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

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2,448 Holiday homes

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 / 14

Apartment pantera - Colle di Val d'Elsa farmhouse sleeps 5

Province of Siena / Colle di Val d'Elsa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 75 km; Swimming pool; Child friendly ;
The apartment, about 55 sqm., Is located on the ground floor, slightly detached from the property and has been obtained from the barn.Is consists of living room with sofa bed, dining table and fireplace, a bathroom with shower, a double bedroom, a bedroom with 2 single  …see more

from £72 / night

£428 - £744 / week

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from £72 / night

1 / 5

Province of Siena / Sovicille

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £60 / night

£300 / week

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from £60 / night

Featured properties

1 / 4

villa giulia - Monteriggioni farmhouse sleeps 2

Province of Siena / Monteriggioni

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
The propertyis a twelth century farmhouse, situated in the heart of Tuscany only 2km from the walled town monteriggioni. and surrounded by the siennese hills. The property is 500 meters above sea level surrounded by olive groves and magnificent woodlands,Peaceful wood  …see more

from £92 / night

£642 / week

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from £92 / night

1 / 7

Lovely countryside Podere San Luigi Apt Tramonto - Pancole farmhouse sleeps 2

San Gimignano / Pancole

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
You can enjoy a relaxing holiday in the center of Tuscany surrounded by nature and the countryside. Very close to San Gimignano, on the "VIA FRANCIGENA", the casale is the starting point for visiting the important Tuscan cities of Art, villages, and the famous  …see more

from £53 / night

£342 / week

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from £53 / 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 / 21

Suite d'Artista: Botto & Bruno - Montalcino apartment sleeps 4

Province of Siena / Montalcino

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
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 £171 / night

£1197 / week

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from £171 / night

1 / 6

Province of Siena / Pienza

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £60 / night

£257 / week

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from £60 / night

(2) Excellent 

1 / 19

Province of Siena / Sovicille

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £48 / night

£274 - £359 / week

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from £48 / night

1 / 4

Magica Toscana immersed in nature in Chianti - Siena b&b sleeps 4

Province of Siena / Siena

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; No pets allowed; Private garden;
In the heart of Tuscany, in the silence of nature among woods and vineyards of the Chianti region, in a dominant position and sunny, sunsets and beautiful landscapes, possibility 'of trekking on foot and horseback tours.The rooms are equipped with a double bed or  …see more

from £65 / night

£449 / week

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from £65 / night

1 / 15

Podernovo Apartment With Pool - San Casciano dei Bagni apartment sleeps 6

Province of Siena / San Casciano dei Bagni

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Agriturismo Podernovo is a beautiful, peaceful and magical Villa amidst 200 hectares of private space nestled on a small hillock in San Casciano dei Bagni's surroundings.The villa is divided into two completely independent apartments that can accommodate over 10 pe  …see more

Pricing unknown

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1 / 20

CAMINO apartment - Monticiano apartment sleeps 2

Province of Siena / Monticiano

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
Romantic and charming 02 people 50 sq.mt first floor apartment in traditional Tuscan villa. Authentic interiors with terracotta floors and chestnut wood beamed ceilings. Double bed. En suite bathroom with shower. Designer ceiling fan for summer cooling. Essential foo  …see more

from £110 / night

£761 - £787 / week

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from £110 / night

1 / 6

Province of Siena / Chianciano Terme

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Child friendly ; Air conditioning; Ask about pets;
 …see more

from £31 / night

£214 / week

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from £31 / night

1 / 10

Province of Siena / Radicofani

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Pet friendly;
 …see more

Pricing unknown

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Pricing unknown

1 / 11

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Car advised;
 …see more

Pricing unknown

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Pricing unknown

1 / 8

Siena / Taverne d'Arbia

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £52 / night

£359 / week

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from £52 / night

1 / 18

galassia 18 - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 3 2 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Not suitable for children;
appartamento, 2 - 3 persone, 2 vano/vani, 1 camera/e da letto, 1 bagno/bagni, ca. 44 m², 1 piano/piani, alloggio al piano terra. Accesso all'alloggio indipendente.TerrenoPorzione privata del terreno, giardino, lastre.Parcheggio: 1 x posto macchina in garage sotter  …see more

from £68 / night

£342 / week

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from £68 / night

(1) Excellent 

1 / 22

Villa Amedeo - Giotto - Val di Merse apartment sleeps 2

Siena / Val di Merse

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 70 km; Child friendly ;
The antique spaces of the apartment have been reinvigorated, made more comfortable and personalized whilst using traditional local materials, rough stone, terracotta, wrought iron, wood.Giotto is one of six complete and elegant, well-appointed apartments, complete with  …see more

from £60 / night

£385 - £471 / week

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from £60 / night

1 / 10

Province of Siena / Sinalunga

5 10 1 night min stay

  • 5 bedrooms
  • Sleeps 10
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £257 / night

