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85 Holiday homes

Filters applied: Pets allowed (85)

1 / 4

Fattoria di Trecento - Trecento farmhouse sleeps 8

Montespertoli / Trecento

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Child friendly ; Ask about pets; Private garden;
A typical Tuscan farm in the center of the Chianti region, surrounded by cypress hills, vineyards and olive-trees;the most important cities of art and culture in Tuscany are just one hour far.The apartment is composed of 3 bedrooms, a large living room, a kitchen and a  …see more

from £154 / night

£1026 / week

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from £154 / night

1 / 14

Province of Florence / Montespertoli

1 5 1 night min stay

  • 1 bedroom
  • Sleeps 5
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £43 / night

£257 - £526 / week

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from £43 / night

(4) Excellent 

1 / 16

Castello Sonnino - Winemaker apartment - Montespertoli apartment sleeps 6

Province of Florence / Montespertoli

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Child friendly ; Car advised; Air conditioning;
At Castello Sonnino you have the chance to stay in exclusive apartments situated in property. The decor has been designed with the greatest care, in harmony with the traditions and taste of Tuscan houses. The traditional materials, the colours with their warm hues and t  …see more

from £129 / night

£1018 / week

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from £129 / night

(1) Excellent 

1 / 17

Castello Sonnino - Farmhouse - Montespertoli apartment sleeps 6

Province of Florence / Montespertoli

3 6 2 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Child friendly ; Ask about pets; Private garden;
At Castello Sonnino you have the chance to stay in an exclusive apartment situated in the thirteenth-century tower. The decor has been designed with the greatest care, in harmony with the traditions and taste of Tuscan houses. The traditional materials, the colours with  …see more

from £116 / night

£812 / week

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from £116 / night

(1) Excellent 

1 / 16

Province of Florence / Montespertoli

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 72 km; Child friendly ; Ask about pets;
 …see more

from £59 / night

£384 / week

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from £59 / night

1 / 19

Province of Florence / Montespertoli

4 8 2 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Child friendly ; Car essential; Ask about pets;
 …see more

from £103 / night

£684 / week

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from £103 / night

1 / 23

Private villa in Chianti, 7 bedrooms, garden, pool - Polvereto villa sleeps 13

Montespertoli / Polvereto

7 13 7 nights min stay

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Nearest beach 88 km; Swimming pool; Child friendly ;
CASALE IL POGGIARELLO - Country Holiday HouseEnclosed in a 5000 sqm area in the heart of the Chianti, it is an oasis where you can enjoy an absolute relax and privacy. Situated in a dominant position on the Virginio Valley, our property will be for your own private use,  …see more

from £245 / night

£1710 / week

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from £245 / night

1 / 9

Country hotel in Chianti - Montespertoli b&b sleeps 36

Province of Florence / Montespertoli

15 36 Min stay varies

  • 15 bedrooms
  • Sleeps 36
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
A charming inn housed in the former premises of a deconsecrated chapel in the vineyards of Chianti. You arrive at the inn along a narrow country road through the vineyards of the Val di Pesa, near Florence. The Old Chapel is situated on a hilltop in a panoramic position  …see more

from £46 / night

£287 - £368 / week

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from £46 / night

1 / 9

Province of Florence / Montespertoli

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Child friendly ; Ask about pets; Private garden;
 …see more

Pricing unknown

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1 / 15

LA MEZZANA APPARTMENT WITH TERRACE AND SHARED POOL - Montespertoli apartment sleeps 2

Province of Florence / Montespertoli

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Child friendly ;
Appartment in small farmhouse (max. 12 people) with private equipped terrace with wonderful view on the sorrounding countryside. The house is situated in a fantastic hilltop position, reached only by a private road that brings you to the small village Martignana in the  …see more

from £60 / night

£300 - £428 / week

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from £60 / night

1 / 16

Montespertoli - 15699054 - Montespertoli farmhouse sleeps 3

Province of Florence / Montespertoli

1 3 3 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Wonderful castle dating back to the 12th century, restored in the 17th century by the noble family of Acciaioli, with a magnificent tower built on the model of the one of Palazzo Vecchio in Florence. Montegufoni castle is part of a large estate comprising vineyards and  …see more

