Watersports holiday villas and apartments Province of Siena | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Siena
  • All locations
  • Abbadia San Salvatore (1)
  • Casole d'Elsa (4)
  • Castellina In Chianti (1)
  • Castelnuovo Berardenga (3)
  • Cetona (9)
  • Chianciano Terme (2)
  • Chiusi (3)
  • Colle di Val d'Elsa (1)
  • Montepulciano (19)
  • Monteriggioni (7)
  • Monteroni d'Arbia (1)
  • Monticiano (2)
  • Murlo (1)
  • Piancastagnaio (1)
  • Pienza (5)
  • Poggibonsi (5)
  • Radda in Chianti (5)
  • Radicondoli (6)
  • Rapolano Terme (4)
  • San Casciano dei Bagni (1)
  • San Gimignano (6)
  • San Giovanni d'Asso (1)
  • Sarteano (2)
  • Siena (15)
  • Sinalunga (5)
  • Sovicille (1)
  • Torrita di Siena (1)

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112 Holiday homes

Filters applied: Water sports (112)

(8) Excellent 

41

Unique, charming farmhouse in Tuscany countryside with shared outdoor pool, sleeps up to 6 - Montepulciano farmhouse sleeps 6

Province of Siena / Montepulciano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
The main arched entrance leads past a utility room and downstairs bathroom into the open plan kitchen and dining room with dining table for 6 guests. The lounge has two sofa's one of which is a comfortable double sofa bed There is a wood burning stove in the lounge  …see more

from £72 / night

£500 - £775 / week

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from £72 / night

(33) Excellent 

25

Tuscan apartment in rural setting with easy access to nearby cities, property has private garden and shared pool - Castel San Gimignano apartment sleeps 6

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
The apartment is located in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the oliv  …see more

from £87 / night

£475 - £733 / week

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from £87 / night

(20) Excellent 

49

3 bedroom holiday apartment near Tuscan cities, staffed property with outdoor pool - Castel San Gimignano apartment sleeps 6

San Gimignano / Castel San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
The apartment is placed in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the olive  …see more

from £87 / night

£475 - £604 / week

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from £87 / night

(43) Excellent 

21

La Casina Toscana, central with parking and wi-fi - Montepulciano cottage sleeps 5

Province of Siena / Montepulciano

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 158 km
  • Child friendly
  • Air conditioning
Placed in the countryside of Montepulciano, near the most important historical towns such as Pienza, Montalcino and Bagno Vignoni, the Casina Toscana is a historical residence of the nineteenth century, which allows guests to enjoy the tranquility and relaxation that th  …see more

from £61 / night

£345 - £604 / week

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from £61 / night

(3) Excellent 

35

The Notary's House - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Small charming flat, old residence of householder's great-grandfather, Notary in Montepulciano. Recently wholly restructured, very quiet, in a very beautiful position: in the centre of town, but facing the walls of the city, in a dominant position.Two nice bedrooms, sma  …see more

from £61 / night

£345 - £518 / week

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from £61 / night

(3) Excellent 

23

Renovated antique apartment in Tuscan countryside - Val di Merse apartment sleeps 5

Siena / Val di Merse

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly
The antique apartment have been reinvigorated, made more comfortable and personalized whilst using traditional local materials, rough stone, terracotta, wrought iron, wood.This elegant, well-appointed apartment is complete with stylish fitted bathroom and kitchen.It has  …see more

from £104 / night

£690 - £733 / week

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from £104 / night

(3) Excellent 

14

New Casa Titta apt 3 bedrooms , amazing view - Castel San Gimignano apartment sleeps 5

San Gimignano / Castel San Gimignano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 55 km
  • Child friendly
  • Ask about pets
C asa Titta is our third apartment ,completely new ,really comfortable, placed on the first floor with three bedrooms for 5 people and a large open space living . A new kitchen equipped with dishwasher , fridge/freezer, microwave and electrical hoven. The bathroom has  …see more

from £87 / night

£475 - £647 / week

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from £87 / night

11

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

 …see more

from £61 / night

£383 / week

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from £61 / night

19

Forsythia Cottage (V041) - Sarteano cottage sleeps 8

Province of Siena / Sarteano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Typical country house, well restructured, Mount Amiata dominates the unique landscape surrounding this property. From the interiors which are refined but cosy, you understand the owners' passion. Very well furnished.On the first floor there is a living room with fi  …see more

from £185 / night

£1294 - £1569 / week

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from £185 / night

(1) Excellent 

14

Tipica dimora toscana - Monticiano apartment sleeps 4

Province of Siena / Monticiano

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets
This apartment is in the historical center of a beautiful town near Siena. Its name is Monticiano. It's composed by 2 bedrooms (for 4 gests), 1 bathroom (with a shower box), 1 indipendent kitchen and a great dining room. The apartment is 75 mq. In the centre of this vi  …see more

from £52 / night

£345 - £388 / week

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from £52 / night

(13) Excellent 

20

Tuscan apartment with pool in Cetona - Cetona apartment sleeps 5

Province of Siena / Cetona

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
The apartment is ideally situated on the outskirts of the medieval town of Cetona, with a splendid view over the valley and distant mountains. It is a short walk from all the local amenities, including restaurants, cafes, and shops. Within a few minutes you can be among  …see more

from £65 / night

£400 - £600 / week

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from £65 / night

(6) Very Good 

45

Province of Siena / Montepulciano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £74 / night

