Pittsylvania County rentals with pool

We found 193 rentals with pool — enter your dates for availability

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November 2025

December 2025

Explore Pittsylvania County rentals with pools

Country Vineyard Escape 5-bedroom farmhouse

Sleeps 12 · 5 bedrooms · 3+ bathrooms

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

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

Sleeps 20 · 7 bedrooms · 5 bathrooms

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

Sleeps 24 · 9 bedrooms · 6 bathrooms

7 BR Manor - Add DIY Wedding 750 dollars, 7th night free ending on a weekday.

Sleeps 24 · 8 bedrooms · 4 bathrooms

Top rated rentals with pools - Pittsylvania County

Premier Host

SML - first lakeside stay

Property was very tidy, comfortable, attention to detail, peaceful and private, and walking distance to additional amenities for Mariners Landing guests.

Lisa D.

Stayed June 2023

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