50 Best Vacation Rentals in Montaione - Holiday Lettings - Cabins

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Alberi
27 properties
San Vivaldo
14 properties
Santo Stefano
11 properties
Sughera
5 properties

Montaione

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5,019 Vacation rentals

(10) Excellent 

48

Villa rental in Collegalli with swimming pool

Montaione / Collegalli

5 10 4 nights min

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Private garden
A beautifully preserved Tuscan villa on the historic Collegalli estate in Montaione, situated on a peaceful hilltop with spectacular views of the countryside. Villa Strozzi offers complete privacy, including a private garden and swimming pool, surrounded by nature and w …see more

from $620 / night

$4,337 / week

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from $620 / night

(1) Excellent 

24

Vacation villa in Montaione

Province of Florence / Montaione

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
Surrounded by five hectares of olive groves and vineyards, situated in an elevated position, this enchanting property overlooks the surrounding countryside, offering a beautiful view of the hills in the distance. San Gimignano, Certaldo and Volterra, musts on every tour …see more

from $284 / night

$1,985 - $5,048 / week

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from $284 / night

36

Apartment rental in Santo Stefano

Montaione / Santo Stefano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 mi
  • Child friendly
  • Pet friendly
Relaxation and comfort characterize this complex in the heart of Toscana, it is made up of a villa in the centre and three groups of independent apartments. They are carefully restored, respecting the environment, so friendly, functional and fully equipped. They have t …see more

from $87 / night

$521 - $1,053 / week

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from $87 / night

(1) Excellent 

29

Vacation apartment with shared pool in Montaione

Province of Florence / Montaione

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
One bedroom apartment of 45sqm with private terrace. Living room with kitchen corner and double sofa bed, double bedroom, bathroom with shower. Sat-Tv, Internet wi-fi connectionThis beautiful holiday accommodation in Chianti is located near the medieval village of Monta …see more

from $137 / night

$422 - $992 / week

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Responds fast!
avg. 1 hour 31 minutes

from $137 / night

(4) Excellent 

25

Vacation apartment rental

Province of Florence / Montaione

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Bouganville is a self catering apartment in the farmhouse Casa Vacanze Amarrante. It's located in the middle of Tuscany between the borders of the province of Firenze, Siena and Pisa: the perfect location to reach the great art cities with daily trip or just get relaxed …see more

from $106 / night

$614 - $1,084 / week

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from $106 / night

47

Vacation apartment in Santo Stefano

Montaione / Santo Stefano

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 mi
  • Child friendly
  • Pet friendly
Relaxation and comfort characterize this complex in the heart of Toscana, it is made up of a villa in the centre and three groups of independent apartments. They are carefully restored, respecting the environment, so friendly, functional and fully equipped. They have t …see more

from $118 / night

$744 - $1,425 / week

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from $118 / night

13

Apartment accommodation in Sughera with shared pool

Montaione / Sughera

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Casa Ilaria: 70 sqm apartment with terrace, located in family-run farmhouse, immersed in the Green Tuscan hills. The apartment consists of a large kitchen with a living room with a sofa bed and a sofa bed, a bedroom and a bathroom. Can indoor parking. The farm is locat …see more

from $107 / night

$746 / week

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from $107 / night

10

Vacation apartment in Alberi

Montaione / Alberi

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
It is a stone farmhouse and accurate renovation recently. Each apartment has central heating, separate entrance, ... The apartment is on the first floor, but in the garden there is a table, chairs and parasol and a quiet place in the middle of the green. . The property …see more

from $112 / night

$744 / week

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from $112 / night

(1) Excellent 

85

Vacation apartment in Montaione

Province of Florence / Montaione

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 73 mi
  • Child friendly
  • Pet friendly
Borgo La Casaccia, renovated 01/2011, born from a medieval village, It is composed of 12 apartments which retain the original architecture of the 17th century, with the ceiling consists of wooden beams and florentine terra-cotta floors. All apartments are equipped with …see more

from $101 / night

$607 / week

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Responds fast!
avg. 24 minutes

from $101 / night

17

Vacation farmhouse with shared pool in Montaione

Province of Florence / Montaione

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The La Valle complex is comprised of seven comfortable apartments situated just a kilometre from the town of Montaione and roughly 45 kilometres from Florence. Each apartment has its own private and furnished outdoor area, perfect for dining alfresco. The complex has …see more