£475 - £518 / week

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from £74 / night

20

Primrose Villa (V039) - Chiusi villa sleeps 8

Province of Siena / Chiusi

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
At Chiusi lake, this beautiful villa is a peaceful and cosy place for a holiday in close contact with nature. The restoration work, using environmentally friendly techniques paid attention to every detail, making the interiors light and comfortable. Extremely well furni  …see more

from £146 / night

£1018 - £2578 / week

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from £146 / night

(3) Excellent 

13

Poggibonsi / Staggia Senese

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 74 km
  • Child friendly
  • Pet friendly

 …see more

from £61 / night

£406 / week

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from £61 / night

(4) Excellent 

14

Apartment in the historic city center of Siena - Siena house sleeps 4

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Ask about pets
This bright and modern apartment totally renovated by just one year, is situated in the charming historic centre of Siena.The apartment is part of a palace complex with other apartments and is located on the ground floor and consists of two floors.The apartment is so co  …see more

from £82 / night

£561 / week

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from £82 / night

(1) Excellent 

29

Province of Siena / Montepulciano

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £233 / night

£1207 - £1897 / week

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from £233 / night

(1) Excellent 

22

Villa Amedeo - Giotto - Val di Merse apartment sleeps 2

Siena / Val di Merse

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly
The antique spaces of the apartment have been reinvigorated, made more comfortable and personalized whilst using traditional local materials, rough stone, terracotta, wrought iron, wood.Giotto is one of six complete and elegant, well-appointed apartments, complete with  …see more

from £61 / night

£388 / week

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from £61 / night

(3) Excellent 

16

Province of Siena / Casole d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 80 km
  • Child friendly

 …see more

from £39 / night

£272 / week

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from £39 / night

(2) Excellent 

24

Balz Tuscan farmholiday Chianti with pond - Radda in Chianti farmhouse sleeps 3

Province of Siena / Radda in Chianti

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the work  …see more

from £52 / night

£302 - £388 / week

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from £52 / night

(2) Excellent 

48

Province of Siena / Castellina In Chianti

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 150 km
  • Child friendly
  • Private garden

 …see more

from £104 / night

£475 - £561 / week

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from £104 / night

24

Province of Siena / Pienza

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly

 …see more

from £302 / night

£1811 - £2699 / week

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from £302 / night

(1) Excellent 

7

Il Casalone Apartment Oliveto - Montepulciano farmhouse sleeps 4

Province of Siena / Montepulciano

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Located in a panoramic position on a hill crest between the Val d'Orcia and Valdichiana near Montepulciano, Agriturismo Il Casalone offers a holiday unit tastefully furnished in Tuscan country style. One double bed room (king size), one bathroom and a living room w  …see more

from £52 / night

£233 - £449 / week

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from £52 / night

27

Province of Siena / Siena

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £179 / night

£1250 - £1682 / week

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from £179 / night

(4) Excellent 

42

Province of Siena / Siena

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

 …see more

from £87 / night

£432 / week

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from £87 / night

25

Lodge Melograno wonderful view in Val D'Orcia - Pienza lodge sleeps 2

Province of Siena / Pienza

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Air conditioning
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £56 / night

£388 - £733 / week

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from £56 / night

20

Orchard Manor (V056) - Chiusi manor house sleeps 20

Province of Siena / Chiusi

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
An independent farmhouse built in stone and bricks with oak beams and terracotta floors, in the heart of a 35 hectare farming estate. The farmhouse is divided into 4 apartments and sleeps 17 + 3.Cypress (sleeps 7) on the first floor there is a living room with a firepla  …see more

from £263 / night

£1837 - £3121 / week

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from £263 / night

(3) Excellent 

32

Tegline Chianti Tuscan accomodation with pond - Radda in Chianti farmhouse sleeps 4

Province of Siena / Radda in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic. We restored the farmhouse of the 15th century and Giovanni has personally followed all the wor  …see more

from £82 / night

£475 - £561 / week

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from £82 / night

(5) Excellent 

35

Torre Farmholiday Tuscan Chianti with pond - Radda in Chianti farmhouse sleeps 3

Province of Siena / Radda in Chianti

2 3 5 nights min

  • 2 bedrooms
  • Sleeps 3
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the wor  …see more

from £69 / night

£432 - £475 / week

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from £69 / night

(1) Excellent 

12

Province of Siena / Cetona

5 6 Min stay varies

  • 5 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 28 km
  • Swimming pool
  • Child friendly

