50 Best Vacation Rentals in Montespertoli - Holiday Lettings - Cabins

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Lucardo
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Montagnana Val di Pesa
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Trecento
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Montespertoli

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307 Vacation rentals

(2) Very Good 

11

Vacation farmhouse rental

Province of Florence / Montespertoli

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • 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 wood …see more

from $133 / night

$927 - $1760 / week

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from $133 / night

(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 $223 / night

$1513 - $2786 / week

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from $223 / night

26

Vacation villa accommodation

Montespertoli / Montagnana Val di Pesa

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Flat furnished with care and fine furniture in a hilly area. The structure consists of 3 double bedrooms and a single. Suitable for families or couples of friends. It has a small garden and can accommodate animals. In a strategic position for visiting the major cities. …see more

from $94 / night

$587 / week

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Responds fast!
avg. 3 hours 39 minutes

from $94 / 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 $141 / night

$481 - $886 / week

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Responds fast!
avg. 3 hours 42 minutes

from $141 / night

(13) Excellent 

25

Vacation cottage with shared pool in Polvereto

Montespertoli / Polvereto

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 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 $129 / night

$845 - $939 / week

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from $129 / 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 $94 / night

$411 - $821 / week

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from $94 / night

(2) Very Good 

24

Trecento Vacation townhouse rental

Montespertoli / Trecento

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • 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 $59 / night

$411 / week

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from $59 / 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 $285 / night

$1995 / week

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from $285 / night

9

Vacation b&b rental

Province of Florence / Montespertoli

15 36 Min stay varies

  • 15 bedrooms
  • Sleeps 36
  • Min stay varies
  • 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 $63 / night

$393 - $505 / week

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from $63 / 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 $352 / night

$2217 - $2663 / week

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from $352 / night

(1) Very Good 

26

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 110 mq on first floor. 5 bed places and composed by kitchen – living room, 1 double bedroom, 1 bedroom with 2 single beds, 1 bedroom with a sin …see more

from $176 / night

$599 - $1138 / week

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Responds fast!
avg. 3 hours 42 minutes

from $176 / night

(4) Excellent 

21

Vacation villa with swimming pool in Montespertoli

Province of Florence / Montespertoli

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Our VILLA CASA DI MONTE is a country-villa that dates back to the beginning of the XIX Century and that has been recently restored preserving the original structure of the house. The whole villa consists of 2 units, but we only rent the VILLA all together to a single g …see more

from $563 / night

$3929 - $5008 / week

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from $563 / 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 $135 / night

$868 - $1115 / week

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from $135 / night

(4) Excellent 

16

Montespertoli Vacation apartment rental

Province of Florence / Montespertoli

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
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 $176 / night

$1396 / week

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from $176 / night

(1) Excellent 

18

Vacation villa in Montagnana Val di Pesa

Montespertoli / Montagnana Val di Pesa

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Private garden
Our Villa is an elegant, aristocratic, sixteenth-century country estate which once belonged to a noble family named Rosselli Del Turco. Complete with vaulted ceilings downstairs and chestnut coffered ones upstairs, stables, a pigeon loft and a graceful loggia on the …see more

from $528 / night

$3519 - $4926 / week

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from $528 / night

18

Montespertoli Vacation farmhouse rental

Province of Florence / Montespertoli

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Traces of ancient cultures fill every corner of the Tuscan landscape and the Cabbiavoli Castle is a shining example! Just 30 minutes from Florence and 50 from Pisa or Siena is the hidden Cabbiavoli estate. It is dominated by a 13th century Castle. The barns built to s …see more

from $125 / night

$728 - $1160 / week

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from $125 / night

20

Vacation farmhouse in Montespertoli

Province of Florence / Montespertoli

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Pet friendly
Traces of ancient cultures fill every corner of the Tuscan landscape and the Cabbiavoli Castle is a shining example! Just 30 minutes from Florence and 50 from Pisa or Siena is the hidden Cabbiavoli estate. It is dominated by a 13th century Castle. The barns built to s …see more

from $115 / night

$680 - $1125 / week

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from $115 / night

20

Vacation farmhouse in Montespertoli

Province of Florence / Montespertoli

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Traces of ancient cultures fill every corner of the Tuscan landscape and the Cabbiavoli Castle is a shining example! Just 30 minutes from Florence and 50 from Pisa or Siena is the hidden Cabbiavoli estate. It is dominated by a 13th century Castle. The barns built to s …see more

from $125 / night

$728 - $1160 / week

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from $125 / 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 $141 / night

