Pittsylvania County rentals with pool

We found 268 rentals with pool — enter your dates for availability

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October 2025

November 2025

Explore Pittsylvania County rentals with pools

New pool liner installed....filling with pool water 7-21

Miles to VIR, Caesar's VA Casino, Martinsv'l , S.Boston, Priv. Pool POOLS OPEN

Sleeps 8 · 3 bedrooms · 2 bathrooms

Premier Host

Beautiful waterfront lodge, private dock and breath taking views of Smith Mt.

Sleeps 8 · 3 bedrooms · 3 bathrooms

Whispering Pines Estate, Waterfront Luxury w/ Covered Verandas + Heated Salt Pool, Hot Tub, Dock!

Sleeps 24 · 9 bedrooms · 6 bathrooms

Premier Host

Lagom at the Lake - Large and Cozy lake front home. Quiet cove, beautiful views!

Sleeps 14 · 7 bedrooms · 6+ bathrooms

Hideaway Ridge, Lakefront NEW Luxury w/ 7-Bedrooms + Heated Salt Pool, Covered Decks, Hot Tub & Dock

Sleeps 20 · 7 bedrooms · 5 bathrooms

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Rentals with Pool in Pittsylvania County

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