Holiday rentals in Province of Siena: Villas, Cottages and Apartments

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4,113 Holiday homes

15

Province of Siena / Murlo

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £35 / night

£173 - £216 / week

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from £35 / night

(1) Excellent 

18

Province of Siena / Siena

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Air conditioning

 …see more

from £78 / night

£475 - £656 / week

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from £78 / night

15

Podere Costarella Apartment Pergola - Radicondoli apartment sleeps 4

Province of Siena / Radicondoli

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Podere Costarella is a farmhouse in the heart of the Tuscan countryside , specifically in Radicondoli .Located in the Chianti area, the farmhouse has four apartments surrounded by nature, a swimming pool and a restaurant serving traditional Tuscan specialty. "Pergo  …see more

from £95 / night

£621 - £739 / week

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from £95 / night

(7) Excellent 

16

OCABIANCA - Casole d'Elsa villa sleeps 4

Province of Siena / Casole d'Elsa

4 4 3 nights min

  • 4 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Lovely independent house with garden, newly built and furnished with care, the Casina dell'Oca Bianca is surrounded by woods and situated on a private road at the edge of the tiny - no more than ten houses - and peaceful hamlet of Marmoraia with its beautiful XII c  …see more

from £69 / night

£483 / week

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from £69 / night

(2) Excellent 

35

Province of Siena / Siena

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £70 / night

£483 - £1087 / week

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from £70 / night

20

Villa Bandini - Val d'Orcia villa sleeps 8

Montalcino / Val d'Orcia

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
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 £332 / night

£2324 - £4013 / week

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from £332 / night

(3) Excellent 

24

Province of Siena / Castiglione D'Orcia

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
  • Pet friendly

 …see more

from £47 / night

£328 - £488 / week

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from £47 / night

25

Province of Siena / San Gimignano

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £74 / night

£449 - £670 / week

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from £74 / night

(3) Excellent 

18

Suite d'Artista: Basilè - Montalcino studio sleeps 2

Province of Siena / Montalcino

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Suite d'Artista is a perfect place to enjoy a relaxing holiday combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. Nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming p  …see more

from £113 / night

£746 / week

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from £113 / night

18

BELLAVALLE - Siena villa sleeps 10

Province of Siena / Siena

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • 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 £850 / night

£3535 - £5949 / week

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from £850 / night

15

Province of Siena / Siena

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from £61 / night

£776 - £1199 / week

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from £61 / night

(1) Excellent 

39

Live Beautifully Five Minutes From Siena - Siena apartment sleeps 5

Province of Siena / Siena

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
Maison CostalpinoThe Maison Costalpino is a fully renovated historical residence 5 minutes driving from Siena city center in the tiny charming village of Costalpino. The Maison has an interesting, colourful history going back over two centuries. During the 19th century  …see more

from £87 / night

£561 / week

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from £87 / night

47

Province of Siena / San Gimignano

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 50 km
  • Child friendly
  • Private garden

 …see more

from £60 / night

£337 / week

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from £60 / night

(2) Excellent 

21

La Casa sulle Mura - Radicondoli guest house sleeps 5

Province of Siena / Radicondoli

3 5 4 nights min

  • 3 bedrooms
  • Sleeps 5
  • 4 nights min
  • Nearest beach 60 km
  • Suitable for children age 5+
  • Ask about pets
A spacious thirteenth century town house built right on the walls of the historic centre of Radicondoli. Here you will be strategically placed on the edge of the village with stunning views at all three levels. On the ground floor you enter a large authentic Tuscan kitc  …see more

from £138 / night

£690 / week

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from £138 / night

(2) Excellent 

31

Tuscan style apartment - Cetona apartment sleeps 4

Province of Siena / Cetona

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Child friendly
Nestled in the heart of the quaint medieval town of Cetona is the gem "Lacittadella", a two bedroom apartment in a 16th century, fully restored family home. The private, quiet apartment features beamed ceilings, antique furnishings, open fireplace, views of  …see more

from £52 / night

£345 / week

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from £52 / 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 £307 / night

