Book Luxury Villas in Radda in Chianti

We selected the 1830 homes worth renting in this location

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Home spotlights in Radda in Chianti

Mulberry & Olive

Mulberry & Olive

  • 6 guests

  • 3 bedrooms

Casanuova di Ama, Gaiole in Chianti

Full of charm, we love this home’s history. It’s hard to imagine its olive press past, save for the very obvious reminder in the living area.

Chianti Lake

Chianti Lake

  • 4 guests

  • 2 bedrooms

Gaiole in Chianti, Siena

Tucked away amid the picturesque Chianti Hills, this charming villa offers a peaceful escape. It’s on an agriturismo with five villas and direct access to a beautiful lake where you can swim and sunbathe.

The Olive Vine

The Olive Vine

  • 6 guests

  • 3 bedrooms

Gaiole in Chianti, Siena

Just outside of Gaiole's idyllic town, serving authentic cuisine and Chianti wine, this hillside home offers pastoral vistas. There's an upside-down layout inside, putting the bedrooms below the living space, which opens out onto several terraces and a leafy garden with an infinity pool.

An Italian Tale

An Italian Tale

  • 14 guests

  • 7 bedrooms

Radda in Chianti, Tuscany

This former lookout tower once guarded the passage between Florence and Siena. Today, it exists as a calm sanctuary offering idyllic views, a private pool and serene grounds.


We selected the top 3% holiday homes in Radda in Chianti Villas

Explore the 1830 most perfect homes in our collection

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Most popular homes in Radda in Chianti

Chianti Classico

Chianti Classico

  • 12 guests

  • 6 bedrooms

Radda in Chianti, Tuscany

The Chianti Essence

The Chianti Essence

  • 8 guests

  • 4 bedrooms

Gaiole in Chianti, Siena

Sangiovesece Scenery

Sangiovesece Scenery

  • 6 guests

  • 3 bedrooms

Gaiole in Chianti, Siena

Chianti Dream

Chianti Dream

  • 4 guests

  • 2 bedrooms

San Sano, Gaiole in Chianti

First Of The Summer Wine

First Of The Summer Wine

  • 6 guests

  • 4 bedrooms

Castellina in Chianti, Tuscany

Citrus Pavillion

Citrus Pavillion

  • 20 guests

  • 9 bedrooms

Gaiole in Chianti, Siena

The Olive Stone

The Olive Stone

  • 6 guests

  • 3 bedrooms

Gaiole in Chianti, Siena

Sweet Tuscany

Sweet Tuscany

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

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Frequently asked questions

Secure a luxury stay in one of the remarkable Villas in our Radda in Chianti, Siena, Tuscany, Italy collection. Our quality and consistency is unmatched, with only the top 3% of homes making it onto our site. Our meticulous home experts test everything from shower pressure to a home's feel and atmosphere, so there really is no need to worry about a thing. Your chosen home is also guaranteed to be fully furnished, with an excellently-equipped kitchen, essential bathroom toiletries, and linens all included. Acquire the help of our friendly experts, on standby 24/7 and always eager to assist you in your hunt for the finest luxury Villa in the entirety of Radda in Chianti.

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