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Chesterfield County rentals with pool

We found 52 rentals with pool — enter your dates for availability

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December 2025

15

January 2026

Explore Chesterfield County rentals with pools

The Pool Pavilion: 3 king beds, 2 full baths and fully stocked kitchen.

Premier Host

2 Water Front homes w/Pool-Enjoy Resort style!

Sleeps 20 · 8 bedrooms · 4+ bathrooms

The Pool Pavilion overlooking the Beautiful Swift Creek Reservoir.

Premier Host

“WaterView" The Pool Pavilion, waterfront property assisted handicap access.

Sleeps 8 · 4 bedrooms · 2 bathrooms

WaterView's "Iconic Gem"
8 bdrm estate home on 100 acre estate property.

Premier Host

3 Family friendly Waterfront homes w/pool, private property with amenities!

Sleeps 16 · 19 bedrooms · 10+ bathrooms

The "Iconic Gem" is the main estate residence, 8 bedrooms sleeping 18.

Premier Host

Water Front Iconic Gem Estate w Pool Pavilion Retreat indoor & outdoor amenities

Sleeps 13 · 13 bedrooms · 8 bathrooms

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Rentals with Pool in Chesterfield County

Holiday Rental options in Chesterfield County

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