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 (33)
  • Castellina In Chianti (18)
  • Castelmuzio (2)
  • Castelnuovo Berardenga (12)
  • Castiglione D'Orcia (7)
  • Cetona (10)
  • Chianciano Terme (5)
  • Chiusdino (7)
  • Chiusi (4)
  • Colle di Val d'Elsa (17)
  • Gaiole in Chianti (13)
  • Montalcino (8)
  • Montepulciano (46)
  • Monteriggioni (19)
  • Monteroni d'Arbia (5)
  • Monticiano (5)
  • Montisi (6)
  • Murlo (6)
  • Palazzone (6)
  • Pienza (22)
  • Pievescola (3)
  • Poggibonsi (17)
  • Radda in Chianti (6)
  • Radicofani (18)
  • Radicondoli (24)
  • Rapolano Terme (17)
  • Rocca d'Orcia (2)
  • San Casciano dei Bagni (9)
  • San Gimignano (51)
  • San Giovanni d'Asso (5)
  • San Quirico d'Orcia (2)
  • Sarteano (7)
  • Siena (128)
  • Sinalunga (17)
  • Sovicille (25)
  • Torrita di Siena (4)
  • Trequanda (3)
  • Vivo d'Orcia (1)

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618 Holiday homes

Filters applied: City breaks (619)

(1) Excellent 

12

Sienahomeandsailing-Green apartment - Siena apartment sleeps 4

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Green apartment is located at ground floor and easily accessible, perfect for a family. It consists of a fully equipped kitchen where a folding sofa bed for two guests is provided, a bedroom with a double bed, a bathroom with shower, toilet, hairdryer, washing machin  …see more

from £39 / night

£268 / week

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from £39 / night

(11) Very Good 

45

Province of Siena / Castelnuovo Berardenga

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £69 / night

£481 / week

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from £69 / night

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

£174 - £218 / week

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from £35 / 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 £209 / night

£714 - £1044 / week

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from £209 / night

5

Province of Siena / Pienza

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £140 / night

£583 - £853 / week

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from £140 / night

(4) Excellent 

30

Live Siena from the very top - Siena apartment sleeps 4

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Car not necessary
Treat yourself with a special holiday. Admire a spectacular, unique panorama from a flat that was built not just at the heart of Siena but also on its highest spot. You will be able to see the whole of Siena and all of its surroundings up to Mount Amiata or Chianti'  …see more

from £73 / night

£409 - £628 / week

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from £73 / night

(1) Excellent 

24

Province of Siena / Colle di Val d'Elsa

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £129 / night

£783 / week

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from £129 / night

(4) Excellent 

19

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £61 / night

£366 - £487 / week

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from £61 / night

26

San Gimignano / Castel San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £44 / night

£296 - £392 / week

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from £44 / night

(1) Excellent 

11

Siena apartments - Siena apartment sleeps 3

Province of Siena / Siena

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Located on the hills of central Tuscany, at only 2 km from the walls of Siena, this charming holiday accommodation in Tuscany has been totally restored into 7 comfortable self-catering apartments with high quality furniture. All the holiday apartments have independent  …see more

from £61 / night

£383 - £479 / week

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from £61 / night

(5) Excellent 

41

Sinalunga / Rigomagno

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly

 …see more

from £70 / night

£435 / week

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from £70 / night

(5) Excellent 

24

Province of Siena / Montepulciano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly

 …see more

from £68 / night

£400 / week

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from £68 / 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 £83 / night

£687 - £740 / week

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from £83 / night

(1) Excellent 

6

Province of Siena / Castiglione D'Orcia

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Ski

 …see more

from £44 / night

£305 / week

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from £44 / night

35

Casa Oliveto - Castelmuzio villa sleeps 10

Province of Siena / Castelmuzio

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
When Eric and Kathy decided they wanted to settle in Tuscany and provide people with the sort of holidays they themselves had always dreamed of - but had rarely been able to find - they knew they had found the ideal property in Castelmuzio for many reasons, amongst whic  …see more

from £370 / night

£2587 - £4131 / week

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from £370 / night

(3) Very Good 

20

Vernianello "Riccio" - Cedda farmhouse sleeps 4

Poggibonsi / Cedda

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Agriturismo VERNIANELLO is a small farm set in the heart of the Chianti hills, surrounded by forests, vineyards and olive groves. Relax , peace and a wonderful panorama view in a pleasant and comfortable homely atmospere will give you the possibility to enjoy your ho  …see more

from £79 / night

£478 - £574 / week

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from £79 / night

5

Province of Siena / Colle di Val d'Elsa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