 …see more

from £302 / night

£2113 / week

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from £302 / night

(1) Good 

4

Province of Siena / Sinalunga

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 25 km
  • Swimming pool

 …see more

from £121 / night

£776 / week

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from £121 / night

(2) Excellent 

19

PALAZZO GIORGI Suite in Piazza del Campo, Siena - Siena apartment sleeps 4

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Child friendly
  • Air conditioning
The apartment overlooks the beautiful Piazza del Campo , with a light coming from the three main windows and invades the entire house is unique about every hour of the day . The apartment has just been renovated and furnished with designer pieces and equipped with every  …see more

from £250 / night

£1638 - £2156 / week

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from £250 / night

27

Podere Staggia - Monteriggioni villa sleeps 5

Province of Siena / Monteriggioni

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
Near to Siena (8 km), in the Chianti region, apartment in farmhouse (size: 170 m2) for max.6 persons. Swimming pool complex and park 3 km far away.Splendid farm house (18 th century) located on the top of a hill. The property apartment offers you the unique and rare pos  …see more

from £93 / night

£647 - £1026 / week

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from £93 / night

(1) Excellent 

54

Province of Siena / Cetona

8 12 2 nights min

  • 8 bedrooms
  • Sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 29 km
  • Child friendly

 …see more

from £302 / night

£2113 / week

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from £302 / night

(2) Excellent 

34

Fonte Tuscany Holiday Apartment Chianti with pond - Radda in Chianti farmhouse sleeps 2

Province of Siena / Radda in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 120 km
  • Child friendly
  • Pet friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce organic Chianti Classico wine and extra virgin olive oil.We restored the farmhouse of the 15th century and Giovanni has personally followed all the work  …see more

from £52 / night

£302 - £397 / week

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from £52 / night

(7) Excellent 

18

Province of Siena / Colle di Val d'Elsa

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 93 km
  • Child friendly
  • Pet friendly

 …see more

from £66 / night

£427 / week

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from £66 / night

20

Chapel Manor (v027) - Chiusi manor house sleeps 21

Province of Siena / Chiusi

8 21 7 nights min

  • 8 bedrooms
  • Sleeps 21
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Swimming pool
This large country house, located in the hills between Lake Chiusi and Lake Trasimeno is an ideal property for a large family or a group of friends that which to spend their holidays together in the beautiful Tuscan countryside.This property is particular suitable for p  …see more

from £307 / night

£2147 / week

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from £307 / night

(1) Very Good 

49

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £130 / night

£604 / week

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from £130 / night

(5) Excellent 

20

Montorio - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Montorio was built in 1300 as a convent and is located in the beautiful sopt in MOntepulciano , on the top of a private hill overlooking the church of San Biagio and the rolling hill. It is in a walking distance to the center of the town but ensure the privacy of a coun  …see more

from £113 / night

£776 / week

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from £113 / night

(2) Excellent 

41

Province of Siena / Cetona

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 28 km
  • Swimming pool

 …see more

from £302 / night

£2113 / week

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from £302 / night

(5) Very Good 

24

Elegant three bedroom Tuscan-style apartment to re - Val di Merse apartment sleeps 7

Siena / Val di Merse

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly
The antique apartment have been reinvigorated, made more comfortable and personalized whilst using traditional local materials, rough stone, terracotta, wrought iron, wood. A large fireplace in the livingThis elegant, well-appointed apartment is complete with stylish fi  …see more

from £173 / night

£949 / week

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from £173 / night

Top Destination reviews

La Casina Toscana, central with parking and wi-fi
Clean, comfortable and cozy house with privacy and convenience to Montepuciano

We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close enough to walk to the Montepulciano town. The place was very clean and thoughtf … see more
Villa Vianci
Best vacation ever!

Our entire experience at Villa Vianci was beyond expectations. We travelled with 4 generations, ages 3 1/2 to 85! The villa was spectacular, spacious & immaculate. The pictures on line don't do it justice. Tommasso & Chiara were the best, any que … see more
Agriturismo Sammonti
Perfect week in Tuscany

All previous positive reviews reflect our experience. Beautiful, quiet location. Lovely hosts. The house was cosy and a great place to come home to after sightseeing. It was also very easy to spend a whole day in the local area or enjoying the pool … see more
Villa Galardini
Great location in heart of Tuscany; wonderful property and very friendly owners

Property is peaceful, clean and ideally located for daytrips to the many nearby villages and Sienna. Grocery stores and restaurants conveniently located in nearby Buonconvento . This was a 50th Birthday celebration vacation to Tuscany with spouse a … see more
Podere Val delle Corti
Very nice and total clean appartment

Beautiful property within a lovely environment Very nice and total clean appartment Landlady and the whole proprietor familiy are very friendly an helpful No kind of weakness has been discovered, at all … see more
Villa PetrAlexa, Tuscany cottage in Chianti area
Villa PetrAlexa - excellent leisure facility

This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfectly prepared. The house was heated up and foo … see more

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