Certaldo villa rentals

We found 332 villa rentals — enter your dates for availability

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August 2025

September 2025

Explore Certaldo villa rentals

Old villa nestled in the hills of Chianti

Sleeps 12 · 5 bedrooms · 6 bathrooms

VILLA BELSOLE - Certaldo Tuscany HEATED POOL and electric car recharge

Sleeps 18 · 9 bedrooms · 0+ bathrooms

Exclusive panoramic villa with private pool between Florence and Siena.

Sleeps 12 · 7 bedrooms · 8+ bathrooms

Top rated villa rentals - Certaldo

Premier Host

San Gimignano Gem

Beautiful. We had 7 wonderful days at La Porticciola. Alessandro the host was very approachable and even arranged for a cook to come in for 2 nights. Imagine sitting on the terrace having a wonderful meal below the lights of San Gimignano. Magical

Debra W.

Stayed Sept 2024

Premier Host

Absolutely amazing! Beat all my families expectations

The property is in excellent condition and the location will truly blow your mind. I was so impressed that I plan on booking again. I honestly cannot fault this property. Gabriele went above and beyond to make sure everything was just perfect.

Samantha W.

Stayed July 2017

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