Vacation rentals with a pool in Cook County

An indoor mosaic-tiled pool is surrounded by a spacious, elegantly arched ceiling. Soft lighting reflects off the water, enhancing the serene atmosphere. Wooden lounge chairs are placed along the poolside, providing a comfortable area to relax.

4.9 out of 5 average rating, 518 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!

Top guest favorite

An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.

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

An inviting backyard scene features a sparkling in-ground pool surrounded by lounge chairs and shaded by greenery. The house's exterior showcases large glass doors that open onto the patio area, providing a seamless connection between indoor and outdoor spaces.

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.

An indoor heated pool area features large glass windows, allowing ample natural light and views of the city. The pool is surrounded by tiled flooring and lounge chairs, with a hot tub located nearby. The space is well-designed for relaxation and enjoyment.

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.

4.98 out of 5 average rating, 88 reviews

Guest suite in Gary

Beachfront- Lake Michigan- 2bd/2bath -Heated Pool

AnnaRating, 5 stars2 weeks ago

Brent was a great host! He consistently checked in to make sure we had what we needed and the space was absolutely stunning. He had a fantastic binder that answered any and all questions. I highly recommend this spot.

A rooftop pool area is surrounded by lounge chairs with vibrant orange cushions. The pool's clear water reflects the colors of a sunset, while city buildings rise majestically in the background, showcasing a blend of urban architecture against a dusk sky.

4.95 out of 5 average rating, 44 reviews

53 Floor MagMile Penthouse Views, Balcony, Pool

GingerRating, 5 stars2 months ago

The condo is in a great location! Very walkable to Navy Pier, Art Institute, Symphony, Plant based restaurants, shows (Drunken Shakespeare recommended). Extremely clean and comfortable. We only used the drip coffee maker but kitchen seemed well equipped. Beds were very comfortable and the view was wonderful, especially at night! Front desk people were friendly and helpful…checkout is early ie 10am but they will look after your bags for $10 per hour. Sleeper sofa is a touch short for adults but worked for my son and his husband for one night.

5 out of 5 average rating, 8 reviews

A cozy interior of a camper is featured, showcasing a spacious bed covered with a white duvet. A mirrored closet area is visible, with hangers neatly aligned. Nearby, an air conditioning unit is placed to ensure comfort, alongside a wooden cabinet for storage.

Camper/RV in Portage

Relaxing*1BR/1BA*Mini Golf*Fishing*Bands*Boating

ScottRating, 5 stars8 months ago

Chris is a phenomenal host. He lives a few minutes away from the RV and is very responsive. Two adults and 2 younger kids were very comfortable and had plenty of space to hangout in the RV. We did not take advantage of the activities at the site, but there was something nearly every hour over the weekend for guests (especially kids) to enjoy. If we are in the area, we would absolutely stay again!

Top guest favorite

A clear swimming pool is surrounded by lush greenery and a wooden deck. Lounge chairs are placed nearby, and a colorful inflatable pool float rests on the water's surface. Sunlight reflects off the pool, enhancing its inviting blue color.

Home in Bloomingdale

4.94 out of 5 average rating, 47 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars1 week ago

Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again

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What guests are saying

3BR Luxury Modern Apartment

4.86 out of 5 average rating, 22 reviews1 month ago

My family and I absolutely loved the apartment. It is clean, modern, spacious and comfortable. The gym is just across the hall from the apartment, which was super convenient for us. The lounge area next to the apartment is also a huge plus for getting some work done. You also get a nice view of the city from the unit and from the gym and lounge area. The building is conveniently located on the north end of River North, walking distance to restaurants, public transport & shops. Despite it's somewhat central location, the unit is quiet inside. Lastly, communication with the host was top notch. Check in & check out process were a breeze. I highly recommend this apartment.

Apartment in Chicago

What guests are saying

The Metropolitan Escape (2BD / 2 BA)

4.79 out of 5 average rating, 29 reviews1 week ago

The apartment was spacious, well furnished, and had a wonderful city view. The building was great and with a lot of amenities. It was in a walkable area (with a Target conveniently next door) and close to public transportation. We would definitely stay here again.

Apartment in Chicago

What guests are saying

Long term rental-Delightful one bdrm pool house

5 out of 5 average rating, 12 reviews31 months ago

Definitely a great stay! October 1st and we were swimming! Decor is amazing! Tv was easy to figure out and had lots of options. We had a busy day before and after our stay so we used Michael’s pool house as a relaxing stay in between and it was perfect

Place to stay in River Forest

What guests are saying

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

4.96 out of 5 average rating, 69 reviews4 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++.

Apartment in Chicago

What guests are saying

Skyline Oasis: City & Lake Views

4.96 out of 5 average rating, 24 reviews2 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!!

Apartment in Chicago

What guests are saying

3BR Elegant Glass Penthouse Pool With Deck & Gym

4.82 out of 5 average rating, 55 reviews1 week ago

Great location, nice building amenities, felt safe and could walk to any and everything but also felt private and quiet, very clean, had everything we needed. Bryan met us for check in and was communicative, prompt, and full of good tips and clear instructions. We are local and would definitely use this space again for visitors or a staycation.

