Province of Siena apartment or villa with a private pool area

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938 Holiday homes

Filters applied: Private pool (938)

34

Villa Fonte all'Oppio Pienza - Pienza villa sleeps 13

Province of Siena / Pienza

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient stone farmhouse, nowadays beautiful holiday villa, set in a very panoramic position inside the Parco Artistico Naturale of Val d'Orcia. Only 2 km far we find the well-known Renaissance village of Pienza. In a short drive there are renowned villages such as Monti  …see more

from £204 / night

£1427 - £2331 / week

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from £204 / night

(2) Good 

14

Villa Verdepino - Rigomagno villa sleeps 10

Sinalunga / Rigomagno

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The villa sits on a hill immersed in the greenery of a peaceful oasis and surrounded by large grounds.Here, where pleasure and nature meet, it is possible to enjoy long walks through the countryside and at the same time be within easy reach of amenities which are just 5  …see more

from £194 / night

£1357 - £9270 / week

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from £194 / night

(5) Excellent 

23

Podere Lo Spadino - San Gimignano villa sleeps 9

Province of Siena / San Gimignano

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The villa, on two floors, is just 5 km from the historic center of San Gimignano, in a secluded location is surrounded by large well kept garden and green, with lawn, where you can spend time and relax. The garden also features a gazebo with garden furniture, barbecue.  …see more

from £305 / night

£1348 - £2174 / week

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from £305 / night

14

Castelnuovo Berardenga / Montaperti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £119 / night

£827 / week

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from £119 / night

19

Fern Cottage (v044) - Cetona cottage sleeps 10

Province of Siena / Cetona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This charming cottage is made up of a kitchen, a living room with fireplace, a dining room, a study, a guest bathroom and a double bedroom with en-suite bathroom with shower on the ground floor. On the first floor there is a double bedroom with en-suite with shower,  …see more

from £327 / night

£2287 - £2687 / week

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from £327 / night

(10) Excellent 

20

Province of Siena / Poggibonsi

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £114 / night

£792 - £1644 / week

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from £114 / night

(5) Excellent 

32

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

Province of Siena / Radicondoli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 £125 / night

£870 / week

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from £125 / night

(2) Excellent 

16

Province of Siena / Sinalunga

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly

 …see more

from £157 / night

£1035 - £1166 / week

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from £157 / night

(11) Excellent 

28

Villa LisiDor, luxury Tuscany cottage in Chianti - Gaiole in Chianti villa sleeps 10

Province of Siena / Gaiole in Chianti

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
* SPECIAL PRICE for a SHORT BREAK: 3-8 October at 2.000€ VILLA LISIDOR: FULLY RENOVATED WITH ALL NEW AMENITIES. The habitable area is doubled: from 150 square meters to 300 square meters. On GROUND FLOOR, which is at garden level, is a large sitting room with Tv  …see more

from £348 / night

£2883 - £4435 / week

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from £348 / night

(6) Very Good 

25

Virgilius - Radicondoli villa sleeps 6

Province of Siena / Radicondoli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
Situated below the mediaeval village of Radicondoli, this property enjoys an exceptional view over the Chianti hills, taking in the towers of San Gimignano and stretching as far as the Apennines.This self standing villa, surrounded by olives groves and fruit trees, has  …see more

from £53 / night

£366 - £1740 / week

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from £53 / night

18

Monks Farm (v023) - Sarteano farmhouse sleeps 14

Province of Siena / Sarteano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This stone house was originally inhabited by a large family of farmers who worked for the monks of the nearby Abbey of Spineto. Excellent furnishing.Ground floor: large kitchen, with wood fired oven, opening directly onto the garden, spacious dining room, study with tab  …see more

from £396 / night

£2766 - £3627 / week

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from £396 / night

23

Province of Siena / Radicondoli

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 56 km
  • Swimming pool
  • Child friendly

 …see more

from £235 / night

£1644 - £2174 / week

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from £235 / night

(6) Very Good 

24

Picturesque Tuscan villa in the hills near Siena features private garden, barbecue and swimming pool, sleeps 6 - Belforte cottage sleeps 6

Radicondoli / Belforte

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
In the picturesque setting of the "Metallifere" hills, west from Siena, is located this characteristic stone built cottage, recently renovated in keeping with the traditional style and character, with wood beams and terracotta floors, furnished in a comfortabl  …see more

from £63 / night

£435 - £653 / week

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from £63 / night

(3) Excellent 

36

Villa La Casella - Cetona villa sleeps 6

Province of Siena / Cetona

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets
Treat yourself to the ideal 2-bedroom home for your dream vacation in Tuscany! La Casella is a luxurious private villa in lush gardens with private pool, outside dining, views and close enough to walk into town. This well furnished villa is set on two levels, and perfec  …see more

from £181 / night

£1224 - £1300 / week

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from £181 / night

(4) Excellent 

19

Chianti, La Pruneta, Masaccio studio - Radda in Chianti farmhouse sleeps 2

Province of Siena / Radda in Chianti

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Podere La Pruneta is an old farmhouse 20 minutes from Radda in Chianti, in the heart of Tuscany, olive trees and vines cover 6 hectares of land on slopes overlooking the Arno Valley. Massacio is one of the tastefully restored studio apartments with wooden-beamed ceili  …see more

from £70 / night

£479 / week

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from £70 / night

(1) Excellent 

24

Villa Montebello - Montalcinello villa sleeps 18

Chiusdino / Montalcinello

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • 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 £342 / night

