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Rent Luxury Holiday Cottages in Castiglion Fiorentino

We selected the 94 homes worth renting in this location

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Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Castiglion Fiorentino

Tuscan Tradition

Tuscan Tradition

  • 8 guests

  • 4 bedrooms

Fratticciola, Cortona

Leave the tourist trail behind and embrace authentic Tuscan village life during a stay at this charming four-bedroom cottage. The charming stone facade is comfortably the oldest in town, with a history dating back hundreds of years, we're sure this place would have some stories to tell.

The Terracotta Sun

The Terracotta Sun

  • 6 guests

  • 4 bedrooms

Arezzo, Tuscany

Surrounded by olive groves and ancient woods, this traditional farmhouse welcomes you to an authentic stay in the heart of Tuscany. Located on Pomaio hill with sweeping views across the countryside, this is a wonderful setting to retreat into the heart of nature.

La Tranquillità

La Tranquillità

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

This quaint redbrick villa with its duck-egg-blue shutters and intoxicating gardens is an enchanting escape in the south of Tuscany. Bordered by thick, leylandii hedges, the hectare of grounds is a symphony of colour, with blooming flowers and lush Mediterranean verdure.

A Tranquil Place

A Tranquil Place

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

Set in the foothills fringing the medieval town of Cortona and surrounded by olive and fir trees, the setting of this traditional cottage couldn't be more Tuscan if it tried. The interiors may be too rustic for some, but they would perfectly suit a small family or group of friends looking for a fuss-free stay.


We selected the top 3% holiday homes in Castiglion Fiorentino Cottages

Explore the 94 most perfect homes in our collection

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Most popular homes in Castiglion Fiorentino

Tuscan Haven

Tuscan Haven

  • 2 guests

  • 2 bedrooms

Sovicille, Tuscany

Chianti Sunrise

Chianti Sunrise

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

A Glass Of Chianti

A Glass Of Chianti

  • 2 guests

  • 1 bedrooms

Montespertoli, Florence

The Valley

The Valley

  • 9 guests

  • 5 bedrooms

Castellina in Chianti, Tuscany

Chianti Hills

Chianti Hills

  • 12 guests

  • 6 bedrooms

Gaiole in Chianti, Siena

Honey & Lavender

Honey & Lavender

  • 10 guests

  • 5 bedrooms

San Casciano dei Bagni, Tuscany

Tuscan Flow

Tuscan Flow

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

A Rustic Reverie

A Rustic Reverie

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Castiglion Fiorentino, Arezzo, Tuscany, Italy. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Castiglion Fiorentino Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

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