Watersports holiday villas and apartments Province of Siena | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Siena
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  • Abbadia San Salvatore (1)
  • Casole d'Elsa (3)
  • Castellina In Chianti (1)
  • Castelnuovo Berardenga (2)
  • Cetona (9)
  • Chianciano Terme (2)
  • Chiusi (3)
  • Colle di Val d'Elsa (1)
  • Montepulciano (17)
  • Monteriggioni (7)
  • Monteroni d'Arbia (1)
  • Monticiano (2)
  • Murlo (1)
  • Piancastagnaio (1)
  • Pienza (5)
  • Poggibonsi (4)
  • Radda in Chianti (5)
  • Radicondoli (6)
  • Rapolano Terme (5)
  • San Casciano dei Bagni (1)
  • San Gimignano (6)
  • San Giovanni d'Asso (1)
  • Sarteano (1)
  • Siena (13)
  • Sinalunga (3)
  • Sovicille (1)
  • Torrita di Siena (1)

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103 Holiday homes

Filters applied: Water sports (103)

1 / 4

Montepulciano / Gracciano

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 200 km; Child friendly ; Car essential;
 …see more

from £43 / night

£300 / week

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from £43 / night

(30) Excellent 

1 / 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
Key info: 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 £86 / night

£471 - £727 / week

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from £86 / night

(18) Excellent 

1 / 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
Key info: 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 £86 / night

£471 - £727 / week

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from £86 / night

Featured properties

(1) Excellent 

1 / 4

Rapolano Terme / Serre di Rapolano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 110 km; Swimming pool; Child friendly ;
 …see more

from £82 / night

£569 / week

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from £82 / night

(1) Excellent 

1 / 37

Province of Siena / Monteroni d'Arbia

1 4 1 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 97 km; Child friendly ; Car advised;
 …see more

from £52 / night

£359 / week

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from £52 / night

(1) Excellent 

1 / 19

Podere Tina - San Casciano dei Bagni villa sleeps 15

Province of Siena / San Casciano dei Bagni

7 15 1 night min stay

  • 7 bedrooms
  • Sleeps 15
  • 1 night min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
La Tina is located on a hilltop in the extreme north of the province of Lazio, bordering on Tuscany and close to Umbria. The hilltop where the former farmhouse, the stables and the swimming pool are located offers a glorious panoramic view of the undulating historical l  …see more

from £616 / night

£4359 / week

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from £616 / night

1 / 4

Province of Siena / Abbadia San Salvatore

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Not suitable for children; No pets allowed;
 …see more

from £69 / night

£274 / week

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from £69 / night

(1) Excellent 

1 / 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
Key info: Nearest beach 55 km; Child friendly ; Car advised;
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 £86 / night

£471 - £727 / week

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from £86 / night

(1) Excellent 

1 / 22

Villa Amedeo - Giotto - Val di Merse apartment sleeps 2

Siena / Val di Merse

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: 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 £60 / night

£385 - £471 / week

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from £60 / night

(3) Excellent 

1 / 13

Poggibonsi / Staggia Senese

2 3 1 night min stay

  • 2 bedrooms
  • Sleeps 3
  • 1 night min stay
Key info: Nearest beach 74 km; Child friendly ; Car advised;
 …see more

from £60 / night

£402 / week

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from £60 / night

1 / 23

Province of Siena / Sovicille

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 80 km; Ask owner if suitable for children; Car essential;
 …see more

from £86 / night

£300 / week

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from £86 / night

(5) Excellent 

1 / 20

Montorio - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; No pets allowed;
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 £112 / night

£770 / week

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from £112 / night

1 / 12

CUZZI COUNTRY HOUSE - Pianella apartment sleeps 6

Castelnuovo Berardenga / Pianella

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 35 km; Child friendly ; Car advised;
Discover Abruzzo with its famous cultural and agricultural sights! The region is famous for its Olive oil and its wine, for excellent and good value for money food and for its kind population. You can go for one day or half a day hiking trips to the beautiful national p  …see more

Pricing unknown

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Pricing unknown

1 / 19

Antico Borgo Poggiarello - Monteriggioni house sleeps 30

Province of Siena / Monteriggioni

15 30 Min stay varies

  • 15 bedrooms
  • Sleeps 30
  • Min stay varies
Key info: Nearest beach 84 km; Swimming pool; Child friendly ;
The structure consists of apartments (surrounded by 30.000 meters of olive trees and wood), charmingly furnished in the old style of Tuscany and telephone line for internet connection. From May 1st until September 15th it's possible to enjoy the swimming pool of 1  …see more

