Short city breaks Province of Siena

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  • Italy
  • Tuscany
  • Province of Siena
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  • Abbadia San Salvatore (1)
  • Asciano (22)
  • Bagni di San Filippo (1)
  • Bagno Vignoni (3)
  • Buonconvento (1)
  • Casciano (1)
  • Casole d'Elsa (32)
  • Castellina In Chianti (16)
  • Castelmuzio (1)
  • Castelnuovo Berardenga (13)
  • Castiglione D'Orcia (7)
  • Cetona (10)
  • Chianciano Terme (5)
  • Chiusdino (7)
  • Chiusi (4)
  • Colle di Val d'Elsa (17)
  • Gaiole in Chianti (12)
  • Montalcino (8)
  • Montepulciano (44)
  • Monteriggioni (18)
  • Monteroni d'Arbia (5)
  • Monticiano (6)
  • Montisi (6)
  • Murlo (5)
  • Palazzone (6)
  • Pienza (22)
  • Pievescola (3)
  • Poggibonsi (21)
  • Radda in Chianti (6)
  • Radicofani (19)
  • Radicondoli (22)
  • Rapolano Terme (17)
  • Rocca d'Orcia (2)
  • San Casciano dei Bagni (9)
  • San Gimignano (50)
  • San Giovanni d'Asso (5)
  • San Quirico d'Orcia (2)
  • Sarteano (7)
  • Siena (110)
  • Sinalunga (8)
  • Sovicille (24)
  • Torrita di Siena (4)
  • Trequanda (2)
  • Vivo d'Orcia (1)

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585 Holiday homes

Filters applied: City breaks (585)

(3) Excellent 

1 / 43

Podere La Casina - Radicondoli villa sleeps 6

Province of Siena / Radicondoli

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 65 km; Child friendly ; Car essential;
The old country villa is composed by a large sitting-room with a huge traditional fireplace and a big sofa, a dining-room provided with a big table for 8 people, two double bedrooms, each with its own private bathroom, a studio with two single beds, a kitchen with store  …see more

from £171 / night

£1026 / week

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from £171 / night

1 / 20

Province of Siena / Gaiole in Chianti

3 5 7 nights min stay

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

from £80 / night

£556 / week

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from £80 / night

1 / 7

Province of Siena / Colle di Val d'Elsa

1 20 Min stay varies

  • 1 bedroom
  • Sleeps 20
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £103 / night

£718 / week

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from £103 / night

Featured properties

1 / 12

Province of Siena / Poggibonsi

1 4 1 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Swimming pool; Suitable for children age 5+; Pet friendly;
 …see more

from £50 / night

£342 - £556 / week

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from £50 / 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 £86 / night

£342 - £607 / week

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from £86 / night

1 / 12

Asciano / Crete Senesi

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 60 km; Child friendly ; Car essential;
 …see more

from £60 / night

£419 / week

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from £60 / night

1 / 5

Province of Siena / Colle di Val d'Elsa

1 2 2 nights min stay

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

from £25 / night

£171 / week

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from £25 / night

1 / 36

Radicofani / Contignano

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; Pet friendly;
 …see more

from £60 / night

£428 - £513 / week

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from £60 / 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 £56 / night

£342 - £744 / week

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from £56 / night

(7) Very Good 

1 / 6

Montepulciano / Valiano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Not suitable for children; Car essential;
 …see more

from £43 / night

£300 / week

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from £43 / night

(1) Excellent 

1 / 28

Il Fienile - Torri barn sleeps 4

Sovicille / Torri

1 4 5 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 5 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
This lovely acommodation for two is in a converted barn just a few meters distant from the main farmhouse. It has two entrances from its spaciuous tiled terrace from where there are great views down the river Arno valley and to the florentine's hills. The terrace i  …see more

from £52 / night

£428 - £548 / week

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from £52 / night

(3) Excellent 

1 / 16

Province of Siena / Casole d'Elsa

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 80 km; Child friendly ; Car advised;
 …see more

from £39 / night

£270 / week

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from £39 / night

1 / 20

Fattoria La Palazzina - Radicofani villa sleeps 22

Province of Siena / Radicofani

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
La Palazzina is a hunting lodge that was built in the second half of the 18th century. It is set on a hill at a height of 580 metres and surrounded by holm oak and cypress trees. Today, the Palazzina is a refined residence, furnished as a private home open to friends a  …see more

from £43 / night

£257 - £4103 / week

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from £43 / night

1 / 14

Province of Siena / Pienza

1 2 2 nights min stay

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

from £60 / night

£300 / week

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from £60 / 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 £86 / night

£300 / week

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from £86 / night

(6) Excellent 

1 / 27

Bright and Spacious Apartment in the heart of town - San Gimignano apartment sleeps 5

Province of Siena / San Gimignano

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Child friendly ; Ask about pets;
Holiday in San Gimignano ... a journey into the heart of Tuscany.Dear Guests, we are the sisters Stefania and Margherita and we are the owners of Appartamento Margherita. We decided to rent the apartment where we were born about 15 years ago, when we understood that it  …see more

from £86 / night

£513 / week

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from £86 / night

1 / 24

Montalcino / Val d'Orcia

1 4 1 night min stay

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

from £171 / night

£1197 / week

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from £171 / night

1 / 14

Province of Siena / Pievescola

1 3 2 nights min stay

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

from £60 / night

£385 / week

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from £60 / night

(1) Excellent 

1 / 13

Holiday cottage in Asciano - Crete Senesi cottage sleeps 2

Asciano / Crete Senesi

1 2 7 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
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 £104 / night

