Photo by Frank Livermore

Calumet County rentals with pool

We found 90 rentals with pool — enter your dates for availability

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September 2025

October 2025

Explore Calumet County rentals with pools

Premier Host

Charming cottage on Lake Winnebago

Sleeps 6 · 3 bedrooms · 2 bathrooms

Pool cover can be closed or open. Here is how it looks being closed.

Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater

Sleeps 30 · 7 bedrooms · 6+ bathrooms

Experience Wisconsin in an old farmhouse in the beautiful Kettle Moraine

Sleeps 5 · 1 bedroom · 1 bathroom

Premier Host

Lovely Lake Winnebago beachfront home, EAA, Packers, water activities, skiing

Sleeps 9 · 3 bedrooms · 3+ bathrooms

Find spaces that suit your style

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Rentals with Pool in Calumet County

Rentals with Pool in Chilton

Rentals with Pool in Sherwood

Rentals with Pool in New Holstein

Rentals with Pool in Stockbridge

Rentals with Pool in Forest Junction

Rentals with Pool in Hilbert

Rentals with Pool in Potter

Rentals with Pool in Brillion

Holiday Rental options in Calumet County

Family-friendly holiday rentals in Calumet County

Oceanfront holiday rentals in Calumet County

Holiday rentals with spa pool in Calumet County

Lake holiday rentals in Calumet County

Beach holiday rentals in Calumet County

Ski holiday rentals in Calumet County

Mountain holiday rentals in Calumet County

Pet-friendly holiday rentals in Calumet County

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