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Holiday stays and homes in Montespertoli| Luxury and Exclusive


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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 (26.52Km from Montespertoli ) 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 Staggia

from 3.990,00 EUR/Week
No booking fees Best Price Guaranteed

Villa Staggia, Domestic help in Tuscany
Area: Poggibonsi - Tuscany (26.73Km from Montespertoli ) View Map 3-OR
  • Property type: Villa
  • Sleeps: 14
  • Double bedrooms: 7
  • Bathrooms: 6
  • Featured pool: Private pool

Rating: 10/10 based upon 2 reviews

Property for exclusive useAncient 18th century Tuscany villa (500 m2) in a dominant position on a Chianti hill, surrounded by olive groves above the old town of Staggia Senese. The villa has undergone attentive restorations, preserving its original structure, making it an ideal setting for a pleasant[...]


Spazzavento

from 1.260,00 EUR/Week
No booking fees Best Price Guaranteed

Spazzavento, Pet allowed in Tuscany
Area: Castellina in Chianti - Tuscany (26.91Km from Montespertoli ) View Map 7-OR
  • Property type: Independent house
  • Sleeps: 8
  • Double bedrooms: 4
  • Bathrooms: 3
  • 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 useStone-built farmhouse (220 m2) situated inside a large property which covers an area of about 460 hectares near Castellina in Chianti. Peaceful and panoramic position amidst the vineyards[...]


Umiliati

from 1.505,00 EUR/Week
No booking fees Best Price Guaranteed

Umiliati, Pet allowed in Tuscany
Area: Castellina in Chianti - Tuscany (27.12Km from Montespertoli ) View Map 7-OR
  • Property type: Independent house
  • Sleeps: 9
  • Double bedrooms: 4
  • Single bedrooms: 1
  • Bathrooms: 3
  • 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 useCharacteristic and small farmhouse inside a large property which covers an area of about 460 hectares near Castellina in Chianti. Peaceful and panoramic position amidst the vineyards[...]


Ceccatelli

from 1.106,00 EUR/Week
No booking fees Best Price Guaranteed

Ceccatelli, Pet allowed in Tuscany
Area: Castellina in Chianti - Tuscany (27.17Km from Montespertoli ) View Map 7-OR
  • Property type: Independent house
  • Sleeps: 7
  • Double bedrooms: 3
  • Single bedrooms: 1
  • Bathrooms: 3
  • Featured pool: Private pool

Rating: 10/10 based upon 1 reviews

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***Property for exclusive useStone-built farmhouse (150 m2) situated inside a large property which covers an area of about 460 hectares near Castellina in Chianti. Peaceful and panoramic position amidst the vineyards[...]


Guidi

from 714,00 EUR/Week
No booking fees Best Price Guaranteed

Guidi, Pet allowed in Tuscany
Area: Castellina in Chianti - Tuscany (27.17Km from Montespertoli ) View Map 7-OR
  • Property type: Apartment
  • Sleeps: 4
  • Double bedrooms: 2
  • Bathrooms: 1
  • Featured pool: Shared pool

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***Characteristic and small group of farmhouses made up of 2 units set inside a large property which covers an area of about 460 hectares near Castellina in Chianti. Peaceful and panoramic position amidst the vineyards[...]


Casali Lilliano B


No booking fees Best Price Guaranteed

Carraretto, Pet allowed in Tuscany
Area: Castellina in Chianti - Tuscany (27.17Km from Montespertoli ) View Map 7-OR

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***Characteristic and small group of farmhouses made up of 2 units set inside a large property which covers an area of about 460 hectares near Castellina in Chianti. Peaceful and panoramic position amidst the vineyards[...]

Carraretto

from 1.022,00 EUR/Week

  • Property type: Apartment
  • Sleeps: 6
  • Double bedrooms: 3
  • Bathrooms: 2
  • Featured pool: Shared pool

Rating: 9/10 based upon 1 reviews

Visentini

from 413,00 EUR/Week

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

Rating: 9/10 based upon 11 reviews


Bettini

from 1.722,00 EUR/Week
No booking fees Best Price Guaranteed

Bettini, Pet allowed in Tuscany
Area: Castellina in Chianti - Tuscany (27.17Km from Montespertoli ) View Map 7-OR
  • Property type: Independent house
  • Sleeps: 11
  • Double bedrooms: 5
  • Single bedrooms: 1
  • Bathrooms: 5
  • Featured pool: Private pool

Rating: 9/10 based upon 4 reviews

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***Property for exclusive useStone-built farmhouse (320 m2) situated inside a large property which covers an area of about 460 hectares near Castellina in Chianti. Peaceful and panoramic position amidst the vineyards[...]