Pricing unknown

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Pricing unknown

(5) Excellent 

1 / 24

Province of Siena / Montepulciano

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Child friendly ; Car advised; No pets allowed;
 …see more

from £67 / night

£394 / week

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from £67 / night

(1) Good 

1 / 4

Province of Siena / Sinalunga

3 8 1 night min stay

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 25 km; Swimming pool;
 …see more

from £120 / night

£770 / week

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from £120 / night

1 / 38

Antico Borgo Poggiarello Due - Monteriggioni apartment sleeps 2

Province of Siena / Monteriggioni

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 84 km; Swimming pool; Child friendly ;
Among woods and vineyard of Siena Chianti, surrounded by a large region considered a natural park , with a dominating and sunny position, you find the ancient rural villane of the XVII century called “Poggiarello”.Unforgettable sunsets, breath-taking landscapes can  …see more

from £86 / night

£513 - £838 / week

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from £86 / night

(2) Excellent 

1 / 40

Monticiano / Iesa Palazzo

6 9 1 night min stay

  • 6 bedrooms
  • Sleeps 9
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £154 / night

£1026 / week

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from £154 / night

(9) Excellent 

1 / 5

Province of Siena / Rapolano Terme

4 4 1 night min stay

  • 4 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; Pet friendly; Private garden;
 …see more

from £112 / night

£778 / week

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from £112 / night

1 / 24

Poggibonsi / Staggia Senese

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
Key info: Child friendly ; Car advised; Ask about pets;
 …see more

from £28 / night

£171 - £283 / week

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from £28 / night

(2) Excellent 

1 / 16

Ulivo - Radicondoli apartment sleeps 5

Province of Siena / Radicondoli

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
The apartment Ulivo is on the first floor of the Villa and has 2 large double/twin bedrooms, a kitchen, sitting/dining room with view and chimney. Kitchen, 1 shower bathroom & 1 guest bathroom.There is a Tv, wifi, and rooms with a view. This apartment is ideal for cultu  …see more

from £86 / night

£599 - £718 / week

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from £86 / night

1 / 10

Agriturismo Terrarossa 2 pax - Valiano apartment sleeps 2

Montepulciano / Valiano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car not necessary;
The apartment "Rosa" (2 persons), with furniture of epoch, is composed of a stay- kitchen with read couch, a double bedroom and a bathroom with shower. In bedroom: tv sat. The Terrarossa agriturism complex is situated on one of the most beautiful and panoramic  …see more

from £82 / night

£385 - £518 / week

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from £82 / night

(1) Excellent 

1 / 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
Key info: 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

£556 / week

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from £82 / night

1 / 11

Province of Siena / Montepulciano

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Not suitable for children; Car advised; No pets allowed;
 …see more

from £60 / night

£377 / week

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from £60 / night

(3) Excellent 

1 / 16

Province of Siena / Casole d'Elsa

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 80 km; Child friendly ; Car advised;
 …see more

from £39 / night

£270 / week

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from £39 / night

(3) Very Good 

1 / 10

Province of Siena / Cetona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Not suitable for children; Car advised; No pets allowed;
 …see more

Pricing unknown

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Pricing unknown

(3) Excellent 

1 / 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
Key info: 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 £60 / night

£342 - £513 / week

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from £60 / night

1 / 24

Agriturismo Podere Le Coste - Rapolano Terme farmhouse sleeps 10

Province of Siena / Rapolano Terme

6 10 1 night min stay

  • 6 bedrooms
  • Sleeps 10
  • 1 night min stay
Key info: Nearest beach 80 km; Swimming pool; Ski;
Immersed in the countryside, in the middle of the woods, the old stone cottage offers splendid apartments which have maintained the architectural features and atmosphere of old times, perfectly integrated with all the modern comforts.The "Le Coste" holiday far  …see more

from £505 / night

£3530 / week

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from £505 / night

1 / 29

Siena holiday apartment rental - Siena apartment sleeps 2

Province of Siena / Siena

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Child friendly ; Air conditioning; Ask about pets;
Located just outside the walls of the historical center, with a 900 square meters private garden and a 30000 square meters private park, 7 minutes walk from Piazza del Campo, 3 minutes walk from Piazza San Francesco, this charming holiday accommodation has been totally  …see more

