Manchester showing a high-rise building and a city

Hillsborough County rentals with pool

We found 44 rentals with pool — enter your dates for availability

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September 2025

13

October 2025

Explore Hillsborough County rentals with pools

Journey Cake Farm, a magical retreat for friends and families to gather.

Charming 1840 Farmhouse ~ Magical Retreat ~ sleeps 14

Sleeps 14 · 7 bedrooms · 4+ bathrooms

Castle in the Fall

Premier Host

Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!

Sleeps 22 · 8 bedrooms · 5+ bathrooms

Find spaces that suit your style

Holiday Rental options in Hillsborough County

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Holiday rentals with spa pool in Hillsborough County

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