Holiday rentals with a pool in West Side

4.9 out of 5 average rating, 517 reviews

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

RenataRating, 5 stars1 week ago

We had such a good time spending a long weekend here to celebrate my spouse’s birthday! My spouse works out of everyday and loves the gym and I enjoyed swimming in the pool. The apartment was clean and cute with everything we needed, and loved the art deco bits in the building, as well as the comfy lobby, easy access to a coffee shop and walking distance to food spots. Would stay here again!

4.96 out of 5 average rating, 24 reviews

Skyline Oasis: City & Lake Views

NatashaRating, 5 stars2 months 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!!

4.96 out of 5 average rating, 69 reviews

Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool

StephanieRating, 5 stars3 weeks ago

We had a great stay and we were so grateful for all the amenities! Washer and dryer and basic necessities like coffee, creamer, paper towels and soaps/detergents were much appreciated! The host was a very effective communicator and was quick to respond. A++.

Top guest favourite

4.97 out of 5 average rating, 104 reviews

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

AngieRating, 5 stars1 week ago

The place had everything we needed for a weekend stay for a comic convention in Chicago. Tamara and Tony were very communicative and kept us updated on early check in availability. We had no problems finding the place and checking ourselves in. Kitchen was fully stocked, they provided a generous amount of towels for us to use. I loved all the board games they had, both old and new games, this place would be great for a lil staycation. They had prepared both sofa beds for us as well, and provided great detail on everything that was available to us during our stay and how we were to check out at the end. I would not hesitate to stay here again, and would reccomend this place to anyone visiting the city!

4.96 out of 5 average rating, 113 reviews

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

XavierRating, 5 stars1 week ago

Great place to stay if you visit your daughter or son at Northwestern. The apartment is modern, clean, comfortable, super quiet, walkable distance from commodities. The communication with Mihyun was flawlessly, proactive, helpful. She offered flexibility on check in/out time as well as responsive advice on the surroundings. Thank you, Michelle

4.96 out of 5 average rating, 27 reviews

Home in Schaumburg

Schaumburg Woodfield Pool House 4bedroom 2.5bath

LindsayRating, 5 stars3 months 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.

4.95 out of 5 average rating, 20 reviews

Home in Schaumburg

Paradise 4BR w/ Pool & Games

JasonRating, 5 stars7 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.

4.85 out of 5 average rating, 89 reviews

Quiet but in the Heart of City walk Everywhere

ChrisRating, 5 stars3 weeks ago

This place was incredible. My kids and I loved staying here. My young daughter had asked to stay in a "fancy hotel" on our trip, and this blew her mind with the views over the city, how nice the space was, and the pool and hot tub that we pretty much had to ourselves every evening. The kitchen had the things we needed to make our own meals. And we were within easy reach of every place we wanted to go. The included parking spot really took things over the top to make this a great deal and an amazing stay for our family.

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Popular amenities for West Side rentals with a pool

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Pool

Free parking on premises

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House rentals with a pool

Home in Glen Ellyn

4.8 out of 5 average rating, 5 reviews

Pardizes Suites

FernandaRating, 5 stars4 days ago

Really nice and spacious place. Everything was clean and comfy.

4.95 out of 5 average rating, 20 reviews

Home in Glen Ellyn

Glen Ellyn Home

TimothyRating, 5 stars4 months ago

The property was very nice. It was well maintained and our family with our grandson were very comfortable. If we were to have a negative comment is that the heat distribution was not even throughout the home. The upstairs where the three bedrooms were located was very warm and the kitchen, living room and family were quite chilly. However, this did not impede us having a comfortable stay.

Home in Schaumburg

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Paradise with Pool & Games

Home in Chicago

New place to stay

Stunning Home in Prime Chicago

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Apartment rentals with a pool

Apartment in Downers Grove

4.92 out of 5 average rating, 62 reviews

Upscale, Washer Dryer, Smoke Free, Pet Free,

NormaRating, 5 stars3 months 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.

4.96 out of 5 average rating, 93 reviews

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

SeanRating, 5 stars1 week ago

Really great place with lots to do nearby!

4.96 out of 5 average rating, 104 reviews

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

JasonRating, 5 stars4 days ago

Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!

Apartment in Chicago

4.2 out of 5 average rating, 5 reviews

voco: Balcony & City View

GavynRating, 5 stars1 month ago

Overall very nice place for the price. Only disappointment was I got to the location listed on the air bnb listing and the actual location was 3 to 4 blocks away which I was a bit upset with. It is closer to the Chicago station on the redline than it is to the river where the listing states. Host was very responsive and allowed me to check out late to avoid waiting around at the airport for a long time.

Apartment in Chicago

4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars23 months ago

Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.

Apartment in Elk Grove Village

4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars1 month ago

I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️