Villas in Gaiole in Chianti, Tuscany, Luxury Villa's with Pool and Holiday Homes in Italy

Gaiole in Chianti Gaiole in Chianti is a medieval city located along the Massellone river and probably named after “gaggiolo” which refers to a big forest. Due to its location, Gaiole has always been an important market centre for the castles and towns in the surrounding. Back in the days, Gaiole was next to being an important market centre also very important to the clergy. This can be traced back to the churches and monasteries that can be found in Gaiole. A church that must be visited is the Parish Church of Spaltenna; consisting of a monastery, church and cluster of farmhouses. Here a valuable 15th century crucifix can be found. A castle situated in this area, also highly recommended to visit is the Castello di Brolio, inhabited by the Ricasoli family since the 12th century, known for producing wine. It isn’t actually possible to enter the castle as descendants of the family still live there, however it is possible to visit the gardens. A wine shop can be found too on the property, offering wine tastings. Of course, the Chianti Classico wine is sold here, but it is also on offer in many other wineries in this region, such as the Abbey of Coltibuono. This former monastery is turned into a wine estate comprising a big forest with a cedar of Lebanon, with a circumference of as much as 7 meters. In order to find some traditional little shops, you must go to the main square where you’ll find a traditional Italian grocery store, an ice cream shop and a cute little pottery shop. Gaiole in Chianti can be reached by flying to Florence and from there taking the car.

The most known and visited area of Tuscany is the Chianti area, comprising around eight Chianti towns. The borders of this area aren’t very clear, but it can be said that in general it extends over the provinces of Florence and Siena, covering all of the area between the two cities and extending to the east toward the Valdarno and to the west to the Val d'Elsa. The Chianti landscape is unique and very beautiful, including picturesque little village, forests and hills covered with vineyards and olive trees. This region is of course also famous for its outstanding red wines, presented in bottles in woven baskets. The Chianti wines are characterized by intense aromas of fruit and flowers, easily drinkable with a smooth aftertaste. Traditional farming is still an everyday part of life in this region, including as afore mentioned wine making, but also olive oil production is very important here, making this region so attractive to tourists.

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Elio (9 persons) - Italy, Tuscany, Buti

Villa popularity 2026: 98% booked

"Elio ", 7-room house 300 m2 on 3 levels. Beautiful and cosy furnishings: living/dining room with open-hearth fireplace, dining table and satellite TV. 1 room with 1 french bed (160 cm), shower/WC. Kitchen (6 hot plates, oven, dishwas... read more »

Amara (4 persons) - Italy, Tuscany, Lucca

Villa popularity 2026: 92% booked

2-room house 40 m2. Bright, practical furnishings: living/sleeping room with 1 double sofabed, dining table and satellite TV. Exit to the terrace. 1 room with 2 beds. Kitchen (4 hot plates, Gas stove, 4 gas rings, toaster, microwave, freezer, electr... read more »

Donatello (5 persons) - Italy, Tuscany, Pergine Valdarno

Villa popularity 2026: 86% booked

4-room house 100 m2 on 2 levels. Comfortable and tasteful furnishings: living/sleeping room with 1 double sofabed, dining table and satellite TV. Exit to the terrace. Open kitchen (oven, dishwasher, 4 induction hot plates, toaster, microwave, freeze... read more »

Filomena (6 persons) - Italy, Tuscany, Vinci

Villa popularity 2026: 89% booked

4-room house 130 m2 on 2 levels. Cosy furnishings: living room with open-hearth fireplace (only for decoration), satellite TV. Exit to the terrace. 1 open room with 1 bed (80 cm), shower/WC. Exit to the garden. Open kitchen (oven, dishwasher, 4 gas ... read more »

Ginevra (7 persons) - Italy, Tuscany, Pergine Valdarno

Villa popularity 2026: 90% booked

4-room house 100 m2 on 3 levels. Rustic furnishings: living room with satellite TV. Exit to the terrace. 2 rooms, each room with 1 double bed. 1 room with 3 beds. Kitchen (oven, dishwasher, 4 gas rings, microwave, electric coffee machine) with dinin... read more »

