Book Family Friendly Rentals in Castiglion Fiorentino

We selected the 2378 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.

Fresh As a Vine

Fresh As a Vine

  • 11 guests

  • 6 bedrooms

Montecchio, Castiglion Fiorentino

Overlooking the lush Chiana Valley, this former farmhouse boasts views you won’t be forgetting any time soon. There are plenty of spots to sit back and soak it all in, but the pergola’s one of our favourites, perched right next to the pool and offering plenty of room for dining alfresco.

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.

Il Sogno

Il Sogno

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

When it comes to Tuscan idylls, this home ticks all the boxes. Set amongst Cortana’s rolling green hills, this renovated 19th century house is full of quiet corners and scenic spots waiting to welcome you into a world of rest and relaxation.


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

Explore the 2378 most perfect homes in our collection

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Most popular homes in Castiglion Fiorentino

Fairytale in Cortona

Fairytale in Cortona

  • 8 guests

  • 3 bedrooms

Cortona, Arezzo

Rosewood Manor

Rosewood Manor

  • 18 guests

  • 9 bedrooms

Castiglion Fiorentino, Arezzo

A Touch Of Ivy

A Touch Of Ivy

  • 7 guests

  • 3 bedrooms

Cortona, Arezzo

La Tranquillità

La Tranquillità

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

By and By

By and By

  • 10 guests

  • 5 bedrooms

Fratticciola, Cortona

Old Tuscan Farmhouse

Old Tuscan Farmhouse

  • 8 guests

  • 3 bedrooms

Castiglion Fiorentino, Arezzo

Vita Toscana

Vita Toscana

  • 12 guests

  • 6 bedrooms

Arezzo, Tuscany

Tuscan Garden

Tuscan Garden

  • 12 guests

  • 6 bedrooms

Castiglion Fiorentino, 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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