Jo Daviess County rentals with pool

We found 446 rentals with pool — enter your dates for availability

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September 2025

October 2025

Explore Jo Daviess County rentals with pools

The Gleneagle Suite (bottom) and our Seven Sisters Suite (Top two levels)

Premier Host

Romantic, Rustic, Secluded, Private

Sleeps 4 · 1 bedroom · 1 bathroom

Premier Host

Beautiful compound, 10 mile views, on 300 acre ranch, next to Galena Territory

Sleeps 24 · 11 bedrooms · 6 bathrooms

43ft x 21ft MASSIVE pool! Splash right in!

Premier Host

Bring Everyone Home for the Holidays! 7 bedrm & 6 baths | 2 game rooms | hot tub

Sleeps 15 · 7 bedrooms · 5+ bathrooms

Premier Host

Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL

Sleeps 12 · 6 bedrooms · 3+ bathrooms

Find spaces that suit your style

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Holiday Rental options in Jo Daviess County

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Explore Jo Daviess County rentals with pools

Romantic, Rustic, Secluded, Private

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

Beautiful compound, 10 mile views, on 300 acre ranch, next to Galena Territory

Bring Everyone Home for the Holidays! 7 bedrm & 6 baths | 2 game rooms | hot tub

Romantic, Secluded, Private, Rustic Cottages

Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL

Find spaces that suit your style

Rentals with Pool in Jo Daviess County

Holiday Rental options in Jo Daviess County