Province of Siena apartment or villa with a private pool area

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538 Holiday homes

Filters applied: Private pool (538)

1 / 24

Province of Siena / Sarteano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £616 / night

£4311 / week

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from £616 / night

1 / 4

Province of Siena / Chiusi

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

Pricing unknown

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1 / 24

Tenuta Val d'Elsa - Siena villa sleeps 35

Province of Siena / Siena

18 35 7 nights min stay

  • 18 bedrooms
  • Sleeps 35
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Total Luxury - Italy special occasion villa with services - this magnificent 14th century estate is situated in the heart of rural Tuscany between San Gimignano and Siena. The villa's hilltop position offers wonderful 360 degree views of the surrounding countryside  …see more

from £4526 / night

£31680 - £45880 / week

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from £4526 / night

(9) Excellent 

1 / 70

VILLA IRIS, LUXURY VILLA IN SAN GIMIGNANO - San Gimignano villa sleeps 12

Province of Siena / San Gimignano

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 71 km; Swimming pool; Child friendly ;
This superb villa, obtained from the careful restoration of an old brick kiln of 1737, is situated in a unique position on a hill opposite the towers of San Gimignano. The villa has been lovingly restored with materials of the highest quality and finished after long and  …see more

from £432 / night

£3018 - £7156 / week

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from £432 / night

(8) Excellent 

1 / 104

Villa Palazzo Bello with Swimming Pool - Cetona villa sleeps 20

Province of Siena / Cetona

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Casale Palazzo Bello is located in a splendid panoramic position, in the middle of the country-side, but only 3 km away from the nice medieval centre of Cetona. Thanks to its geographic location, the property offer an enchanting immersion in nature and an extremely rela  …see more

from £604 / night

£2199 - £3490 / week

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from £604 / night

(1) Very Good 

1 / 24

Beautiful detached Tuscan villa in Chianti hills featuring private outdoor pool, terrace and garden - San Gimignano cottage sleeps 8

Province of Siena / San Gimignano

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
Tameriggio is a beautiful detached villa converted from a lovely, old hay store situated in the Chianti hills half way (35 km) between Florence and Siena.In the well kept garden there is an inviting swimming pool (8 x 5 m) available from May to October for exclusive use  …see more

from £87 / night

£604 - £1682 / week

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from £87 / night

1 / 27

Casa Rosanna - Radicondoli house sleeps 8

Province of Siena / Radicondoli

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 50 km; Swimming pool; Child friendly ;
This typical stone house is situated in a panoramic position about 200 m. from Radicondoli, a characteristic and attractive mediaeval village (population 1.000) situated in a hilly position about 45 km from Siena. Guests can therefore avail of all the facilities availa  …see more

from £87 / night

£604 - £1294 / week

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from £87 / night

(5) Very Good 

1 / 20

Secluded villa with private pool Chianciano Terme - Chianciano Terme villa sleeps 10

Province of Siena / Chianciano Terme

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
The villa lies at 3 kms from the town of Chianciano Terme, one of the most popular thermal Spas in Italy. The villa is located among the hills dividing Val d'Orcia and Valdichiana. The whole property is for your private use and not shared with any other person. The vill  …see more

from £216 / night

£1294 - £2285 / week

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from £216 / 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 £621 / night

£4397 / week

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from £621 / night

1 / 23

Villa Leccio - Monticiano villa sleeps 9

Province of Siena / Monticiano

9 9 Min stay varies

  • 9 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Villa Leccio is a world apart set in a charming and peaceful place where guests can truly relax and rediscover a calmer pace of life, away from the city. The villa is nesteled in the beautiful unspoiled widerness of a natural reserve. It is close to Siena and to San Gal  …see more

from £1523 / night

£6091 / week

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from £1523 / night

1 / 29

Province of Siena / Montepulciano

5 9 1 night min stay

  • 5 bedrooms
  • Sleeps 9
  • 1 night min stay
Key info: Swimming pool; Not suitable for children; Car advised;
 …see more

from £863 / night

£6035 / week

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from £863 / night

1 / 20

The Spring (v024) - Pienza villa sleeps 12

Province of Siena / Pienza

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below. The house, built in the first half of the eighteenth century, has been renovated carefully by the couple  …see more

from £488 / night

£3414 - £4526 / week

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from £488 / night

(1) Excellent 

1 / 16

Province of Siena / Sarteano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £185 / night

