Province of Siena apartment or villa with a private pool area

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991 Holiday homes

Filters applied: Private pool (991)

1 / 24

I5.167 - Villa with pool i... - Vagliagli villa sleeps 6

Castelnuovo Berardenga / Vagliagli

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 0 km; Swimming pool; Child friendly ;
Lovely house in the heart of the Chianti area, just 15 km from Siena. Situated in peaceful position, even though a secondary road passes 50 m away. The property is partly closed and the swimming pool, just below the house ground, has a lovely view over the valley and th  …see more

from £185 / night

£1294 - £2088 / week

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from £185 / 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 £147 / night

£1027 - £2600 / week

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from £147 / night

(1) Excellent 

1 / 20

Podere le Monache 1 - San Gimignano farmhouse sleeps 4

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • 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 £57 / night

£345 - £750 / week

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from £57 / night

Featured properties

(55) Excellent 

1 / 52

Incredible, large Tuscan villa boasts jacuzzi, private outdoor pool, billiard room, tennis court, tripadvisor Certificate of Excellence

Province of Siena / Sinalunga

12 26 Min stay varies

  • 12 bedrooms
  • Sleeps 26
  • Min stay varies
Key info: Nearest beach 170 km; Swimming pool; Child friendly ;
Villa Scopetello is the perfect holiday home for large groups and families who wish to spend their holidays together. (Between September and May it is also possible to rent just a portion of the Villa or even one bedroom) The 1000 square meter large Villa with 12 bedro  …see more

from £346 / night

£2419 - £7827 / week

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from £346 / 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

(5) Excellent 

1 / 20

Secluded villa with private pool Chianciano Terme

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 £218 / night

£1305 - £2305 / week

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from £218 / 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 £783 / night

£5479 / week

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from £783 / night

1 / 20

Villa delle Crete - Rapolano Terme villa sleeps 24

Province of Siena / Rapolano Terme

10 24 7 nights min stay

  • 10 bedrooms
  • Sleeps 24
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Name: Villa delle CreteAccommodation: VilleLocation: Rapolano TermeSleep: 24 Bedrooms: 10 Bathrooms: 10DescriptionVilla delle Crete is an amazing property that rests on the gentle and inspiring hills of Crete Senesi, near the natural thermal spa of Rapolano, in the marv  …see more

from £609 / night

£4261 / week

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from £609 / night

(15) Excellent 

1 / 23

Podere Scopicciolo - Casole d'Elsa villa sleeps 12

Province of Siena / Casole d'Elsa

7 12 7 nights min stay

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 75 km; Swimming pool; Child friendly ;
Villa Podere Scopicciolo is located about 30 miles from Florence. It is 900 ft above sea level in the heart of Tuscany surruonded by cultivated farm land and well preserved forests. It is fully immersed in the countryside enjoying peace and tranquillity, yet convenientl  …see more

from £895 / night

£6261 - £9131 / week

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from £895 / night

(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 £83 / night

£566 / week

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from £83 / night

(4) Excellent 

1 / 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
Key info: Swimming pool; Child friendly ; Car essential;
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

(2) Excellent 

1 / 40

Monticiano / Iesa Palazzo

6 9 1 night min stay

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

from £157 / night

£1044 / week

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from £157 / night

1 / 15

Lovely 3 bedroom villa in the scenic Tuscan countryside wih large private garden and swimming pool

Province of Siena / Montisi

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Villa Montisi has been restored over the last few years with all the modern facilities within a traditional tuscan villa this makes for a truly unique holiday experience.Located in the scenic Val d'Orcia region which was declared a world heritage site by UNESCO.Thr  …see more

from £150 / night

£1044 - £1953 / week

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from £150 / 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 ;
 …see more

from £70 / night

£392 / week

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from £70 / 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 £157 / night

£1096 / week

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from £157 / night

(4) Excellent 

1 / 19

Gorgeous 5 bedroom villa in Siena, Tuscany boasts

Province of Siena / Siena

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Child friendly ;
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 £156 / night

£1087 - £2166 / week

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from £156 / night

1 / 17

Province of Siena / Sinalunga

3 9 3 nights min stay

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £235 / night

£1644 / week

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from £235 / 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 £119 / night

£827 - £1914 / week

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from £119 / night

1 / 20

Province of Siena / Chiusdino

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 50 km; Swimming pool; Child friendly ;
 …see more

from £373 / night

£2609 - £3305 / week

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from £373 / night

(6) Excellent 

1 / 10

Province of Siena / Sovicille

2 5 2 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Nearest beach 72 km; Swimming pool; Child friendly ;
 …see more

from £40 / night

£487 - £2192 / week

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from £40 / night

1 / 17

Old Brick Farm (v034) - Radicofani farmhouse sleeps 8

Province of Siena / Radicofani

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
This beautifully renovated farmhouse is ideal positioned for touring the area.On the ground floor there is a living room with double sofa bed, a double room with door on to the garden, a small kitchen, a bathroom with shower. On the first floor there is another living r  …see more

from £125 / night

£870 - £1496 / week

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from £125 / 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 £342 / night

