Book Family Friendly Rentals in Castiglion Fiorentino

We selected the 2316 homes worth renting in this location

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Home spotlights in Castiglion Fiorentino

Timeless Harmony

Timeless Harmony

  • 14 guests

  • 5 bedrooms

Arezzo, Tuscany

Made up of a main building and two annexes, nestled on a promontory and enjoying stunning views of the city and surrounding countryside, this home is a gorgeous blend of the traditional and the super modern. Sit by the fireplace in the main building or admire the art adorning the walls, or out by the private pool and catch some sun on the poolside loungers under the trees.

Tuscan Garden

Tuscan Garden

  • 12 guests

  • 6 bedrooms

Castiglion Fiorentino, Arezzo

Tucked away in Val di Chiana in the heart of the Tuscan countryside, this home promises an escape from it all. Ideal for larger groups, the main villa sleeps eight guests across four bedrooms.

Dreams of Yesterday

Dreams of Yesterday

  • 10 guests

  • 5 bedrooms

Santa Firmina, Arezzo

This is not your typical Italian villa. Sure, on the outside it looks familiar with its rustic stone walls and quaint shutters.

Wild Rosemary

Wild Rosemary

  • 10 guests

  • 5 bedrooms

Castiglion Fiorentino, Arezzo

A truly idyllic escape to rural Tuscany requires rolling hills, a rustic farmhouse and panoramic views across olive groves and vineyards. And you'll have all of this and more at this beautiful home deep in the countryside between Arezzo and Cortona.


We selected the top 3% holiday homes in Castiglion Fiorentino Family Friendly Rentals

Explore the 2316 most perfect homes in our collection

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Most popular homes in Castiglion Fiorentino

Ten Green Bottles

Ten Green Bottles

  • 17 guests

  • 6 bedrooms

Foiano della Chiana, Tuscany

The Terracotta Sun

The Terracotta Sun

  • 6 guests

  • 4 bedrooms

Arezzo, Tuscany

Timeless in Tuscany

Timeless in Tuscany

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

The Whispering Hills

The Whispering Hills

  • 6 guests

  • 2 bedrooms

Arezzo, Tuscany

The Ancient Stone

The Ancient Stone

  • 11 guests

  • 5 bedrooms

Cortona, Arezzo

Il Sogno

Il Sogno

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

The Softest Crimson

The Softest Crimson

  • 8 guests

  • 4 bedrooms

Le Corchie, Cortona

The Lucia

The Lucia

  • 10 guests

  • 5 bedrooms

Cortona, Arezzo

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Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Castiglion Fiorentino, Arezzo, Tuscany, Italy. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Castiglion Fiorentino Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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