Cortona In the region of Arezzo, on the border of Tuscany and Umbria lies the Etruscan town of Cortona, which offers stunning views of Lake Trasimeno. The city had an important position in the Middle Ages which can still be seen in the historic buildings and monuments. Some popular buildings include the old city wall with gates and towers, the Palazzo Communale, the town hall and the Museo dell'Academia Etrusca, where findings from the Etruscan and Roman times can be found, but also paintings. Cortona also has several old churches, with as its most important one Santuario di Santa Margarita, named after the holy Margaret of Cortona, whose embalmed body lies on the altar for everyone to behold. At the highest point of Cortona is the castle Fortezza Medicea di Girifalco located which is well worth a visit! Nowadays Cortona is also known because of the fact that several scenes from the Oscar-winning film "La vita è bella" were shot here, and because of the book "Under the Tuscan Sun" by Frances Mayes, in which she tells about renovating an old house in Cortona. In this city you can stroll through the narrow, historic streets leading onto the Piazza della Repubblica where you can relax on the terrace or eat some delicious Italian ice cream. Cortona is about a half hour drive from Florence Airport, so the best option is to first fly there first, hire a car and drive to your destination.

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There are 155 villas still available of the total of 2 villas

Emiliano (8 persons) - Italy, Tuscany, Montaione

Villa popularity 2024: 74% booked

Montaione, a cozy, small hamlet in Tuscany near Florence, hailing from the earliest settlements during the Etruscan and Roman age, is also famous because of its location a few kilometers only from the Sacro Monte di San Vivaldo, that is an exact rep... read more »

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Pool
Lowest week price
8
private pool
€ 4.802,-

Norah (8 persons) - Italy, Tuscany, Gaiole in Chianti

Villa popularity 2024: 98% booked

This splendid property is located in one of the most beautiful parts of the Chianti Classico area. The complex has recently been very carefully and tastefully renovated, and is perfectly furnished with traditional Tuscan pieces and fitted with all m... read more »

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8
private pool
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Paola (10 persons) - Italy, Tuscany, Siena

Villa popularity 2024: 100% booked

An old farmhouse, 4 Km from the center of Siena, situated on the top of a hill from which it is possible to admire the Chianti hills on one side and the Val d'Orcia on the other.  The stone building is surrounded by a beautiful, completely fenc... read more »

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Citycenter
Lowest week price
10
private pool
4 km
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Ludovica (8 persons) - Italy, Tuscany, Porto Ercole

Villa popularity 2024: 71% booked

Porto Ercole is a delightful seaside resort located on the promontory of Argentario.  It is an ancient fishing village which lies at the foot of a 16th century Spanish Fortress. Visitors can enjoy pleasant walks around the town’s alleyway... read more »

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Pool
Beach
Lowest week price
8
private pool
1 km
€ 8.673,-

Sienna (6 persons) - Italy, Tuscany, Buonconvento

Villa popularity 2024: 100% booked

This characteristic detached house is located amidst the Crete Senesi, 6 Km from Buonconvento and 13 Km from Montalcino, on top of one of the area’s typical gentle hills that offer stunning panoramic views of the valleys that change color acco... read more »

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6
private pool
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Martina 22 (16 persons) - Italy, Tuscany, Buonconvento

Villa popularity 2024: 78% booked

The prestigious Martina 22 is located within a 600 hectare estate on the hills of the Val d'Orcia, between Siena and Montalcino.   This historic place has been recognized by UNESCO as a key reference point for the area. The Castello... read more »

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Pool
Lowest week price
16
private pool
€ 35.973,-

Martina 16 (16 persons) - Italy, Tuscany, Buonconvento

Villa popularity 2024: 98% booked

The prestigious Martina 16 is located within a 600 hectare estate on the hills of the Val d'Orcia, between Siena and Montalcino.   This historic place has been recognized by UNESCO as a key reference point for the area. The Castello... read more »

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Lowest week price
16
private pool
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Beatrice (13 persons) - Italy, Tuscany, Monteroni d'Arbia

Villa popularity 2024: 99% booked

Beatrice is located in the middle of a 400 hectare organic farm, delimited by a small, very ancient village. It is situated within the Crete Senesi, a very atmospheric landscape dominated by harsh, bare hills worn away over the centuries but wh... read more »

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Lowest week price
13
private pool
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Elisabetta (8 persons) - Italy, Tuscany, Vertine

Villa popularity 2024: 65% booked

Elisabetta is situated in a little village that dates back to the Middle Ages, 40 Km from Siena and 3 Km from Gaiole in Chianti, in an area filled with castles and magnificent vineyards: the birthplace of Chianti Classico wine. The village of Vertine ... read more »

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Pool
Lowest week price
8
private pool
€ 3.150,-

Xavier 12 (12 persons) - Italy, Tuscany, Gaiole in Chianti

Villa popularity 2024: 98% booked

The Chianti region is not large but it is very rich from a naturalistic viewpoint, with a valuable historic and artistic profile and a generous offering of food and wine. The Chiantigiana, one of the most beautiful roads in Italy, crosses the whole ... read more »

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Lowest week price
12
private pool
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Xavier 8 (8 persons) - Italy, Tuscany, Gaiole in Chianti

Villa popularity 2024: 98% booked

The Chianti region is not large but it is very rich from a naturalistic viewpoint, with a valuable historic and artistic profile and a generous offering of food and wine. The Chiantigiana, one of the most beautiful roads in Italy, crosses the whole ... read more »

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Pool
Lowest week price
8
private pool
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Margo (11 persons) - Italy, Tuscany, Peccioli

Villa popularity 2024: 98% booked

Margo is 8 Km away from Peccioli, a charming medieval village perched on a hill with a wonderful view of the Tuscan countryside. In the village guests will find a selection of restaurants, bars, a historic cake shop and stores for everyday ... read more »

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Lowest week price
11
private pool
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Sophia (13 persons) - Italy, Tuscany, Peccioli

Villa popularity 2024: 98% booked

This elegant liberty style villa dating back to the mid 1900s has been renovated without altering its architectural features.  Furnished extremely tastefully in every detail, the original 19th century pieces and ornaments give the villa a parti... read more »

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Lowest week price
13
private pool
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Diego (12 persons) - Italy, Tuscany, San Donato in Poggio

Villa popularity 2024: 98% booked

The Chianti region is made up of gentle valleys and picturesque villages that will capture your imagination, offering breathtaking natural and architectural landscapes and giving you a taste of the warm Tuscan welcome for which this area is so famou... read more »

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Pool
Lowest week price
12
private pool
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Irene (14 persons) - Italy, Tuscany, Montenero

Villa popularity 2024: 90% booked

Old detached farmhouse dating back to 1800 situated in the green Tuscan countryside along the coast of Livorno just 4.5 km from the area’s small beaches and 8 km from the center of Livorno. The farmhouse has been renovated without altering the... read more »

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Beach
Lowest week price
14
private pool
4 km
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