Daniella (12 persons) - Italy, Tuscany, Florence

Villa popularity 2026: 95% booked

"Daniella", 8-room house 240 m2 on 4 levels, on the ground floor. Entrance hall. Shower/WC. Upper floor: open living room with open-hearth fireplace and satellite TV. Lounge. Exit to the terrace. 2 double bedrooms. Open kitchen (4 hot plates,... read more »

Santa (6 persons) - Italy, Tuscany, Certaldo

Villa popularity 2026: 95% booked

4-room house 140 m2 on 2 levels, on the ground floor. Very tasteful and stylish furnishings: large living/dining room with open-hearth fireplace and satellite TV. Exit to the terrace. Large, open kitchen (5 hot plates, oven, dishwasher, microwave, e... read more »

Celestina (4 persons) - Italy, Tuscany, Scansano

Villa popularity 2026: 88% booked

2-room house 60 m2 on 2 levels. Spacious and bright, renovated, comfortable and beautiful furnishings: large living room with open-hearth fireplace and satellite TV. Exit to the loggia. Kitchenette (5 hot plates, oven). Upper floor: 1 room with 1 be... read more »

Fernanda (6 persons) - Italy, Tuscany, Roccastrada

Villa popularity 2026: 94% booked

3-room house 60 m2 on 2 levels, on the ground floor. Rustic furnishings: living room with 1 sofabed, dining table and satellite TV (flat screen). Exit to the garden. 1 room with panoramic window with 1 french bed (120 cm). Open kitchen (4 hot plates... read more »

Fiorella (6 persons) - Italy, Tuscany, Montevarchi

Villa popularity 2026: 96% booked

"Fiorella ", 4-room house 110 m2 on 2 levels, on the ground floor. Comfortable and beautiful furnishings: living/dining room with open-hearth fireplace and satellite TV. Exit to the veranda. 1 double bedroom with bath/bidet/WC. 1 room with 2 beds. Op... read more »

Corrado (6 persons) - Italy, Tuscany, Scansano

Villa popularity 2026: 99% booked

"Corrado", 4-room house 90 m2 on 2 levels. Rustic furnishings: living/dining room, on 2 levels with open-hearth fireplace, dining table, satellite TV and air conditioning. Exit to the terrace. 1 room with 2 beds, shower/WC and air conditioning. Exi... read more »

Bella (7 persons) - Italy, Tuscany, Ravi

Villa popularity 2026: 93% booked

"Bella", 4-room house 86 m2, on the upper ground floor. Practical furnishings: living/dining room with open-hearth fireplace, dining table and satellite TV. Exit to the terrace. 1 room with 1 sofabed and 1 double bed. 1 room with 1 double bed... read more »

Felice (8 persons) - Italy, Tuscany, San Casciano Val di Pesa

Villa popularity 2026: 80% booked

7-room house 220 m2 on 2 levels. Comfortable and tasteful furnishings: living/dining room with open-hearth fireplace, dining table, satellite TV, radio, CD-player, hi-fi system and DVD. Exit to the terrace. Living room. Kitchen (oven, dishwasher, 5 ... read more »

Alonzo (10 persons) - Italy, Tuscany, Rufina

Villa popularity 2026: 85% booked

5-room house 180 m2 on 2 levels. Simple and rustic furnishings: living/dining room with open-hearth fireplace, dining table, satellite TV and DVD. 2 rooms, each room with 1 french bed (160 cm). Open kitchen (oven, dishwasher, 5 gas rings, toaster, k... read more »

Mafalda (8 persons) - Italy, Tuscany, Monte San Savino

Villa popularity 2026: 75% booked

5-room house 150 m2 on 2 levels. Renovated, rustic and tasteful furnishings: living/dining room with open-hearth fireplace, dining table, kitchen corner and satellite TV. Exit to the garden. 3 rooms, each room with 1 french bed (160 cm). Kitchen (1 ... read more »

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