from £76 / night

£440 - £979 / week

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from £76 / night

1 / 20

Piandaccoli - Botticelli - Polvereto apartment sleeps 4

Montespertoli / Polvereto

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
Large apartment for 4 people located in Residenze Piandaccoli farmhouse. The apartment has: kitchen, living room with LCD TV, large bathroom, 1 double bedroom and 1 twin bedroom. Residenze Piandaccoli is an old farmhouse divided into holiday apartments, recently restore  …see more

from £105 / night

£730 - £1215 / week

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from £105 / night

1 / 20

Villa Il Nido, Montespertoli - Montespertoli villa sleeps 5

Province of Florence / Montespertoli

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Villa Il Nido (The Nest), part of an ancient mansion on Chianti hills, is perfectly named, nestled in a lovely park with centennial cypresses and olive trees, amidst the sweet bird song: a little heaven of quiet and beauty on a sea of hills rolling to the horizon.Only 5  …see more

from £109 / night

£761 - £1026 / week

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from £109 / night

1 / 13

Montespertoli - 15699005 - Montespertoli farmhouse sleeps 3

Province of Florence / Montespertoli

1 3 3 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Wonderful castle dating back to the 12th century, restored in the 17th century by the noble family of Acciaioli, with a magnificent tower built on the model of the one of Palazzo Vecchio in Florence. Montegufoni castle is part of a large estate comprising vineyards and  …see more

from £66 / night

£387 - £742 / week

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from £66 / night

1 / 24

Province of Florence / Montespertoli

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 55 km; Child friendly ; Car essential;
 …see more

from £81 / night

£565 - £941 / week

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from £81 / night

1 / 20

Villa in Montespertoli - Montespertoli villa sleeps 5

Province of Florence / Montespertoli

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Villa Gasparri, stylish restored mansion on Chianti Hills, with private pool in exclusive use, is perfectly placed for exploring this fascinating area and glorious cities as Florence (25 km), Siena (55 km), San Gimignano (35 km), Pisa (60 km), offering a first class acc  …see more

from £109 / night

£761 - £1026 / week

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from £109 / night

1 / 9

Province of Florence / Montespertoli

1 5 1 night min stay

  • 1 bedroom
  • Sleeps 5
  • 1 night min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £69 / night

£428 / week

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from £69 / night

(3) Excellent 

1 / 28

La Rocca di Montalbino_App. TORRE - Montespertoli hotel apartment sleeps 10

Province of Florence / Montespertoli

2 10 2 nights min stay

  • 2 bedrooms
  • Sleeps 10
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
La Rocca di Montalbino stands on one of the hilltops surrounding Montespertoli. This location offers a splendid view of the Chianti landscape and all the peace and quiet of the Tuscan countryside.Surrounded by thirty hectares of vineyards, olive groves, and woodlands, o  …see more

from £163 / night

£1018 - £1274 / week

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from £163 / night

1 / 19

Amazing SPA Apartment in the wineyards_LA ROCCA - Trecento apartment sleeps 8

Montespertoli / Trecento

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
Superior Apartment with3 double bedroom with ensuite bathroom, one additional bathroom at ground floor, dining room + living room, full equipped kitchen and direct access to a private garden with an amazing panoramic view where you can have relaxing time or breakfast, l  …see more

from £109 / night

£761 - £1317 / week

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from £109 / night

1 / 20

Piandaccoli - Giotto - Polvereto apartment sleeps 2

Montespertoli / Polvereto

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Giotto is a large apartment for 2 people located inside a typical Tuscan farmhouse. The apartment is composed of: built-in kitchen, living room with LCD TV, large bathroom also suitable for disables and double bedroom with queen-size bed.Residenze Piandaccoli is an old  …see more

from £79 / night

£551 - £910 / week

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from £79 / night

(1) Excellent 

1 / 20

Montespertoli - 15699053 - Montespertoli farmhouse sleeps 6

Province of Florence / Montespertoli

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Wonderful castle dating back to the 12th century, restored in the 17th century by the noble family of Acciaioli, with a magnificent tower built on the model of the one of Palazzo Vecchio in Florence. Montegufoni castle is part of a large estate comprising vineyards and  …see more

from £140 / night

£813 - £1459 / week

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from £140 / night

(31) Very Good 

1 / 23

Detached Tuscan villa with private garden - Montespertoli farmhouse sleeps 13

Province of Florence / Montespertoli

7 13 Min stay varies

  • 7 bedrooms
  • Sleeps 13
  • Min stay varies
Key info: Nearest beach 40 km; Swimming pool; Child friendly ;
A lovely, comfortable house [200m2] situated in a wonderful hilltop position,reached only by a private road and surrounded by the hills and valleys of the Florentine countryside. The house is divided into three apartments of various sizes located on two levels that can  …see more

from £300 / night

£1368 - £2223 / week

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from £300 / night

1 / 21

MULINO A VENTO Appartment with private terrace - Montespertoli apartment sleeps 4

