Book Luxury Villas in Castellina in Chianti

We selected the 1992 homes worth renting in this location

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Home spotlights in Castellina in Chianti

The Summer Harvest

The Summer Harvest

  • 14 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

Nestled among hills dotted with olive groves and vineyards, this villa makes a comfortable base for large groups and family gatherings. Inside, you'll find two sitting rooms, two kitchens, and an array of cosy bedrooms.

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.

The Moon Sanctuary

The Moon Sanctuary

  • 22 guests

  • 11 bedrooms

Greve in Chianti, Florence

Immersed in the natural beauty of the Chianti hills, this home opens its doors to a magical stay with idyllic views. Consisting of a main house and three independent apartments, this is the perfect setting for families and groups in search of space to stretch out and spend quality time together.

Chianti Nights

Chianti Nights

  • 9 guests

  • 5 bedrooms

Barberino Tavarnelle, Florence

If you’re searching for somewhere to escape the hustle and bustle of everyday life, this Tuscan villa will be right up your street. Ideal for larger groups of friends or family, the countryside location is as peaceful as it gets.


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

Explore the 1992 most perfect homes in our collection

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Most popular homes in Castellina in Chianti

A Touch of Chianti

A Touch of Chianti

  • 8 guests

  • 4 bedrooms

Castellina in Chianti, Tuscany

Tuscan Hues

Tuscan Hues

  • 39 guests

  • 15 bedrooms

Greve in Chianti, Florence

Sweet Tuscany

Sweet Tuscany

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

Chianti Sunrise

Chianti Sunrise

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Chianti Breeze

Chianti Breeze

  • 10 guests

  • 5 bedrooms

Gaiole in Chianti, Siena

Sun of Splendour

Sun of Splendour

  • 15 guests

  • 7 bedrooms

Fonterutoli, Castellina in Chianti

Chianti Memories

Chianti Memories

  • 10 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

The Olive Tint

The Olive Tint

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

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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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