menu

Holiday Villas in Chianti

Select a location
Photo of Casa Roseto

Casa Roseto

Sleeps: 9 Rooms: 4 From €1,386 weekly
Views over Tuscany Once a fine old 17th century Tuscan barn, this beautiful, restored property with air conditioning has its own private swimming pool. The house lies in its own grounds with views ove...
From €1,386 weekly
Request to book
Photo of Podere Villetta 2

Podere Villetta 2

Sleeps: 7 Rooms: 3 From €577 weekly
This pretty, detached, stone holiday property (ref ITC250) and apartment, which adjoins the owner’s home (ref ITC251), are set in the beautiful countryside of the Chianti hills, just 5km away from Sa...
From €577 weekly
Request to book
Photo of Casa Antica

Casa Antica

Sleeps: 5 Rooms: 2
Several contemporary features make this semi-detached house with air-conditioning stand out from the rest. The open-plan living/dining and kitchen area with their clean lines give the impression of s...
Request to book
Photo of Ademollo

Ademollo

Sleeps: 8 Rooms: 3 From €1,014 weekly
This cosy farmhouse, accessed via a rough track, has been transformed into a beautiful holiday property from a former hayloft. It is perfect for hot summer days by the outdoor swimming pool or cold a...
From €1,014 weekly
Request to book
Photo of Le Masse 1

Le Masse 1

Sleeps: 8 Rooms: 3 From €1,146 weekly
This attractive holiday cottage, formally a farmhouse, is situated amidst the green hills of the Chianti Classico. It is comfortably furnished and boasts a pretty and broad view of the countryside, r...
From €1,146 weekly
Request to book
Photo of Camelia 2

Camelia 2

Sleeps: 2 Rooms: 1 From €262 weekly
This great holiday apartment is one of six lovely apartments in a beautiful farmhouse. The farmhouse itself belongs to a company who produces excellent wines that can be tasted and purchased by guest...
From €262 weekly
Request to book
Photo of La Fornacina

La Fornacina

Sleeps: 8 Rooms: 4 From €1,734 weekly
Transformed in to a delightful holiday home, retaining its original characteristics, this charming property is located in the lovely hills of Chianti, in the neighborhood of Tavarnelle Val di Pesa. T...
From €1,734 weekly
Request to book
Photo of Podere Villetta 1

Podere Villetta 1

Sleeps: 6 Rooms: 2 From €577 weekly
This pretty, detached, stone holiday property (ref ITC250) and apartment, which adjoins the owner’s home (ref ITC251), are set in the beautiful countryside of the Chianti hills, just 5km away from Sa...
From €577 weekly
Request to book
Photo of Olivo

Olivo

Sleeps: 5 Rooms: 2
This fantastic holiday house, one of a number of other holiday properties, is set within the charming medieval village in the heart of Chianti Classico in a breathtaking landscape of olive trees, vin...
Request to book
Photo of Ormanni 3

Ormanni 3

Sleeps: 4 Rooms: 2
This beautifully restored farmhouse, accessed via unmade road, is set in the heart of the Chianti region, to which holds five fantastic holiday apartments. Here guests will find an impressive stone b...
Request to book
Photo of Ormanni 5

Ormanni 5

Sleeps: 2 Rooms: 1
This beautiful farmhouse is located in the heart of the Chianti region and has been divided into 5 nice apartments. In this holiday apartment, guests can enjoy a great view of the surrounding landsc...
Request to book
Photo of Michele

Michele

Sleeps: 4 Rooms: 1 From €447 weekly
This lovely apartment is located in the heart of the Chianti area, about 4 km from Barberino Val D’Elsa (in the province of Florence). It is set in a brick and stone building dating back to the 17th...
From €447 weekly
Request to book
Photo of Poggio Agli Ulivi

Poggio Agli Ulivi

Sleeps: 4 Rooms: 2
This cosy barn conversion is just 3km from Poggibonsi. It has been beautifully restored and has successfully preserved the original structure of the building. It enjoys a wonderful location amidst th...
Request to book
Photo of Gallonero 2

Gallonero 2

Sleeps: 10 Rooms: 3 From €872 weekly
This small rural complex of holiday properties is located in the region surrounding the villages of Tavarnelle Val di Pesa and Marcialla. It is situated on a hillside in a tranquil position, overlook...
From €872 weekly
Request to book
Photo of Casa Padronale 1

Casa Padronale 1

Sleeps: 8 Rooms: 4
This lovely holiday house, one of a number of other holiday properties, is set within the charming medieval village in the heart of Chianti Classico, in breathtaking landscapes surrounded by olive tr...
Request to book
Photo of Fonte Nuova

Fonte Nuova

Sleeps: 15 Rooms: 6 From €1,057 weekly
This large, spacious and comfortable, stone-built, detached farmhouse is peacefully located between the gently sloping hills of Chianti and the Valdarno. The house enjoys views over the landscape and...
From €1,057 weekly
Request to book
Photo of Ormanni 1

