Book Family Friendly Rentals in Castiglion Fiorentino

We selected the 2322 homes worth renting in this location

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Home spotlights in Castiglion Fiorentino

Ten Green Bottles

Ten Green Bottles

  • 17 guests

  • 6 bedrooms

Foiano della Chiana, Tuscany

Set in 30,000 square metres of grounds, this home is the Tuscan dream. There’s a turquoise swimming pool for hot summer days, a volleyball and football pitch, and a well-tended orto (vegetable garden) where you can help yourself to seasonal sun-ripened produce and cook just like a local.

Valley Vista Villa

Valley Vista Villa

  • 10 guests

  • 5 bedrooms

Cortona, Arezzo

Located just one mile from the hilltop town of Cortona, this Tuscan villa is made up of two apartments in one charming and traditional farmhouse. Both apartments have their own separate entrances, making this a great choice for large groups.

Now and Forever

Now and Forever

  • 18 guests

  • 9 bedrooms

Castiglion Fiorentino, Arezzo

A traditional Tuscan villa nestled in the pristine countryside just a thirty-five-minute drive from Arezzo, this home is every bit as magical as it looks. Steeped in history and packed with period features and antiques, it's a slice of old-world romance that's suitable for a large group holiday or a special celebration.

The Ancient Stone

The Ancient Stone

  • 11 guests

  • 5 bedrooms

Cortona, Arezzo

Perched on the hills overlooking the Val di Chiana, this beautiful home seamlessly blends rustic charm with elegant Tuscan style to create a truly unforgettable stay. Less than a fifteen–minute walk from the centre of Cortona, the owners have thoughtfully restored this traditional farmhouse into a welcoming space that exudes charm.


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

Explore the 2322 most perfect homes in our collection

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Most popular homes in Castiglion Fiorentino

The Valley of Angels

The Valley of Angels

  • 14 guests

  • 7 bedrooms

Cortona, Arezzo

Fairytale in Cortona

Fairytale in Cortona

  • 8 guests

  • 3 bedrooms

Cortona, Arezzo

Italian Iced Tea

Italian Iced Tea

  • 8 guests

  • 4 bedrooms

Pieve al Toppo, Civitella in Val di Chiana

A Touch Of Ivy

A Touch Of Ivy

  • 7 guests

  • 3 bedrooms

Cortona, Arezzo

The Main Event

The Main Event

  • 10 guests

  • 5 bedrooms

Metelliano, Cortona

View From The Evening

View From The Evening

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

Rosewood Manor

Rosewood Manor

  • 18 guests

  • 9 bedrooms

Castiglion Fiorentino, Arezzo

Timeless in Tuscany

Timeless in Tuscany

  • 8 guests

  • 4 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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