Vacation rentals with a pool in Illinois

4.97 out of 5 average rating, 116 reviews

A spacious pool area is surrounded by vibrant flower beds and lush green landscaping. Comfortable lounge chairs are arranged around the pool, which is flanked by a shaded gazebo area with seating. The house is visible in the background, reflecting a tranquil outdoor setting.

Home in Farmer City

Platypus Hills, Lake, Heated Pool, Hot tub,Firepit

This cozy 2-bedroom country house sits on 8 acres, sleeps 6 and overlooks Clinton Lake with amazing views. We offer a hot tub, heated pool, kayaks, and 10 miles of hiking, hunting, and horse trails.Boat ramp is located at the end of the driveway. We are located 30 minutes between Bloomington & Champaign. There is a $50 charge per day for each guest over 2 regardless whether they stay overnight. Guests must be 18+. Pool open May-Sept. PLEASE READ THE ENTIRE LISTING TO ENSURE IT MEETS YOUR NEEDS.

An indoor pool area is presented with a spacious swimming pool, surrounded by large windows allowing natural light to fill the space. Comfortable lounge chairs are arranged along the poolside, with towels neatly placed on the side. The ceiling showcases exposed wooden beams, adding a warm touch to the atmosphere.

4.97 out of 5 average rating, 143 reviews

Pools, Hot Tub, Fire tables, dog friendly

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

4.91 out of 5 average rating, 294 reviews

An outdoor living area features a spacious swim spa, partially covered by a wooden structure. The water appears green and inviting, surrounded by the natural setting of trees and open lawn. Additional outdoor amenities are visible nearby, enhancing the open space.

Barn in Carthage

Cozy Garden Studio in Lake Linda Barn w/swimspa

This spacious studio in a shady forest is a clean newly remodeled open unit. A 50 in smart TV is provided. It has a comfy queen sized bed, a full sized fridge, sink and microwave and a new cozy gas stove/fireplace. Guests have access to a shared space with electric stove, washer and dryer and additional bathroom with large shower. You will be surrounded by scenery consisting of a 44 acre lake, gardens, and woodlands filled with animals and a vast variety of birds and a new swimspa to share.

4.94 out of 5 average rating, 150 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!

4.98 out of 5 average rating, 120 reviews

A spacious outdoor area is highlighted by a large swimming pool with inviting waters. Surrounding the pool, sun loungers provide ample relaxation space. The cabin features a wooden exterior and a large patio area, framed by vibrant trees and landscaping that showcases the beauty of the surroundings.

Home in Murphysboro

Embers of Murphysboro

Escape to the beauty of Embers of Murphysboro. The sprawling landscapes and cabin with high end amenities have everything to offer for a weekend getaway or larger gathering. Sucumb to the beauty of nature around you that will awaken your inner senses and relax your mind. Nestled upon a 26 acre property the cabin will astound you with picturesque landscapes and a lodging infused with both character and luxury. Explore local wineries, hiking trails, fishing, boating , dining and more...

4.98 out of 5 average rating, 157 reviews

The living area features mid-century modern furniture with vibrant green and orange chairs surrounding a coffee table. A gas fireplace is centered under a unique light fixture, and large windows allow views of the surrounding woods. A dining area is visible in the background.

Treehouse in Galena

Octagon treehouse Hottub-pool-fireplace-firepit

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

4.94 out of 5 average rating, 363 reviews

A circular swimming pool is surrounded by a wooden deck, featuring whimsical inflatable floats in various shapes. Lush greenery and trees provide shade around the pool area, creating a relaxing outdoor space for leisure and enjoyment.

Apartment in Ottawa

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.

4.99 out of 5 average rating, 254 reviews

A serene view of the Pool House from the swimming pool, showcasing a welcoming porch adorned with colorful flowers. The pool's clear blue water reflects the bright sunlight, and vibrant, large-colored balls float gracefully on the surface.

Guesthouse in Carbondale

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.

4.95 out of 5 average rating, 235 reviews

A sparkling pool is surrounded by a spacious patio featuring several green plants in blue pots. A decorative wall with an American flag adds character, while the area is bordered by a white fence and trees provide a natural backdrop.

Home in Belleville

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".

4.98 out of 5 average rating, 113 reviews

An outdoor fire pit is surrounded by several black Adirondack chairs, set among fallen leaves. The cabin is visible in the background, illuminated by warm lights, creating a cozy ambiance. Tall trees frame the scene, providing a sense of seclusion.