from $144 / night

$1,005 - $1,423 / week

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from $144 / night

12

Montaione Vacation apartment rental

Province of Florence / Montaione

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
81 House: 40 sqm apartment with terrace, located in family-run farmhouse, immersed in the Green Tuscan hills. The apartment consists of a large kitchen with living room, bedroom, bathroom and closet. Can indoor parking. The farm is located a few kilometres from the most …see more

from $100 / night

$694 / week

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from $100 / night

11

Montaione Vacation farmhouse rental

Province of Florence / Montaione

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Nice complex comprising 5 units quietly located near the small town of Montaione. This property is part of a large farming estate producing wine, olive oil, saffron and “cinta senese” prosciutto and salami (cold cuts from a special Tuscan pig). Rigoletto is ideal for th …see more

from $122 / night

$744 - $1,053 / week

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from $122 / night

(1) Excellent 

12

Vacation apartment rental

Montaione / Alberi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The LEBBIO is situated in the heart of Tuscany, on the hills of Chianti, famous for its woods and poplars, grapevines and olive trees, where history has its mark in the little hamlets, stone farmhouses, castles and villas standing near "via francigena".The Lebbio, tucke …see more

from $180 / night

$1,115 - $2,255 / week

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from $180 / night

38

Apartment rental in Santo Stefano

Montaione / Santo Stefano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 mi
  • Child friendly
  • Pet friendly
Relaxation and comfort characterize this complex in the heart of Toscana, it is made up of a villa in the centre and three groups of independent apartments. They are carefully restored, respecting the environment, so friendly, functional and fully equipped. They have t …see more

from $93 / night

$558 - $1,215 / week

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from $93 / night

8

Vacation apartment with shared pool in Alberi

Montaione / Alberi

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
It is in a stone farmhouse and accurate renovation recently.It is divided into 6 independent apartments.The property is located in the heart of Tuscany, 6 km from the medieval village of Montaione.In less than an hour you can go to visit our most beautiful cities of art …see more

from $93 / night

$607 / week

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from $93 / night

17

Farmhouse rental in Montaione with shared pool

Province of Florence / Montaione

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Nice complex comprising 8 units located near the small town of Montaione. This property is part of a large 105-hectare farming estate producing wine, olive oil, saffron and “cinta senese” prosciutto and salami (cold cuts from a special Tuscan pig). Outside guests can en …see more

from $160 / night

$1,053 - $1,735 / week

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from $160 / night

(5) Excellent 

37

Vacation apartment in Montaione

Province of Florence / Montaione

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Air conditioning
Located in the historical village centre of Montaione (Florence region), the apartment has been restored to a high standard with 2 bedroom, 2 bathroom. It is conveniently located in the main pedestrian street of town surrounded by restaurants, shops, local markets and …see more

from $87 / night

$607 / week

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Responds fast!
avg. 3 hours 3 minutes

from $87 / night

55

Farmhouse rental in Montaione with shared pool

Province of Florence / Montaione

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The Agritourism Le Capanne, immersed in the Tuscany countryside among Florence, Pisa and Siena, offers warm and family hospitality. Without sacrificing modern convenience, it maintains the tradition of the past, between the garden and farmyard animals. In the fa …see more

from $73 / night

$512 - $642 / week

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from $73 / night

28

Montaione Vacation villa rental

Province of Florence / Montaione

9 17 7 nights min

  • 9 bedrooms
  • Sleeps 17
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Montaione Luxury villa - Casa Francigena enjoys an enviable location in the heart of the Tuscan countryside. Surrounded by its own vineyards and olive groves, this elegant two-storey villa has a history dating back 1,000 years to its origins as a cloister on the Via Fra …see more

from $870 / night

$6,090 - $14,602 / week

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from $870 / night

7

Vacation home with shared pool in Montaione

Province of Florence / Montaione

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
CASAVACANZE MONTERICCO IS IN TUSCANY MONTAIONE (FI). FLAT 2 + 2 PLACES CONSISTS OF: 1 DOUBLE, 1 BATHROOM AND KITCHEN AND SOFA BED 1 X2. LARGE GARDEN, BARBECUE, POOL AND PRIVATE PARKING. IDEAL STARTING POINT TO VISIT Florence, Siena and Pisa. THE THERMAL CENTER OF GAMBAS …see more

