumburg Vacation rentals
- Chicago Vacation rentals
- Rentals with pools United States
- Rentals with pools Chicago
- Rentals with pools Downtown Chicago
- Rentals with pools Milwaukee
- Rentals with pools Illinois
- Rentals with a hot tub North Side
- Monthly Rentals North Side
- Rentals with a patio North Side
- Rentals with beach access North Side
- Townhouse rentals North Side
- Hotel rentals North Side
- Rentals with outdoor seating North Side
- Rentals with a balcony North Side
- Rentals with a fire pit North Side
- Rentals with breakfast North Side
- Fitness-friendly rentals North Side
- Smoking-friendly rentals North Side
- Waterfront rentals North Side
- Family-friendly rentals North Side
- Pet-friendly rentals North Side
- Rentals with a washer and dryer North Side
- Private suite rentals North Side
- Rentals with an EV charger North Side
- House rentals North Side
- Kid-friendly rentals North Side
- Beachfront rentals North Side
- Rentals with a fireplace North Side
- Rentals with lake access North Side
- Apartment rentals North Side
- Loft rentals North Side
- Condo rentals North Side
- Bed and breakfasts North Side
- 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
- Things to do United States
- Sports activities United States
- Nature and outdoors United States
- Entertainment United States
- Art and culture United States
- Sightseeing United States
- Food and drink United States
- Wellness United States
- Things to do Illinois
- Art and culture Illinois
- Sightseeing Illinois
- Food and drink Illinois
- Things to do North Side