Province of Siena apartment or villa with a private pool area

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952 Holiday homes

Filters applied: Private pool (952)

1 / 34

Podere Sant' Albino - Sant'Albino villa sleeps 14

Montepulciano / Sant'Albino

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Nearest beach 115 km; Swimming pool; Great for children of all ages ;
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 £358 / night

£2500 - £5167 / week

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from £358 / night

(11) Excellent 

1 / 27

Villa LisiDor, luxury Tuscany cottage in Chianti

Province of Siena / Gaiole in Chianti

4 bedroomsSleeps 107 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 110 km; Swimming pool; Great for children of all ages ;
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 Sat area, a dining room in front of the pool, a professional  …see more

from £395 / night

£2763 - £4250 / week

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from £395 / night

1 / 23

Villa Erinni with sauna and a private pool

Province of Siena / Cetona

5 bedroomsSleeps 97 nights min stay

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
The villa is located in the southermost corner of Tuscany on top of a hill facing Cetona. The views are breathtaking and stretch as far as Città delle Pieve and Orvieto. A short walk (1km) takes guests to the lovely medieval town of Cetona, where they can get fresh bre  …see more

from £215 / night

£1500 - £3000 / week

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from £215 / night

(1) Excellent 

1 / 24

Villa Paradiso - Radda in Chianti villa sleeps 14

Province of Siena / Radda in Chianti

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
The house has been lovingly restored and furnished with careful attention and eye for detail.The lovely gardens, which are to the rear of the property have an array of aromatic plants such as lavender with shady corners and a magnificent pergola for dining outdoors. Pri  …see more

from £233 / night

£1625 - £3142 / week

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from £233 / night

1 / 100

Castiglione D'orcia 62100 - Castiglione D'Orcia villa sleeps 19

Province of Siena / Castiglione D'Orcia

8 bedroomsSleeps 197 nights min stay

  • 8 bedrooms
  • Sleeps 19
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Beautiful independent villa with private pool situated in the Orcia valley area, a splendid region south of Siena rich in charming villages and hamlets such us Montalcino, Pienza, San Quirico dOrcia, Castiglione dOrcia. This property has been recently restored and turne  …see more

from £275 / night

£1923 - £3540 / week

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from £275 / night

(5) Excellent 

1 / 24

Villa Vianci - Staggia Senese villa sleeps 12

Poggibonsi / Staggia Senese

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Great for children of all ages ;
Villa Vianci is luxurious villa dating back to the eighteenth century, located in the heart of Chianti, just 17 Km away from Siena and 45 Km from Florence. It is located on hill overlooking the medieval Castle of Monteriggioni Recently subjected to an attentive renova  …see more

from £500 / night

£3500 / week

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from £500 / night

1 / 100

Gaiole - Gaiole in Chianti villa sleeps 8

Province of Siena / Gaiole in Chianti

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
ExteriorsVilla Gaiole is an authentic Sienese-style retreat with total privacy and comfort. Located in a natural environment of absolute privacy Villa Gaiole has recently  been remodeled and elegantly furnished. All rooms and bedrooms are air conditioned to allow a  …see more

from £417 / night

£2500 - £3750 / week

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from £417 / night

(1) Excellent 

1 / 100

Magda - San Gimignano villa sleeps 12

Province of Siena / San Gimignano

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 90 km; Swimming pool; Great for children of all ages ;
Exterior:Perched on top on a hill, in the heart of Chianti countryside, Villa Magda boasts what must be one of the most enviable views of Tuscany: rolling Chianti hills decked with vines and olives, crowned by the incredible profile of San Gimignano's towers (locat  …see more

from £709 / night

£4500 - £5417 / week

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from £709 / night

1 / 18

Villa Monica - Chiusi villa sleeps 12

Province of Siena / Chiusi

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
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 £288 / night