£1294 - £2587 / week

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from £185 / night

1 / 12

APARTMENT 804 - Cedda apartment sleeps 4

Poggibonsi / Cedda

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
60 sqm apartment located on the first floor, Podere Santa Filomena. It 'consists of large living room with fireplace, kitchen, one double bedroom and one twin bedroom. Bathroom with bath and shower. The rental price includes: bed linen and towels changed weekly, fi  …see more

from £71 / night

£496 / week

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from £71 / night

1 / 22

46441001 - Castellina In Chian - Castellina In Chianti farmhouse sleeps 16

Province of Siena / Castellina In Chianti

8 16 7 nights min stay

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Beautiful restored farmhouse with swimming-pool situated in the heart of the Chianti Classico area, a few kilometers away from Castellina in Chianti. This property is quietly situated on a large 220-hectare farming estate producing excellent wines. Tastefully furnished,  …see more

from £388 / night

£2716 - £3703 / week

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from £388 / night

1 / 22

Province of Siena / Monticiano

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
 …see more

from £153 / night

£1035 - £1337 / week

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from £153 / night

1 / 26

Charming Villa in the Crete Senesi - San Giovanni d'Asso villa sleeps 8

Province of Siena / San Giovanni d'Asso

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
This charming old hamlet is located at 5 km from San Giovanni d'Asso, in the heart of the Crete Senesi, at just 13 km from Pienza and 16 km from Montalcino. The estate belonged for six hundred years to the notorious Piccolomini family, a protagonist of Italian Ren  …see more

from £350 / night

£4557 / week

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from £350 / night

(16) Excellent 

1 / 24

Attractive stone-built villa in extraordinary Tuscan locale, private terrace and swimming pool, incredible views, sleeps up to 9 - San Gimignano villa sleeps 9

Province of Siena / San Gimignano

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
Villa La Porticciola take its charm from the extroardinary position in front of the silhouette of San Gimignano towers. Everywhere it is possible to admire the unforgettable panoramic view of the town or the hilly landscape of the Chianti region. Ideal position for excu  …see more

from £345 / night

£1466 - £2500 / week

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from £345 / night

1 / 20

Cypress Villa (v008) - Pienza farmhouse sleeps 13

Province of Siena / Pienza

6 13 7 nights min stay

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Nearest beach 44 km; Swimming pool; Child friendly ;
Ground floor: a large living room with fireplace, small kitchen, a double bedroom with a separate entrance from the outside with an en-suite bathroom with washing machine.First floor: a double bedroom with Jacuzzi inside the room and en-suite bathroom with shower, a dou  …see more

from £355 / night

£2483 - £5932 / week

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from £355 / night

1 / 20

Chapel Manor (v027) - Chiusi manor house sleeps 21

Province of Siena / Chiusi

8 21 7 nights min stay

  • 8 bedrooms
  • Sleeps 21
  • 7 nights min stay
Key info: 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 - £3216 / week

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from £307 / night

1 / 14

Monteroni d'Arbia Villa - Monteroni d'Arbia villa sleeps 14

Province of Siena / Monteroni d'Arbia

7 14 7 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
This detached house with private garden and pool inside an agricultural business cultivated with olive trees, features also a park and views of Siena and is set in the beautiful Sienese countryside, just 3 km from Vescovado and 5 km from Monteroni away. It consists of t  …see more

from £444 / night

£3104 / week

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from £444 / night

1 / 31

Villa Colombaio - Asciano villa sleeps 9

Province of Siena / Asciano

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
As guests enter the property there is an entrance hall leading off to a living area on the right and large kitchen on the left. This area has an open plan feel to it. The kitchen is superbly equipped with everything guests could possibly need and want during their stay.  …see more

from £300 / night

£1667 - £3590 / week

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from £300 / night

1 / 6

Le Tortore villa - Monteroni d'Arbia villa sleeps 6

Province of Siena / Monteroni d'Arbia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
The Siena rolling hills, the valley of the Arbia river, the castle of San fabiano and the farm estate with pheasants,and white truffles:a dream!Come to this villa unique for her comforts!Air conditioning, DVD , HI-FI, fully equipped kitchen,balcony with view on the sunf  …see more

from £173 / night

£1121 - £1552 / week

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from £173 / night

1 / 31

Il Poggiarone Montepulciano - Montepulciano villa sleeps 14

Province of Siena / Montepulciano

7 14 7 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Car advised;
Il Poggiarone is a splendid farmhouse with typical Tuscan architectural features, set in an extremely panoramic position and the ideal destination for those who are looking for a holiday which is a mix of art, history and nature. The beautiful villa is near the owner's  …see more

from £163 / night

£1138 - £2104 / week

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from £163 / night

1 / 18

Apartment Cocchieri 101 - Caprera apartment sleeps 6

Siena / Caprera

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; No pets allowed;
Recently renovated apartment over two floors, situated on top of the old riding stables, comfortably equipped and elegantly furnished with antique pieces of furniture. Main floor: living room/dining room, kitchen, 1 double room with a double bed, 1 double room, bathroom  …see more

from £233 / night

£807 - £897 / week

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from £233 / night

1 / 24

Province of Siena / San Casciano dei Bagni

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
 …see more

from £345 / night

£1294 - £2932 / week

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from £345 / night

1 / 12

10319 - Villa Dan - Gracciano di Colle Val d'Elsa villa sleeps 10

Siena / Gracciano di Colle Val d'Elsa

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Pet friendly;
Villa Dan is located between the cities of Arezzo, Florence and Siena, at the quaint old town of Figline Valdarno with its ancient piazza and historical buildings. The Villa Dan has 5 bedrooms and 3bathrooms, situated in Figline Valdarno, with a magnicificient view. On  …see more

