Book Luxury Villas in Castellina in Chianti

We selected the 2070 homes worth renting in this location

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Home spotlights in Castellina in Chianti

The Ode to Beauty

The Ode to Beauty

  • 14 guests

  • 7 bedrooms

Radda in Chianti, Tuscany

This traditional Tuscan home opens its doors to the natural beauty of the Chianti region. Nestled amid the trees, the private garden lends itself perfectly to lazy days by the pool.

The Rosso

The Rosso

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

Perched on the slopes of the Chianti hills, this stone villa effortlessly blends traditional Tuscan farmhouse charm with modern comforts. Since children under six aren’t permitted here, this villa is a perfect spot for a group seeking a retreat amongst sprawling gardens.

Old Vine's Jewel

Old Vine's Jewel

  • 12 guests

  • 6 bedrooms

Greve in Chianti, Florence

Tucked away in the hills of Chianti, among the vineyards and olive groves, this typically Tuscan villa is a real charmer. There’s a sunny swimming pool for leisurely laps or poolside lounging, a vine-covered terrace for dining al fresco, and plenty of peace and tranquillity to savour.

Grapes & Olives

Grapes & Olives

  • 10 guests

  • 5 bedrooms

Castellina in Chianti, Tuscany

Tucked into the rolling hills of Chianti, this villa sits on a working winery and olive oil farm – and yes, they do offer tastings. The lower half of the main villa is where the magic happens while upstairs has been transformed into a cosy apartment with exposed beams, a fireplace, modern kitchen and three characterful bedrooms.


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

Explore the 2070 most perfect homes in our collection

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Most popular homes in Castellina in Chianti

Vineyard Estate

Vineyard Estate

  • 4 guests

  • 2 bedrooms

Castellina in Chianti, Tuscany

First Of The Summer Wine

First Of The Summer Wine

  • 6 guests

  • 4 bedrooms

Castellina in Chianti, Tuscany

Village & Grape

Village & Grape

  • 10 guests

  • 5 bedrooms

Castellina in Chianti, Tuscany

Toscana Per Sempre

Toscana Per Sempre

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

Vino Classico

Vino Classico

  • 8 guests

  • 3 bedrooms

Villa, Radda in Chianti

Being of Beauty

Being of Beauty

  • 18 guests

  • 9 bedrooms

Lilliano, Castellina in Chianti

Eternal Etruscan

Eternal Etruscan

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

Tuscan Hilltop

Tuscan Hilltop

  • 37 guests

  • 18 bedrooms

Greve in Chianti, Florence

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Frequently asked questions

Secure a luxury stay in one of the remarkable Villas in our Castellina 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 Castellina in Chianti.

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