Dickinson County rentals with pool

We found 238 rentals with pool — enter your dates for availability

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September 2025

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October 2025

Explore Dickinson County rentals with pools

One of the best places to see the sunset in Okoboji!

Premier Host

Lakefront Luxury! Spacious corner condo, wrap around deck. 6 BB waterpark passes

Sleeps 12 · 4 bedrooms · 2 bathrooms

Exterior

Premier Host

Heart Of Arnold's Park Near West Lake. Family And Friends Sleeps 18

Sleeps 21 · 7 bedrooms · 4 bathrooms

Enjoy a gorgeous lake view while seated comfortably around the fire table.

Premier Host

Lake view condo! Updated unit with 8 beds and 6 waterpark passes at Bridges Bay.

Sleeps 10 · 3 bedrooms · 2 bathrooms

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Rentals with Pool in Dickinson County

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Rentals with Pool in Okoboji

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Rentals with Pool in Milford

Holiday Rental options in Dickinson County

Oceanfront holiday rentals in Dickinson County

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Lake holiday rentals in Dickinson County

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Family-friendly holiday rentals in Dickinson County

Beach holiday rentals in Dickinson County

Ski holiday rentals in Dickinson County

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