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Holiday stays, homes and villas in Italy in San Gimignano| Luxury and Exclusive


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Vignalsole

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

Vignalsole, Domestic help in Tuscany
Area: Radda in Chianti - Tuscany (26.14Km from San Gimignano ) 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 delle Fate

from 1.484,00 EUR/Week
No booking fees Best Price Guaranteed

Casina delle Fate, Children friendly in Tuscany
Area: Montespertoli - Tuscany (26.32Km from San Gimignano ) View Map 7
  • Property type: Independent house
  • Sleeps: 6
  • Double bedrooms: 3
  • Bathrooms: 1
  • Featured pool: Private pool

Rating: 9/10 based upon 2 reviews

Property for exclusive useExclusive villa of 180 sq.mt with swimming pool, for up to 6 persons with two double bedrooms, one bedroom with two beds, one bathroom with shower, one small bathroom with sink. Guests will find a large fenced garden, a furnished terrace for outdoor breakfasts, beach umbrellas[...]


Antica Torre

from 2.331,00 2.051,00 EUR/Week
No booking fees Best Price Guaranteed

Antica Torre, Children friendly in Tuscany
Area: Greve in Chianti - Tuscany (26.82Km from San Gimignano ) View Map 2

12% off6% off

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

Rating: 9/10 based upon 8 reviews

Property for exclusive useAncient stone house, 210 sq. m., holding up to 10 persons in 5 double bedrooms, 3 bathrooms with shower, one bathroom with bathtub. Guests can use a garden with table and chairs for outdoor breakfasts, a barbecue, wood-burning stove, shared parking 30 metres away. The property[...]


Dolcicolline

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

Dolcicolline, Children friendly in Tuscany
Area: Montelupo Fiorentino - Tuscany (27.19Km from San Gimignano ) View Map 4-OR
  • Property type: Independent house
  • Sleeps: 4-6
  • Double bedrooms: 2
  • Bathrooms: 2
  • Featured pool: Private pool

Property for exclusive useBeautiful and comfortable barn situated deep in the heart of the green Tuscan countryside in the whereabouts of Montelupo Fiorentino, a town famous for its pottery and terracotta in a strategic position for excursions. Only 20 minutes by car and you are in Florence and in less[...]


Casale del Lago

from 1.400,00 1.232,00 EUR/Week
No booking fees Best Price Guaranteed

Casale del Lago, Children friendly in Tuscany
Area: San Casciano Val di Pesa - Tuscany (27.35Km from San Gimignano ) View Map 3-OR

12% off6% off

  • Property type: Independent house
  • Sleeps: 8-12
  • Double bedrooms: 4
  • Bathrooms: 3
  • 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 useCasale del Lago is an long-standing property, 160 sq.m. sleeping up to 12 people made up of 4 double bedrooms, 3 bathrooms one of which has a Jacuzzi and two sitting rooms each with a[...]


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 (27.93Km from San Gimignano ) 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[...]


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 (28.35Km from San Gimignano ) 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[...]


Villa Spicchio

from 3.297,00 2.800,00 EUR/Week
No booking fees Best Price Guaranteed

Villa Spicchio, Children friendly in Tuscany
Area: Gaiole In Chianti - Tuscany (28.57Km from San Gimignano ) View Map 7-OR

15% off12% off6% off

  • Property type: Independent house
  • Sleeps: 6
  • Double bedrooms: 3
  • Bathrooms: 3
  • Featured pool: Private pool

Property in exclusive use.Beautiful, completely independent stone farmhouse with exclusive swimming pool, outdoor Jacuzzi, able to accommodate 6 people with 3 double bedrooms and 3 bathrooms. The farmhouse has a large garden, shed with sitting area, panoramic terrace equipped for alfresco dining, barbecue,[...]


Il Nibbio

from 1.400,00 EUR/Week
No booking fees Best Price Guaranteed

Il Nibbio, Children friendly in Tuscany
Area: Gaiole in Chianti - Tuscany (29.01Km from San Gimignano ) View Map 7-OR
  • Property type: Independent house
  • Sleeps: 5
  • Double bedrooms: 2
  • Single bedrooms: 1
  • Bathrooms: 2
  • 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 useHoliday home made from a ancient medieval fortress in stone, 140 sq. m., holding up to 5 persons with 2 double bedrooms, 1 single and 2 bathrooms. The property has a private swimming[...]


Dimora Boccaccio

from 2.163,00 EUR/Week
No booking fees Best Price Guaranteed

Dimora Boccaccio, Children friendly in Tuscany
Area: Greve in Chianti - Tuscany (29.35Km from San Gimignano ) View Map 3
  • 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 useExclusive villa with swimming pool, suitable for 6 people, with 3 double bedrooms and 3 bathrooms, an enclosed garden equipped for outdoor dining, a portable barbecue. The villa is furnished with heating, smart TV, wi-fi internet connection, baby bed, high chair, fans in each[...]


Villa la Strega

from 5.628,00 4.781,00 EUR/Week
No booking fees Best Price Guaranteed

Villa la Strega, Children friendly in Tuscany
Area: Siena - Tuscany (29.41Km from San Gimignano ) View Map 3-OR

15% off

  • Property type: Villa
  • Sleeps: 13
  • Double bedrooms: 6
  • Single bedrooms: 1
  • Bathrooms: 4
  • Featured pool: Private pool

Rating: 10/10 based upon 5 reviews

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***Property for exclusive use“Villa la Strega” dates back to the 18th century and has been refurbished recently keeping its sober Tuscan elegance. The view of the city that can be enjoyed from here is unique,[...]