Casali Lilliano A


No booking fees Best Price Guaranteed

Boschi, Pet allowed in Tuscany
Area: Castellina in Chianti - Tuscany (27.17Km from Montespertoli ) 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

Fontani

from 1.057,00 EUR/Week

  • Property type: Independent house
  • Sleeps: 7
  • Double bedrooms: 3
  • Single bedrooms: 1
  • Bathrooms: 3
  • Featured pool: Shared pool

Rating: 9/10 based upon 4 reviews


Santantimo

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

Santantimo, Children friendly in Tuscany
Area: Castellina in Chianti - Tuscany (27.82Km from Montespertoli ) 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[...]


Fiorita

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

Fiorita, Children friendly in Tuscany
Area: Radda in Chianti - Tuscany (27.92Km from Montespertoli ) View Map 7-OR
  • Property type: Independent house
  • Sleeps: 8
  • Double bedrooms: 4
  • Bathrooms: 3
  • Featured pool: Swimming Pool

Rating: 9/10 based upon 5 reviews

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***Property for exclusive useTypical country house in stone, 150 sq. m., with 4 double bedrooms and 3 bathrooms, holding up to 8 persons. The villa has a large garden with private swimming pool, an outdoor area for[...]


Villa Montespertoli

from 3.073,00 EUR/Week
No booking fees Best Price Guaranteed

Villa Montespertoli, Suitable for weddings in Tuscany
Area: Castellina in Chianti - Tuscany (28.29Km from Montespertoli ) View Map 3-OR
  • Property type: Independent house
  • Sleeps: 12
  • Double bedrooms: 6
  • Bathrooms: 7
  • 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 stone-built farmhouse (480 m2) completely restored farmhouse, situated inside a large property which covers an area of about 460 hectares near Castellina in Chianti in a peaceful[...]


Casale il Gualdo

from 3.164,00 2.849,00 EUR/Week
No booking fees Best Price Guaranteed

Casale il Gualdo, Children friendly in Tuscany
Area: Radda in Chianti - Tuscany (28.72Km from Montespertoli ) View Map 3

10% off5% off

  • Property type: Independent house
  • Sleeps: 16
  • Double bedrooms: 8
  • Bathrooms: 6
  • Featured pool: Private pool

Rating: 10/10 based upon 13 reviews

Property for exclusive useCasale il Gualdo is an old stone house, completely independent, measuring 300 sq. m. and capable of holding up to 16 people with 8 double bedrooms and 6 bathrooms. The farmhouse, with an exclusive pool with Infinity edge, Wi-Fi, satellite TV and air conditioning in the bedrooms,[...]


Vignalsole

from 10.703,00 EUR/Week
No booking fees Best Price Guaranteed

Vignalsole, Domestic help in Tuscany
Area: Radda in Chianti - Tuscany (29.22Km from Montespertoli ) View Map 7-OR
  • Property type: Villa
  • Sleeps: 9
  • Double bedrooms: 4
  • Single bedrooms: 1
  • Bathrooms: 4
  • Featured pool: Private pool

Property for exclusive useLarge country house, entirely built in stone, in the heart of the Chianti hills. This is one of the most popular international tourist destinations which lovers of the Tuscan countryside all ask for. Everywhere there are vineyards which, in October, are tinted with numerous[...]


Casina di Teo

from 1.379,00 EUR/Week
No booking fees Best Price Guaranteed

Casina di Teo, Children friendly in Tuscany
Area: Monteriggioni - Tuscany (29.27Km from Montespertoli ) View Map 3
  • Property type: Independent house
  • Sleeps: 2-4
  • Double bedrooms: 1
  • Bathrooms: 2
  • Featured pool: Private pool

Rating: 10/10 based upon 8 reviews

Property for exclusive useLa Casina di Teo is a small converted barn, 75 sq. m. and completely independent, holding up to 4 persons with a double bedroom, a double sofa bed and two bathrooms. The house has a large private garden, completely enclosed and furnished, with private swimming pool, barbecue[...]


Villa Poggio Tondo

from 2.632,00 EUR/Week
No booking fees Best Price Guaranteed

Villa Poggio Tondo, Children friendly in Tuscany
Area: Castellina In Chianti - Tuscany (29.32Km from Montespertoli ) View Map 7
  • Property type: Independent house
  • Sleeps: 6
  • Double bedrooms: 3
  • Bathrooms: 3
  • Featured pool: Private pool

Rating: 10/10 based upon 2 reviews

Property for exclusive useVilla with exclusive pool able to accommodate 6 people in 2 double bedrooms, 1 bedroom with 2 single beds, 3 complete bathrooms. At guests' disposal 2 complete kitchens and 1 large dining room for the entire group, equipped area with table and chairs for outdoor dining, 1 built-in[...]


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 (29.34Km from Montespertoli ) 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 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 (29.62Km from Montespertoli ) 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[...]

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