from £90 / night

£449 / week

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from £90 / night

1 / 11

Murlo / Vescovado di Murlo

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 70 km; Suitable for children age 5+; Car advised;
 …see more

from £65 / night

£385 / week

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from £65 / night

1 / 11

Province of Siena / Rapolano Terme

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; Pet friendly;
 …see more

from £52 / night

£325 / week

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from £52 / night

(2) Excellent 

1 / 19

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

Province of Siena / Siena

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 95 km; Child friendly ; Car advised;
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 £248 / night

£1701 - £2052 / week

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from £248 / night

(14) Excellent 

1 / 17

Fabio Apartments San Gimignano - San Gimignano apartment sleeps 4

Province of Siena / San Gimignano

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 65 km; Child friendly ; Car advised;
Apartment "Il Duca" (2-6 beds)Bright three-roomed apartment (85 mq). With its twelve windows it offers a beautiful panoramic view of the surrounding Chianti countryside, the nearby gardens, the ancient buildings and the legendary Torre del Diavolo. It is finel  …see more

from £88 / night

£616 / week

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from £88 / night

1 / 25

Province of Siena / Chianciano Terme

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; Car advised;
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from £137 / night

£847 - £1086 / week

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from £137 / night

(1) Excellent 

1 / 14

Tipica dimora toscana - Monticiano apartment sleeps 4

Province of Siena / Monticiano

2 4 4 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay
Key info: Nearest beach 60 km; Child friendly ; Car essential;
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

£342 - £385 / week

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from £52 / night

(2) Very Good 

1 / 13

Province of Siena / San Gimignano

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; Car not necessary; No pets allowed;
 …see more

from £112 / night

£684 / week

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from £112 / night

(41) Excellent 

1 / 21

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

Province of Siena / Montepulciano

3 5 3 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 158 km; Child friendly ; Car advised;
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 £60 / night

£342 - £599 / week

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from £60 / night

1 / 24

Luxury renovated Tuscan holiday apartment rental i - Val di Merse apartment sleeps 14

Siena / Val di Merse

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 70 km; Child friendly ;
The antique spaces have been reinvigorated, made more comfortable and personalized whilst using traditional local materials, rough stone, terra cotta, wrought iron, wood. There are six complete and elegant, well-appointed apartments, complete with stylish fitted bathroo  …see more

from £257 / night

£1710 - £2052 / week

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from £257 / night

1 / 36

Antico Borgo Poggiarello Suite - Monteriggioni apartment sleeps 4

Province of Siena / Monteriggioni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 84 km; Swimming pool; Child friendly ;
The suite includes a large kitchen and living-room with sofa double bed, 1 double bedroom and 1 bathroom. From this suite you can reach a private terrace with garden furniture and a fantastic view on the Elsa Valley.Unforgettable sunsets, breath-taking landscapes can be  …see more

from £129 / night

£770 - £1197 / week

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from £129 / night

1 / 24

Le Contessine - Magical Tuscan Villa - Cetona farmhouse sleeps 8

Province of Siena / Cetona

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
Le Contessine is a beautiful villa of 300 sqm located at the foot of Mount Cetona 10 minutes drive from the village within the idyllic Tuscan landscape of vine-clad hills, extensive olive groves and cypress trees.The house is a precious gem shining among the tree-lined  …see more

from £214 / night

£1496 - £2026 / week

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from £214 / night

Top Destination reviews

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
Casa Degli Olivi Cetona , Siena Tuscany
Italian friendliness, food, wine and culture at its best - Cetona - Tuscany

What a fantastic experience in the Italian countryside. Two weeks tucked away from tourist mayhem. Even prior to our departure from the Middle East to start our holiday, the owners answered all our enquiries quickly,efficiently with sound advice. The … see more
I MELOGRANI II: 3BDR Tuscan villa,view,pool,WiFi
Perfect.

The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arrive on a S … see more
Tuscan apartment with pool in Cetona
Excellent, centrally located apartment in a charming village

We thoroughly enjoyed our stay in Cetona and, given half a chance, would go back tomorrow! We booked the apartment for two weeks with my husband and I spending the first week on our own, and our two sons and one girlfriend joined us for the second w … 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

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