Holiday rentals with a pool in Illinois

4.97 out of 5 average rating, 116 reviews

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.

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

4.98 out of 5 average rating, 133 reviews

Villa in Galena

King Bd, Well-located Near Pool, Spa, Golf, Trails

✓Semi-private outdoor pool, steps away ✓Lake access ✓Well equipped kitchen w/modern appliances ✓Smart TV on each level w/Roku & YouTube TV ✓Computer desk ✓Fireplace w/supply of firewood ✓Queen sofa bed ✓2 Full baths ✓Gas grill ✓Indoor pool ✓Near hiking trails & paved walking trails ✓North Course & Driving Range, 2 min drive ✓Owner's Club access ✓Stonedrift Spa, 3 min drive ✓Downtown Galena, 15 min drive ✓Chestnut Mountain (Ski & Zipline), 25 min drive ✓Guest favorites: "cleanliness & comfort"

4.91 out of 5 average rating, 294 reviews

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.

4.98 out of 5 average rating, 120 reviews

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

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

Flat 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.

4.94 out of 5 average rating, 154 reviews

The Beauty on Belden: Owners' Club access & more!

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.

Guest house in Carbondale

4.99 out of 5 average rating, 254 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.

4.95 out of 5 average rating, 235 reviews

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

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

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!

Holiday rentals for every style

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Convenient locations with everyday essentials

Popular amenities for Illinois rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 25 reviews

Home in Benton

Rend Lake Retreat

WillRating, 5 stars2 weeks ago

This house is amazing. Breakfast while overlooking the horse pasture, dinner out on the back deck. Everything in the house was spotless! The shower was so great. It had good water pressure! The beds were so comfy, I got the best sleep here. Better than I've gotten in a long time! The pool was clean. My kids enjoyed it, even though it was chilly out! They also enjoyed the games in the garage. My kids loved the popcorn machine, what a fun touch! The location is perfect. It's out in the country, but close enough to other towns that a run to the store doesn't take all day. It's very close to several Rend Lake Day Use Areas, which makes going out fun and easy! 10/10 Will stay again.

4.98 out of 5 average rating, 66 reviews

Home in Urbana

Cozy Cottage on Mumford

AntheaRating, 5 stars2 days ago

Pictures don’t do this place justice! Nicely decorated; gorgeous and private back yard; kitchen well-stocked and beds very comfortable. Pool was an extra bonus. Neighborhood was nice as well. We will definitely be back!

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.

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. ❤️

4.94 out of 5 average rating, 64 reviews

Galena Getaway Retreat | 3BD/3BA | Hot Tub + Games

StaceyRating, 5 stars1 week ago

The Ravine Lodge is a relaxing spot to truly getaway and unplug. A short distance to downtown Galena and a few miles to the main Owners Lodge where the pool and gym are located. Windy roads so driving at night may not be ideal for some. Home was very clean and had all the amenities. We would come back!!

4.95 out of 5 average rating, 38 reviews

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.

4.95 out of 5 average rating, 19 reviews

Home in Geneseo

Charming Geneseo Farmhouse

MaryRating, 5 stars2 days ago

My friend wanted a place to hang out and relax with her bridesmaids for her bachlorette party and this was the perfect place! we were never bored. The pool was amazing, plenty of land to play wiffleball and corn hole and the house was absolutley gorgeous! The host was very responsive and answered any questions I had. I would highly recommend this place!

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Apartment rentals with a pool

Apartment in Downers Grove

4.92 out of 5 average rating, 63 reviews

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

Apartment 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.

Apartment 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.

Apartment 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

Apartment 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

Apartment 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.

Apartment 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.