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Holiday stays and homes in Chianti| Luxury and Exclusive


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Casa al Monte

from 2.128,00 EUR/Week
No booking fees Best Price Guaranteed

Casa al Monte, Children friendly in Tuscany
Area: Greve in Chianti - Tuscany View Map 3
  • Property type: Independent house
  • Sleeps: 14
  • Double bedrooms: 7
  • Bathrooms: 6
  • Featured pool: Private pool

Rating: 10/10 based upon 8 reviews

Property for exclusive useProperty at exclusive use. Tuscan farmhouse (400 sq. m.) with private swimming pool and Jacuzzi, hosting up to 14 persons in 5 double bedrooms, 2 bedrooms with two beds, 6 bathrooms. Guests can use 2 living rooms and 2 kitchens, the gym, and the fenced garden complete with[...]


Casa Rebecca

from 1.442,00 1.225,00 EUR/Week
No booking fees Best Price Guaranteed

Casa Rebecca, Children friendly in Tuscany
Area: Greve in Chianti - Tuscany View Map 3

15% off

  • Property type: Independent house
  • Sleeps: 8
  • Double bedrooms: 4
  • Bathrooms: 2
  • Featured pool: Private pool

Rating: 10/10 based upon 5 reviews

Property for exclusive useOld stone property, 150 sq. m., for up to 8 persons with 4 double bedrooms and 2 bathrooms with shower. There is a garden, a swimming pool exclusively for guests, as is the barbecue. Parking for 2 cars is shared with others. The owners live in a small and completely independent[...]


Villa Setona

from 4.382,00 EUR/Week
No booking fees Best Price Guaranteed

Villa Setona 24, Children friendly in Tuscany
Area: Bucine - Tuscany View Map 3
  • Property type: Independent house
  • Sleeps: 24
  • Double bedrooms: 12
  • Bathrooms: 12
  • Featured pool: Private pool

Rating: 10/10 based upon 3 reviews

Property for exclusive useElegant property made up of the main villa and an outbuilding for 24 persons, with 9 double bedrooms each with its own private bathroom with shower in the main building, plus three double bedrooms each with its own private bathroom with shower in the outbuilding. There is a[...]

Also available as:


Il Casalone

from 1.603,00 EUR/Week
No booking fees Best Price Guaranteed

Il Casalone, Domestic help in Tuscany
Area: Greve in Chianti - Tuscany View Map 7-OR
  • Property type: Independent house
  • Sleeps: 9-10
  • Double bedrooms: 4
  • Single bedrooms: 1
  • Bathrooms: 2
  • Featured pool: Private pool

Rating: 10/10 based upon 3 reviews

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***Property for exclusive useOverlooking a green valley in the Chianti, in the small, picturesque village of Lucolena in Chianti, Il Casalone is a comfortable country house with a private swimming pool and rooftop[...]


Villa Belvedere

from 8.001,00 EUR/Week
No booking fees Best Price Guaranteed

Villa Belvedere, Suitable for weddings in Tuscany
Area: Poggibonsi - Tuscany View Map 4-OR
  • Property type: Villa
  • Sleeps: 12
  • Double bedrooms: 6
  • Bathrooms: 6
  • Featured pool: Private pool

Rating: 10/10 based upon 6 reviews

Property for exclusive useBeautiful independent villa, 550 sq. m., made up of a main house and an annex 30 metres away, holding up to 12 people with 6 double bedrooms and 6 bathrooms. The property has a swimming pool and private outdoor space, Wi-Fi, air conditioning and is the perfect solution for[...]


Villa di Tizzano

from 11.200,00 EUR/Week
No booking fees Best Price Guaranteed

Villa di Tizzano, Children friendly in Tuscany
Area: Greve in Chianti - Tuscany View Map 3-OR
  • Property type: Villa
  • Sleeps: 16
  • Double bedrooms: 8
  • Bathrooms: 8
  • Featured pool: Private pool

Property for exclusive useThe villa is situated in the hills that ascend from the city of Florence towards Chianti. It is part of a large historic estate belonging to an aristocratic Florentine family. The countryside all around is a succession of woods, olive groves and vineyards, dotted with farmhouses[...]


