50 Best Vacation Rentals in Montespertoli - Holiday Lettings - Cabins

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Lucardo
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Montagnana Val di Pesa
24 properties
Trecento
14 properties
Polvereto
12 properties

Montespertoli

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289 Vacation rentals

(3) Excellent 

28

Hotel apartment rental in Montespertoli with shared pool

Province of Florence / Montespertoli

2 10 2 nights min

  • 2 bedrooms
  • Sleeps 10
  • 2 nights min
  • 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 wood …see more

from $213 / night

$1446 - $2662 / week

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from $213 / night

25

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Apartment in the old "Borgo". Close to the restaurant. About 500 meters from the farmhouse and the swimming pool.Apartment on ground floor,60 mq, 4 bed places, kitchen (Micro wave oven),- living room, 1 double bedroom, 1 bedroom with 2 single beds, bathroom with shower. …see more

from $135 / night

$460 - $847 / week

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from $135 / night

(11) Excellent 

25

Vacation cottage with shared pool in Polvereto

Montespertoli / Polvereto

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
Situated in a strategic position halfway between Florence and Siena and within easy access of all the most important tourist sites, yet immersed in the quiet of the countryside where the birds sing and in the hot summer evenings the fireflies glow. Far from major roads …see more

from $107 / night

$718 - $897 / week

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from $107 / night

(4) Excellent 

25

Vacation cottage in Polvereto

Montespertoli / Polvereto

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 90 mi
  • Swimming pool
Situated in a strategic position halfway between Florence and Siena and within easy access of all the most important tourist sites, yet immersed in the quiet of the countryside where the birds sing and in the hot summer evenings the fireflies glow. Far from major roads …see more

from $113 / night

$819 - $1043 / week

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from $113 / night

(1) Excellent 

21

Montespertoli Vacation apartment rental

Province of Florence / Montespertoli

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Nearest beach 45 mi
  • Swimming pool
  • Child friendly
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 …see more

from $90 / night

$393 - $785 / week

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from $90 / night

(6) Excellent 

20

Vacation villa with swimming pool in Montespertoli

Province of Florence / Montespertoli

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
Le Torri Tuscany . Villa rentals apartments Le Torri is a Tuscan farmhouse built in the XIII century and located in the beautiful Chianti area. All your needs will be taken care of by the owners themselves, ensuring a relaxing break. The stone farmhouse has a swimmi …see more

from $78 / night

$544 - $875 / week

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from $78 / night

12

Vacation apartment with shared pool in Trecento

Montespertoli / Trecento

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $94 / night

$659 - $1075 / week

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from $94 / night

(5) Excellent 

24

Polvereto Vacation cottage rental

Montespertoli / Polvereto

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 90 mi
  • Swimming pool
Situated in a strategic position halfway between Florence and Siena and within easy access of all the most important tourist sites, yet immersed in the quiet of the countryside where the birds sing and in the hot summer evenings the fireflies glow. Far from major roads …see more

from $118 / night

$830 - $1065 / week

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from $118 / night

19

Montespertoli Vacation farmhouse rental

Province of Florence / Montespertoli

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min
  • 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 $115 / night

$673 - $1457 / week

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from $115 / night

(2) Excellent 

15

Vacation cottage in Montespertoli

Province of Florence / Montespertoli

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Cottage in the heart of Tuscany, surrounded by the colors of the hills and close to places of art. To spend a unique stay in a land cultivated with passion from a peasant family. The House is a single unit with access from the ground floor to the living room and the ki …see more

from $337 / night

$2119 - $2544 / week

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from $337 / night

21

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Apartment in the old "Borgo". Close to the restaurant. About 500 meters from the farmhouse and the swimming pool. Apartment of 80 mq on two floors. 5 bed places and composed by kitchen-dining room, 1 double bedroom, 1 single bedroom, 1 bedroom with two single beds, bath …see more

from $169 / night

$538 - $1054 / week

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from $169 / night

18

Vacation apartment with shared pool in Trecento

Montespertoli / Trecento

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $94 / night

$659 - $1075 / week

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from $94 / night

23

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
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 $107 / night

