Castellina in Chianti Family Friendly Hotel Alternatives

We selected the 3058 homes worth renting in this location

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Age 1 to 12

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Home spotlights in Castellina in Chianti

A Truffled Retreat

A Truffled Retreat

  • 19 guests

  • 10 bedrooms

Castellina in Chianti, Siena

This Italian villa caught our eye for its panoramic views of the Tuscan countryside. There’s plenty to make your holiday memorable here, including both indoor and outdoor pools, a sauna, and a private wine cellar.

Il Nocino

Il Nocino

  • 8 guests

  • 4 bedrooms

Castellina in Chianti, Tuscany

This charming cottage is tucked away on an authentic working vineyard, beside a family farmhouse. It’s just 1 kilometre from Castellina in Chianti, and within driving distance of Sam Gimignano, Siena, and Florence – you’ll have plenty of options for day trips.

Tuscan Orgins

Tuscan Orgins

  • 10 guests

  • 5 bedrooms

Castellina in Chianti, Tuscany

From the countryside views to the traditional character inside, there's no denying that this home is unmistakably Tuscan. It's situated among a working vineyard, offering access to the estate's communal pool and a shared garden.

First Of The Summer Wine

First Of The Summer Wine

  • 6 guests

  • 4 bedrooms

Castellina in Chianti, Tuscany

Surrounded by olive trees and vast swathes of vineyards, this Tuscan home in the heart of the Chianti wine region is a haven of rural relaxation. Its exposed stone exterior gives way to a bright interior, where farmhouse simplicity meets elegant design in the living room.


We selected the top 3% holiday homes in Castellina in Chianti Family Friendly Hotel Alternatives

Explore the 3058 most perfect homes in our collection

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Most popular homes in Castellina in Chianti

Classic Moments

Classic Moments

  • 10 guests

  • 5 bedrooms

Castellina in Chianti, Tuscany

Being of Beauty

Being of Beauty

  • 18 guests

  • 9 bedrooms

Lilliano, Castellina in Chianti

The Rosso

The Rosso

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

Wild Onion

Wild Onion

  • 4 guests

  • 2 bedrooms

Fonterutoli, Castellina in Chianti

My Chianti Heart

My Chianti Heart

  • 12 guests

  • 4 bedrooms

Gaiole in Chianti, Siena

Wild Roses

Wild Roses

  • 10 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

Tales of Sunsets

Tales of Sunsets

  • 4 guests

  • 2 bedrooms

Barberino Tavarnelle, Florence

A Taste of the Hills

A Taste of the Hills

  • 2 guests

  • 1 bedrooms

Castellina in Chianti, Tuscany

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Frequently asked questions

Explore our family friendly hotel alternatives in Castellina in Chianti, Siena, Tuscany, Italy. We’ve cherry-picked a collection of spacious homes in safe, residential neighbourhoods popular with local parents. Find a fully furnished home with fun kids' bedrooms, well-equipped kitchens, multiple bathrooms and often outdoor space too. Our friendly team of Plum Experts are on-hand 24/7 to help you book your dream family friendly hotel alternative in Castellina in Chianti, Siena, Tuscany, Italy.

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