Apartment in Chicago

What guests are saying

Happy Glamper Camper lakeshore 1 bed Room sleeps 5

4.71 out of 5 average rating, 21 reviews7 months ago

Emily is a fantastic host. Anything I needed during my stay, her or her husband were right there to assist with. She was very responsive & accommodating to all my needs. My stay was extremely peaceful, private, & exactly what i needed. My stay was very affordable & a perfect little getaway for me. Thank you for being such a considerate & thoughtful host, Emily.

Campsite in Portage

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Popular amenities for Cook County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area is characterized by a plush gray sofa and a round coffee table. Decorative wall elements and a vibrant red holiday tree enhance the modern decor. Soft lighting is provided by a statement chandelier hanging from the ceiling.

Home in Glen Ellyn

4.8 out of 5 average rating, 5 reviews

Pardizes Suites

FernandaRating, 5 stars6 days ago

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

4.94 out of 5 average rating, 51 reviews

An outdoor deck features a modest above-ground pool surrounded by wooden fencing. Two lounge chairs are placed on a textured rug, providing a relaxing seating area. Lush greenery is visible in the background, under a clear blue sky.

Home in Schererville

Cozy house in Schererville

CarlosRating, 5 stars4 days ago

Kate’s place was exactly what I expected. Pristine condition and spotless. Kate accommodated my early arrival which was greatly appreciated. I would 100% book this place again. Highly recommend her place to anyone in the area for a weekend or just to get away from the city. Thank you again for your attention on such a short notice on my booking.

4.95 out of 5 average rating, 20 reviews

A swimming pool is seen surrounded by a white fence, with colorful pool floats inviting fun. Sunlight reflects off the clear blue water, and lush green trees provide a natural backdrop. A patterned mat lies at the edge, enhancing the relaxing atmosphere.

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.

The exterior of a three-story townhome is presented, featuring light-colored siding and a brick accent. A single-car garage is visible, along with a small front lawn. Large windows allow natural light to enter, while a tree branch extends above, casting gentle shadows.

Home in Schaumburg

4.71 out of 5 average rating, 7 reviews

Spacious 3 Floor Townhome

MelissaRating, 5 stars3 weeks ago

This spot is awesome. Close to the mall and lots of places to eat and things to do. Very spacious tri level. Free Parking on premises. Lots of room for people to sleep very spacious. Comfy couches. The bed I had was great. Our venue was very close for the event we attended we will be back!

A comfortable living room features a dark leather sofa centered in the space. Two bright red chairs are positioned around a small table. Natural light enters through large windows adorned with sheer curtains, illuminating the floral-patterned rug on the hardwood floor.

Home in Gary

4.81 out of 5 average rating, 226 reviews

Oasis , Near Beach, Hard Rock and Dunes

AlisonRating, 5 stars7 months ago

We enjoyed our weekend trip close to the beach!

4.91 out of 5 average rating, 22 reviews

Home in Schaumburg

Schaumburg Oasis with a Pool and Hidden Garden

GotimukulRating, 5 stars2 weeks ago

had such a wonderful stay! The place was exactly as described—clean, cozy, and beautifully maintained. The host was incredibly kind and responsive, making the whole experience smooth and stress-free. Would definitely stay here again and highly recommend it to anyone looking for a comfortable and welcoming place to stay!

4.93 out of 5 average rating, 75 reviews

A modern hallway features arched openings along white walls, accented by warm lighting that highlights the dark wood flooring. Dark doors are positioned at either end, providing a clean and sophisticated look.

Home in Plainfield

Relaxing Spanish style Home (w/inground pool)

DevonRating, 5 stars7 months ago

House was lovely. I enjoyed the homes decor. Every day I woke up with something else I loved. The house had everything we needed. Only thing I wished the pool heater was working and the pillows were flat. I would definitely stay here again.

A spacious living area is highlighted by two navy blue sofas and a modern coffee table, with a wood piano situated against the wall. Large windows allow natural light to flow in, illuminating the soft carpeting and neutral wall colors.

Home in Glenwood

4.8 out of 5 average rating, 56 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

Nicole And ArnoRating, 5 stars1 month ago

Loved this Airbnb! Didn’t want to leave.

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Condo rentals with a pool

4.92 out of 5 average rating, 62 reviews

A modern living area features a blue sofa accented by colorful pillows. A flat-screen TV is positioned on a white media console. A round coffee table sits on a textured area rug, with plants adding a touch of greenery. The open kitchen is visible, showcasing light wood cabinetry.

Condo in Downers Grove

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.

An outdoor pool area is shown, featuring a clear blue pool surrounded by lounge chairs. Trees provide a touch of greenery, while a modern glass structure offers shaded seating. Sunshine reflects off the water, creating a bright and inviting atmosphere.

4.96 out of 5 average rating, 93 reviews

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

SeanRating, 5 stars2 weeks 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 stars6 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!

A serene bedroom is illuminated by soft purple lighting. A spacious bed with a polka dot blanket is centered in the room. Floor-to-ceiling glass doors reveal a view of a vibrant city skyline at night, with city lights twinkling in the background.

Condo 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.

An outdoor pool area features a clear, blue body of water surrounded by lounge chairs. Lush greenery is placed in large planters along the perimeter, with a backdrop of modern high-rise buildings and a cloudy sky.

Condo 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.

Condo in Elk Grove Village

The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.

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! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

An outdoor swimming pool is surrounded by lounge chairs, offering a relaxing space. Trees are strategically placed around the area, and large glass walls provide views to the inside. Sunlight reflects off the water, enhancing the serene setting.