Castellina in Chianti Unique Homes

We selected the 3876 homes worth renting in this location

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Home spotlights in Castellina in Chianti

The Hilltop Dream

The Hilltop Dream

  • 12 guests

  • 6 bedrooms

Radda in Chianti, Tuscany

With breathtaking views across the Chianti countryside, this home will captivate you from the moment of arrival. There’s also a private pool, a peaceful garden and a pergola with a barbecue – perfect for alfresco dining.

Cypress Reflections

Cypress Reflections

  • 14 guests

  • 7 bedrooms

Barberino Tavarnelle, Florence

Step back in time and experience this Tuscan home, a beautifully restored estate dating back to around 1000 AD. This luxurious countryside escape has a private riverside beach, a swimming pool and plenty of areas to relax and dine in the sun.

Tuscan Hues

Tuscan Hues

  • 39 guests

  • 15 bedrooms

Greve in Chianti, Florence

Sitting atop the Chianti hills overlooking the Vignamaggio Valley, this stone estate blends traditional Tuscan charm with modern comforts. It’s perfect for a large group, with a main villa and a renovated barn offering three apartments.

Eternal Etruscan

Eternal Etruscan

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

Sit back, relax and soak up the sunshine at this characterful villa in Chianti. It may be a little dated inside, but the twin apartment layout is perfect for families and groups that want their own space.

We selected the top 3% holiday homes in Castellina in Chianti Unique Homes

Explore the 3876 most perfect homes in our collection

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Most popular homes in Castellina in Chianti

Il Nocino

Il Nocino

  • 8 guests

  • 4 bedrooms

Castellina in Chianti, Tuscany

The Etruscan View

The Etruscan View

  • 4 guests

  • 2 bedrooms

Galenda, Gaiole in Chianti

Vino Classico

Vino Classico

  • 8 guests

  • 3 bedrooms

Villa, Radda in Chianti

Rose Garden

Rose Garden

  • 2 guests

  • 2 bedrooms

Radda in Chianti, Tuscany

Terracotta & Vine

Terracotta & Vine

  • 6 guests

  • 3 bedrooms

San Sano, Gaiole in Chianti

Chianti Sunset

Chianti Sunset

  • 10 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

The Tuscan Moon

The Tuscan Moon

  • 10 guests

  • 5 bedrooms

Castellina in Chianti, Tuscany

The Vine Vineyard

The Vine Vineyard

  • 18 guests

  • 11 bedrooms

Castelnuovo Berardenga, Siena

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Frequently asked questions

Plum guide offers a handpicked selection of the most unique homes in Castellina in Chianti, Siena, Tuscany, Italy. Our homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book a short or extended stay and secure the most unique home in Castellina in Chianti, Siena, Tuscany, Italy for your next getaway. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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