Villa Pisana

from 7.700,00 EUR/Week
No booking fees Best Price Guaranteed

Villa Pisana, Domestic help in Tuscany
Area: Palaia - Tuscany (30.10Km from San Gimignano ) View Map 3-OR
  • Property type: Villa
  • Sleeps: 8
  • Double bedrooms: 4
  • Bathrooms: 3
  • Featured pool: Private pool

Property for exclusive useVilla Pisana is a villa for rent situated in the hills overlooking a valley not far from Pisa, west of Florence and Siena. The landscape is typical of the Tuscan hills with olive tree groves on the terraced land, vineyards and small groves. The extensive view allows you to[...]


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 (30.42Km from San Gimignano ) 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[...]


Casale la Monta

from 2.401,00 2.037,00 EUR/Week
No booking fees Best Price Guaranteed

Casale la Monta, Children friendly in Tuscany
Area: Greve in Chianti - Tuscany (30.63Km from San Gimignano ) View Map 4

15% off12% off6% off

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

Rating: 10/10 based upon 2 reviews

Property for exclusive useTuscan farmhouse, 285 sq. m., with a private swimming pool, for up to 8 persons in 4 double bedrooms and 4 bathrooms. The outdoor area features a fenced garden, a covered loggia with a table for outdoor meals and a stonework barbecue. The property also has satellite TV, wifi,[...]


Torreantica

from 7.938,00 EUR/Week
No booking fees Best Price Guaranteed

Torreantica, Children friendly in Tuscany
Area: Castelnuovo Berardenga - Tuscany (30.91Km from San Gimignano ) View Map 4-OR
  • Property type: Villa
  • Sleeps: 12
  • Double bedrooms: 6
  • Bathrooms: 7
  • Featured pool: Private pool

Rating: 10/10 based upon 2 reviews

Property for exclusive useIn the gently rolling hills of the Sienese Chianti region stands Torreantica, whose origins date back to the 13th century when it was a watchtower dominating over the streets and possessions of the lords of the valley. Centuries have passed but the beauty of the landscape has[...]


Castello di Cacchiano

from 2.975,00 EUR/Week
No booking fees Best Price Guaranteed

Castello di Cacchiano, Children friendly in Tuscany
Area: Gaiole in Chianti - Tuscany (31.51Km from San Gimignano ) View Map 4-OR
  • Property type: Independent house
  • Sleeps: 7
  • Double bedrooms: 3
  • Single bedrooms: 1
  • Bathrooms: 4
  • Featured pool: Private pool

Rating: 10/10 based upon 6 reviews

Property for exclusive useIl Bindaccio is an independent part of the castle with private swimming pool and Jacuzzi, holding up to 7 persons with 2 double bedrooms with bathroom with bathtub and shower, one bedroom with two beds, one single bedroom, one bathroom with shower and one bathroom with hydromassage[...]


Il Colombaio

from 1.477,00 EUR/Week
No booking fees Best Price Guaranteed

Il Colombaio, Children friendly in Tuscany
Area: Gaiole in Chianti - Tuscany (32.04Km from San Gimignano ) View Map 3
  • Property type: Independent house
  • Sleeps: 8
  • Double bedrooms: 4
  • Bathrooms: 3
  • Featured pool: Private pool

Rating: 10/10 based upon 10 reviews

Property for exclusive useAncient tower dating back to the 1600s with an apartment in a separate farmhouse, hosting a total of 8 persons in 3 double bedrooms, one bedroom with two beds, 3 bathrooms and one small bathroom. Guests can use the exclusive fenced swimming pool with outdoor shower, private[...]


Casa Betta

from 2.016,00 EUR/Week
No booking fees Best Price Guaranteed

Casa Betta, Children friendly in Tuscany
Area: Vinci - Tuscany (32.40Km from San Gimignano ) View Map 3-OR
  • Property type: Independent house
  • Sleeps: 6
  • Double bedrooms: 3
  • Bathrooms: 2

Property for exclusive useBeautiful house, fully renovated, located on the Florentine hills only a short distance from Vinci and only 35km from Florence, tastefully fitted out with comfortable furniture. The house is semi-detached and is in an ideal position to visit the main Tuscan art cities such[...]


Villino le Viole

from 1.813,00 EUR/Week
No booking fees Best Price Guaranteed

Villino le Viole, Children friendly in Tuscany
Area: Fucecchio - Tuscany (32.45Km from San Gimignano ) View Map 2
  • Property type: Independent house
  • Sleeps: 4-6
  • Double bedrooms: 2
  • Bathrooms: 2
  • Featured pool: Private pool

Rating: 10/10 based upon 6 reviews

Property for exclusive useSmall villa for 6 persons with private swimming pool, two double bedrooms, a double sofa bed in the living room, and two bathrooms with shower. The property has air conditioning, internet, central heating and mosquito screens. The outdoor area features a large fenced garden,[...]


Villa dei Medici

from 6.300,00 EUR/Week
No booking fees Best Price Guaranteed

Villa dei Medici, Children friendly in Tuscany
Area: Vinci - Tuscany (32.54Km from San Gimignano ) View Map 3-OR
  • Property type: Villa
  • Sleeps: 6
  • Double bedrooms: 3
  • Bathrooms: 2
  • Featured pool: Private pool

Rating: 10/10 based upon 4 reviews

Property in exclusive useVilla renovated with great care and equipped with every comfort, with a total surface area of ​​150 m2, able to accommodate up to 6 people in 2 double bedrooms, 1 bedroom with bunk bed, 2 bathrooms and a guest bathroom. The villa offers a private and panoramic swimming pool,[...]