£2174 - £3914 / week

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from £342 / night

(5) Excellent 

22

Apartment "Casa Laura" - Monteriggioni apartment sleeps 5

Province of Siena / Monteriggioni

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Casa Laura is an independent apartment in a restored farmhouse Agriturismo la Magione that is situated on an agricultural estate on a hilltop at about 300 meters above sea level. It offers a wonderful panorama of the surrounding countryside with fields, olive groves, vi  …see more

from £61 / night

£392 - £505 / week

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from £61 / night

22

Province of Siena / Monticiano

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

 …see more

from £154 / night

£1044 - £1087 / week

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from £154 / night

(4) Excellent 

44

I MELOGRANI I:5 BDR Tuscan villa,view,pool ,WiFi - San Giovanni d'Asso villa sleeps 10

Province of Siena / San Giovanni d'Asso

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
You could not ask for a more special place in which to celebrate an important anniversary or simply spend a vacation with your family and friends ! I Melograni is a beautiful antique,indipendent, "casale" with a large fenced swimming pool (5x12 mt), 1km away (walking  …see more

from £472 / night

£3305 - £4261 / week

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from £472 / night

16

Villa - Asciano farmhouse sleeps 11

Province of Siena / Asciano

6 11 1 night min

  • 6 bedrooms
  • Sleeps 11
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
he beautiful master's villa has an austere Tuscan architectural structure, of some 600 square metres distributed on two floors.On the ground floor you will find the entrance, a large sitting room with Tuscan-style fireplace, a sitting-room, a dining room, a card ro  …see more

from £653 / night

£4696 / week

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from £653 / night

(2) Excellent 

35

Agriturismo Sammonti - Monteriggioni farmhouse sleeps 2

Province of Siena / Monteriggioni

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The “borgo Sammonti” was built in the beginning of the 13th century as a fortress in the county of Scorgiano, and it is located near most beautiful and important tuscan cities. The structure is surrounded by woods and it offers many paths for walks and escursions.Th  …see more

from £66 / night

£435 - £479 / week

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from £66 / night

(4) Excellent 

21

La Chiesina - Casaglia villa sleeps 6

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
The villa was an ancient historical structure going back to before the year 1200, originally the chapel "Santa Maria Church", near the burg of Casaglia. Over the centuries, the chapel was deconsecrated to become, first a watchtower, and then a place where the  …see more

from £131 / night

£870 - £2000 / week

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from £131 / night

32

Leccetino - Trequanda villa sleeps 6

Province of Siena / Trequanda

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
Villa Leccetino Tuscany Arriving at Leccetino, down a short tree covered road is like arriving at a very secret location. Tucked into the hillside surrounded by olive trees, this is a spectacular masonry villa, made with stones dug up from the ground on this terraced p  …see more

from £280 / night

£1957 - £3470 / week

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from £280 / night

(1) Excellent 

20

Villa Cafaggiola 3 bedroom villa with private pool - San Gimignano villa sleeps 6

Province of Siena / San Gimignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
The Villa has been completely renovated from an old barn and materials have been used for its original restructuring terracotta floors and exposed beams on the ceilings. It 'a great place to spend a quiet holiday without sacrificing the various excursions just a short d  …see more

from £162 / night

£1131 / week

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from £162 / night

(3) Good 

32

chianti, olive groves, vines, views, relax. - Radda in Chianti farmhouse sleeps 6

Province of Siena / Radda in Chianti

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden
La Pruneta is a beautifully restructured old farmhouse surrounded by olive trees in the middle of Tuscany, 20 minutes from Radda in Chianti, 50 minutes from Florence, Siena and Arezzo. Two self contained studios and a one bedroom apartment available for rent separately  …see more

from £70 / night

£479 - £966 / week

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from £70 / night

(4) Excellent 

17

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £105 / night

£522 - £1131 / week

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from £105 / night

(7) Very Good 

24

Just outside of medieval Tuscan village, beautiful 2 bedroom hillside cottage with private pool and garden - Radicondoli cottage sleeps 5