Ormanni 1

Sleeps: 5 Rooms: 3
This lovely farmhouse is situated in the heart of the Chianti region. It comprises 5 apartments (ITC461, ITC463, ITC464, ITC465 and ITC402) in an impressive stone building which is superbly located...
Request to book
Photo of Gallonero 1

Gallonero 1

Sleeps: 8 Rooms: 3 From €642 weekly
This small rural complex of holiday properties is located in the region surrounding the villages of Tavarnelle Val di Pesa and Marcialla. It is situated on a hillside in a tranquil position, overlook...
From €642 weekly
Request to book
Photo of Ulivo 5

Ulivo 5

Sleeps: 4 Rooms: 2 From €435 weekly
This traditional farmhouse complex is set amidst the woods, vineyards and century-old olive tree groves in the typical landscape of the Chianti Classico, and is accessed via a 1.6km country lane. The...
From €435 weekly
Request to book
Photo of Villa Claudia

Villa Claudia

Sleeps: 10 Rooms: 5 From €5,184 weekly
This lovely holiday home, with air-conditioning and traditional charm, is located in the quiet countryside just outside the ancient hamlet of Castellinuzza. Boasting panoramic views over the Chianti...
From €5,184 weekly
Request to book
Photo of Villa Rebecca

Villa Rebecca

Sleeps: 10 Rooms: 5 From €3,164 weekly
This semi-detached holiday home within a panoramic position can be found in the heart of the Chianti Classico area, about 8km from Greve in Chianti. Surrounded by vineyards and olive trees, this hous...
From €3,164 weekly
Request to book
Photo of Farmhouse 1

Farmhouse 1

Sleeps: 11 Rooms: 6 From €1,243 weekly
These beautiful stone-built holiday farmhouses are located in the heart of Chianti Classico, 5km from Castellina in Chianti. The properties are situated on a renowned Tuscan estate, accessed via a ro...
From €1,243 weekly
Request to book
Photo of Borgo La Casina

Borgo La Casina

Sleeps: 22 Rooms: 9 From €1,932 weekly
This ancient complex includes an old stone country house and a building which was originally a medieval fort dating back to the 11th century, and enjoys views over the landscape. The complex is locat...
From €1,932 weekly
Request to book
Photo of Serristori 4

Serristori 4

Sleeps: 6 Rooms: 2 From €578 weekly
This traditional farmhouse complex is set amidst the woods, vineyards and century-old olive tree groves in the typical landscape of the Chianti Classico, and is accessed via a 1.6km country lane. The...
From €578 weekly
Request to book
Photo of S 7

S 7

Sleeps: 6 Rooms: 3 From €599 weekly
This traditional farmhouse complex is set amidst the woods, vineyards and century-old olive tree groves in the typical landscape of the Chianti Classico, and is accessed via a 1.6km country lane. The...
From €599 weekly
Request to book
Photo of San Gusme 1

San Gusme 1

Sleeps: 4 From €480 weekly
This characteristic, restored, stone-built hayloft with air-conditioning is set amid the Chianti hills and only 200m from the picturesque medieval hamlet of San Gusmè. This property has an extensive...
From €480 weekly
Request to book
Photo of Casa Le Ginestre

Casa Le Ginestre

Sleeps: 4 Rooms: 2 From €698 weekly
This very comfortable holiday home is located in a stunning setting within the Chianti Mountains. The very tasteful and charming furnishings, the large, natural grounds and the superb views towards A...
From €698 weekly
Request to book
Photo of La Stalla

La Stalla

Sleeps: 6 Rooms: 2 From €435 weekly
This lovely holiday home is part of a stone house in an old farm complex which has been renovated, in a panoramic location, on the edge of the small village of Lucignano on Chianti hills between San...
From €435 weekly
Request to book
Photo of Sangiovese 5

Sangiovese 5

Sleeps: 4 Rooms: 2 From €349 weekly
This first floor holiday apartment forms part of an ancient farmhouse in the Chianti hills with 5 other properties (ITC638, ITC617, ITC623, ITC631 and ITC635). Surrounded by vineyards and olive trees...
From €349 weekly
Request to book
Photo of Casato 2

Casato 2

Sleeps: 2 Rooms: 1 From €435 weekly
This pleasant and characteristic holiday apartment, which is part of a former convent, is set on the gentle hills typical of the Chianti, rich in olive groves and vineyards. In a peaceful location, t...
From €435 weekly
Request to book
Photo of Magnolia

Magnolia

Sleeps: 5 Rooms: 2 From €370 weekly
This fantastic apartment, one of six apartments, is situated in a beautiful stone farmhouse. The farmhouse has been renovated in keeping with the typical building characteristics of the site, and is...
From €370 weekly
Request to book
Photo of Sangiovese 3

Sangiovese 3

Sleeps: 5 Rooms: 2 From €435 weekly
This holiday apartment forms part of an ancient farmhouse in the Chianti hills with 5 other properties (ITC638, ITC617, ITC623, ITC637 and ITC635). Surrounded by vineyards and olive trees, it has bee...
From €435 weekly
Request to book
Photo of Sangiovese 11

