Vacation Rentals with Pool in Illinois

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Filtering by: Swimming pool

37 vacation rentals

(6) Very Good 

34

Large Executive Estate with pool in Quiet Neighborhood

Illinois / Carbondale

Carbondale house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$178

Price per night from

$178

(2) Excellent 

24

Spacious Utica Townhouse w/ Private Deck & Views!

Illinois / Utica

Utica house

3 18 min stay varies

  • 3 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$309

Responds fast!
avg. 39 minutes

Price per night from

$309

(6) Excellent 

Certificate of Excellence

32

GRAND BEAR RESORT LUXURY CABIN - 40% OFF!

Illinois / Utica

Utica townhouse

3 15 2 nights min

  • 3 bedrooms
  • sleeps 15
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Certificate of Excellence

Price per night from

$372

Responds fast!
avg. 2 hours 48 minutes

Price per night from

$372

(1) Excellent 

11

Adorable Park Model On The Water In Lake Sara Camp

Illinois / Effingham

Effingham house

2 10 2 nights min

  • 2 bedrooms
  • sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$143

Price per night from

$143

(4) Excellent 

12

The Carbondale Pool House

Illinois / Carbondale

Carbondale guest house

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$143

Price per night from

$143

(1) Excellent 

20

Serenity Cabins - Rustic, modern cabin w/fireplace, pool table & wifi

Illinois / Galena

Galena log cabin

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$297

Responds fast!
avg. 9 minutes

Price per night from

$297

(7) Excellent 

24

Inviting, Serene Golf Villa in Galena Territory

Illinois / Galena

Galena villa

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Nice peaceful stay” I enjoyed my stay at the SeRene Golf Villa. It was very peaceful, and the drive to get there was beautiful! It wasn't that far from Galena, and I enjoyed the views as I drove to town. The owner's club was a short drive, and I en
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Price per night from

$114

Responds fast!
avg. 53 minutes

Price per night from

$114

(17) Excellent 

Certificate of Excellence

16

Enjoy 4 Bed/3Bath and true resort living

Illinois / Galena

Galena house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Wonderful!!” Traveled with family. We had a great time. The location and property was exactly what we needed. We really enjoyed the fully stocked house. Literally you don't need to bring anything. And Galena. Wonderful. The kids really enjoyed the
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Certificate of Excellence

Price per night from

$287

Responds fast!
avg. 1 hour 35 minutes

Price per night from

$287

(1) Very Good 

15

Beautiful Home near Chicago, IL

Illinois / Tinley Park

Tinley Park house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$487

Price per night from

$487

(4) Excellent 

23

Stunning Home Away From Home.

Illinois / Galena

Galena house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$344

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$344

(13) Very Good 

13

Family Friendly; Pet friendly Settlement Home

Illinois / Galena

Galena cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$170

Responds fast!
avg. 2 hours 31 minutes

Price per night from

$170

(3) Excellent 

15

Comfort House

Illinois / Galena

Galena house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$367

Price per night from

$367

24

Peaceful Custom Carbondale Home w/Pool Near SIU!

Illinois / Carbondale

Carbondale house

3 9 min stay varies

  • 3 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$246

Responds fast!
avg. 39 minutes

Price per night from

$246

24

Cozy 2BR Utica Townhouse w/Resort-Style Amenities!

Illinois / Utica

Utica villa

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$189

Responds fast!
avg. 7 minutes

Price per night from

$189

(2) Excellent 

15

Perfect Getaway -Quiet Cul de Sac-Lg 3 bdrm 3 bath

Illinois / Galena

Galena townhouse

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$201

Responds fast!
avg. 1 hour 5 minutes

Price per night from

$201

(1) Excellent 

30

NEWLY RENOVATED!! Beautiful Golf Villa Waiting Just For You!

Illinois / Galena

Galena villa

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$155

Price per night from

$155

25

Utica Resort Townhome by Starved Rock State Park!

Illinois / Utica

Utica house

3 18 min stay varies

  • 3 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$407

Responds fast!
avg. 36 minutes

Price per night from

$407

(1) Excellent 

46

Starved Rock Country Estate

Illinois / Peru

Peru house

5 16 2 nights min

  • 5 bedrooms
  • sleeps 16
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$785

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$785

24

NEW! 2BR South Beloit Apartment w/ Pool & Hot Tub!

Illinois / South Beloit

South Beloit apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$126

Responds fast!
avg. 39 minutes

Price per night from

$126

(24) Excellent 

18

Enjoy a Cozy, Secluded, Affordable Galena Retreat!