Province of Siena / Radicondoli

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
Situated below the mediaeval village of Radicondoli, west from Siena, is located this characteristic farm house, recently renovated in keeping with the traditional style and character, with wood beams and terra cotta floors, furnished in a comfortable, rustic style. In  …see more

from £50 / night

£348 - £1522 / week

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from £50 / night

5

Apartment Il Pino - San Fabiano apartment sleeps 4

Monteroni d'Arbia / San Fabiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The Il Pino apartment is located in the villa Podernovo at San Fabiano farmestate. It offers stunning views on the Arbia valleys and the skyline of Montalcino, and an authenitc athmosphere of a Tuscan home.The furnitures ,the air conditioning, the TV satellite with Sky  …see more

from £114 / night

£653 - £870 / week

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from £114 / night

(5) Excellent 

26

Impressive stone-built cottage with private grounds and pool close to medieval Tuscan town of Colle Val d'Elsa - Colle di Val d'Elsa cottage sleeps 5

Province of Siena / Colle di Val d'Elsa

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly
This interesting and beautiful stone-built house is peacefully located in the country side just 1 km way from the mediaeval town of Colle Val d'Elsa. Casavico is the result of a recent renovation which has transformed this ancient barn (once belonging to the nearby  …see more

from £63 / night

£435 - £1305 / week

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from £63 / 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 £310 / night

£2166 / week

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from £310 / night

43

Villa La Casella - Cetona villa sleeps 4

Province of Siena / Cetona

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Treat yourself to the ideal 2-bedroom home for your dream vacation in Tuscany! La Casella is a luxurious private villa set on a gentle hillside with lush gardens and private pool, outside dining, views and close enough to walk into town. This well furnished villa is set  …see more

from £170 / night

£1187 - £2444 / week

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from £170 / night

(2) Excellent 

24

Stunning Villa in Siena with exclusive spa - Siena villa sleeps 10

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful villa in Siena with private Spa-Wellness Center room is situated on the hills with a breathtaking view over the vineyards up to Siena. An ideal accommodation for all those seeking peace and quiet but also a perfect point of departure for visiting the beau  …see more

from £237 / night

£1653 - £3477 / week

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from £237 / night

(42) Excellent 

35

Beautiful Private Villa, pool, hot tub,wi-fi,Siena - Siena villa sleeps 12

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
JUST RELAX...... YOUR VACATION IN TUSCANY BEGINS NOW!!!! What we want is to make this holiday as pleasant and relaxing as possible, so we want to make available to you our Villa, that for a time, long or short it might be, will be YOUR HOME in Tuscany. A HOLIDAY WITHOUT  …see more

from £243 / night

£1696 - £4348 / week

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from £243 / night

100

Ville Di Corsano 44299 - Monteroni d'Arbia villa sleeps 14

Province of Siena / Monteroni d'Arbia

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Spacious and beautiful farmhouse with outbuilding and private swimming-pool situated in peaceful location on a large estate enjoying extensive views over the Crete Senesi area and Siena in the distance. This villas has been tastefully restored and turned into a splendid  …see more

from £1936 / night

£11293 - £16311 / week

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from £1936 / night

(1) Excellent 

24

24091-Holiday house Siena - Radicondoli villa sleeps 6

Province of Siena / Radicondoli

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Situated at the edge of a park, just within 5 minutes walk to the mediaeval hilltop village of Radicondoli, the property enjoys an exceptional view over the Metallifere Hills and those of Chianti, taking in the towers of San Gimignano and stretching as far as the Apenni  …see more

from £56 / night

£386 - £1542 / week

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from £56 / night

(3) Excellent 

24

Radicondoli / Belforte

4 9 4 nights min

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £200 / night

£1305 - £1566 / week

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from £200 / night

(2) Excellent 

40

Siena / Val di Merse

6 11 Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £109 / night

£774 - £1722 / week

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from £109 / night

24

Villa in Tuscany - Montepulciano villa sleeps 12

Province of Siena / Montepulciano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The Poggio Golo holiday villa has been restored to its original splendour after long and careful renovation, giving you the possibility to savor the atmosphere of a holiday from past times in an old 17th century villa with original furniture and accessories. The well-tr  …see more

from £218 / night

£2131 / week

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from £218 / night

(2) Very Good 

10

Cosy Tuscan villa for friends or family - San Gimignano apartment sleeps 7

Province of Siena / San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Splendid three bedroom two bathroom villa located right outside of San Gimignano. Absolut privacy and quiet location !! Incredible private pool with a panoramic position over the Tuscan landscape Three double bedrooms - perfect for couples or friends travelling to  …see more

from £140 / night

£957 - £1218 / week

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from £140 / night

18

Villa Monica - Chiusi villa sleeps 12

Province of Siena / Chiusi

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The farmhouse was inhabited by a family of Umbrian farmers whose main occupation was cultivating their land, picking up its hard-earned fruits.The house is now surrounded by a garden with oak-trees, mulberry-trees, laurels, maples and lime-treesOn the inside walls, the  …see more

from £298 / night

£1827 - £2696 / week

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from £298 / night

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