Vacation rentals with a pool in Illinois

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Illinois

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Bartlett

4.96 out of 5 average rating, 185 reviews

Cozy & Spacious Suite in Quiet Neighborhood

This 950 sq. ft. guest suite is in a quiet, upscale neighborhood, less than 1/2 mile from Bartlett Hills Golf Club and a mile from Metra Train Station. 50 min. train ride to downtown Chicago. 10 min. walk to downtown Bartlett. A private entrance makes check-in easy and convenient, while offering privacy during your stay. Full kitchen, accessible bathroom, WIFI, and cable provided. Washer/Dryer available upon request. Pool is for registered guests only. Owners on site to assist if needed.

Sep 9 – 16

G$22,794 GYD per night

Guest favorite

Home in Putnam

4.88 out of 5 average rating, 104 reviews

The Beach House

We have completely remodeled the inside and believe you will thoroughly enjoy this perfect lake home getaway. The inside features 3 bedrooms, 2 baths, 2 living areas, kitchen, and laundry room. The outside speaks for itself with its own private beach, wrap around dock, beautiful lake views from anywhere on the property, and great outdoor hang out areas both on upper level deck and lower level patio with camp fire. The home is on a picturesque lake- you will love having your own private beach!

Sep 8 – 15

G$82,333 GYD per night

Guest favorite

Home in Galena

4.97 out of 5 average rating, 101 reviews

Summer Fun! Hot tub/game rm/scenic views/6BR/6BA

Welcome to The Double Eagle! Experience Galena and the Territory while you relax in this 6 bedroom/6 bath home overlooking the fairway. This well-stocked and spacious three story home easily accommodates multiple families or large groups and has many outdoor spaces to enjoy! Sip your morning coffee in the 3-season room with cozy sectional, make the most of your afternoon playing pool or foosball in the game room, and finish the day by grilling out on the back deck and relaxing in the hot tub.

Nov 15 – 22

G$130,441 GYD per night

Guest favorite

Guest suite in St. Charles

5.0 out of 5 average rating, 250 reviews

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed, studio area includes blue ray player, reverse osmosis drinking water, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

Oct 6 – 13

G$19,336 GYD per night

Guest favorite

Home in Galena

4.95 out of 5 average rating, 106 reviews

Awesome Lodge in Galena Territory

Bring the whole family to our Galena home for fun, games, and making memories! Located 1.3 miles from the Owner's Club in The Galena Territory, enjoy many amenities and everything Galena has to offer! 15 mins to downtown! 3 bedrooms and 3 full bathrooms, the house is equipped with great Wi-Fi and 8 key cards to access Territory amenities! There is tons of space to spread out across 3 floors . Enjoy the game room, hot tub, three seasons room, deck, and outdoor space in this awesome home!

Jan 12 – 19

G$87,410 GYD per night

Guest favorite

Guesthouse in Lebanon

4.96 out of 5 average rating, 179 reviews

Pool, Hot Tub and Dog Paradise

As of 10/4/23 the pool is closed. Our pool house is close to Scott Air Force Base and STL. Home is on 5 acres and has plenty of privacy. Beds are memory foam mattresses. Heated pool (May-September). Pet friendly (dog/cat) & have 1 XL kennel and 1 small pet carrier we can set up. Our home has a large circle drive that goes behind the barn. There is more than enough room for Handicap parking, the gate and sidewalk to the main patio are 48 inches wide. We have a handicap shower seat as well.

Mar 24 – 31

G$25,770 GYD per night

Guest favorite

Guesthouse in Carbondale

4.99 out of 5 average rating, 226 reviews

Carbondale Pool House - Sauna, Hot Tub, Dogs OK

The Pool House is a separate cottage surrounded by gardens and swimming pool, with retro "Danish Modern" furniture, a gourmet kitchen and plush beds. We have recently added a Finnish Sauna and Japanese Ofuro Soaking Tub. We accept well behaved dogs for a fee of $35 a night. We allow only guests of the Pool House on the grounds, gardens or pool. Covid protocols are followed. Hosts are Jane, anthropologist and D. a retired photojournalist for the New York Times. City License # 24-04

Dec 29 – Jan 5

G$50,850 GYD per night

Guest favorite

Home in Galena

4.95 out of 5 average rating, 201 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

Welcome to the Toasted Marshmallow; your cozy escape from reality. Enjoy the peace and quiet of this charming three bedroom, two bath home in The Galena Territories. Kitchen is fully equipped to meet your needs. Enjoy the additional lower level family room w/ 2nd fireplace so your group may spread out. Deck with ample room for dining outside and enjoying your coffee or wine. Home includes six access passes to the GTA Owner's Club and pools. Strong Wi-Fi for remote work, if needed.

Dec 27 – Jan 3

G$38,202 GYD per night

Guest favorite

Home in Galena

4.97 out of 5 average rating, 174 reviews

Newly Renovated. Gorgeous Retreat!

Newly Renovated. Gorgeous Retreat w/seasonal waterfall view! *This home has Large flat screen TV's in Living Room and Both BDRMS. All new kitchen cabinets, Side by Side Refrigerator with Ice Maker, Electric Stove, Microwave, and includes Dishwasher, Keurig Coffee pot, Regular 12 c coffee pot. New Flooring through out, and new Furniture.. Relax by the electric fireplace indoor or the backyard firepit. NO SMOKING IN UNIT New windows coming in the near future. Minimum 2 night stay

Apr 24 – May 1

G$33,733 GYD per night

Guest favorite

Home in Fairview Heights

4.88 out of 5 average rating, 347 reviews

Near STL, Pool, Jacuzzi, Fire Pit, Lrg Yard!

Don’t see the dates you need? Message me! Two king beds, 2 queen beds, and 2 futons for sleeping. This 1900 sq ft 4 bed/2 bath ranch style home is situated in a peaceful neighborhood less than 20 minutes from the Arch & zoo and within 1-2 miles of multiple grocery stores, restaurants, and shopping. Home offers a beautiful large yard with privacy fence, pool, oversized jacuzzi, fire pit, fully stocked kitchen, pack n’ play, high chair, yard games, and so much more! No pets please!

Oct 2 – 9

G$71,263 GYD per night

Guest favorite

Guesthouse in Ottawa

4.95 out of 5 average rating, 270 reviews

Detached, private guest house!

Come stay in our carriage house turned guest house!, the property has a swimming pool available during swimming season, which is June thru September. a separate Hot Tub and new BBQ for your private use; please indicate if you intend to use the pool during your stay, we need an hours notice to remove the cover; the hot tub is always ready to use. You will be sure to enjoy the proximity to restaurants, shopping in Ottawa, parks such as Starved Rock, and a variety of festivals.

Mar 16 – 23

G$14,378 GYD per night

Guest favorite

Home in Galena

4.93 out of 5 average rating, 121 reviews

The Beauty on Belden: minutes from amenities!

Our 3 bedroom, 3 bathroom retreat located in the Galena Territory is the perfect choice for your getaway with access to the Owners' Club. Each bedroom has its own private bathroom. The four seasons room is perfect for relaxing. The home has a spacious back deck for cookouts and entertaining. The house is a 3 minute drive from the Owners' Club and minutes away from 4 golf courses, Shenandoah Riding Center and Marina. 10 minutes to downtown Galena, 15 min to Chestnut Mountain.

Dec 12 – 19

G$73,130 GYD per night