Photo by Jocey Hurt

Chesterfield County rentals with pool

We found 61 rentals with pool — enter your dates for availability

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September 2025

16

October 2025

Explore Chesterfield County rentals with pools

Interior

Premier Host

Charming 1-bedroom suite with WiFi and AC in Bon Air

Sleeps 7 · 1 bedroom · 1 bathroom

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

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

Find spaces that suit your style

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Rentals with Pool in Chesterfield County

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Holiday rentals with spa pool in Chesterfield County

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