Photo by Ginie Ying

Town of Highland rentals with pool

We found 240 rentals with pool — enter your dates for availability

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October 2025

November 2025

Explore Town of Highland rentals with pools

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The Cabin at Deep Hollow

Sleeps 16 · 5 bedrooms · 2+ bathrooms

Indoor/ outdoor pool partially open (surrounding pool fence not shown)

Premier Host

Indoor Pool, 11 yrs hosting, 7 bdrm, Hot Tub, Designer Home, Stunning Kitchen

Sleeps 18 · 7 bedrooms · 5+ bathrooms

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