Illinois Vacation Rentals with Pools
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $261/Night
For 7 Nights US $1,826
452.08 ft²
4 Guests
1 Bedroom
1 Bathroom
Apartment
- Private Pool
- Oceanfront
- Fireplace/Heating
US $117/Night
For 7 Nights US $819
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $1,306/Night
For 7 Nights US $9,143
8 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $165/Night
For 7 Nights US $1,153
1435.19 ft²
32 Guests
13 Bedrooms
12 Bathrooms
Apartment
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,582/Night
For 7 Nights US $11,076
1557 ft²
7 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $368/Night
For 7 Nights US $2,579
3003.13 ft²
14 Guests
6 Bedrooms
6 Bathrooms
Villa
- Private Pool
- Hot Tub
- Spa
US $717/Night
For 7 Nights US $5,017
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $230/Night
For 7 Nights US $1,610
1571.53 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $314/Night
For 7 Nights US $2,199
1500 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $211/Night
For 7 Nights US $1,480
2400.35 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Free Cancellation
House
- Private Pool
- Spa
- Fireplace/Heating
US $494/Night
For 7 Nights US $3,456
970 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $146/Night
For 7 Nights US $1,020
Why Choose Rent By Owner for your Illinois Vacation Rentals with Pools?
What makes our Vacation Rentals with Pools special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Illinois
How to Book Your Illinois Vacation Rentals with Pools
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals with pools. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Illinois
Common Vacation Rentals with Pools Amenities
What amenities can you expect?
Our Vacation Rentals with Pools are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Illinois, IL
Chicago
Cook County
Chicago
Central Chicago
Downtown Chicago
West Side
North Side
The Loop
Jo Daviess County
Lake County
Near North Side
Galena
Illinois Vacation Rentals with Pools Frequently Asked Questions
1. What are the top Rentals With Pools in Illinois?
There are a lot of options in Illinois. If you plan on staying in the Illinois area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Rentals With Pools in Illinois:
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- Escape! Hot Tub, Fire Pit, 3 Decks, WiFi, Pool Table
- Westaway-Spacious Home w/Private Hot Tub, Fireplace, Amazing 1st Floor Layout
- Charming 3BR/3BA With Hot Tub, Fireplace & Pool Table
- Galena Oak Glen Getaway near Shopping, Golfing, Hiking
- Picture Perfect Galena Getaway on Golf Course | 4 Bed 4 Bath | Hot Tub & FirePit
- 55th Floor Penthouse with Award-Winning Views
- Welcome to your Galena Get Away!
- The Cottage on Lake Galena
- North Woods Inspired Lodge Hot Tub + Fire Pit Galena Territory Retreat
2. How many Rentals With Pools are available in Illinois?
Currently, the total number of properties listed by RBO in 2026 is over 3859 in the Illinois area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Illinois.
More Rentals You May Like Near Illinois
1603.82 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $454/Night
For 7 Nights US $3,178
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
US $80/Night
For 7 Nights US $560
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $223/Night
For 7 Nights US $1,558
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Private Pool
- Fireplace/Heating
- Pool
US $142/Night
For 7 Nights US $994
560 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Pool
US $230/Night
For 7 Nights US $1,608
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $150/Night
For 7 Nights US $1,049
900 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $102/Night
For 7 Nights US $712
600 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Pool
US $258/Night
For 7 Nights US $1,805
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Pool
- Kitchen
- Air Conditioner
US $323/Night
For 7 Nights US $2,258
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $173/Night
For 7 Nights US $1,209
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $112/Night
For 7 Nights US $785
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $115/Night
For 7 Nights US $808