$746 - $1177 / week

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from $107 / night

14

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
MARGHERITE apartment is made of 2 double bedrooms, 2 bathrooms (one with a Jacuzzi-type bath-tub, WC, basin, bidet; the other is with shower, WC, basin, bidet), a large living-room with a double sofa bed, a dining room able to sit up to 15 persons, a kitchen fully equip …see more

from $152 / night

$919 - $1794 / week

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from $152 / night

20

Montespertoli Vacation apartment rental

Province of Florence / Montespertoli

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Large apartment for 6 people located in Residenze Piandaccoli farmhouse. The apartment has: 2 kitchens, 2 living rooms with LCD TV and one of each with a sofa bed with a double bed in fron of a lovely fireplace, 2 large bathrooms with shower, 2 double bedrooms with a do …see more

from $273 / night

$1907 / week

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from $273 / night

17

Vacation farmhouse with shared pool in Montespertoli

Province of Florence / Montespertoli

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • 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 $113 / night

$649 - $1325 / week

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from $113 / night

(1) Excellent 

18

Vacation villa in Montespertoli

Province of Florence / Montespertoli

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Private garden
Part of a big countryside house with garden, composed of two floors. Postion: between Florence and Siena, well situated to visit Tuscany. You will be the only tenants relaxing in the garden! Groundfloor with a big dining romm/living room with kitchen, first floor wit …see more

from $79 / night

$550 / week

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from $79 / night

(1) Excellent 

19

Vacation farmhouse in Montespertoli

Province of Florence / Montespertoli

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • 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 $182 / night

$1055 - $1896 / week

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from $182 / night

19

Vacation farmhouse accommodation

Province of Florence / Montespertoli

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • 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 $157 / night

$919 - $1723 / week

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from $157 / night

(1) Excellent 

15

Apartment rental in Montagnana Val di Pesa with shared pool, golf nearby

Montespertoli / Montagnana Val di Pesa

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
The apartment orange and cinnamon, is a lovely one bedroom apartment inside the Torricella Farmahouse. The apartament have a large and very well equipped (kettle, toaster, American coffee machine) kitchen and living room in orange tones, is very bright with an outside …see more

from $135 / night

$729 / week

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from $135 / night

24

Vacation villa with swimming pool in Montespertoli

Province of Florence / Montespertoli

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 45 mi
  • Swimming pool
  • Child friendly
The villa is situated in a small and charming village called Renai, 3 km from Castelfiorentino, surrounded by vineyards and olive groves. In the small village of Castelfiorentino you will find: railway station, supermarket, banks, post office, pharmacies, hospital, all …see more

from $277 / night

$1939 - $3135 / week

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from $277 / night

22

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Apartment in the old "Borgo". Close to the restaurant. About 500 meters from the farmhouse and the swimming pool.Apartment on first floor. Apartment of 50 mq, 2 bed places and composed by kitchen - living room, 1 double bedroom, bathroom with shower. TV SAT. Internet wi …see more

from $113 / night

$370 - $667 / week

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from $113 / night

(1) Excellent 

24

Trecento Vacation townhouse rental

Montespertoli / Trecento

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Nestled in the hills of Chianti stands the Casa Rossa: property consists of two apartments; one consists of a large kitchen/living room with fireplace, sofa-bed and access to a terrace, a double room and a bathroom with bathtub on the second apartment consists of living …see more

from $57 / night

$337 / week

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from $57 / night

15

Vacation farmhouse in Trecento

Montespertoli / Trecento

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Accommodation in Chianti for luxury holidays. Farming estate producing wine and olive oil with a charming farmhouse situated in a small luxury hamlet of houses in panoramic and quiet location amidst the hills surrounding Montespertoli, in Chianti. The farmhouse, is divi …see more

from $97 / night

$563 - $1051 / week

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from $97 / night

9

Montespertoli Vacation home rental

Province of Florence / Montespertoli

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Ask about pets
David and Eleanor are Tuscan DOCG and want to share the taste of local hospitality in a modern setting and with an eye on design and comfort. This is not a House but a recovery that would lead to atypical building something personal, close to amenities but away from the …see more

from $90 / night

$561 / week

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from $90 / night

20

Vacation apartment with shared pool, golf nearby in Polvereto

Montespertoli / Polvereto

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • 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 $228 / night

