50 Best Vacation Rentals in Montespertoli - Holiday Lettings - Cabins

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8,821 Vacation rentals

15

Vacation cottage rental

Province of Florence / Montespertoli

2 7 4 nights min

  • 2 bedrooms
  • sleeps 7
  • 4 nights min
  • Ask about children
  • Ask about pets
  • Private garden
Recently restored in typical Tuscan Country Style Ex Priest Residence accomodates up to 7 guests. Located on top of a hill which offers astonishing views of the surrounding hills. Lovely Cosy Garden with Old Olive Tree and Sundeck with Outdoor Shower. Situated only at 3 …see more

from $177 / night

$1,081 - $1,439 / week

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from $177 / night

23

Vacation villa with swimming pool in Montespertoli

Province of Florence / Montespertoli

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Le Torri Tuscany. Villa apartments with pool, 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 s …see more

from $104 / night

$725 / week

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from $104 / 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
Special offer: July and August price includes a typical Tuscan dinner ; aqua gym lesson, horse-drawn coach tour of the vineyard Apartment in the farm about 200 meters from the main farmhouse, from the swimming pool and from the restaurant. Apartment on ground floor.60 …see more

from $115 / night

$411 - $920 / week

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from $115 / night

24

Vacation apartment in Montagnana Val di Pesa

Montespertoli / Montagnana Val di Pesa

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 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 $170 / night

$1,133 / week

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from $170 / night

23

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
Special offer: July and August price includes a typical Tuscan dinner ; aqua gym lesson, horse-drawn coach tour of the vineyard Apartment in the old "Borgo". Close to the restaurant. About 500 meters from the farmhouse and the swimming pool. Apartment on ground floor,s …see more

from $137 / night

$489 - $984 / week

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from $137 / night

(9) Excellent 

20

Vacation villa with swimming pool in Montespertoli

Province of Florence / Montespertoli

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • 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 $85 / night

$561 - $725 / week

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from $85 / 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
Special offer: July and August price includes a typical Tuscan dinner ; aqua gym lesson, horse-drawn coach tour of the vineyard Apartment in the farm about 200 meters from the main farmhouse, from the swimming pool and from the restaurant. Apartment on first floor. Apa …see more

from $91 / night

$363 - $685 / week

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Responds fast!
avg. 3 hours 44 minutes

from $91 / night

(1) Excellent 

24

Vacation townhouse in Montespertoli

Province of Florence / Montespertoli

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 76 mi
In the very heart of Tuscany you will find on the top of a hill a very cozy accommodation and an incomparable view ranging from San Gimignano towers to the harsh Alpi Apuane will welcome you with a warm hug. The apartment is located at ground floor and is composed of a …see more

from $56 / night

$390 / week

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from $56 / 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
Special offer: July and August price includes a typical Tuscan dinner ; aqua gym lesson, horse-drawn coach tour of the vineyard Apartment in the old "Borgo". Close to the restaurant. About 500 meters from the farmhouse and the swimming pool.Apartment on ground floor,60 …see more

from $137 / night

$469 - $914 / week

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from $137 / night

(31) Very Good 

27

Farmhouse rental in Montespertoli with swimming pool

Province of Florence / Montespertoli

7 13 1 night min

  • 7 bedrooms
  • sleeps 13
  • 1 night min
  • Nearest beach 40 mi
  • 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 t …see more

from $455 / night

$2,161 / week

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from $455 / 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 $125 / night

$819 - $1,075 / week

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Responds fast!
avg. 2 hours 43 minutes

from $125 / night

28

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
Tucked away among the gently rolling hills near Florence, Tenuta Moriano is an antique farmhouse turned vacation rental apartments. Our apartments are furnished in typical rustic Tuscan style, with high quality handmade furniture. Tenuta Moriano is the perfect location …see more

from $137 / night

$955 / week

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from $137 / night

(2) Very Good 

76

Vacation farmhouse rental

Province of Florence / Montespertoli

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
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, …see more

from $160 / night

$1,478 / week

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Responds fast!
avg. 35 minutes

from $160 / night

10

Montespertoli Vacation home rental

Province of Florence / Montespertoli

3 12 1 night min

  • 3 bedrooms
  • sleeps 12
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Enormous Room + Apartment for planning to organize celebrations Birthdays, The room is independent and equipped with everything: audio / lights, console tables, chairs Private events of all kinds. Apartment with kitchen and beds with possibility We add other beds garden …see more

from $398 / night

$2,786 / week

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from $398 / night

(1) Excellent 

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 $160 / night

$546 - $1,081 / week

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from $160 / night

(1) Excellent 

23

Vacation apartment with shared pool in Polvereto

Montespertoli / Polvereto

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 67 mi
  • 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 …see more

from $91 / night

$609 / week

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from $91 / 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 $115 / night

$686 / week

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from $115 / 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 $130 / night

$906 - $1,302 / week

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from $130 / night

(6) 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 $120 / night

$842 - $1,115 / week

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Responds fast!
avg. 2 hours 43 minutes

from $120 / 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
Special offer: July and August price includes a typical Tuscan dinner ; aqua gym lesson, horse-drawn coach tour of the vineyard Apartment in the old "Borgo". Close to the restaurant. About 500 meters from the farmhouse and the swimming pool.Apartment on first floor. 60 …see more

from $125 / night

$421 - $808 / week

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from $125 / 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 $114 / night