£727 / week

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from £104 / night

1 / 12

Villetta Bruco - Asciano villa sleeps 6

Province of Siena / Asciano

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 90 km; Swimming pool;
This large, 124 square metre, two-floor independent small villa has been created by connecting the old priest's accommodation with the coach-house.The ground floor is subdivided by an arch in the living room with fireplace and kitchen/dining room. On the ground flo  …see more

from £206 / night

£1453 - £1881 / week

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from £206 / night

1 / 24

Province of Siena / Castiglione D'Orcia

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Child friendly ; Car essential; Ask about pets;
 …see more

from £411 / night

£2462 / week

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from £411 / night

(1) Excellent 

1 / 12

Pienza / Monticchiello

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £77 / night

£428 / week

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from £77 / night

(18) Excellent 

1 / 24

The Beautiful Sun Apartment - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Nearest beach 170 km; Child friendly ; Car not necessary;
This spacious and modern apartment (140sq.mt.) offers a pleasant, shining, fresh and convenient permanence in the core of Tuscany. It has two large bed rooms (25 sq.mt.), two large living rooms whose one with a new and fully equipped kitchen (dish washer machine include  …see more

from £102 / night

£598 - £1042 / week

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from £102 / night

(10) Excellent 

1 / 24

Romantic Tuscan cottage, sleeps four, total priva - Casole d'Elsa cottage sleeps 6

Province of Siena / Casole d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
Casa Daniela' is a well farm into a romantic country cottage. The house ( Total independent ) - in the surroundings of Casole d'Elsa, a medieval village with Etruscan origins – is located on a hill surrounded by a large olive grove and a pretty garden. Inside the ma  …see more

from £116 / night

£684 - £983 / week

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from £116 / night

1 / 40

Province of Siena / Castelnuovo Berardenga

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Child friendly ; Car essential; Pet friendly;
 …see more

from £43 / night

£300 / week

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from £43 / night

(1) Excellent 

1 / 12

Pienza / Monticchiello

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £77 / night

£428 / week

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from £77 / 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 £39 / night

£479 - £1347 / week

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from £39 / night

1 / 18

La Guardiola - Crete Senesi cottage sleeps 4

Asciano / Crete Senesi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 50 km; Child friendly ; Car advised;
The cosy cottage "La Guardiola" was once the house of the castle's guardian. It is now a 2 bedroom stone house which can accommodate up to 4 guests. The cottage has been completely restored and consists of 5 rooms: 2 bedrooms, a comfortable sitting room  …see more

from £163 / night

£624 / week

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from £163 / night

1 / 22

Province of Siena / Siena

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Not suitable for children;
 …see more

from £85 / night

£593 / week

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from £85 / 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

£287 - £415 / week

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from £48 / night

1 / 12

private room for a family holiday - Siena private room sleeps 3

Province of Siena / Siena

1 3 2 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Nearest beach 75 km; Child friendly ; Car not necessary;
The apartment is very large, equipped with all comforts and a private garden, is situated in the North of Siena, just minutes from downtown and the famous Sienese countryside. In the home there is only the owning family that offers a large and comfortable double room wi  …see more

from £56 / night

£334 / week

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from £56 / night

1 / 12

Province of Siena / Radicofani

2 3 1 night min stay

  • 2 bedrooms
  • Sleeps 3
  • 1 night min stay
Key info: Child friendly ; Air conditioning; Pet friendly;
 …see more

from £52 / night

£300 / week

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from £52 / night

1 / 21

Gaiole in Chianti / Lecchi

1 5 1 night min stay

  • 1 bedroom
  • Sleeps 5
  • 1 night min stay
Key info: Child friendly ; No pets allowed;
 …see more

from £60 / night

£385 - £654 / week

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from £60 / night

1 / 13

Province of Siena / San Gimignano

1 2 Min stay varies

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

from £60 / night

£419 / week

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from £60 / night

1 / 83

il Molinaccio Montepulciano 3 - Montepulciano farmhouse sleeps 6

Province of Siena / Montepulciano

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 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 £257 / night

£1496 / week

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from £257 / night

1 / 22

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
 …see more

Pricing unknown

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Pricing unknown

1 / 24

Poggibonsi / Staggia Senese

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
Key info: Child friendly ; Car advised; Ask about pets;
 …see more

from £28 / night

£171 - £283 / week

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from £28 / night

1 / 23

Tuscan villa in 1000 year old church - Casciano di Murlo villa sleeps 12

Murlo / Casciano di Murlo

5 12 7 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
This impressive villa is the perfect for you if you would like to explore Tuscany's culture and atmosphere. It is surrounded by impressive serene views of woods and vineyards that stretch as far as the eye can see.*** Please note that from the 27th of June to the 4  …see more

from £252 / night

£1761 / week

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from £252 / night

(2) Excellent 

1 / 18

Province of Siena / Gaiole in Chianti

2 2 7 nights min stay

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Pet friendly;
 …see more

from £77 / night

£539 / week

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from £77 / night

1 / 11

Province of Siena / Siena

1 4 2 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 70 km; Child friendly ; Car essential;
 …see more

from £112 / night

£642 / week

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from £112 / night

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