£2174 - £3914 / week

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from £342 / night

(5) Excellent 

1 / 20

Villa Reggello between Pienza and Montepulciano

Torrita di Siena / Montefollonico

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
Villa Reggello is located amidst the gently rolling Tuscan hills, between Pienza and Montepulciano, complitely surrounded by organic plantations. Careful restoration, using original period materials, has maintained the style of the farm and ensured an ancient atmosphere  …see more

from £435 / night

£2087 - £3131 / week

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from £435 / night

1 / 16

Castle Cottage (v011) - San Casciano dei Bagni cottage sleeps 6

Province of Siena / San Casciano dei Bagni

2 6 7 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 40 km; Swimming pool; Child friendly ;
The cottage is in the heart of the hamlet which is completely surrounded by ancient walls, and has a splendid view of the parish church and all the valley. It is independent and surrounded by a large garden. All the ceramics in the house were painted by the owner and ha  …see more

from £123 / night

£861 - £1105 / week

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from £123 / night

1 / 18

The Old Villa (v055) - Siena villa sleeps 7

Province of Siena / Siena

1 7 Min stay varies

  • 1 bedroom
  • Sleeps 7
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
Just 10 minutes from Siena, this fine residence has been knowingly restored by a careful and sensitive owner. It is situated on the edge of a small hamlet dominated by a medieval tower. There is a large garden with a solarium paved with terracotta. Extremely well furnis  …see more

from £207 / night

£1444 - £2044 / week

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from £207 / night

1 / 36

Charming old farmhouse with pool 10 km from Siena

Province of Siena / Sovicille

6 11 7 nights min stay

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min stay
Key info: Nearest beach 90 km; Swimming pool; Child friendly ;
Podere Rota is a charming and characteristic farmhouse (200 m2), medieval origin, which has been created from the careful restoration with bio-architecture technicians. It is very comfortable and the property has 7000 m3 green and wood around. The pool is 9,15 m long x  …see more

from £109 / night

£766 - £1705 / week

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from £109 / night

1 / 10

Province of Siena / Rapolano Terme

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

Pricing unknown

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(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 £627 / night

£4435 / week

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from £627 / night

(16) Excellent 

1 / 24

Attractive stone-built villa in extraordinary Tuscan locale, private terrace and swimming pool, incredible views, sleeps up to 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 £348 / night

£1479 - £2522 / week

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from £348 / night

1 / 20

PIERFANTINI - San Gusme villa sleeps 8

Castelnuovo Berardenga / San Gusme

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 90 km; Swimming pool; Child friendly ;
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 / 36

Villa Le Crete - Castelmuzio villa sleeps 6

Province of Siena / Castelmuzio

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
This little, two-storey, converted Tuscany farmhouse has been meticulously restored in a simple, rustic style, employing high-quality traditional materials. Set on a gentle elevation in a remote spot, it is entirely surrounded by the clay hills called “Crete Senesi”  …see more

from £157 / night

£914 - £1305 / week

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from £157 / night

1 / 20

Torrita Di Siena - 81890001 - Torrita di Siena farmhouse sleeps 12

Province of Siena / Torrita di Siena

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Large and bright villa situated a short distance away from Torrita di Siena, a small village in the Val D’Orcia region, near the beautiful town of Montepulciano, renowned for the production of the “DOCG Nobile di Montepulciano” wine. This villas offers large outdo  …see more

from £219 / night

£1528 - £2548 / week

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from £219 / night

1 / 16

Villa Rombi - Contignano villa sleeps 18

Radicofani / Contignano

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Villa Rombi is a beautiful Tuscan property located in Contignano. The spacious villa sleeps up to 19 guests in the main house and annex. It is surrounded by breathtaking views over the Italian countryside.Villa Rombi has been beautiful decorated with a relaxed modern Tu  …see more

from £2813 / night

£11250 / week

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from £2813 / night

1 / 22

la lodola - Crete Senesi apartment sleeps 4

Asciano / Crete Senesi

1 4 1 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
In Lodola the guest enjoys reserve, relax and comfort, plunging into an absolutely bucolic environment. The oval swimming-pool with its wide sun- parlour is situated in the big surrounding park, where there is also a wide path for jogging and walking.The farmhouse is  …see more

from £105 / night

£731 / week

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from £105 / night

(6) Very Good 

1 / 25

Virgilius - Radicondoli villa 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 ;
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 £63 / night

£435 - £1740 / week

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from £63 / night

1 / 24

Province of Siena / Murlo

4 10 Min stay varies

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

from £157 / night

£1348 / week

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from £157 / night

1 / 4

Apartment Il Vino - San Fabiano apartment sleeps 5

Monteroni d'Arbia / San Fabiano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Large apartment at the ground floor of the villa.Vaulted ceilings, large rooms, all comforts. Large master bedroom om with king size bed, living room with two beds, large dining and cooking room, bathroom with shower.The area is famous for the Dante Alighieri Divina Com  …see more

from £131 / night

£696 - £1044 / week

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from £131 / 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 £182 / night

£1270 - £1966 / week

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from £182 / night

1 / 20

Montefollonico - 65998001 - Pienza farmhouse sleeps 10

Province of Siena / Pienza

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
Large Tuscan farmhouse dating back to the 15trh century built on the ruins of an ancient convent of the year 1200. This property with a charming inner courtyard, is situated in quiet and panoramic location on a large 100-hectare estate producing olive oil and wine. Thi  …see more

from £431 / night

£2516 - £3444 / week

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from £431 / 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 £622 / night

£4348 / week

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from £622 / night

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