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

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4,227 Holiday homes

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 / 18

Province of Siena / Siena

1 4 2 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Car not necessary; Ask about pets;
 …see more

from £66 / night

£392 / week

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from £66 / night

1 / 13

SERRA - Siena apartment sleeps 4

Province of Siena / Siena

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Car advised;
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANYVilla Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city that they c  …see more

from £122 / night

£853 / week

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from £122 / night

Featured properties

1 / 11

Ground floor apartment for 2 in Tuscan countryside

Sovicille / San Rocco a Pilli

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Not suitable for children; Car essential; No pets allowed;
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 £105 / night

£731 / week

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from £105 / 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 / 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 £94 / night

£653 / week

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from £94 / 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 £74 / night

£435 - £757 / week

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from £74 / night

1 / 101

Emma - Melograno - 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 ;
Melograno apartment on the ground floor of the main farmhouse is traditional in style with high, beamed ceilings and an original stone wall, adding lots of character. It can accommodate up to four, offering one double bedroom and a double sofa bed in the living room. Th  …see more

from £70 / night

£427 - £609 / week

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from £70 / night

1 / 6

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; No pets allowed;
 …see more

from £61 / night

£383 - £670 / week

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from £61 / night

1 / 12

Montepulciano / Abbadia di Montepulciano

3 7 1 night min stay

  • 3 bedrooms
  • Sleeps 7
  • 1 night min stay
Key info: Child friendly ; Car advised; Pet friendly;
 …see more

from £53 / night

£261 / week

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from £53 / night

(3) Excellent 

1 / 26

Agriturismo Casanova di Lucignano (Rosmarino)

Province of Siena / Monteroni d'Arbia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Not suitable for children;
Casanova di Lucignano has three apartments - Rosmarino, Lavanda and Maggiorana – all containing a bedroom, bathroom and a living room with an attached kitchen. All apartments also have a fireplace and a color TV; free Wi-fi Internet access is available for guests.The  …see more

from £74 / night

£457 - £487 / week

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from £74 / night

1 / 28

Radicondoli / Belforte

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 75 km; Swimming pool; Child friendly ;
 …see more

from £117 / night

£814 - £948 / week

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from £117 / 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 £479 / night

£1740 - £2522 / week

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from £479 / night

1 / 23

Province of Siena / Sovicille

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 80 km; Ask owner if suitable for children; Car essential;
 …see more

from £87 / night

£305 / week

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from £87 / night

1 / 18

Province of Siena / Castelmuzio

2 6 3 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Child friendly ; Car advised; Ask about pets;
 …see more

from £70 / night

£435 - £705 / week

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from £70 / night

(21) Excellent 

1 / 60

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 90 km; Child friendly ; Car essential;
 …see more

from £48 / night

£292 - £422 / week

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from £48 / night

1 / 18

APARTMENT FIORDALISO 2603 - Colle di Val d'Elsa apartment sleeps 2

Province of Siena / Colle di Val d'Elsa

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Every apartment has its own outside space with table and chairs for outside eating (directly in front of the entrance of the apartments) and offer a fantastic panorama over the whole valley of the river Elsa. The furniture is in the typical country style used in Tuscany  …see more

from £68 / night

£476 - £635 / week

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from £68 / night

1 / 17

Province of Siena / Chiusdino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; No pets allowed;
 …see more

from £87 / night

£348 - £618 / week

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from £87 / night

1 / 24

Galileo apt on ground floor very typical

Province of Siena / Sovicille

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 80 km; Child friendly ;
Galileo Surface: 102 M2Located on the ground floor it has an independent entrance on the secondary patio but is also connected with the central courtyard through a large kitchen/dining area. VIRTUAL VISITThe living has been organized inside the old cellar with preserved  …see more

from £83 / night

£566 - £696 / week

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from £83 / night

1 / 5

Province of Siena / San Quirico d'Orcia

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; No pets allowed;
 …see more

from £83 / night

£435 / week

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from £83 / night

1 / 10

LA CORTE - Monteriggioni house sleeps 4

Province of Siena / Monteriggioni

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
Perfect base for seeing Siena, Florence, San Gimignano and other Chianti towns. Borgo Stomennano is composed by 5 different accommodations that can hos a total of 34 pax. Each villa is beautifully unique, stunning decor and full of character La Corte is at the ground fl  …see more

from £153 / night

£1044 - £1392 / week

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from £153 / 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