from $186 / night

$434 / week

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from $186 / night

46

Vacation villa in San Vivaldo

Montaione / San Vivaldo

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Pet friendly
Pian of the oaks is an eighty-hectare estate consisting of cherry orchards and nuts and for the most part by woods wild chestnut. The environment is an extraordinary refuge for deer, wild boar and many other wild animals, and for a variety of native tree species. This u …see more

from $471 / night

$3,296 - $4,163 / week

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from $471 / night

(1) Excellent 

24

Vacation villa with swimming pool in Alberi

Montaione / Alberi

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villino Santo Stefano is a beautiful private Villa in the Florentine Chianti area. It has been recently restored and it is fully equipped. It overlooks the gently Tuscan rolling hills and it is surrounded by a typical Tuscan landscape: hills, olive trees and vineyards. …see more

from $217 / night

$1,487 - $2,416 / week

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from $217 / night

18

Vacation home with shared pool in Montaione

Province of Florence / Montaione

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Beautiful holiday home in the heart of Tuscany. Ideal for a family vacation or couple. Two bedrooms, two bathrooms, kitchen and living room with fireplace. Patio on the terrace with breathtaking views. Wi Fi is free and available throughout the property. Frame the struc …see more

from $161 / night

$1,115 - $1,797 / week

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from $161 / night

42

Vacation villa rental

Montaione / Santo Stefano

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 65 mi
  • Swimming pool
  • Child friendly
!!!EARLY BOOKING DISCOUNT!!! FOR STAYS IN HSS1 & HS (2018): 10% discount for bookings confirmed within 45 days before the arrival date. FOR STAYS IN MS and HSS Seasons (2018): 15% discount for bookings confirmed within 30 days before the arrival date. FOR STAYS IN LS a …see more

from $1,022 / night

$7,149 - $12,006 / week

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from $1,022 / night

14

Montaione Vacation farmhouse rental

Province of Florence / Montaione

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Nice complex comprising 8 units located near the small town of Montaione. This property is part of a large 105-hectare farming estate producing wine, olive oil, saffron and “cinta senese” prosciutto and salami (cold cuts from a special Tuscan pig). Outside guests can en …see more

from $147 / night

$930 - $1,487 / week

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from $147 / night

7

Alberi Vacation townhouse rental

Montaione / Alberi

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
It is a stone farmhouse and accurate renovation recently. It is divided into 6 independent apartments. The property is located in the heart of Tuscany, 6 km from the medieval village of Montaione.In less than an hour you can go to visit our most beautiful cities of art: …see more

from $137 / night

$954 / week

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from $137 / night

(3) Excellent 

36

Vacation villa with swimming pool in Montaione

Province of Florence / Montaione

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
The villa is located right outside the picturesque hamlet of Iano, whose origins date back to the Etruscan times. This is the territory of Montaione which lies on the triangle of the provinces of Pisa, Florence and Siena, ideal starting point to visit S. Gimignano, Volt …see more

from $317 / night

$2,218 - $3,705 / week

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from $317 / night

7

Vacation apartment in Alberi

Montaione / Alberi

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 60 mi
  • Swimming pool
It is a stone farmhouse and accurate renovation recently.It is divided into 6 independent apartments.The property is located in the heart of Tuscany, 6 km from the medieval village of Montaione.In less than an hour you can go to visit our most beautiful cities of art: F …see more

from $112 / night

$744 / week

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from $112 / night

18

Montaione Vacation apartment rental

Province of Florence / Montaione

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 70 mi
  • Child friendly
  • Pet friendly
The house is part of the tourist complex called "Agriturismo La Valle" The building is an old Tuscan farmhouse, recently renovated and equipped with modern facilities, while retaining the style and atmosphere typical of this type of construction: Inside the floors are …see more

from $148 / night

$1,032 / week

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from $148 / night

(2) Excellent 

28

Vacation apartment with shared pool in Montaione

Province of Florence / Montaione

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Limonaia is a self catering apartment in the farmhouse Casa Vacanze Amarrante. It's located in the middle of Tuscany between the borders of the province of Firenze, Siena and Pisa: the perfect location to reach the great art cities with daily trip or just get relaxed in …see more

