Holiday 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 favourite

Cabin

4.96 out of 5 average rating, 116 reviews

Winter Getaway! <-Hot tub- Fire place-Game room->

Escape to our cozy luxe cabin in Galena Territory, the perfect retreat for winter! Start your mornings sipping coffee by the gas fireplace, then warm up each evening in the hot tub! Enjoy friendly competition with arcade games, board games, air hockey, and darts. With 10 amenity cards, you can access the owner’s club for swimming and exercise including indoor pickle ball-rackets and balls at the house! Experience relaxation and adventure in this tranquil haven—your unforgettable getaway awaits!

Guest favourite

Home

4.97 out of 5 average rating, 126 reviews

Newly Remodeled! Hot tub, 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.

Guest favourite

Home

4.96 out of 5 average rating, 114 reviews

Holiday Hot Tub Escape-Open for Christmas!

Step into Rolling Hills Retreat, a sanctuary from the everyday bustle! Our dog-friendly rental offers breathtaking views and numerous amenities for your pleasure and relaxation. Enjoy a swim in the indoor or outdoor pool, and discover a variety of amenities that promise an unforgettable stay. *Pickle Ball *Basketball *Pool Tables *Hiking Trails *Workout Room *Tennis Courts *Brand new (June 2024) Marina with boat rental (additional charge) *Ping Pong tables *Arcade *Scenic Waterfall *Kayaking

Guest favourite

Villa

4.98 out of 5 average rating, 110 reviews

King Bed, Woodburning Fireplace, Indoor Pool

◆ Quiet, wooded retreat ◆ King bed ◆ Indoor pool, year round access ◆ Well equipped kitchen ◆ Smart TV on each level w/Roku & YouTube TV ◆ Woodburning fireplace w/supply of firewood ◆ Computer desk ◆ 2 Full baths ◆ Queen sofa bed ◆ Gas grill ◆ Fitness center ◆ Paved walking trails nearby ◆ North Course & driving range conveniently up the road ◆ Stonedrift Spa, 3 min. drive ◆ Downtown Galena, approx. 15 min drive ◆ Winter sports at Nordic Center ◆ Chestnut Mountain Ski , approx. 25 min drive

Guest favourite

Guest suite

4.96 out of 5 average rating, 207 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.

Guest favourite

Guest suite

5 out of 5 average rating, 274 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 with mattress topper, studio area includes Smart TV, water station, 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.

Guest favourite

Treehouse

4.98 out of 5 average rating, 114 reviews

Retro octagon house in woods- Hot tub, fireplace,

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

Guest favourite

Home

4.95 out of 5 average rating, 230 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.

Guest favourite

Rental unit

4.94 out of 5 average rating, 326 reviews

Detached, private guest house! a ms

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.

Guest favourite

Guest house

4.99 out of 5 average rating, 241 reviews

Carbondale Pool House - Sauna, Hot Tub, Dogs OK

Rated in “Top 1%” by Airbnb, 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 and friends of the Pool House on the grounds, gardens or pool. Hosts are Jane, anthropologist and D. a retired photojournalist for the New York Times.

Guest favourite

Home

4.98 out of 5 average rating, 204 reviews

The Pool House 1-Bedroom Home with Hot Tub & Pool

Soak in the hot tub or relax poolside at The Pool House! Its rural setting is perfect for a relaxing stay, romantic getaway, business trip or spending time with your family. Enjoy a full kitchen, electric fireplace and spacious bedroom. *No parties allowed *No pets allowed *No smoking allowed *No photo shoots allowed Maximum guest number is 5. We DO NOT have a TV, but do have WIFI. **Military discount is available. Please message us first by clicking "Contact host".

Guest favourite

Home

4.91 out of 5 average rating, 128 reviews

Private Cabin w/Pool on Lake Centralia, sleeps 12.

Welcome to Deer Creek Cabin on Lake Centralia. Relax with the whole family at this peaceful private retreat. A large deck surrounds the pool for all your family fun. Fishing and kayaking are just steps away. Enjoy your morning coffee in the screened-in porch overlooking a quiet cove of the beautiful lake. It is common to see deer, geese, ducks, turtles, and blue heron. As night falls, cozy up around the fire pit to make more family memories.