$796 / week

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from $114 / night

(1) Excellent 

17

Apartment rental in Montespertoli

Province of Florence / Montespertoli

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • 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 $154 / night

$1,081 / week

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from $154 / night

22

Vacation apartment with shared pool in Montespertoli

Province of Florence / Montespertoli

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Special offer: July and August price includes a typical Tuscan dinner ; aqua gym lesson, horse-drawn coach tour of the vineyard Apartment in the old "Borgo". Close to the restaurant. About 500 meters from the farmhouse and the swimming pool. Apartment of 100 mq on two …see more

from $159 / night

$567 - $1,099 / week

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Responds fast!
avg. 3 hours 44 minutes

from $159 / night

(5) Very Good 

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 $171 / night

$1,353 / week

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from $171 / 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 $92 / night

$640 / week

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from $92 / night

26

Vacation chalet with shared pool in Montespertoli

Province of Florence / Montespertoli

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Nearest beach 65 mi
  • Swimming pool
  • Child friendly
In the heart of Tuscan Chianti, surrounded by green hills of Florence, you can come and spend a nice relaxing holiday in the countryside, where you can enjoy a glass of wine at the swimming pool, alternating visits to nearby cities, such as Florence, Siena, Pisa, Volter …see more

from $75 / night

$366 / week

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from $75 / night

4

Montespertoli Vacation hotel apartment rental

Province of Florence / Montespertoli

21 2 1 night min

  • 21 bedrooms
  • sleeps 2
  • 1 night min
  • Nearest beach 70 mi
  • Swimming pool
  • Air conditioning
Hotel Il Molino del Ponte is located in Montespertoli, Chianti, Tuscany, in an ideal location for visiting all the art cities like Florence, Siena, Pisa, Luca, San Gimignano, Volterra ... with 15 apartments and 6 rooms, all furnished in typical Tuscan style, with air co …see more

from $75 / night

$478 / week

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from $75 / night

(7) 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 $120 / night

$830 - $1,115 / week

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Responds fast!
avg. 2 hours 43 minutes

from $120 / night

49

Montespertoli Vacation apartment rental

Province of Florence / Montespertoli

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • 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 $137 / night

$960 / week

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from $137 / 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 $380 / night

$2,655 / week

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Responds fast!
avg. 3 hours 22 minutes

from $380 / night

(4) Excellent 

38

Vacation villa with swimming pool in Polvereto

Montespertoli / Polvereto

13 29 min stay varies

  • 13 bedrooms
  • sleeps 29
  • min stay varies
  • Nearest beach 100 mi
  • 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 $1,024 / night

$6,822 - $13,569 / week

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from $1,024 / night

113

Trecento Vacation apartment rental

Montespertoli / Trecento

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 50 mi
  • Swimming pool
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 $137 / night

$1,353 - $1,751 / week

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Responds fast!
avg. 35 minutes

from $137 / 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
Special offer: July and August price includes a typical Tuscan dinner ; aqua gym lesson, horse-drawn coach tour of the vineyard Apartment in the old "Borgo". Close to the restaurant. About 500 meters from the farmhouse and the swimming pool.Apartment on first floor. Ap …see more

from $108 / night

$397 - $691 / week

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Responds fast!
avg. 3 hours 44 minutes

from $108 / 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
Special offer: July and August price includes a typical Tuscan dinner ; aqua gym lesson, horse-drawn coach tour of the vineyard Apartment in the old "Borgo". Close to the restaurant. About 500 meters from the farmhouse and the swimming pool. Apartment of 110 mq on firs …see more

from $160 / night

$537 - $1,108 / week

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from $160 / night

15

Vacation home rental

Province of Florence / Montespertoli

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
This surprising tuscan house, newly rifurbished and ristructured, distinguishes itself for its brightness and its furniture and decor unusually modern and elegant. Developed on 3 floors, it overspreads for about 200 Mq, over 20 Mq of panoramic terrace and a fenced garde …see more

from $136 / night

$951 / week

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from $136 / 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 $341 / night

$2,388 / week

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from $341 / 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 $153 / night

$1,131 - $1,903 / week

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from $153 / night

(4) Excellent 

34

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 $546 / night

$3,809 - $4,855 / week

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from $546 / night

13

Vacation farmhouse in Montespertoli

Province of Florence / Montespertoli

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
The farmhouse "Galletti" farm belonging to the farm "Fonte Bugliana", is located in the area of ​​Chianti Colli Fiorentini, 1.5 km from the village of San Quirico in Collina, a district of Montespertoli, in a particularly panoramic position with view over the Val di Pes …see more

from $155 / night

$914 / week

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from $155 / night

11

Vacation cottage in Polvereto

Montespertoli / Polvereto

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 70 mi
  • Swimming pool
GIRASOLE Property 55sqm - Sleeps 2 The apartment is on a ground floor . Externally there is a large porch with a table and chairs and a sofa . The kitchen has an open floor plan with the living room with a sofa with TV . The kitchen is complete with oven , dishwasher, f …see more

from $91 / night

$626 / week

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from $91 / night