from £358 / night

£2500 / week

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from £358 / night

(1) Excellent 

1 / 17

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £104 / night

£518 - £1121 / week

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from £104 / night

1 / 16

Villa Casella - Contignano villa sleeps 18

Radicofani / Contignano

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
For those in search of an exceptional and luxurious Italian retreat, Villa Casella is the perfect choice. The exquisite villa is located in Contignano surrounded by spectacular views of rolling clay hills and countryside.The villa sleeps up to 19 in 8 very spacious bedr  …see more

from £2813 / night

£11250 / week

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from £2813 / night

(3) Excellent 

1 / 32

Rustic home Il Torrione, private garden and pool - Radicondoli house sleeps 6

Province of Siena / Radicondoli

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 50 km; Swimming pool; Child friendly ;
In our rustic house Il Torrione you will find all the peacefulness that only Tuscany can offer the visitor. Our customers will find this large apartment in Radicondoli, town in the green of Tuscany hills, composed by three bedrooms, bathrooms, a kitchen, a living room a  …see more

from £124 / night

£863 - £1078 / week

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from £124 / night

1 / 20

Primrose Villa (V039) - Chiusi villa sleeps 8

Province of Siena / Chiusi

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: 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

1 / 24

23916-Holiday house San Gimign - Badia A Elmi villa sleeps 8

Siena / Badia A Elmi

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
The property is a beautiful detached villa converted from a lovely, old hay store situated in the Chianti hills half way (35 km) between Florence and Siena.<br><br>In the well kept garden there is an inviting swimming pool (8 x 5 m) available from May to Oct  …see more

from £103 / night

£717 - £1939 / week

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from £103 / night

1 / 24

Province of Siena / Pienza

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Nearest beach 95 km; Swimming pool; Child friendly ;
 …see more

from £302 / night

£1811 - £3044 / week

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from £302 / night

(1) Excellent 

1 / 25

Villa Corsano, SIENA - Ville di Corsano villa sleeps 20

Province of Siena / Ville di Corsano

10 20 6 nights min stay

  • 10 bedrooms
  • Sleeps 20
  • 6 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Typical Tuscan villa, ancient and charming. Large Dining room with huge fireplace (15 century). Frescoed ballroom. Some of the bedrooms are frescoed too. Extensive gardens with table to have dinners outside. Panoramic pool area overlooking Siena, the Crete Senesi and th  …see more

from £776 / night

£5432 / week

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from £776 / night

(1) Excellent 

1 / 24

Villa Montebello - Montalcinello villa sleeps 18

Chiusdino / Montalcinello

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Child friendly ;
Characteristic Tuscan stone farmhouse situated in a dominant position just 5 minutes’ walk from a magical medieval village 35 km west of Siena . The property has been completely renovated a few years ago and turned into a most cozy and comfortable luxury holiday vill  …see more

from £339 / night

£2156 - £3880 / week

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from £339 / night

(2) Very Good 

1 / 17

Il Borgo del Grillo - Sarteano villa sleeps 50

Province of Siena / Sarteano

23 50 3 nights min stay

  • 23 bedrooms
  • Sleeps 50
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Il Borgo del grillo, originally registered as Borgo Fastelli in its 1765 Catasto Leopoldino entry (the local land registry of the time) is an historical abode which has been towering over the Val d'Orcia for centuries. Located in the western part of Monte Cetona, i  …see more

from £61 / night

£423 / week

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from £61 / night

(9) Excellent 

1 / 20

Province of Siena / Poggibonsi

2 8 3 nights min stay

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £112 / night

£778 - £1616 / week

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from £112 / night

1 / 19

Stunning Villa near Pienza - Pienza villa sleeps 10

Province of Siena / Pienza

4 10 7 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
This lovely holiday home in the Middle Ages was probably a resting place for pilgrims travelling on the Via Francigena, that passes nearby. Furthermore, opposite the property is the 13th century Castello di Spedaletto, one of the most important monastic granges of the S  …see more

from £158 / night

£1104 - £2069 / week

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from £158 / night

1 / 34

Podere Sant' Albino - Sant'Albino villa sleeps 14

Montepulciano / Sant'Albino

7 14 7 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Nearest beach 115 km; Swimming pool; Child friendly ;
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves. It has been turned into a residence of refined charm that retains an atmosphere of informal welcome. The landscape and environment of Montepulciano are amo  …see more

from £370 / night

£2587 - £5345 / week

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from £370 / night

(28) Excellent 

1 / 26

Fonte Aulente Montalcino - Val d'Orcia farmhouse sleeps 5

Montalcino / Val d'Orcia

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored and surrounded by beautiful garden-park, 2 km from Montalcino, in a panoramic position with amazing views over the Tuscan hills. The apartment is a part of the old farmhouse, with its own ent  …see more

from £116 / night

£808 / week

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from £116 / night

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