1 / 25

Chianti, La Pruneta, Raffaello Apartment

Province of Siena / Radda in Chianti

1 4 2 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; No pets allowed; Private garden;
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. Raffaello is a beautifully restored one bedroom apartment with antique furniture, woo  …see more

from £70 / night

£479 - £722 / week

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from £70 / night

1 / 36

Province of Siena / Radicondoli

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 70 km; Child friendly ; Car advised;
 …see more

from £131 / night

£609 / week

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from £131 / night

1 / 18

APARTMENT 904 - Colle di Val d'Elsa apartment sleeps 6

Province of Siena / Colle di Val d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
Double room with a double bed, bedroom with two single beds, living room with fireplace and double sofa bed, kitchenette, bathroom. The apartment has got beautiful arches and stone walls. Heating. Ground floor.50 years ago we ran into Podere La Pieve, whose name derives  …see more

from £105 / night

£653 / week

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from £105 / night

1 / 15

Apartment 507 - Castellina In Chianti apartment sleeps 2

Province of Siena / Castellina In Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; No pets allowed;
Bed places : 2Two Rooms, 40 sqm, a kitchen and tv, a double bedroom, a bathroom with shower. The apartments are at the first floor. On the ground floor externally there are tables, chairs and umbrellas for common use. Can host one more child (max 12 years) with accommod  …see more

from £61 / night

£427 - £518 / week

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from £61 / night

(11) Excellent 

1 / 33

Pretty 2 bedroom holiday apartment in the heart of

Province of Siena / Montepulciano

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Car not necessary; Ask about pets;
CasaMontepulciano is a flat of roughly 60 sq m (646 sq ft), located in via Cagnano 9. Restored in 2011 it is has high quality finishes and exposed beams. It consists of a large living room/kitchen, two bedrooms (one of which is a master bedroom but in the other room i  …see more

from £66 / night

£348 - £576 / week

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from £66 / night

1 / 100

Castellina - middle - Castellina In Chianti apartment sleeps 5

Province of Siena / Castellina In Chianti

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
Some of the middle  size apartments are located in the old school for children of the hamlet while some others are located in the old house of the estate ranger and in the oldest building of the farm called Darios House. All middle size apartment two double bedroom  …see more

from £106 / night

£737 - £1054 / week

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from £106 / night

(5) Very Good 

1 / 23

Province of Siena / Montepulciano

1 2 Min stay varies

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

from £74 / night

£479 - £574 / week

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from £74 / night

1 / 5

Macciangrosso - Chiusi apartment sleeps 5

Province of Siena / Chiusi

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
Ancient Villa (XVI century) divided into elegant apartments of various size, immersed in the quiet of a secular italian garden, with swimmingpool and tennis court. Conveniently positioned to visit both Tuscany and Umbria. Few chilometers far from SPA centers such as San  …see more

from £140 / night

£740 / week

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from £140 / night

1 / 7

10392 - Farmhouse Graziano Sta - San Gimignano farmhouse sleeps 2

Province of Siena / San Gimignano

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Not suitable for children; Air conditioning; No pets allowed;
Farmhouse Graziano Stalla is one of 3 independent country homes located on a vast farm estate, where stately cypress trees welcome you to a captivating Tuscan experience.andnbsp;The house is at the medieval town of San Gimignano with its well-known towers, as well as a  …see more

from £166 / night

£922 / week

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from £166 / night

(1) Excellent 

1 / 20

Villa Caprera Suite Le Camelie - Caprera apartment sleeps 2

Siena / Caprera

1 2 5 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 5 nights min stay
Key info: Nearest beach 100 km; Child friendly ; Car advised;
Caprera is an elegant village in Liberty Style built at the end of 19th Century. The place has retained its original charm, still offers all modern comforts and facilities; Ideally located for visiting Siena and its countryside, the Chianti area, the 'crete senesi&  …see more

from £79 / night

£392 / week

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from £79 / night

1 / 43

Province of Siena / Vivo d'Orcia

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Ski; Child friendly ; Ask about pets;
 …see more

from £61 / night

£427 / week

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from £61 / night

(4) Excellent 

1 / 18

Province of Siena / Siena

1 2 7 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Car essential;
 …see more

from £44 / night

£305 / week

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from £44 / night

(3) Excellent 

1 / 18

Suite d'Artista: Basilè - Montalcino studio sleeps 2

Province of Siena / Montalcino

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
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 £114 / night

£753 / week

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from £114 / night

1 / 45

Province of Siena / Siena

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
Key info: Child friendly ; Ask about pets;
 …see more

Pricing unknown

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Pricing unknown

1 / 20

Province of Siena / Radda in Chianti

1 2 1 night min stay

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

from £61 / night

£348 / week

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from £61 / night

(7) Excellent 

1 / 41

Unique, charming farmhouse in Tuscany countryside with shared outdoor pool, sleeps up to 6

Province of Siena / Montepulciano

2 6 7 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 0 km; Swimming pool; Child friendly ;
The main arched entrance leads past a utility room and downstairs bathroom into the open plan kitchen and dining room with dining table for 6 guests. The lounge has two sofa's one of which is a comfortable double sofa bed There is a wood burning stove in the lounge  …see more

from £72 / night

£500 - £890 / week

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from £72 / night

(5) Excellent 

1 / 24

Province of Siena / Montepulciano

1 4 3 nights min stay

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

from £68 / night

£400 / week

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from £68 / 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

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