50 Best Vacation Rentals in Montespertoli - Holiday Lettings - Cabins

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8,908 Vacation rentals

(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

$412 - $921 / week

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Responds fast!
avg. 3 hours 5 minutes

from $115 / 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 $92 / night

$367 - $693 / week

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Responds fast!
avg. 3 hours 5 minutes

from $92 / 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

$393 / week

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from $56 / night

14

Vacation apartment in Montespertoli

Province of Florence / Montespertoli

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Small jewelry, in the heart of the center of the country, halfway between Siena and Florence, apartment complete with bedroom, living room, equipped kitchen, with views mozzafiatto, 2 bordered by gardens on the sides, one with gazebo, parking private and 2 minutes from …see more

from $52 / night

$229 / week

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from $52 / 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 $86 / night

$567 - $904 / week

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from $86 / 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 $92 / night

$630 / week

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from $92 / 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 $138 / night

$481 - $916 / week

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Responds fast!
avg. 3 hours 5 minutes

from $138 / night

(2) Excellent 

22

Montespertoli Vacation b&b rental

Province of Florence / Montespertoli

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 76 mi
In the heart of the enchanting Tuscany you will find on the top of a hill the lovely B&B Il Poggetto, and an amazing view ranging from San Gimignano towers to the harsh Alpi Apuane will welcome you with a warm hug. The room is located at the first floor and guests can e …see more

from $63 / night

$441 / week

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from $63 / 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 $149 / night

$1,145 / week

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from $149 / night

(1) Excellent 

15

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

Montespertoli / Montagnana Val di Pesa

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights 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 $126 / night

$973 / week

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from $126 / 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 $1,030 / night

$6,865 - $13,654 / week

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from $1,030 / night

40

Vacation farmhouse with shared pool in Lucardo

Montespertoli / Lucardo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
Nice complex in Chianti, with pool, for rent. A villa comprising 3 buildings recently restored preserving its original architectural features and turned into 6 apartments and a small independent villa. The property for rent is situated in panoramic location on the hills …see more

from $101 / night

$704 - $1,261 / week

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from $101 / 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 $115 / night

$801 / week

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Responds fast!
avg. 3 hours 47 minutes

from $115 / night

43

Vacation farmhouse with shared pool in Lucardo

Montespertoli / Lucardo

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
Nice complex in Chianti, with pool, for rent. A villa comprising 3 buildings recently restored preserving its original architectural features and turned into 6 apartments and a small independent villa. The property for rent is situated in panoramic location on the hills …see more

from $111 / night

$772 - $1,386 / week

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from $111 / 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 70 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 $285 / night

$1,993 - $3,201 / week

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from $285 / 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 $92 / night

$613 / week

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from $92 / night

12

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
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 $69 / night

$455 - $683 / week

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from $69 / 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 $105 / night

$733 - $1,167 / week

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from $105 / 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

$367 / week

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from $75 / 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 $161 / night

$550 - $1,087 / week

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Responds fast!
avg. 3 hours 5 minutes

from $161 / 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 $344 / night

$2,403 / week

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from $344 / night

(31) Very Good 

27

Farmhouse rental in Montespertoli with swimming pool

Province of Florence / Montespertoli

7 13 min stay varies

  • 7 bedrooms
  • sleeps 13
  • min stay varies
  • 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 $458 / night

$2,174 - $2,975 / week

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from $458 / 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 $155 / night

$1,087 / week

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from $155 / night

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 $178 / night

$1,087 - $1,448 / week

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from $178 / night

27

Vacation farmhouse in Lucardo

Montespertoli / Lucardo

3 9 min stay varies

  • 3 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $83 / night

$575 - $1,072 / week

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from $83 / 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 $149 / night

$492 - $990 / week

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Responds fast!
avg. 3 hours 5 minutes

from $149 / 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 $76 / night

$481 / week

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from $76 / 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 $109 / night

$761 - $998 / week

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from $109 / 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 $138 / night

$962 / week

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from $138 / 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 $121 / night

$687 - $996 / week

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from $121 / 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 $126 / night

$447 - $813 / week

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Responds fast!
avg. 3 hours 5 minutes

from $126 / night

27

Vacation townhouse with swimming pool in Montespertoli

Province of Florence / Montespertoli

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
CASANOVA 1Casanova 1 is the largest of the apartments, about 100 m2 for a receptivity of 5/6 people, and is located on the first floor of the main building of podere Casanova. After a flight of stairs you have access to the large room where the large old fireplace. On t …see more

from $121 / night

$710 - $1,019 / week

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from $121 / 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 $109 / night

$761 - $998 / week

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from $109 / 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 $161 / night

$538 - $1,110 / week

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Responds fast!
avg. 3 hours 5 minutes

from $161 / 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 $109 / night

$407 - $698 / week

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Responds fast!
avg. 3 hours 5 minutes

from $109 / 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 $559 / night

$3,908 - $4,566 / week

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from $559 / night

23

Montespertoli Vacation apartment rental

Province of Florence / Montespertoli

3 3 1 night min

  • 3 bedrooms
  • sleeps 3
  • 1 night min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
The house is situated on a wonderful Florentine hills few Km. From Florence. For guests do not drive you the property will be happy to do service to the railway station of Montelupo F.no (from Florence about 15 minutes by train). After a day immersed in the history and …see more

from $91 / night

$633 / week

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from $91 / 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 $103 / night

$721 - $824 / week

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from $103 / 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 - $1,100 / week

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Responds fast!
avg. 2 hours 51 minutes

from $159 / 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 $138 / night

$1,362 - $2,174 / week

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Responds fast!
avg. 35 minutes

from $138 / night