Pittsylvania County rentals with pool

We found 192 rentals with pool — enter your dates for availability

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December 2025

January 2026

Explore Pittsylvania County rentals with pools

Exterior

Country Vineyard Escape 5-bedroom farmhouse

Sleeps 12 · 5 bedrooms · 3+ bathrooms

Exterior

Premier Host

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

Sleeps 8 · 3 bedrooms · 3 bathrooms

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

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

Sleeps 8 · 3 bedrooms · 2 bathrooms

Heated Salt Pool

Firefly Estate, Lakefront Luxury w/ Covered Verandas + Heated Salt Pool, Hot Tub, Dock!

Sleeps 24 · 9 bedrooms · 6 bathrooms

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Rentals with Pool in Pittsylvania County

Holiday Rental options in Pittsylvania County

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