from $100 / night

$533 - $1,084 / week

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from $100 / night

(1) Excellent 

7

Casicello Vacation townhouse rental

Montaione / Casicello

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 55 mi
  • Swimming pool
  • Child friendly
Casa Vacanze Antica Pietra is a beautiful property in the green Tuscan hills. Our vacation home is in the small medieval village of Casicello, few kilometers from the most beautiful cities of Tuscany of art and culture , such as Montaione, Volterra, San Gimignano , Cer …see more

from $121 / night

$793 / week

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from $121 / night

18

Vacation villa with swimming pool in Montaione

Province of Florence / Montaione

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Right on this special place, VILLA Torresassa was built. With its 270 sq. meters living space and its elegant and luxurious rooms on 2 floors, as well as the well groomed garden and the private swimming pool, in this property you will find the enchantment of a luxury ho …see more

from $496 / night

$3,469 / week

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from $496 / night

21

Apartment rental in Montaione with shared pool

Province of Florence / Montaione

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly
These holiday homes in Chianti are located near the medieval village of Montaione, right within the heart of the Tuscan triangle created by Florence, Pisa and Siena. Situated on the hills, the apartments enjoy a breathtaking view over the valleys, Val d'Elsa and Val d'E …see more

from $77 / night

$347 - $682 / week

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Responds fast!
avg. 1 hour 31 minutes

from $77 / night

(1) Very Good 

24

Vacation villa with swimming pool in Montaione

Province of Florence / Montaione

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Villa Montaione Hills has been recently renovated respecting his traditional Tuscan architecture, characterized by lining on the floor (the famous Tuscan cotto), kitchen in brickwork, soft coloured tiles of the bathrooms and beautiful tapestries. The Villa can comfort …see more

from $434 / night

$2,788 - $4,832 / week

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from $434 / night

10

Vacation apartment rental

Province of Florence / Montaione

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Casavacanze Montericco si trova nella campagna Toscana a Montaione(FI) ed è il punto di partenza ideale per visitare Firenze, Pisa e Siena. La struttura ha 1 appartamento grande (8 posti)composto da: 4 camere, 2 bagni e una cucina All'esterno c'è un ampio giardino, i …see more

from $149 / night

$744 / week

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from $149 / night

(2) Excellent 

17

Vacation apartment rental

Province of Florence / Montaione

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Le Case di San Vivaldo is situated in the countryside of Tuscany Region. Is 40 km away from Florence, 42 km from Siena, 45 km from Pisa and 17 km from San Gimignano. The houses for rent are equipped with all amenities (kitchen with dishwasher, private bathroom, TV). We …see more

from $149 / night

$930 / week

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Responds fast!
avg. 3 hours 26 minutes

from $149 / night

14

Vacation farmhouse rental

Province of Florence / Montaione

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The La Valle complex is comprised of seven comfortable apartments situated just a kilometre from the town of Montaione and roughly 45 kilometres from Florence. Each apartment has its own private and furnished outdoor area, perfect for dining alfresco. The complex has …see more

from $104 / night

$736 - $1,083 / week

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from $104 / night

(2) Excellent 

24

Vacation villa with tennis court in Collegalli

Montaione / Collegalli

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 50 mi
  • Child friendly
  • Air conditioning
San Paolo di Collegalli: in the middle of the green Tuscany countryside, amidst rolling hills, cypresses and olive trees 50 Km from Florence, 50 Km from Pisa and 50 Km from Siena We offer a villa and an annexed guest house , a private half Olympic pool (25x12,5 m) wit …see more

from $530 / night

$3,705 / week

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from $530 / night

25

Vacation apartment with shared pool in Montaione

Province of Florence / Montaione

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
These holiday homes in Chianti are located near the medieval village of Montaione, right within the heart of the Tuscan triangle created by Florence, Pisa and Siena. Situated on the hills, the apartments enjoy a breathtaking view over the valleys, Val d'Elsa and Val d'E …see more

from $106 / night

$459 - $812 / week

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Responds fast!
avg. 1 hour 31 minutes

from $106 / night

20

Collegalli Vacation farmhouse rental

Montaione / Collegalli

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Rich with local history, this estate in Tuscany is a splendid example of the struggle for power played out between the various ages here between Florence and Pisa. This lovely rental home was once one of the many from the Buonaparte family of San Minato dating back to t …see more

from $496 / night

$1,797 - $3,593 / week

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from $496 / night