Cabin in Galena

Family Time! Hot Tub•Fire Pit•Game Room•3 Kings!

Ultimate Family Escape in Galena Territory! Unwind, explore, and make memories at this chic, spacious cabin! Sip coffee on the deck as deer wander by, soak in the hot tub, and gather around the fire pit for s’mores. Stay cozy by the wood fireplace or challenge the family with arcade games, air hockey, pinball, and darts! Enjoy Owner’s Club access with a pool, fitness center & pickleball (8 amenity cards). Adventure awaits—book your perfect getaway today!

4.97 out of 5 average rating, 109 reviews

An above-ground pool is set amidst a lush green lawn, surrounded by trees. The deck area features steps leading up to the pool's edge, where colorful pool floats are visible. The peaceful outdoor space invites relaxation and enjoyment.

Yurt in Homewood

Glamping Yurt&RV-Game Room-Pool-Sauna-Hotub Court

Glamping Experience to the NEXT LEVEL! Opened April - Nov. Contact during off season. Mini Resort Includes: RV w/bathroom - 2 beds & sofa sleeper 20' Safari Yurt - 4 beds w/sofa sleeper Game Room w/bathroom 1 bed & sofa sleeper Gazebo w/2 twin beds Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court Breakfast included is 1 dozen fresh eggs!

4.9 out of 5 average rating, 145 reviews

A refreshing above-ground pool is surrounded by a wooden deck, leading to a serene lake view. Lush green trees frame the area, and the calm water reflects the surrounding nature. Sunlight filters through the branches, enhancing the tranquil setting.

Home in Salem

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.

Vacation rentals for every style

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Popular amenities for Illinois rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious outdoor area is showcased with a hot tub situated beneath a wooden deck. The hot tub is surrounded by a stone patio and features steps leading up to it. Natural stone walls provide a rustic backdrop, enhancing the tranquil environment.

4.96 out of 5 average rating, 280 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

SofRating, 5 stars2 weeks ago

Beautiful place and James is very good host . Thank you

Superhost

An indoor pool area features large windows allowing natural light to illuminate the space. Two green inflatable floats rest in the water. Comfortable blue lounge chairs are arranged along the perimeter, while a patterned rug adds texture to the floor.

Home in Marion

4.85 out of 5 average rating, 40 reviews

Lakehouse-indoor pool and hottub

SamanthaRating, 5 stars2 days ago

We loved staying here! It was a great way to get together. Wineries were an easy drive and it was a beautiful weekend trip

A round dining table is set outdoors with four yellow plates, each topped with a drink garnished with olives and celery. A bottle of cocktail mix rests beside the glasses, surrounded by textured placemats. Lush greenery provides a natural backdrop.

4.92 out of 5 average rating, 101 reviews

Perfect Location! Owner Club Access, Dog Friendly!

TaewonRating, 5 stars1 week ago

Our family—including me, my wife, our daughter, and our puppy—had a wonderful time. Ginger was very kind and provided detailed information, including how to use the amenities like the swimming pools. The property was clean, cozy, and conveniently located near downtown, where we had a great time exploring. We’d definitely recommend this place to any family and would love to return on our next trip to Galena.

The modern home is set against a backdrop of trees, with a flat grassy area in the foreground. The structure features large windows and a prominent stone chimney, offering ample outdoor seating on the deck. The natural surroundings create a peaceful atmosphere.

4.89 out of 5 average rating, 121 reviews

Modern Home w/Amazing Views, Hot Tub, Game Room

RobinRating, 5 stars2 months ago

We had such a great time! We took the whole family (10 people) and there was plenty of room. The basement was great for keeping the kids entertained. They were wore out from playing video games, air hockey, basketball, and hot rubbing. The area has beautiful views, and feels very private even though there are houses close buy - which we prefer just in case we would need help. We all wished we could have stayed longer! We highly recommend and will definitely be back!

4.94 out of 5 average rating, 69 reviews

Treehouse Getaway | Hot Tub • Firepit • Games

LisaRating, 5 stars2 weeks ago

Wonderful home to enjoy for our family getaway! The house is beautifully decorated and truly feels like a treehouse with huge windows surrounded by woods. Every need was thought out…we enjoyed comfy beds, the smokeless firepit, games and puzzles, and a brand new hot tub! Truly a great place to chillax and the hosts were so quick to reply and helpful. Lots to do around Galena but we mostly enjoyed hanging at the house. ❤️

4.95 out of 5 average rating, 38 reviews

An inviting in-ground pool is set within a private yard, featuring clear blue water that reflects the surrounding greenery. A pool float is visible on the water's surface. The area is bordered by a hedged fence, providing a sense of seclusion and relaxation.