Casale Sandonatino

from 2.751,00 EUR/Week
No booking fees Best Price Guaranteed

Casale Sandonatino, Children friendly in Tuscany
Area: Castellina in Chianti - Tuscany View Map 5
  • Property type: Villa
  • Sleeps: 12
  • Double bedrooms: 6
  • Bathrooms: 3
  • Featured pool: Private pool

Rating: 9/10 based upon 4 reviews

Property for exclusive useCasale San Donatino is an old stone house, 480 sq. m., holding up to 12 persons with 6 double bedrooms and 3 bathrooms. The house has a splendid, panoramic, private swimming pool, WiFi and a barbecue. It is ideal for groups of friends or large families.Outdoors and Swimming[...]


Casa Talciona

from 1.638,00 EUR/Week
No booking fees Best Price Guaranteed

Talciona, Children friendly in Tuscany
Area: Poggibonsi - Tuscany View Map 3-OR
  • Property type: Apartment
  • Sleeps: 4
  • Double bedrooms: 2
  • Bathrooms: 1
  • Featured pool: Private pool

Rating: 10/10 based upon 1 reviews

Comfortable apartment (110 m2) in a small villa built in the 1970s situated in the hills of Chianti, about 5 km from Poggibonsi, halfway between Florence and Siena. The most beautiful villages of the Chianti like Castellina and Radda in Chianti or the village of San Gimignano with its famous towers can[...]

Also available as:


Villa Mary

from 2.065,00 EUR/Week
No booking fees Best Price Guaranteed

Villa Mary, Children friendly in Tuscany
Area: Poggibonsi - Tuscany View Map 3
  • Property type: Independent house
  • Sleeps: 12
  • Double bedrooms: 6
  • Bathrooms: 3
  • Featured pool: Private pool

Rating: 10/10 based upon 3 reviews

Villa with exclusive swimming pool, divided into 2 apartments, able to accommodate 12 people in 6 double bedrooms, 3 bathrooms with shower and 1 service bathroom. At guests' disposal 2 complete kitchens and 2 dining rooms, a garden with two porches equipped with tables and chairs for outdoor dining,[...]

Also available as:


San Romolo

from 1.386,00 1.176,00 EUR/Week
No booking fees Best Price Guaranteed

San Romolo, Children friendly in Tuscany
Area: Barberino Val d'Elsa - Tuscany View Map 4-OR

15% off12% off6% off

  • Property type: Independent house
  • Sleeps: 10
  • Double bedrooms: 5
  • Bathrooms: 4
  • Featured pool: Private pool

Rating: 10/10 based upon 11 reviews

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***Property for exclusive useSan Romolo is an ancient stone farmhouse immersed in the Chianti countryside. Typical of the farmhouses in the area, it has several floors and includes an outbuilding, totalling 210 sq.[...]


Dimora del Castello

from 8.701,00 EUR/Week
No booking fees Best Price Guaranteed

Dimora del Castello, Domestic help in Tuscany
Area: Castelfiorentino - Tuscany View Map 7-OR
  • Property type: Villa
  • Sleeps: 12
  • Double bedrooms: 6
  • Bathrooms: 6
  • Featured pool: Private pool

Rating: 10/10 based upon 11 reviews

Property for exclusive useIn a beautiful position in the Chianti hills near San Gimignano, just 30 km from Florence, is located the Dimora del Castello, built on the ancient Via Francigena, that connected France to Rome during the Middle-age. The origins of the Dimora del Castello date back to the early[...]


L'Angolino

from 1.652,00 EUR/Week
No booking fees Best Price Guaranteed

L'Angolino, Children friendly in Tuscany
Area: Radda in Chianti - Tuscany View Map 7-OR
  • Property type: Independent house
  • Sleeps: 6
  • Double bedrooms: 3
  • Bathrooms: 2
  • Featured pool: Private pool

Rating: 10/10 based upon 13 reviews

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***Property for exclusive useBeautiful stone farmhouse, completely independent, 120 sq. m., holding up to 6 persons with two double bedrooms and 2 bathrooms. The property has a swimming pool, large garden, furnished[...]


Santantimo

from 2.982,00 EUR/Week
No booking fees Best Price Guaranteed

Santantimo, Children friendly in Tuscany
Area: Castellina in Chianti - Tuscany View Map 3-OR
  • Property type: Villa
  • Sleeps: 10
  • Double bedrooms: 5
  • Bathrooms: 5
  • Featured pool: Private pool

Rating: 10/10 based upon 2 reviews

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***Property for exclusive useThe villa in Chianti (400 m2) was built in the early 16th century as an ancient oratory. In 1876 it underwent its first transformation into a farmhouse and only today, thanks to a skilful[...]