£2147 / week

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from £307 / night

(1) Excellent 

24

Villa Maura - Cetona farmhouse sleeps 10

Province of Siena / Cetona

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Private garden
This characteristic farmhouse is located close to Cetona, a little village in the Siena countryside, close to the San Casciano and Chianciano baths. It is developed in three levels and can host up to 10 people. It comprises a large and comfortable living room with dinin  …see more

from £130 / night

£906 - £1449 / week

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from £130 / night

(8) Excellent 

31

Close to the historic Tuscan town of Radicondoli, - Belforte farmhouse sleeps 6

Radicondoli / Belforte

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Just 12 km from the historic town of Radicondoli, La Boscaglia is the perfect place to experience the beautiful Tuscan countryside hidden in the hills above Siena.La Boscaglia farmhouse is divided into 5 separate spacious self catering apartments with their very own kit  …see more

from £104 / night

£725 / week

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from £104 / night

(1) Excellent 

13

Holiday cottage in Asciano - Crete Senesi cottage sleeps 2

Asciano / Crete Senesi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
Featuring an outdoor pool and a garden with views of the Tuscan countryside, Agriturismo Podernuovo offers rustic-style accommodation outside Asciano. The property produces olive oil and honey and organizes dinner on request.The cottage I MANDORLI was an ancient hayloft  …see more

from £82 / night

£682 - £733 / week

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from £82 / 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

£388 - £500 / week

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from £61 / night

16

NIDO apartment - Monticiano apartment sleeps 2

Province of Siena / Monticiano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Cozy 02 people first floor34 sq.mt. apartment in Tuscan villa. Authentic interiors with terracotta floors and chestnut wood beamed ceilings. Double bed. Bathroom with shower. Designer ceiling fan for summer cooling. Essential food facilities: 2-ring gas hob, extracto  …see more

from £102 / night

£712 - £733 / week

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from £102 / 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 £62 / night

£432 - £1294 / week

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from £62 / 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 £392 / night

£2742 - £3595 / week

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from £392 / night

(1) Excellent 

19

La Fonte San Gimignano, Prov. Siena - San Gimignano apartment sleeps 2

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
Gelsomino: is one of four, very comfortable, quiet self catering apartments in a traditional Tuscan country villa. It comands fabulous views over the rolling hills, vineyards and olive groves. It has been completely refurbished yet retains all the original features  …see more

from £103 / night

£719 - £960 / week

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from £103 / night

39

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £115 / night

£802 - £962 / week

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from £115 / night

15

Province of Siena / Pienza

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £207 / night

£707 - £1035 / week

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from £207 / night

14

Province of Siena / Montepulciano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £65 / night

£432 - £509 / week

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from £65 / night

(2) Very Good 

27

San Donato - San Gusme villa sleeps 4

Castelnuovo Berardenga / San Gusme

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Private garden
San Donato is an exquisite gem set in rolling Chianti vineyards with views that stretch 360 degrees past a nearby 13th century hill town to Siena and into infinity. Part of the original estate of Villa Arceno, San Donato has a history that goes back many 100's of years  …see more

from £184 / night

£1285 - £1716 / week

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from £184 / night

24

Orcia Valley country house - Castiglione D'Orcia villa sleeps 21

Province of Siena / Castiglione D'Orcia

8 21 Min stay varies

  • 8 bedrooms
  • Sleeps 21
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful holiday home in the Val d'Orcia, surrounded by gently rolling hills, is near Castiglione d'Orcia (12km), just a few kilometres from the famous spa waters at Bagno Vignoni (10km) and Bagni San Filippo (7km). Surrounded by peace and quiet this lovely farmho  …see more

