Province of Siena apartment or villa with a private pool area | Holiday Lettings

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  • Asciano (8)
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  • Buonconvento (6)
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  • Castiglioncello del Trinoro (1)
  • Castiglione D'Orcia (6)
  • Cetona (20)
  • Chianciano Terme (4)
  • Chiusdino (6)
  • Chiusi (8)
  • Colle di Val d'Elsa (4)
  • Gaiole in Chianti (20)
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  • Montalcino (21)
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  • Montepulciano (40)
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  • Monticiano (9)
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  • Murlo (7)
  • Palazzone (5)
  • Pienza (26)
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  • Radda in Chianti (10)
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  • Radicondoli (18)
  • Rapolano Terme (5)
  • Rosia (1)
  • San Casciano dei Bagni (11)
  • San Gimignano (54)
  • San Giovanni d'Asso (17)
  • San Quirico d'Orcia (2)
  • Sarteano (18)
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538 Holiday homes

Filters applied: Private pool (538)

(7) Excellent 

1 / 24

Rapolano Terme / Serre di Rapolano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 120 km; Swimming pool; Child friendly ;
 …see more

from £82 / night

£556 / week

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from £82 / 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 £86 / night

£599 - £1334 / week

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from £86 / night

1 / 47

Villa Brunello - Castelnuovo dell'Abate villa sleeps 8

Montalcino / Castelnuovo dell'Abate

5 8 3 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Nearest beach 90 km; Swimming pool; Child friendly ;
This comfortable, cosy villa nestles on a sheltered incline among gently rolling hills. These are covered in Brunello wine-producing vineyards, which border the lower pool-terrace. The San Giuseppe winery, from which the house takes its name, is situated nearby. Wonderf  …see more

from £1146 / night

£5983 / week

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from £1146 / night

Featured properties

1 / 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
Key info: 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 £112 / night

£642 - £855 / week

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from £112 / night

(3) Very Good 

1 / 21

Sovicille / Torri

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £77 / night

£471 / week

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from £77 / night

1 / 12

Agriturismo Terrarossa 4px - Valiano apartment sleeps 4

Montepulciano / Valiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
The Terrarossa farm holiday resort is deep in the stunning hills around Montepulciano. It is part of an ancient country estate counting 130 acrwes land, where with respect for the land and its natural balance wheat, sunflowers and, above all, the vines for Vino Nobile  …see more

from £129 / night

£513 - £761 / week

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from £129 / night

1 / 5

VILLA TINAIO - Monteroni d'Arbia house sleeps 10

Province of Siena / Monteroni d'Arbia

8 10 Min stay varies

  • 8 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; No pets allowed;
Monteroni d'Arbia: Villa Tinaio was originally the estate wine cellar. Because of its size, it can accomodate families or groups of friends up to 24 people who can enjoy moments of absolute relax, on the border of the private pool, surrounded by ancient trees.On th  …see more

from £464 / night

£3248 - £4958 / week

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from £464 / night

(15) Excellent 

1 / 22

Lovely Independent cottage with private pool - Monteguidi cottage sleeps 5

Casole d'Elsa / Monteguidi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 40 km; Swimming pool; Child friendly ;
La Casa Dei Nonni is a beautiful villa located just outside the tiny village of Monteguidi, immersed in the beautiful Tuscan countryside. The villa has a spacious living room with fireplace, a fitted kitchen with a second fireplace, a bedroom with two single beds and a  …see more

from £129 / night

£770 - £1154 / week

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from £129 / night

(2) Excellent 

1 / 24

Province of Siena / Palazzone

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
 …see more

from £257 / night

£2137 / week

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from £257 / night

(42) Excellent 

1 / 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
Key info: 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 £239 / night

£1667 - £4274 / week

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from £239 / night

1 / 24

Province of Siena / Palazzone

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 106 km; Swimming pool; Child friendly ;
 …see more

from £214 / night

£1197 - £2137 / week

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from £214 / night

1 / 100

Gianluca - Guazzino villa sleeps 20

Sinalunga / Guazzino

11 20 Min stay varies

  • 11 bedrooms
  • Sleeps 20
  • Min stay varies
Key info: Nearest beach 140 km; Swimming pool; Child friendly ;
ExteriorsIf guests are in search of convenience and luxury, this Italian villa in Tuscany makes the perfect choice. All Tuscan and Umbrian treasures are easily accessible as this ancient 18th century residence is located nearby the highway and toll-free roads. The area  …see more

from £855 / night

£5983 - £6582 / week

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from £855 / night

(1) Excellent 

1 / 14

Villa Verdepino - Rigomagno villa sleeps 10

Sinalunga / Rigomagno

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
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 £191 / night