Villa Beba

from 1.806,00 EUR/Week
No booking fees Best Price Guaranteed

Villa Beba 6, Children friendly in Tuscany
Area: Castellina in Chianti - Tuscany View Map 5
  • Property type: Villa
  • Sleeps: 6
  • Double bedrooms: 3
  • Bathrooms: 2
  • Featured pool: Private pool

Rating: 8/10 based upon 1 reviews

Property for exclusive useHistorical 18th Century villa on two floors, 280 sq. m. with 3 double bedrooms and 2 bathrooms capable of holding up to 6 persons. The villa has a large terraced and enclosed park with a private swimming pool, an outdoor eating area with stonework barbecue, Wi-Fi and satellite[...]

Also available as:

Villa Beba with 10 Sleeps

from 2.653,00 EUR/Week


Il Torrino

from 3.689,00 EUR/Week
No booking fees Best Price Guaranteed

Il Torrino, Children friendly in Tuscany
Area: Radda in Chianti - Tuscany View Map 5-OR
  • Property type: Independent house
  • Sleeps: 12
  • Double bedrooms: 6
  • Bathrooms: 6
  • Featured pool: Private pool

Property for exclusive useIl Torrino is a beautiful country home, composed of a main house and an annex, sleeping 12 in its 6 double bedrooms with 6 bathrooms. The house, which has recently been restored maintaining beam ceilings and cotto floors, has internet connection and all the bedrooms have an[...]


Villa Martina

from 8.498,00 EUR/Week
No booking fees Best Price Guaranteed

Villa Martina, Children friendly in Tuscany
Area: Tavarnelle Val di Pesa - Tuscany View Map 7-OR
  • Property type: Villa
  • Sleeps: 12
  • Double bedrooms: 6
  • Bathrooms: 5
  • Featured pool: Private pool

Rating: 9/10 based upon 1 reviews

Property for exclusive useVilla Martina is a luxurious farmhouse with outbuilding, ideal for 12 persons with 6 double bedrooms, 5 complete bathrooms and a small one. It boasts a private spa, a swimming pool, a heated Jacuzzi, a large garden with gazebo, stone barbecue and children’s games. The villa[...]


Villa Pergine

from 3.374,00 EUR/Week
No booking fees Best Price Guaranteed

Villa Pergine, Children friendly in Tuscany
Area: Pergine Valdarno - Tuscany View Map 7-OR
  • Property type: Villa
  • Sleeps: 12
  • Double bedrooms: 6
  • Bathrooms: 6
  • Featured pool: Private pool

Rating: 10/10 based upon 4 reviews

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***Property for exclusive useLarge villa of approximately 350 m2 created from the restoration of an ancient farmhouse, whose owners have left its ancient country characteristics intact. The stone walls have preserved[...]


Casali Lilliano A


No booking fees Best Price Guaranteed

Boschi, Pet allowed in Tuscany
Area: Castellina in Chianti - Tuscany View Map 7-OR

Characteristic and small group of farmhouses set inside a large property which covers an area of about 460 hectares near Castellina in Chianti. Panoramic position amidst the vineyards and gently rolling hills of Chianti Classico (350 m a.s.l.). The structures has been restored and furnished in accordance[...]

Boschi

from 707,00 EUR/Week

  • Property type: Apartment
  • Sleeps: 4
  • Double bedrooms: 2
  • Bathrooms: 1
  • Featured pool: Shared pool

Rating: 10/10 based upon 2 reviews


Casa Belmonte

from 2.282,00 2.009,00 EUR/Week
No booking fees Best Price Guaranteed

Casa Belmonte, Children friendly in Tuscany
Area: Castellina in Chianti - Tuscany View Map 7-OR

12% off

  • Property type: Independent house
  • Sleeps: 8
  • Double bedrooms: 4
  • Bathrooms: 4
  • Featured pool: Private pool

Rating: 10/10 based upon 3 reviews

Property for exclusive useTypical farmhouse with annexe, recently restructured and complete with every luxury, with a total area of 180 sq. m., holding up to 8 persons with 4 double bedrooms and 4 bathrooms. The private swimming pool is in a panoramic position surrounded by large outdoor areas which,[...]