from £432 / night

£1638 - £3595 / week

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from £432 / night

24

Villa La Strega luxury 6 bedroom villa in Tuscany - Siena villa sleeps 11

Province of Siena / Siena

6 11 Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
This is a stunning eighteenth century villa situated on a hill just 2 kilometres from Siena and enjoying stunning views of the city. With a lovely terrace and informal private outdoor pool overlooking Siena, it's a great setting to enjoy a holiday with family and friend  …see more

from £370 / night

£2587 - £3880 / week

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from £370 / night

100

Emma - Olivo - Bagno Vignoni apartment sleeps 6

Province of Siena / Bagno Vignoni

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Olivo apartment is situated on the first floor of this lovely farmhouse. It is decorated in a delightful, traditional style with pretty floral fabrics and sunny colours to make you feel welcome. The original wooden beams and terracotta tiled flooring have also been kept  …see more

from £104 / night

£604 - £845 / week

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from £104 / night

27

Casa Rosanna - Radicondoli house sleeps 8

Province of Siena / Radicondoli

3 8 7 nights min

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

from £87 / night

£604 - £970 / week

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from £87 / night

27

La Pieve Marsina - Gaiole in Chianti villa sleeps 5

Province of Siena / Gaiole in Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
In the top of a hill set in the patchwork of vineyards that characterizes the area of Chianti Classico, in the heart of an ancient medieval village, was born a few years ago Pieve Marsina.The structure, made up of nice apartments, has as principal objective to allow our  …see more

from £104 / night

£815 - £1147 / week

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from £104 / night

(4) Very Good 

12

Sienahomeandsailing-Red apartment - Siena apartment sleeps 5

Province of Siena / Siena

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Red apartment consists of a living room with sofa bed for two guests, a fully equipped kitchenette, bedroom with a double bed, a single bed, bathroom with shower, toilet, hairdryer, washing machine/tumble dryer. WI FI sat TV in each room, heating/air conditioning,  …see more

from £43 / night

£296 / week

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from £43 / night

100

Emma - Corbezzolo - Bagno Vignoni apartment sleeps 8

Province of Siena / Bagno Vignoni

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
This large apartment on the ground floor of the barn consists of three en suite double bedrooms, two of which have private bathrooms with both showers and hydro-massage bathtubs. It is a real fairy-tale apartment with its light and spacious rooms, draping fabrics, prett  …see more

from £199 / night

£1268 - £1690 / week

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from £199 / night

25

Holiday lodging near Pienza D - Torrita di Siena apartment sleeps 4

Province of Siena / Torrita di Siena

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
This lovely country house with pool in Tuscany is located at 1.5km from the beautiful medieval village of Torrita di Siena, in the heart of Val di Chiana, only 15 km from Pienza and Montepulciano, and 48 km from Siena. Situated on a knoll, the 18th-century farmhouse is  …see more

from £42 / night

£294 - £587 / week

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from £42 / night

11

Ground floor apartment for 2 in Tuscan countryside - San Rocco a Pilli apartment sleeps 2

Sovicille / San Rocco a Pilli

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
Our Holiday Home is located in an old farmhouse surrounded by nature, just 8 kilometers from the center of the beautiful city of Siena. After 10 years of renovation we are proud to offer you a unique stay in a special setting which preserve the structural, architectural  …see more

from £104 / night

£725 / week

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from £104 / night

24

Province of Siena / Pienza

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly

 …see more

from £302 / night

£1811 - £2699 / week

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from £302 / night

44

Province of Siena / Monticiano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly

 …see more

from £61 / night

£414 - £475 / week

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from £61 / night

(5) Excellent 

16

PODERE SAN PIETRO - Montepulciano farmhouse sleeps 10

Province of Siena / Montepulciano

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Podere san Pietro is an ancient country house held in brick and stones with a living surface of 350 sqm. for a total of 3bathroom and 4 bedrooms, which accommodate up to 10 people , in addition to private swimming pool of 11X5 mt The house has been recently restored (20  …see more

from £173 / night

£1207 - £1544 / week

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from £173 / night

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