£1334 - £9112 / week

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from £191 / night

1 / 20

San Gimignano / Ulignano

4 9 7 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Nearest beach 90 km; Swimming pool; Suitable for children age 5+;
 …see more

from £361 / night

£2522 / week

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from £361 / night

1 / 14

Castelnuovo Berardenga / Montaperti

5 9 7 nights min stay

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £116 / night

£812 - £1283 / week

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from £116 / night

(5) Excellent 

1 / 46

Villa Sangimignano - Montauto farmhouse sleeps 5

San Gimignano / Montauto

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
The 200 sqm villa is a typical stone barn in an early '900 style, characterized by the tranquility of the Tuscan countryside of San Gimignano in which it is immersed.It can be accessed via a large private and completely fenced garden of 2,000 sqm.The house is the r  …see more

from £199 / night

£1453 - £1966 / week

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from £199 / night

(4) Excellent 

1 / 24

Pretty Tuscan cottage surrounded by stunning hills with private pool and terrace, sleeps up to 5 - Casole d'Elsa cottage sleeps 5

Province of Siena / Casole d'Elsa

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Nearest beach 65 km; Swimming pool; Child friendly ;
Stone cottage situated in the green, panoramic hills at 1.5 km from the hilltop town of Casole d'Elsa. Accommodation is offered on the elevated ground floor composed by a cosy leaving room with a double sofa bed and access onto a large panoramic terrace (50 m2), 1  …see more

from £80 / night

£556 - £898 / week

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from £80 / night

(7) Excellent 

1 / 18

3 bedroom farmhouse in the picturesque Tuscan hills boasting private pool, terrace and garden, sleeps 6 - San Gimignano farmhouse sleeps 6

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Child friendly ;
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from £84 / night

£565 - £941 / week

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from £84 / night

(1) Excellent 

1 / 24

Casa Giovanni - San Giovanni d'Asso villa sleeps 5

Province of Siena / San Giovanni d'Asso

3 5 7 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Italian village rental - This charming historic residence is part of a larger building, located in the village of San Giovanni d'Asso, just beyond the original castle walls and a short walk to the centre.With origins dating back to the 15th century this property ce  …see more

from £240 / night

£1680 - £2360 / week

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from £240 / night

(13) Excellent 

1 / 24

Charming 2 bedroom Tuscan villa with private pool - San Gimignano villa sleeps 5

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 85 km; Swimming pool; Child friendly ;
Charming stone-built house located in a peaceful and panoramic position on the green, rolling hills near San Gimignano.The villa is the result of a recent renovation which has transformed this ancient barn into a beautiful and comfortable detached villa, ideal for spend  …see more

from £171 / night

£471 - £1539 / week

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from £171 / night

1 / 13

Casa Ciaccheri - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
The house is located in the heart of the Chianti Classico, inside the town of Gaiole in Chianti (all kinds of shops). The apartment is on the ground floor and is part of a building where the owners reside.Outside a portion of an equipped courtyard is available for the e  …see more

from £69 / night

£300 / week

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from £69 / night

(15) Very Good 

1 / 97

7 bedroom Tuscan farmhouse near rennaissance town of Montepulciano, features include jacuzzi, private garden and pool - Montepulciano farmhouse sleeps 16

Province of Siena / Montepulciano

7 16 1 night min stay

  • 7 bedrooms
  • Sleeps 16
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Car essential;
The watermill “Il Molinaccio”, near the renaissance town of Montepulciano, was already present in the old maps of the Granduchy of Tuscany . The original building, duly and let me say passionately restored, now reopens as a luxury country house where the guests may  …see more

from £513 / night

£2992 / week

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from £513 / night

1 / 25

Province of Siena / Gallina

2 6 2 nights min stay

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

from £154 / night

£1077 / week

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from £154 / night

1 / 24

I5.348 - Holiday house wit... - Celle sul Rigo villa sleeps 16

San Casciano dei Bagni / Celle sul Rigo

7 16 7 nights min stay

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Nearest beach 0 km; Swimming pool; Child friendly ;
The farmhouse is located near Radicofani, under the UNESCO Patrimony (being a part of the Val d'Orcia) 4.5 km from the town centre along the old dirt Francigena Road. The ancient house, restructured with a rustic style, is part of a farm with 96 hectars of cultivated f  …see more

from £196 / night

£1368 - £2455 / week

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from £196 / night

1 / 11

Province of Siena / Sinalunga

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £86 / night

£582 / week

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from £86 / night

(13) Excellent 

1 / 24

Renovated 5 bedroom villa surrounded by Tuscan vineyards, fetures private pool, log fire and terrace - San Gimignano villa sleeps 12