£1795 / week

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from £257 / night

1 / 14

Province of Siena / Pievescola

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Suitable for children age 5+;
 …see more

from £60 / night

£385 - £471 / week

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from £60 / night

(3) Excellent 

1 / 25

Province of Siena / Vivo d'Orcia

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 70 km; Ski; Child friendly ;
 …see more

from £60 / night

£385 / week

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from £60 / night

(3) Excellent 

1 / 13

Poggibonsi / Staggia Senese

2 3 1 night min stay

  • 2 bedrooms
  • Sleeps 3
  • 1 night min stay
Key info: Nearest beach 74 km; Child friendly ; Car advised;
 …see more

from £60 / night

£402 / week

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from £60 / night

1 / 100

Emma - Laghetto - Bagno Vignoni apartment sleeps 4

Province of Siena / Bagno Vignoni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
On the first floor of the barns can be found Laghetto apartment. This apartment includes one double bedroom and a double sofa bed and therefore can accommodate up to four guests. It has a very fresh feel with light rooms and neutral colours. A four-poster bed with drapi  …see more

from £69 / night

£419 - £599 / week

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from £69 / night

(2) Very Good 

1 / 26

Il Portico - Torri farmhouse sleeps 5

Sovicille / Torri

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
Apartment Il Portico is at the ground floor of the main building and can host 4 people (or five in the double sofa bed that is in the living room). As you enter the front door you have a sejour that leads you to a spacious and well equipped kitchen with large semicircu  …see more

from £77 / night

£513 - £642 / week

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from £77 / night

(1) Very Good 

1 / 17

Province of Siena / Sovicille

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Car essential; Ask about pets;
 …see more

from £52 / night

£325 / week

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from £52 / night

(22) Excellent 

1 / 19

Casa Parva - Montisi apartment sleeps 4

Province of Siena / Montisi

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Suitable for children age 5+; No pets allowed;
A one-bedroom romantic apartment in a charming Medieval village in Tuscany. The village is off the beaten track and yet very close to the world known countryside of Tuscany and its most important art cities and wine districts. Pienza and Montepulciano are only 20 minute  …see more

from £120 / night

£770 / week

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from £120 / night

(1) Excellent 

1 / 21

Province of Siena / Abbadia San Salvatore

8 12 Min stay varies

  • 8 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Suitable for children age 5+; Car essential; Pet friendly;
 …see more

from £257 / night

£1539 - £1881 / week

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from £257 / night

1 / 6

Castelnuovo Berardenga / San Gusme

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

Pricing unknown

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Pricing unknown

1 / 10

Province of Siena / Colle di Val d'Elsa

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Ask owner if suitable for children; No pets allowed;
 …see more

from £39 / night

£270 / week

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from £39 / night

1 / 20

Cypress Manor (V037) - Sarteano manor house sleeps 18

Province of Siena / Sarteano

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
Beautifully renovated and furnished, luxury manor house with air conditioning in each room, underfloor heating, large paved stone patio that surrounds the whole house with pergola to eat outside and a laundry room. The house is divided as follows:.On the ground floor fo  …see more

from £1020 / night

£7137 - £14060 / week

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from £1020 / night

1 / 12

Province of Siena / Montalcino

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £103 / night

£684 / week

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from £103 / night

1 / 15

Holiday cottage near Siena - Sinalunga cottage sleeps 4

Province of Siena / Sinalunga

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Car advised; Air conditioning;
This one-bedroom cottage is the perfect location for those who want to have a place to rest after a busy day spent exploring Tuscany.It consists of a living room, a double bedroom, a fully equipped kitchen with fireplace and a bathroom.The kitchen leads to a small court  …see more

from £70 / night

£400 / week

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from £70 / night

1 / 14

villa in the heart of Tuscany - Montisi villa sleeps 14

Province of Siena / Montisi

6 14 4 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 4 nights min stay
Key info: Child friendly ; Ask about pets; Private garden;
Poggio is a typical Tuscan villa of the 17th century, built entirely of stone, situated 3 km from the medieval village of Montisi and plunged the unmistakable landscape of the Crete Senesi. Its dominating position overlooks the area from Montalcino, Trequanda until Sien  …see more

from £471 / night

£1710 - £2479 / week

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from £471 / 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 / 8

Province of Siena / Siena

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £114 / night

£796 / week

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from £114 / night

1 / 4

Ortensia - Radda in Chianti apartment sleeps 4

Province of Siena / Radda in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Suitable for children age 5+; Air conditioning; Ask about pets;
Resort Olmo is situated in the historical heart of Tuscany and Chianti, halfway between Siena and Firenze.It is situated in a picturesque village called “Borgo di Campomaggio", which dates back to 1700. After some years of careful restoring works, that kept una  …see more

from £129 / night

£898 - £1077 / week

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from £129 / night

(3) Excellent 

1 / 31

Stunning views at Siena's doorstep - Free WiFi - Costalpino villa sleeps 6

Siena / Costalpino

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Child friendly ; Car advised; No pets allowed;
This beautifully renovated rustic villa is only 10 minutes' drive from the heart of Siena. Built in the 1500's, Belvedere (beautiful view) is situated on a remote hilltop with breathtaking views of the Tuscan countryside with vineyards and olive trees in the i  …see more

from £213 / night

£1368 - £1539 / week

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from £213 / night

1 / 20

Podere la Marronaia Blue 2p - San Gimignano farmhouse sleeps 2

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Podere la Marronaia is a small and welcoming farmhouse situated on a small hill among vineyards and olive groves, close to the historical centre of San Gimignano (2km). The central part of this historical building is the watching tower built in 1200 ad as part of the c  …see more

Pricing unknown

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1 / 20

Il Ciliegio - Belforte farmhouse sleeps 8

Radicondoli / Belforte

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
The main house 'Il Ciliegio' is a very old farm, dated around 1200, on the road which goes from Belforte to the sea. The house is exposed to the south, between the forest and the valley of the cultivated fields surrounded by tranquility and nature. We are not far from B  …see more

Pricing unknown

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(7) Excellent 

1 / 12

Province of Siena / Monteriggioni

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Ask about pets;
 …see more

from £52 / night

£342 / week

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from £52 / night

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