£1765 - £2606 / week

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from £288 / night

1 / 15

Old Home Farm (v017) - Cetona farmhouse sleeps 20

Province of Siena / Cetona

8 bedroomsSleeps 207 nights min stay

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
This farmhouse is located in an exceptional panoramic position on the slopes of the Cetona mountain, it was probably an ancient fortified farm. It has recently been completed renovated and is divided into apartments but has a large common room with fireplace, bathroom a  …see more

from £287 / night

£2009 - £2834 / week

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from £287 / night

(1) Excellent 

1 / 24

Villa Bossona - Montepulciano villa sleeps 16

Province of Siena / Montepulciano

8 bedroomsSleeps 16Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
Key info: Nearest beach 115 km; Swimming pool; Great for children of all ages ;
Villa Bossona is an impressive villa which dates back to the eighteenth century. Ideal for quiet and relaxing holidays it is located in the sweet Montepulciano hills few minutes from the town. A small church with an enchanting bell tower is preserved in its original for  …see more

from £500 / night

£3250 - £3584 / week

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from £500 / night

1 / 23

Province of Siena / Radicondoli

3 bedroomsSleeps 9Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Nearest beach 56 km; Swimming pool; Great for children of all ages ;
 …see more

from £225 / night

£1575 - £2084 / week

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from £225 / night

1 / 24

Villa San Biagio - Montepulciano villa sleeps 16

Province of Siena / Montepulciano

7 bedroomsSleeps 167 nights min stay

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Nearest beach 115 km; Swimming pool; Great for children of all ages ;
Villa San Biagio is situated close to the hilltop town of Montepulciano renowned for its historical importance and for its wine Nobile. This magnificent country house is one of the most exclusive and stunning farmhouses in the area. The restoration works carefully prese  …see more

from £521 / night

£3646 - £5730 / week

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from £521 / night

1 / 20

Villa Cafaggiola 3 bedroom villa with private pool

Province of Siena / San Gimignano

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 75 km; Swimming pool; Great for children of all ages ;
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 £155 / night

£1084 - £1875 / week

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from £155 / night

(8) Excellent 

1 / 20

Three bedroom apartment in stunning villa

Province of Siena / San Gimignano

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Car advised;
Osservatorio is a stunning villa for up to 11guests divided into two independent units. Orione apartment for up to 6 guests.The property is extraordinarily cool and pleasant throughout the summer, thanks to its location on a higher altitude (about 500 AMSL) and the beau  …see more

from £179 / night

£1250 - £1917 / week

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from £179 / night

1 / 100

Albino - Montepulciano villa sleeps 14

Province of Siena / Montepulciano

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Nearest beach 180 km; Swimming pool; Great for children of all ages ;
ExteriorVilla Albino is a sophisticated and at the same time relaxed villa for 14 people in Tuscany. It is conveniently located just 5km away from Montepulciano, a privileged position to explore all of central Italy. It is within easy reach of Pienza, Montalcino, Bagno,  …see more

from £334 / night

£2334 - £5167 / week

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from £334 / night

1 / 22

Tuscan Villa Nr. San Gimignano large gardens

Colle di Val d'Elsa / Campiglia dei Foci

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 60 km; Swimming pool; Great for children of all ages ;
Villa Nr. San Gimignano, Siena Province, Tuscany, ItalyTypical Tuscan Style Villa with Private Pool and Large Private garden.12.000 Square Metres Of Gardens, With Pine Trees, Monumental Oaks And Olive GroveWonderful stone building situated in a peaceful position with a  …see more

from £155 / night

£1084 - £2084 / week

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from £155 / night

(3) Excellent 

1 / 19

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

Province of Siena / Radda in Chianti

1 bedroomSleeps 22 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £67 / night

£459 / week

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from £67 / night

1 / 20

PIERFANTINI - San Gusme villa sleeps 8

Castelnuovo Berardenga / San Gusme

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 90 km; Swimming pool; Great for children of all ages ;
Pierfantini is a rustic villa located in the Chianti just a few kilometres away from the medieval village San Gusme. The completely private villa in its nestled hillside position provides a refreshing retreat from the hot Tuscan days that cover the valley below. In the  …see more