Illinois / Galena

Galena apartment

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Amazing deal!” I came with a small group for a weekend getaway in March 2013. Unlike other rentals, this place was fully stocked with the little things most people forget. (Coffee, ketchup, syrup, cooking oil, face wipes etc.) This is an end unit and
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Price per night from

$157

Responds fast!
avg. 1 hour 33 minutes

Price per night from

$157

9

6 Bedroom Home in Western Suburbs with Heated Pool

DuPage County / Downers Grove

Downers Grove house

6 15 3 nights min

  • 6 bedrooms
  • sleeps 15
  • 3 nights min
  • Nearest beach 27 mi
  • Swimming pool
  • Child Friendly

Price per night from

$744

Responds fast!
avg. 2 hours 27 minutes

Price per night from

$744

(4) Excellent 

12

Walnut Hill House

Illinois / Galena

Galena house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary
“Beautiful vacation home” We loved this perfectly maintained home.Everything we wanted was in the area biking,hiking,pool, golf and restaurants. Great location and views.
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Price per night from

$338

Responds fast!
avg. 33 minutes

Price per night from

$338

(2) Excellent 

24

Nice Galena Home w/Huge Patio, Hot Tub & Fire Pit!

Illinois / Galena

Galena house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$361

Responds fast!
avg. 7 minutes

Price per night from

$361

(10) Very Good 

7

Marsha's Guesthouse Rental

Illinois / DuQuoin

DuQuoin house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“This is truly a hidden treasure!!!” The guesthouse is gorgeous and private. There was everything we needed including full kitchen with dishes, internet, bath towels and 3 TVs. They gave us the whole pool area to ourselves and we only saw them about
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Price per night from

$92

Responds fast!
avg. 2 hours 40 minutes

Price per night from

$92

(1) Excellent 

28

The Cedar Rim Home

Illinois / Galena

Galena house

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$743

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$743

6

Best Waterfront Luxury Property in Chain of Lakes Brand New Villa Private Events

Lake County / Lake Villa

Lake Villa house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,400

Price per night from

$1,400

7

Awesome Value! Spacious Loft for 6 with Pool + Free Daily Breakfast

Illinois / Bloomington-Normal

Bloomington-Normal condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$55

Price per night from

$55

(5) Excellent 

10

Grand Bear Updated Lux Cabin: Chef kitch,Wi-Fi,Sleep 12 SWIM/HIKE/FISH/BOAT/GOLF

Illinois / Utica

Utica townhouse

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$430

Responds fast!
avg. 1 hour 10 minutes

Price per night from

$430

(8) Excellent 

10

Fall Rates /Stay 7 nights for the price of 5 /Wifi

Illinois / Galena

Galena house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Wonderful Experience” What a great place to celebrate a family milestone, my parents 50th Wedding annivewrsary. We had both adults and children traveling with us to enjoy all of the amenties that the house offers. The owner has done a fantastic job
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Price per night from

$487

Responds fast!
avg. 3 hours 54 minutes

Price per night from

$487

41

⭐ Hot Tub, Sauna, Steam Shower & Chefs Kitchen ⭐

Illinois / Galena

Galena house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$516

Price per night from

$516

(10) Very Good 

22

Fox River Resort

Illinois / Sheridan

Sheridan condo

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$103

Price per night from

$103

16

Craig Manor - - Pool Open -Book Events

Illinois / Godfrey

Godfrey house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$86

Price per night from

$86

9

Awesome Value! Spacious Rental for 4 with Pool + Free Daily Breakfast

Illinois / Bloomington-Normal

Bloomington-Normal condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$109

Price per night from

$109

61

Chicago Countryside Condo

Illinois / Sheridan

Sheridan condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 46 mi
  • Swimming pool
  • Ski

Price per night from

$94

Responds fast!
avg. 2 hours 9 minutes

Price per night from

$94

6

Wyndham Galena - a Resort Close to Shopping and Sk

Illinois / Galena

Galena hotel apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$458

Price per night from

$458

7

Awesome Value! Spacious Suite for 4 with Pool + Free Daily Breakfast

Illinois / Bloomington-Normal

Bloomington-Normal studio

Studio 4 min stay varies

  • Studio
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$98

Price per night from

$98

9

Two Bedroom Family Cottage at Sunset Lakes RV Resort in Hillsdale

Illinois / Hillsdale

Hillsdale house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$185

Price per night from

$185