$1593 / week

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from $228 / night

(17) Excellent 

13

Polvereto Vacation barn rental

Montespertoli / Polvereto

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Private garden
This traditional Tuscan barn has been lovingly restored by the current owner to a very high standard. They have maintained all of the original charm whist making it a luxurious and stylish holiday home. On the ground floor there is a family room with a comfortable d …see more

from $113 / night

$785 / week

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from $113 / night

14

Vacation farmhouse in Montespertoli

Province of Florence / Montespertoli

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • 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 $99 / night

$570 - $1271 / week

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from $99 / night

13

Montespertoli Vacation farmhouse rental

Province of Florence / Montespertoli

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • 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

$503 - $963 / week

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from $87 / night

17

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly
Apartment in the farm about 200 meters from the main farmhouse, from the swimming pool and from the restaurant. Apartment on first floor. Apartment of 45 mq., 2 bed places and composed by kitchen - living room, 1 double bedroom, bathroom with shower. TV SAT. Internet wi …see more

from $113 / night

$382 - $679 / week

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from $113 / night

24

Montespertoli Vacation apartment rental

Province of Florence / Montespertoli

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
HOLIDAYS AND BUSINESS Wonderful farmhouse in the middle of a landscape of extraordinary beauty, in the heart of the Tuscan hills just 20 Km from the city of Florence and not far from other cities and art centers such as Siena, Pisa, San Gimignano, Volterra. Only 45 min …see more

from $213 / night

$1446 - $2427 / week

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from $213 / night

23

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Apartment in the old "Borgo". Close to the restaurant. About 500 meters from the farmhouse and the swimming pool.Apartment on first floor. 60 mq., 3 bed places and composed by entrance - living room, kitchen, 1 double bedroom, 1 single bedroom, bathroom with shower. Int …see more

from $124 / night

$415 - $796 / week

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from $124 / night

21

Montagnana Val di Pesa Vacation villa accommodation

Montespertoli / Montagnana Val di Pesa

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 75 mi
  • Swimming pool
  • Child friendly
Enjoy noble splendor in this gracious antique villa which is both close to Florence and immersed in tranquility. Villa Il Turco is an elegant, aristocratic, sixteenth-century country estate which once belonged to a noble family named Rosselli Del Turco. Complete with …see more

from $472 / night

$3301 - $4472 / week

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from $472 / night

19

Vacation home rental

Province of Florence / Montespertoli

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Casa indipendente di campagna in bellissima posizione collinare e panoramica. E' situata nel comune di Montespertoli, la città del vino, nella zona del Chianti e da qui sono facilmente raggiungibili Firenze, Siena, San Gimignano, Pisa, Volterra. E' spaziosa e confortevo …see more

from $129 / night

$897 - $1289 / week

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from $129 / night

7

Vacation home in Montespertoli

Province of Florence / Montespertoli

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Ask about pets
David and Eleanor are Tuscan DOCG and want to share the taste of local hospitality in a modern setting and with an eye on design and comfort. This is not a House but a recovery that would lead to atypical building something personal, close to amenities but away from the …see more

from $45 / night

$281 / week

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from $45 / night

24

Vacation apartment in Montagnana Val di Pesa

Montespertoli / Montagnana Val di Pesa

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
Romantic and cosy apartment with wooden beams and terracotta floors within a farm with pool and green area, can accommodate up to 6 people using the double sofa bed in the living-room/kitchen. The apartment has a large kitchen (very well equipped) with 4 burners and ref …see more

from $157 / night

$897 / week

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from $157 / night

(1) Excellent 

16

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Apartment in the farm about 200 meters from the main farmhouse, from the swimming pool and from the restaurant. Apartment on ground floor.60 mq, 4 bed places and composed by kitchen - living room with oven, 1 double bedroom, 1 bedroom with 2 single beds, bathroom with …see more

from $135 / night

$471 - $903 / week

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from $135 / night

15

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 45 mi
  • 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 …see more

from $73 / night

$393 - $561 / week

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from $73 / night

49

Montespertoli Vacation apartment rental

Province of Florence / Montespertoli

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
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 $135 / night

$942 - $1609 / week

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from $135 / night

12

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
My accommodation is located in the center of Tuscany, right between the main art cities: Florence, Pisa and Siena. my accommodation is also equipped with TV, laundry and dishes, in addition to the pool, tennis, table tennis and many barbecue areas. The parking lot is pr …see more

from $113 / night

$673 / week

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from $113 / night

1