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Castelnuovo Berardenga rentals with pool

We found 2,488 rentals with pool — enter your dates for availability

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August 2025

September 2025

Explore Castelnuovo Berardenga rentals with pools

BEAUTIFUL VILLA with private Pool in the heart of Chianti

Sleeps 14 · 7 bedrooms · 6 bathrooms

Back of house with covered terrace for alfresco dining

Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Sleeps 10 · 5 bedrooms · 3 bathrooms

Beautiful Private & Luxurious Tuscan Villa Near Siena/Scenic Views/Crete Senesi

Sleeps 7 · 3 bedrooms · 3+ bathrooms

FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI

Sleeps 9 · 5 bedrooms · 4+ bathrooms

Top rated rentals with pools - Castelnuovo Berardenga

Premier Host

Spectacular!

Would highly recommend! The property is stunning - perfect for our extended family, with everything you could need for young and old. The views are breathtaking! Gaia was incredibly communicative and a generous and responsive host. Thank you for such a wonderful stay!

Simone L.

Stayed Sept 2024

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