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Holiday rentals with a pool in Illinois

Find and book unique homes with a pool on Airbnb

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Popular amenities for Illinois rentals with a pool

House rentals with a pool

Guest favourite
Home in Galena
4.95 out of 5 average rating, 243 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

KellyRating, 5 stars2 weeks ago
We had a wonderful stay! The house was stocked with everything we needed. The kids had so much fun with all the toys and games and us adults loved the deck and firepit. It was the perfect place for our family. We saw a bunch of wild turkeys, a few deer and lots of other wild life. Everything was clean, the beds were comfortable and the thoughtful extras were much appreciated. Brittany and Tim were great hosts!
Top Guest favourite
Home in Cobden
4.94 out of 5 average rating, 68 reviews

Wine trail, views, hot tub, pool…

ErikaRating, 5 stars2 weeks ago
Four of us stayed in Lisa's place for the weekend and we had more than enough space. The outdoor area was definitely our favorite amenity. Sitting outside anytime of the day with a beautiful view of the bluffs was special. I highly recommend staying here if you're in the area. It was a wonderful time.
Guest favourite
Home in Galena
4.94 out of 5 average rating, 67 reviews

Fox Wood Path l HOT TUB l A&D Rise Getaways

MaryRating, 5 stars1 week ago
It was our first time to Galena. We were looking for a relaxing weekend getaway to celebrate our 20th. The house was exactly as described in a serene setting within Galena Territory. We enjoyed hiking, biking, and wineries all within a short drive, and then relaxing in the hot tub in the evenings. We didn't partake in any of the included amenities within Galena Territory, but noted it as a positive that we would take advantage of for future trips. We very much enjoyed our stay and hope to return soon!
Top Guest favourite
Home in Galena
4.94 out of 5 average rating, 150 reviews

Awesome Lodge in Galena Territory

TaylorRating, 5 stars1 week ago
We had a great stay at the cabin for my brother’s bachelor party weekend. We played 2 golf courses, ate at one of the resort restaurants, and went downtown for dinner one night. It’s a 2 minute drive to the courses and 10 minutes to downtown. Great location that sat on one of the par 4s.
Top Guest favourite
Home in Galena
4.97 out of 5 average rating, 145 reviews

Pools, Hot Tub, Fire tables, dog friendly

KimberlyRating, 5 stars1 week ago
We had a wonderful stay! Doreen was always in communication making sure we had everything we needed. Our family of 5 was looking to getaway for a few days and this was a great place for it! The home was clean and cozy with lots of thoughtful touches throughout to make us feel welcome. We got to enjoy the amenities at the club house, and were just close enough to town to enjoy the restaurants and shops. My kids want to come back already!
Top Guest favourite
Home in Oregon
4.97 out of 5 average rating, 39 reviews

Rock River Relaxation Home

BrentRating, 5 stars1 week ago
Beautiful home to stay in for a nice long weekend away from the city. Very quick access to town and to various nature attractions. The house was very clean and just overall a very comfortable stay.
Guest favourite
Home in Washington
4.95 out of 5 average rating, 39 reviews

A Luxe Pool & Hot Tub Retreat~ Westgate Oasis

GraceRating, 5 stars4 months ago
Absolutely wonderful experience from beginning to end. Well-maintained, relaxing, soothing, and just all around beautiful. Hope to visit again.
Top Guest favourite
Home in Galena
5 out of 5 average rating, 39 reviews

Golden Meadows Escape: A Luxurious Country Retreat

AdamRating, 5 stars1 week ago
This place was exactly what we were looking for. We had a group of 9 coming from different cities, all meet at this beautiful location. Check-in was flawless and the entire house was spotless when we arrived. There was plenty of space to accommodate our entire group and we immediately felt right at home. The scenery was absolutely gorgeous. We enjoyed time on the deck in front of the gas fire as well as the spacious fire pit just off the house. The yard was plenty big for games and although we had beautiful weather during our trip, we had a big theatre room to ourselves when we wanted some inside time. Our host was very helpful from start to finish. We always got a quick response and he worked with us to make sure our trip was special. We highly recommend this spot and would love to come back someday.

Condo rentals with a pool

Guest favourite
Condo in Downers Grove
4.92 out of 5 average rating, 63 reviews

Upscale, Washer Dryer, Smoke Free, Pet Free,

ChidoRating, 5 stars3 months ago
I really loved the place—it was cozy, soundproof, and felt just like home. It had a warm, inviting atmosphere and a great sense of comfort. Plus, the neighborhood felt very safe, which made our stay even better.
Top Guest favourite
Condo in Champaign
5 out of 5 average rating, 39 reviews

Modern Feel Condo 2 bd /2 bath 1 car garage

DanRating, 5 stars2 weeks ago
The best AirBnB we have stayed in while visiting family in champaign . Definitely will stay here again if it's available next time we come up.
Superhost
Condo in Chicago
4.73 out of 5 average rating, 55 reviews

2BD Central Downtown Location! Spacious & Cozy

MadleneRating, 5 stars1 month ago
We were very happy with the Apartment, it was clean and perfect size for 4 people. Ana was super helpful and responded immediately, we loved talking to her 😄 For me due to Images, and wrong adress on the public profile, there has been some confusion about the location of the Apartment. All in all: The views are not stunning, but the location is perfect for sightseeing (and price was great location wise)! 😉
Condo in Jo Daviess County
4.83 out of 5 average rating, 6 reviews

Lake Links Loft in Galena, Illinois

DavidRating, 5 stars5 months ago
Our family had a fantastic job at Dan's place. The location is great - close enough to the Eagle Ridge Inn and Owners Club, but very private location with a beautiful view of the lake. The unit had everything we need and was much larger than the pictures made it seem. Galena had great shopping and restaurants. Galena Territory Owners Club indoor pool was perfect for the kids. I'd recommend staying here anytime we make it back to Galena Territory!
Guest favourite
Condo in Evanston
4.95 out of 5 average rating, 108 reviews

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

StaciRating, 5 stars2 weeks ago
Always responded quickly. When we had trouble with front door lock they came out quickly and addressed the problem.
Superhost
Condo in Jo Daviess County
4.8 out of 5 average rating, 5 reviews

Long Bay Point Unit C5

AlyxRating, 5 stars7 months ago
My husband and I stayed here for 4 nights. It's a 10 min drive from downtown Galena in a quiet wooded area with paved trails that you can take to the nearby amenities. The place was clean, quiet, and the bathtub was amazing! The gym and indoor/outdoor pool are very nice but about 1.5 miles from the condo which wasn't stated anywhere (or at least not anywhere we saw) and was a little disappointing but overall wasn't a huge deal. The restaurant is a short walk through the trails or you can drive to it. It's right next door. Also, the initial message you get after booking with the rules and asking to email them out of the app was a little daunting and not normal for Airbnb bookings. It just had a less "homey" experience that you expect from Airbnb. It made me slightly nervous but after everything I would certainly stay here again.
Condo in Galena
4.6 out of 5 average rating, 5 reviews

Tranquil Retreat: Cozy Studio @ Wyndham Galena

DinaRating, 5 stars21 months ago
This place was absolutely B.E.A.U.T.F.U.L! The staff were super sweet and friendly. So many things to do at Galena. Also, there was a table with “to do activities” That was very helpful. I would 100% come back. Thank you all staff for being such a good host.
Guest favourite
Condo in Elk Grove Village
4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars2 months 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! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

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