Home in Washington

A Luxe Pool & Hot Tub Retreat~ Westgate Oasis

GraceRating, 5 stars3 months ago

Absolutely wonderful experience from beginning to end. Well-maintained, relaxing, soothing, and just all around beautiful. Hope to visit again.

An outdoor seating area is arranged around a central fire pit on a spacious deck. Comfortable chairs with decorative pillows face the fire, surrounded by a plaid rug. Lush green hills are visible in the background, enhancing the tranquil outdoor setting.

5 out of 5 average rating, 37 reviews

Golden Meadows Escape: A Luxurious Country Retreat

SimoneRating, 5 stars1 week ago

This place was incredible! We almost thought it was too good to be true but it was completely how it was described. The surrounding area was beautiful and we’re definitely interested in coming back now.

5 out of 5 average rating, 42 reviews

A spacious outdoor area is presented, featuring a heated swimming pool surrounded by lounge chairs. A shaded seating arrangement includes a fire table, complemented by cozy blankets. The backdrop displays a vibrant sunset sky, enhancing the serene ambiance of the space.

Home in Normal

"Not so Normal" Oasis w/unique Pool House Bar

RachelRating, 5 stars6 days ago

This Daisy Lane property was a dream location for a “destination staycation” — The property immediately felt like “home” and was extremely clean & well stocked with great amenities throughout!! 😍🤩 The pool glistened & hot tub was wonderfully steamy & super relaxing!! **We stayed the first week in June & paid to have the pool heated. We would recommend heating the pool to anyone staying in the Midwest before July/August (when regular seasonal temps would naturally heat the water to a more comfortable temperature).** The game table was also a very fun & unique feature — it provided great indoor entertainment when the weather outside wasn’t cooperating. 😁 Our hosts were quick to respond to any questions & were very friendly & eager to make sure we had an enjoyable stay!! 🥰 We will definitely recommend this Beyond The Path listing to friends & family & will be keeping it on our short list of places to return to in the future!! Happy Travels!!

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Condo rentals with a pool

4.92 out of 5 average rating, 63 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,

ChidoRating, 5 stars2 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.

5 out of 5 average rating, 38 reviews

A welcoming living area is filled with natural light, featuring a circular dining table surrounded by four upholstered chairs. A comfortable seating arrangement is positioned nearby, complemented by a ceiling fan and a flat-screen TV mounted on the wall. A modern fireplace adds warmth to the space.

Condo in Champaign

Modern Feel Condo 2 bd /2 bath 1 car garage

DanRating, 5 stars4 days 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.

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

4.4 out of 5 average rating, 10 reviews

voco: Balcony & City View

BrookeRating, 5 stars3 weeks ago

Our stay here worked out perfectly. The host was nice, and the location was centrally located to great shopping and restaurants. Very private and safe. The view at night was beautiful.

A bright living space is showcased, featuring large windows that invite natural light. A stone fireplace is positioned against the wall, complemented by a wooden mantel with artwork above. A television stands on a stand nearby, and a cozy seating area is arranged for relaxation.

Condo in Jo Daviess County

4.83 out of 5 average rating, 6 reviews

Lake Links Loft in Galena, Illinois

DavidRating, 5 stars4 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!

4.95 out of 5 average rating, 106 reviews

Condo in Evanston

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

JasonRating, 5 stars1 month 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!

Superhost

An indoor pool area features a clear blue pool surrounded by lounge chairs. Large windows allow natural light to fill the space, highlighting the stone accent wall. Lush greenery is placed strategically around the pool for a refreshing touch.

Condo in Galena

4.75 out of 5 average rating, 32 reviews

Galena, IL, Studio 2

MariaRating, 5 stars23 months ago

Great place to stay very close to downtown Galena.

The resort's brick and timber façade is framed by lush greenery and a spacious lawn. Large windows are visible, hinting at comfortable accommodations within. The sun casts a warm glow over the building, highlighting its lodge-like design amidst a serene, tree-lined setting.

Condo in Galena

4.6 out of 5 average rating, 5 reviews

Tranquil Retreat: Cozy Studio @ Wyndham Galena

DinaRating, 5 stars20 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.