Holiday rentals with a pool in North Side

4.9 out of 5 average rating, 511 reviews

Flat

Whole Flat in Private Club. Walk to L, Dining & Shows

JessicaRating, 5 stars4 days ago

What an awesome apartment! The location was perfect for a show at the Aragon. We easily found parking right around the corner and were thrilled to not have to pay for daily parking. We never had to move our car once! We walked to restaurants, an awesome deli for sandwiches, and did karaoke at the local lounge. The apartment itself was spotless, and I am very picky about cleanliness! The building had amazing amenities and we enjoyed the coffee shop and bar. We didn't use the pool or gym areas but they have quality machines and rival a gym membership. We also spent time in the rooftop lounge, which we had to ourselves to enjoy the view. We will definitely stay again if we find ourselves returning to the area.

4.96 out of 5 average rating, 24 reviews

Flat

Skyline Oasis: City & Lake Views

NatashaRating, 5 stars4 days ago

Let me just say, the pictures don’t do this cute, cozy place justice! I’m big on hospitality and customer service, and Johana and Akos were beyond accommodating and communicative. I would dare to say this is the most accommodating place I’ve experienced so far! The space has such a good energy and flow to it — cozy, inviting, and with a beautiful sunset view from the kitchen window that you can enjoy right from the living room sofa. The views are stunning, and the building itself is upscale, clean, and even smells great! I enjoy playing some of the games that were pervaded( Uno and Jenga) and I appreciated that the TVs had all the apps, HBO, Disney, prime, Netflix etc. It’s in a great location, and I felt very safe throughout my stay. The only con would be some city noise, but it didn’t bother me at all. There’s a nearby train that doesn’t pass often, and again, it wasn’t an issue for me. I would definitely recommend this place!!

4.97 out of 5 average rating, 98 reviews

Flat

Fun & cozy getaway w/POOL/game room/FREE parking

RyanRating, 5 stars2 months ago

Tamara and Tony were kind, responsive and accommodating. Everything you could ask for in an Airbnb host! The place was easy to find and access was quick and simple. The space was clean, welcoming and well appointed. The coffee machine was well stocked and the bed was comfy. Plenty of space and places to hang around. Great location in Logan Square! Want to come back in the summer and take a dip in the pool! 10/10. Would rent again.

4.96 out of 5 average rating, 109 reviews

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

PaulRating, 5 stars1 week ago

Good location to most of the places like restaurants and shops, still walking distance to Northwestern University as well. Very easy to communicate with Mihyun who is very helpful during our stay. Will definitely book again next time

4.96 out of 5 average rating, 27 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

LindsayRating, 5 stars1 month ago

Everything went perfect for us. We flew in from out of town, and some plans fell through. We asked Mike if it was possible to check in a couple hours early and he was very flexible. We really appreciate you and your home. Thanks for letting us stay.

4.92 out of 5 average rating, 142 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

JeffRating, 5 stars2 months ago

We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.

Holiday rentals for every style

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Popular amenities for North Side rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 6 reviews

Luxury Condo Downtown Chicago

CarsonRating, 5 stars15 months ago

Paras was an extremely friendly host. He provided a long list of recommendations and made sure we were aware he was only a message or call away.

4.88 out of 5 average rating, 16 reviews

Schaumburg Oasis with a Pool and Hidden Garden

BrianRating, 5 stars3 days ago

This property had exactly what I needed. It was a secluded place to get a great peace of mind. The pictures did not do justice. The host was very proactive with the snow storm that was going on. Some of the best communications and updates during my visit. I will definitely look to rent from this host again when I come back to Chicago.

4.86 out of 5 average rating, 7 reviews

Spacious 4 Bed/3.5 Bath Sleeps 8+

CarmenRating, 5 stars4 months ago

Beautiful house very clean and comfortable. We'll be back very soon

4.95 out of 5 average rating, 20 reviews

Paradise 4BR w/ Pool & Games

JasonRating, 5 stars5 months ago

We really enjoyed our stay at this beautiful home. It is close to everything. The place is clean and very organized. Lily and Nathan has been wonderful and very responsive and communicated well with us. I definitely recommend this place when you visit Schaumburg. Thank you guys for everything.

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Apartment rentals with a pool

4.92 out of 5 average rating, 61 reviews

Upscale, Washer Dryer, Smoke Free, Pet Free,

NormaRating, 5 stars1 month ago

My husband and I stayed here over the holidays. The apartment was pretty well appointed, clean and is in a good location- centrally located for our purposes of being near family and close enough to the expressway to get to the city.

4.95 out of 5 average rating, 88 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

MelanieRating, 5 stars2 weeks ago

Very nice place, convenient location if you have students at NU. I was surprised by how firm the mattresses were, all are a really hard foam not a traditional spring mattress. A word of caution regarding parking, bring only compact cars! It was very tricky to navigate into and out of the garage and parking spot with a SUV. Other than that, great stay!

4.96 out of 5 average rating, 100 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

SarahRating, 5 stars1 week ago

Mihyun was a terrific host and the place was extremely comfortable and inviting. We asked for a late check out when our plans changed and she was accommodating to the best she was able to be. The glass windows all around made it possible to watch the weather, it was very peaceful. Thank you!

TamonRating, 5 stars3 weeks ago

New place to stay

voco: Balcony & City View

Great stay and location. Immaculate views of the city. Close walk to the Chicago and Goodman theaters. Also great breakfast and brunch spots. And some good ole’ Chicago deep dish pizza at Giordano’s. The River Walk is about a 8 minute drive and a nice 22 minute walk. Which the walk is worth it even in the cold.

4.95 out of 5 average rating, 78 reviews

Just remodeled apartment close to airport and mall

Ralf OliverRating, 5 stars2 months ago

Great apartment. Super host. Everything was great.

4.91 out of 5 average rating, 120 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

DominicRating, 5 stars2 weeks ago

We loved our stay here! The apartment is clean, modern and well taken care of. The instructions for check in and check out were clear and easy. The building is nice and has an underground garage and fitness center. It is an easy walk into the center of evanston. Se would definitely return!

4.9 out of 5 average rating, 63 reviews

Peaceful Condo in Lisle, Illinois

JoanneRating, 5 stars6 months ago

Sara responded well, both by text and phone call, to my inability to enter the building. Once in the apartment, I was pleased with all the amenities, cleanliness, and quiet.