Sangiovese 11

Sleeps: 6 Rooms: 3 From €502 weekly
This holiday apartment forms part of an ancient farmhouse in the Chianti hills with 5 other properties (ITC637, ITC617, ITC623, ITC631 and ITC635). Surrounded by vineyards and olive trees, it has bee...
From €502 weekly
Request to book
Photo of Piazzale 2

Piazzale 2

Sleeps: 4 Rooms: 2 From €513 weekly
This property is made up of three great apartments, with independent entrances, one of which is inhabited by the owners, in a beautiful and characteristic farmhouse in the heart of the Chianti Classi...
From €513 weekly
Request to book
Photo of Piazzale 1

Piazzale 1

Sleeps: 4 Rooms: 2 From €544 weekly
This property is made up of three great apartments, with independent entrances, one of which is inhabited by the owners, in a beautiful and characteristic farmhouse in the heart of the Chianti Classi...
From €544 weekly
Request to book
Photo of S 3

S 3

Sleeps: 5 Rooms: 2 From €490 weekly
This traditional farmhouse complex is set amidst the woods, vineyards and century-old olive tree groves in the typical landscape of the Chianti Classico, and is accessed via a 1.6km country lane. The...
From €490 weekly
Request to book
Photo of Gardenia

Gardenia

Sleeps: 4 Rooms: 2 From €326 weekly
Located in a beautiful stone farmhouse, this delightful holiday apartment has been renovated, yet keeping its typical building characteristics. The lovely apartments are among olive trees and vineyar...
From €326 weekly
Request to book
Photo of Serristori 1

Serristori 1

Sleeps: 6 Rooms: 2 From €480 weekly
This traditional farmhouse complex is set amidst the woods, vineyards and century-old olive tree groves in the typical landscape of the Chianti Classico, and is accessed via a 1.6km country lane. The...
From €480 weekly
Request to book
Photo of Dahlia

Dahlia

Sleeps: 4 Rooms: 2 From €305 weekly
This fantastic apartment, one of six apartments, is situated in a beautiful stone farmhouse. The farmhouse has been renovated in keeping with the typical building characteristics of the site, and is...
From €305 weekly
Request to book
Photo of Sangiovese 1

Sangiovese 1

Sleeps: 2 Rooms: 1 From €272 weekly
This ground floor holiday apartment forms part of an ancient farmhouse in the Chianti hills with 5 other properties (ITC638, ITC637, ITC623, ITC631 and ITC635). Surrounded by vineyards and olive tre...
From €272 weekly
Request to book
Photo of Sangiovese 9

Sangiovese 9

Sleeps: 4 Rooms: 2 From €349 weekly
This first floor apartment forms part of an ancient farmhouse in the Chianti hills with 5 other holiday properties (ITC638, ITC617, ITC623, ITC631 and ITC637). Surrounded by vineyards and olive trees...
From €349 weekly
Request to book
Photo of Gaiole

Gaiole

Sleeps: 4 Rooms: 2 From €359 weekly
This renovated stone house is located in the medieval village of Gaiole which the American magazine Forbes named number one in its list of "Europe’s Most Idyllic Places to Live”. The region of Chiant...
From €359 weekly
Request to book
Photo of Farmhouse 2

Farmhouse 2

Sleeps: 7 Rooms: 4 From €796 weekly
These beautiful stone-built holiday farmhouses are located in the heart of Chianti Classico, 5km from Castellina in Chianti. The properties are situated on a renowned Tuscan estate, accessed via a ro...
From €796 weekly
Request to book
Photo of Sangiovese 2

Sangiovese 2

Sleeps: 3 Rooms: 2 From €304 weekly
This ground floor holiday apartment forms part of an ancient farmhouse in the Chianti hills with 5 other properties (ITC638, ITC617, ITC637, ITC631 and ITC635). Surrounded by vineyards and olive tree...
From €304 weekly
Request to book
Photo of Cappella

Cappella

Sleeps: 14 Rooms: 7 From €1,287 weekly
This pretty, stone-built farmhouse situated amidst the green hills of the Florentine Chianti, is in a very peaceful and panoramic location while being surrounded by olive trees and very beautiful vie...
From €1,287 weekly
Request to book
Photo of Michelangelo 2

Michelangelo 2

Sleeps: 3 Rooms: 1
These terraced houses, two of four, are well-kept and comfortably and tastily decorated. Each house has its own private entrance and private area with gazebo and barbecue in front of the kitchen. The...
Request to book
Photo of Masaccio

Masaccio

Sleeps: 8 Rooms: 4
These terraced houses, two of four, are well-kept and comfortably and tastily decorated. Each house has its own private entrance and private area with gazebo and barbecue in front of the kitchen. The...
Request to book
Photo of Ormanni 2

Ormanni 2

Sleeps: 4 Rooms: 2
This lovely farm house, accessed via a rough track, has been renovated into five holiday apartments and is situated in the heart of the Chianti region on a hill with exceptional views. Surrounded by...
Request to book
Holiday rental locations
Listing 1-48 of 48 Top Holiday Rentals
Results per page:
  • 10
  • 20
  • 50
With cookies we can give you the best experience on selfcatering.travel. By using our website, you consent to the use of cookies.