Province of Florence / Montespertoli

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Ask about pets;
Appartment in a small farmhouse (composed by three appartments) situated in a wonderful hilltop position with a large (more that 4.000 sqm.) garden with stunning views on the sorrounding countryside. Pool and parking area withing the grounds.The appartment is about 55 s  …see more

from £82 / night

£359 - £642 / week

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from £82 / night

1 / 18

Montespertoli - 15699052 - Montespertoli farmhouse sleeps 5

Province of Florence / Montespertoli

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Wonderful castle dating back to the 12th century, restored in the 17th century by the noble family of Acciaioli, with a magnificent tower built on the model of the one of Palazzo Vecchio in Florence. Montegufoni castle is part of a large estate comprising vineyards and  …see more

from £122 / night

£708 - £1328 / week

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from £122 / night

(3) Excellent 

1 / 21

PODERE LE RONDINI - Polvereto villa sleeps 29

Montespertoli / Polvereto

13 29 Min stay varies

  • 13 bedrooms
  • Sleeps 29
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
Our ancient master-house called COLONICA villa, has been recently restored originating a villa made of 9 bedrooms (of which 5 double-bedrooms and 4 rooms that can be used as triple-, twin- or double-bedrooms), 10 bathrooms (each one with shower, bidet, wc, basin; one is  …see more

from £1112 / night

£6838 - £9402 / week

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from £1112 / night

1 / 49

Tenuta Moriano - Apart trilo 1 - Montespertoli apartment sleeps 5

Province of Florence / Montespertoli

2 5 2 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Tenuta Moriano is part of an antique territory, the Chianti, dedicated to the agricultural tradition and culture of its wines. Immersed by the atmosphere of the Tuscan country and located very closely to the heart of one of the most antique art cities in the entire worl  …see more

from £95 / night

£582 / week

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from £95 / night

1 / 17

LA MASSERIA CHARMING APPARTMENT WITH GREAT VIEW - Montespertoli apartment sleeps 7

Province of Florence / Montespertoli

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Nearest beach 40 km; Swimming pool; Child friendly ;
Ample appartment in farmhouse (composed of 3 appartments max 12 guests) in a wonderful peacefull hilltop position reached only by a 600 metres private road.The appartment has two private terraces with breathtaking views on the sorrounding countryside. Around the house  …see more

from £129 / night

£599 - £1069 / week

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from £129 / night

(1) Excellent 

1 / 23

Polvereto - Polvereto apartment sleeps 4

Montespertoli / Polvereto

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 67 km; Swimming pool;
This beautiful and well equipped apartment with exposed beams and terracotta floor,sits on a large estate (10.000 square meters) with olive groves and vineyards with pool directly by the house.It is well connected to the most important Tuscan cities.Polvereto is set on  …see more

from £69 / night

£458 / week

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from £69 / night

1 / 16

Montespertoli - 15699009 - Montespertoli farmhouse sleeps 5

Province of Florence / Montespertoli

1 5 3 nights min stay

  • 1 bedroom
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Wonderful castle dating back to the 12th century, restored in the 17th century by the noble family of Acciaioli, with a magnificent tower built on the model of the one of Palazzo Vecchio in Florence. Montegufoni castle is part of a large estate comprising vineyards and  …see more

from £87 / night

£500 - £1020 / week

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from £87 / night

1 / 11

Province of Florence / Montespertoli

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £86 / night

£599 - £992 / week

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from £86 / night

1 / 12

Montespertoli - 45485002 - Trecento farmhouse sleeps 4

Montespertoli / Trecento

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Beautiful property with swimming-pool comprising 3 apartments situated in panoramic location on the hills surrounding Florence. The 3 units are nicely furnished in a rustic style and provide furnished outdoor areas. The owners live in a fourth apartment on the premises  …see more