$763 / week

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from $141 / night

(2) Excellent 

19

Vacation apartment in Montespertoli

Province of Florence / Montespertoli

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Casanova 3 is located on the ground floor of a small house independent, behind the main structure of Podere Casanova. Apartment of 80 m2, for a maximum capacity of 4 people. It is surrounded by an English lawn and the sidebar has a large private terrace equipped for eat …see more

from $112 / night

$716 - $950 / week

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from $112 / night

14

Vacation chalet with shared pool in Montespertoli

Province of Florence / Montespertoli

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
In the heart of Chianti in Tuscany, immersed in the green of the hills, you can come and spend a pleasant relaxing countryside, where you can enjoy a good wine in front of the swimming pool, alternating visits to the nearby cities of art like Florence, Siena, Pisa, Volt …see more

from $59 / night

$352 - $722 / week

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from $59 / 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 $165 / night

$939 / week

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from $165 / 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 $223 / night

$1513 - $2539 / week

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from $223 / 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 $82 / night

$569 - $915 / week

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from $82 / 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 $190 / night

$1104 - $1984 / week

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from $190 / night

(5) 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 $124 / night

$857 - $1009 / week

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from $124 / 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 $165 / night

$962 - $1803 / week

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from $165 / 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 $94 / night

$587 / week

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Responds fast!
avg. 58 minutes

from $94 / night

(1)  

17

Vacation apartment rental

Province of Florence / Montespertoli

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 40 mi
  • 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 ho …see more

from $176 / night

$821 - $1466 / week

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from $176 / night

4

Montespertoli Vacation apartment rental

Province of Florence / Montespertoli

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
apartment for rent ideal for holiday in contact with nature mq 50 local number five 60 Euro per day apartments equipped with all the comfort of Apartments equip you th Rent Apartments for weekends (minimum 2 days ... 30 minutes from Florence, san gimignano 25 minutes .4 …see more

from $71 / night

$493 / week

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from $71 / night

36

Vacation villa rental

Province of Florence / Montespertoli

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 75 mi
  • Swimming pool
  • Private garden
Villa Florence Casa Serena consists of about half of an ancient farm, whose first foundations date back to the 15th century. Renovated and expanded several times, it was definitely used as a country house Restored, totally independent property and surrounded by cypress …see more

from $310 / night

$2170 - $3457 / week

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from $310 / 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 $176 / night

$575 - $1103 / week

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Responds fast!
avg. 3 hours 42 minutes

from $176 / 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 $98 / night

$690 - $1125 / week

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from $98 / night

21

Vacation farmhouse in Montespertoli

Province of Florence / Montespertoli

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Traces of ancient cultures fill every corner of the Tuscan landscape and the Cabbiavoli Castle is a shining example! Just 30 minutes from Florence and 50 from Pisa or Siena is the hidden Cabbiavoli estate. It is dominated by a 13th century Castle. The barns built to s …see more

from $135 / night

$785 - $1302 / week

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from $135 / 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 $141 / night

$493 - $945 / week

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Responds fast!
avg. 3 hours 42 minutes

from $141 / 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 $118 / night

$821 / week

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from $118 / 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 $47 / night

$294 / week

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Responds fast!
avg. 58 minutes

from $47 / night

6

Vacation apartment rental

Province of Florence / Montespertoli

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The farm holidays “Il Gufo del Chianti” is located in the countryside. The apartment “Il grano” with its 53sqm, is suitable for up to 5 people. Rooms: a bedroom with double bed and single bed, living room (very large) with sofa bed and kitchenette. The apartment i …see more

Pricing unknown

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Pricing unknown

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 $141 / night

$986 - $1683 / week

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from $141 / night

11

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
appartamento indipendente piano terra arredato con biancheria , giardino con barbecue, piscina e tennis , 25 minuti da Firenze 35 minuti da pisa , Empoli ,vinci 20 minuti da San Gimignano 40 minuti a Siena, siamo a centro toscana nella campagna delle colline del chia …see more

from $94 / night

$657 / week

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from $94 / night