from £107 / night

£746 - £1194 / week

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from £107 / night

1 / 100

Il Cervo - Province of Siena villa sleeps 19

Tuscany / Province of Siena

10 bedroomsSleeps 197 nights min stay

  • 10 bedrooms
  • Sleeps 19
  • 7 nights min stay
Key info: Nearest beach 115 km; Swimming pool; Great for children of all ages ;
ExteriorsLocated in San Casciano dei Bagni, Siena, this complex is the perfect starting point for a tour in the Tuscan region. The characteristic countryside with its rolling hills, vineyards and olive groves are a wonderful setting for long walks or bicycle rides.The n  …see more

from £310 / night

£2167 / week

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from £310 / night

(2) Very Good 

1 / 100

Castellina In Chianti 81687 - Castellina In Chianti villa sleeps 10

Province of Siena / Castellina In Chianti

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
The villa dating back to the first 800 as is present in the Catasto Leopoldino (the first inventory in Tuscany), it has been restructured maintaining it Tuscan typical style with ceilings with beams in wood and floors in cooked and window "mandorlate" that the  …see more

from £327 / night

£1910 - £2862 / week

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from £327 / night

1 / 45

Province of Siena / Gaiole in Chianti

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
 …see more

from £596 / night

£4167 - £6667 / week

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from £596 / night

1 / 20

Rose Farm (v048) - Castiglione D'Orcia villa sleeps 21

Province of Siena / Castiglione D'Orcia

1 bedroomSleeps 217 nights min stay

  • 1 bedroom
  • Sleeps 21
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
Large farmhouse divided into 4 apartments and 2 double bedrooms with bathrooms. Each apartment has a private entrance and two bedrooms (double, single or twin) each with bathrooms, kitchenette or kitchen. Laundry room. A large communal living room with fireplace is av  …see more

from £439 / night

£3067 - £4750 / week

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from £439 / night

(3) Excellent 

1 / 24

Lovingly renovated Tuscan Farmhouse with pool and garden, sleeps 6

Province of Siena / Casole d'Elsa

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 60 km; Swimming pool; Great for children of all ages ;
Casa Panoramica is a lovingly renovated farmhouse situated at the edge of the small hamlet of Lucciana, just 4 km from the lager hill town of Casole d’Elsa.Internally the house is attractively furnished with a practical kitchen opening onto the dining room with direct  …see more

from £78 / night

£542 - £1417 / week

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from £78 / night

1 / 18

Monks Farm (v023) - Sarteano farmhouse sleeps 14

Province of Siena / Sarteano

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
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 £379 / night

£2650 - £4384 / week

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from £379 / night

1 / 32

Leccetino - Trequanda villa sleeps 6

Province of Siena / Trequanda

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Car essential;
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 £271 / night

£1891 - £3353 / week

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from £271 / night

1 / 100

Nobile - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 200 km; Swimming pool; Great for children of all ages ;
ExteriorVilla Nobile, a lovely farmhouse within a wine and olive oil producing estate boasts a perfect location, on a hill with panoramic views of the area, conveniently situated a few minutes drive from Montepulciano and well located to explore the wider area. Guests a  …see more

from £227 / night

£1584 - £2417 / week

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from £227 / night

(7) Very Good 

1 / 24

Typically Tuscan stone farmouse with 6 bedrooms, brilliant views and private swimming pool

Province of Siena / Radicondoli

6 bedroomsSleeps 13Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
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 £107 / night

£542 - £2459 / week

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from £107 / night

(1) Excellent 

1 / 32

chianti, olive groves, vines, views, relax.

Province of Siena / Radda in Chianti

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
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 £67 / night

£459 - £925 / week

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from £67 / night

(4) Excellent 

1 / 19

Gorgeous 5 bedroom villa in Siena, Tuscany boasts

Province of Siena / Siena

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Great for children of all ages ;
Villa Le Tolfe is so close to Siena you can almost touch it (only 3 kilometres away). With stunning views and beautiful antique gardens this villa is perfect for relaxed stress free holidays. The house is built on top of a hill covered with olive groves and vineyards.  …see more