from £49 / night

£285 - £518 / week

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from £49 / night

1 / 20

Montespertoli - 15699025 - Montespertoli farmhouse sleeps 6

Province of Florence / Montespertoli

4 6 3 nights min stay

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Wonderful castle dating back to the 12th century, restored in the 17th century by the noble family of Acciaioli, with a magnificent tower built on the model of the one of Palazzo Vecchio in Florence. Montegufoni castle is part of a large estate comprising vineyards and  …see more

from £94 / night

£541 - £1152 / week

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from £94 / night

1 / 18

Montespertoli - 45485003 - Trecento farmhouse sleeps 4

Montespertoli / Trecento

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Beautiful property with swimming-pool comprising 3 apartments situated in panoramic location on the hills surrounding Florence. The 3 units are nicely furnished in a rustic style and provide furnished outdoor areas. The owners live in a fourth apartment on the premises  …see more

from £59 / night

£336 - £570 / week

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from £59 / night

1 / 11

Marvellous Apartment in Chianti. Special Offer - Montespertoli farmhouse sleeps 8

Province of Florence / Montespertoli

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
La Rocca di Montalbino stands on one of the hilltops surrounding Montespertoli. This location offers a splendid view of the Chianti landscape and all the peace and quiet of the Tuscan countryside.Surrounded by thirty hectares of vineyards, olive groves, and woodlands, o  …see more

from £97 / night

£676 - £1231 / week

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from £97 / night

1 / 19

Montespertoli - 84456001 - Montespertoli farmhouse sleeps 6

Province of Florence / Montespertoli

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Comfortable portion of a country house very close to Montespertoli, a town in the Tuscan hills about 25 km from Florence and 30 km from San Gimignano. The country house is made up of the apartment for rent, and the apartment of the owners, who are nice, discreet and wel  …see more

from £111 / night

£648 - £1382 / week

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from £111 / night

1 / 20

Montespertoli - 15699050 - Montespertoli farmhouse sleeps 2

Province of Florence / Montespertoli

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Wonderful castle dating back to the 12th century, restored in the 17th century by the noble family of Acciaioli, with a magnificent tower built on the model of the one of Palazzo Vecchio in Florence. Montegufoni castle is part of a large estate comprising vineyards and  …see more

from £82 / night

£476 - £793 / week

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from £82 / night

1 / 15

Polvereto - 124470005 - Lucardo farmhouse sleeps 2

Montespertoli / Lucardo

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
In the southern part of Florence in the direction of Siena (Heart of Tuscany) a majestic farmhouse rises on a hill at the crossing point of a valley, la Valle a Polvereto. Fully integrated in its rural surroundings the restoration of this characteristic Tuscan accommoda  …see more

from £60 / night

£419 - £659 / week

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from £60 / night

1 / 20

Montespertoli - 15699016 - Montespertoli farmhouse sleeps 3

Province of Florence / Montespertoli

2 3 3 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Wonderful castle dating back to the 12th century, restored in the 17th century by the noble family of Acciaioli, with a magnificent tower built on the model of the one of Palazzo Vecchio in Florence. Montegufoni castle is part of a large estate comprising vineyards and  …see more

from £72 / night

£422 - £812 / week

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from £72 / night

1 / 16

Montespertoli - 15699018 - Montespertoli farmhouse sleeps 2

Province of Florence / Montespertoli

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Wonderful castle dating back to the 12th century, restored in the 17th century by the noble family of Acciaioli, with a magnificent tower built on the model of the one of Palazzo Vecchio in Florence. Montegufoni castle is part of a large estate comprising vineyards and  …see more

from £76 / night

£440 - £1036 / week

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from £76 / night

1 / 15

Montespertoli - 15699038 - Montespertoli farmhouse sleeps 4

Province of Florence / Montespertoli

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Wonderful castle dating back to the 12th century, restored in the 17th century by the noble family of Acciaioli, with a magnificent tower built on the model of the one of Palazzo Vecchio in Florence. Montegufoni castle is part of a large estate comprising vineyards and  …see more

from £76 / night

£440 - £979 / week

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from £76 / night

Top Destination reviews

Poppiano Chianti Hill WiFi
memorable stay

My family and I enjoyed our recent stay at Simone and Susanne's apartment. Susanne was a nice and helpful host who assisted us to locate her apartment in Poppiano as we drove in from Rome. The apartment was as depicted in her listing. It was very spa … see more

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