Province of Siena / San Gimignano

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
The completely renovated property occupies a panoramic position within an estate of olive groves and vineyards, boasting an entrancing view of the famous towers of San Gimignano 4 km away. The characteristic architecture enables guests to experience a specifically Tusc  …see more

from £342 / night

£1539 - £2479 / week

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from £342 / night

1 / 25

A paradise for families and couples!!! - Radda in Chianti tower sleeps 4

Province of Siena / Radda in Chianti

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
A view on a scenic wine and olive oil country. The ancient farmhouse of Augusto and Lele Vitali is an excellent base from which to explore the "heart" of Tuscany. A few meters off the road to the village, the Torre, facing Radda, stands in an olive grove overlooking vin  …see more

from £120 / night

£812 / week

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from £120 / night

1 / 12

Il Casale di Piera - Castiglione D'Orcia villa sleeps 25

Province of Siena / Castiglione D'Orcia

8 25 7 nights min stay

  • 8 bedrooms
  • Sleeps 25
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car not necessary;
The farm 'Moro Fiacchi' that hosts "Il Casale di Piera" holiday house, is a typical Tuscan country mansion from the XVII century, with a spectacular pool overlooking the boundless valley, it sits in the very heart of the Val D'Orcia Artistic, Na  …see more

from £611 / night

£4274 / week

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from £611 / night

1 / 16

Farmhouse Podere Pienza - Val d'Orcia farmhouse sleeps 12

Montalcino / Val d'Orcia

5 12 3 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
The 300 m2 farmhouse has been beautifully restored. Split into 2 levels, the farmhouse has a huge open living room that has access to the terrace with outdoor furnishings for dining and relaxing. The farmhouse is adorned with fine Tuscan country furnishings.The farmhous  …see more

from £257 / night

£1966 / week

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from £257 / 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 £145 / night

£1009 - £2556 / week

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from £145 / night

(1) Excellent 

1 / 17

Tuscan hillside farmhouse with private pool, terrace and garden, great for family holidays - San Gimignano farmhouse sleeps 6

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Child friendly ;
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from £56 / night

£342 - £812 / week

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from £56 / night

(7) Very Good 

1 / 24

Delightful holiday house at the edge of Tuscan village of Casciano di Murlo, features private garden, terrace and pool - Casciano di Murlo house sleeps 5

Murlo / Casciano di Murlo

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 50 km; Swimming pool; Child friendly ;
Situated at the edge of the village of Casciano di Murlo, about 20 km away from Siena, in the heart of the gorgeous Tuscan countryside. Lovely views over the hills, private veranda with garden furniture and barbecue. Very tranquil location.The house (about 55 square met  …see more

from £56 / night

£368 - £471 / week

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from £56 / night

1 / 15

Province of Siena / Radicofani

1 4 1 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
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from £69 / night

£385 / week

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from £69 / 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 £342 / night

£1453 - £2308 / week

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from £342 / 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

1 / 27

Province of Siena / Montisi

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £248 / night

£1736 / week

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from £248 / night

(3) Excellent 

1 / 19

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

Province of Siena / Radda in Chianti

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
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 £69 / night

£471 / week

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from £69 / night

(10) Excellent 

1 / 24

Romantic Tuscan cottage, sleeps four, total priva - Casole d'Elsa cottage sleeps 6

Province of Siena / Casole d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
Casa Daniela' is a well farm into a romantic country cottage. The house ( Total independent ) - in the surroundings of Casole d'Elsa, a medieval village with Etruscan origins – is located on a hill surrounded by a large olive grove and a pretty garden. Inside the ma  …see more

from £116 / night

£684 - £983 / week

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from £116 / night

(7) Excellent 

1 / 24

Typically Tuscan stone farmouse with 6 bedrooms, brilliant views and private swimming pool - Radicondoli farmhouse sleeps 13

Province of Siena / Radicondoli

6 13 7 nights min stay

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Nearest beach 55 km; Swimming pool; Child friendly ;
This property is a typical stone farmhouse with dependance recently transformed into an enchanting holiday villa, conveniently located at just 3 km from the characteristic medieval village of Radicondoli. This area, west of Siena is characterised by the gentle rolling h  …see more

from £80 / night

£556 - £2522 / week

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from £80 / night

1 / 20

The Convent (v019) - Radicofani villa sleeps 12

Province of Siena / Radicofani

1 12 7 nights min stay

  • 1 bedroom
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
This was an old monastery during the first half of the sixteenth century and went on to become a summer residence for the friars of Monte Oliveto Maggiore. It enjoys beautiful views across a valley. Old farmhouse, well restored, divided into three apartments. Snowdrop (  …see more

from £179 / night

£1248 - £1530 / week

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from £179 / night

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I MELOGRANI II: 3BDR Tuscan villa,view,pool,WiFi
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