from £149 / night

£1042 - £2075 / week

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from £149 / night

1 / 100

Fiordaliso - San Giovanni d'Asso villa sleeps 10

Province of Siena / San Giovanni d'Asso

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 70 km; Swimming pool; Great for children of all ages ;
Exterior This enchanting villa is located in the heart of Tuscany, near Pienza. It is situated in the middle of an old olive grove and has one of the most stunning views in all of Tuscany. Besides the lovely city of Pienza, you'll also be near Montepulciano, Corton  …see more

from £417 / night

£2917 - £3959 / week

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from £417 / night

1 / 100

Ester - Castellina In Chianti villa sleeps 12

Province of Siena / Castellina In Chianti

5 bedroomsSleeps 127 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 85 km; Swimming pool; Great for children of all ages ;
ExteriorsLocated in the heart of the Chianti region, this extraordinary villa boasts views over the hills, the valleys and the countryside at its fullest. It is situated very close to Castellina in Chianti, a town in the province of Siena with ancient constructions, an  …see more

from £335 / night

£2345 - £3401 / week

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from £335 / night

1 / 23

Villa Giusy - Casole d'Elsa villa sleeps 14

Province of Siena / Casole d'Elsa

5 bedroomsSleeps 147 nights min stay

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
Recently renovated farmhouse, divided into two independent apartments, but let as one unit. Panoramic position, 3 km from Casole d'Elsa, lovely small town at the edge of the Chianti region. Made of stone, the house has maintained its rural architecture with terraco  …see more

from £120 / night

£834 - £2167 / week

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from £120 / night

1 / 20

Villa Bandini - Val d'Orcia villa sleeps 8

Montalcino / Val d'Orcia

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 95 km; Swimming pool; Great for children of all ages ;
Villa Bandini is located only 300 meters from the hamlet of Lucignano d’Asso on top of a hill on the border between the Val d’Orcia and the Sienese clay hills. Lucignano d’Asso is a medieval ancient hamlet which, since the XV century, has belonged to the Piccolomi  …see more

from £321 / night

£2246 - £4288 / week

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from £321 / night

1 / 18

BELLAVALLE - Siena villa sleeps 10

Province of Siena / Siena

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
An eighteenth century Tuscan farmhouse in a delightful little valley along the historic Via Francigena, surrounded by 14 hectares of privately owned vines, olive trees and woods that ensure utter privacy and tranquillity – this is Bellavalle, just 3.5 kilometres from  …see more

from £822 / night

£3417 - £5750 / week

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from £822 / night

1 / 43

Villa La Casella - Cetona villa sleeps 4

Province of Siena / Cetona

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
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 £164 / night

£1148 - £2614 / week

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from £164 / night

1 / 15

DELICIOUS BEDROOMS IN FARMHOUSE IN TUSCANY

Province of Siena / Radicofani

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
We offer hospitality in two delightful double rooms, each with private bath, elegantly furnished exclusively with antique furniture. Each room is accessed directly from the garden with a separate entrance to ensure complete privacy.From the private garden and decorated  …see more

from £59 / night

£295 - £421 / week

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from £59 / night

1 / 22

Villa Baiocco - Chiusi villa sleeps 14

Province of Siena / Chiusi

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
Villa Baiocco is a typical Tuscan, historic farm house from 1700, recently converted to a prestigious holiday home - without losing its unique character and charm. Surrounded by 20'000m2 of well kept gardens, for your private use only, it offers all the peace and t  …see more

from £238 / night

£1667 - £3750 / week

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from £238 / night

(1) Excellent 

1 / 24

I Cipressi - San Gimignano cottage sleeps 7

Province of Siena / San Gimignano

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Nearest beach 97 km; Swimming pool; Great for children of all ages ;
A charming villa set in a cypress-tree-lined garden with a lovely pool at just 4 km from the historic town of San Gimignano famous for its medieval towers, historical sights and craft shops, as well as having an excellent selection of restaurants and local amenities. T  …see more

from £120 / night

£792 - £2125 / week

Enquire Enquire View

from £120 / night

(1) Very Good 

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Province of Siena / San Gimignano

7 bedroomsSleeps 10Min stay varies

  • 7 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Not suitable for children; No pets allowed;
 …see more

from £242 / night

£1584 - £2250 / week

Book Book View

from £242 / night

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