 …see more

from £26 / night

£174 / week

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from £26 / night

14

Province of Siena / Pievescola

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £61 / night

£392 / week

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from £61 / night

(1) Excellent 

23

Province of Siena / Siena

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £66 / night

£457 - £518 / week

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from £66 / night

(2) Very Good 

12

Podere Remignoli Apt Luna - San Gimignano farmhouse sleeps 2

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
The farm Podere Remignoli is set halfway between Florence and Siena on top of a hill overlooking the unique scenery of San Gimignano, from where you can admire the Chianti hills on the east, the Elsa valley on the north and the Montagnola Senese on the south. The farmho  …see more

from £79 / night

£522 / week

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from £79 / night

(2) Excellent 

40

Monticiano / Iesa Palazzo

6 9 1 night min

  • 6 bedrooms
  • Sleeps 9
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £157 / night

£1044 / week

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from £157 / night

(4) Excellent 

28

Apartment near San Gimignano - San Gimignano farmhouse sleeps 4

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
'Podere Collinella' has been re-built to a high standard, retaining the charm of a Tuscan farmhouse.The walls are of the old stone, chestnut beams support the ceiling, and positioned on a slight hill has wonderful views of the surrounding countryside. Podere C  …see more

from £61 / night

£314 - £427 / week

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from £61 / night

(1) Excellent 

24

Province of Siena / Sarteano

4 9 1 night min

  • 4 bedrooms
  • Sleeps 9
  • 1 night min
  • Nearest beach 120 km
  • Child friendly
  • Private garden

 …see more

from £44 / night

£305 / week

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from £44 / night

(4) Excellent 

19

San Giacomo, home with a view - San Casciano dei Bagni farmhouse sleeps 12

Province of Siena / San Casciano dei Bagni

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
San Giacomo is a charming country house set in one of the most enchanting Tuscan landscape. The property is close to the medieval village of SAN CASCIANO DEI BAGNI, known since the Etruscan times for its thermal hot springs. SAN GIACOMO sleeps 8 peple in the main hous  …see more

from £209 / night

£696 - £1948 / week

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from £209 / night

(1) Excellent 

39

Bright, spacious villa with pool near Siena - Siena villa sleeps 7

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Key points: large apartment (140 m2) in a farmhouse renovated with taste and attention to details. Terrace and independent entrance into the courtyard of the property, large pool with view and garden-park with olive grove. Fully equipped kitchen, comfortable living room  …see more

from £157 / night

£853 - £1314 / week

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from £157 / night

6

Apartment "IL MANGIA" in Siena - Siena apartment sleeps 2

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
This cosy and refined two roomed unit (40 sqm) takes its name from the Tower which dominates Siena's main square “il Campo”. The apartment is located on the 2nd floor of my historical palace (a a splendid aristocratic Villa from the first part of the C17th - just  …see more

from £79 / night

£522 - £696 / week

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from £79 / 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

£299 / week

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from £43 / night

(2) Excellent 

28

Il Fienile - Torri barn sleeps 4

Sovicille / Torri

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • 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 £53 / night

£435 - £557 / week

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from £53 / night

13

Province of Siena / Pievescola

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £53 / night

£348 / week

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from £53 / night

(3) Excellent 

32

Province of Siena / Siena

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Suitable for children age 5+
  • Car not necessary

 …see more

from £105 / night

£627 - £1114 / week

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from £105 / night

(15) Very Good 

27

The Perfect Base For Your Tuscan Adventure - Sant Andrea a Montecchio apartment sleeps 4

Siena / Sant Andrea a Montecchio

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 120 km
  • Child friendly
  • Car not necessary
Located in the quiet countryside 5 km south of the beautiful medieval city of Siena, the Sant'Andrea apartment is part of a fully restored 15th century monastery.Only 5 minutes from the superstrada linking Siena to Florence and the Grosseto beaches, this residence is an  …see more

from £61 / night

£435 / week

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from £61 / night

(4) Excellent 

42

Province of Siena / Siena

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

 …see more

from £87 / night

£435 / week

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from £87 / night

(5) Excellent 

35

Monticiano / Tocchi

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 50 km
  • Child friendly
  • Pet friendly

 …see more

from £61 / night

£400 - £887 / week

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from £61 / 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

£392 - £505 / week

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from £61 / 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 £71 / night

£487 - £1096 / week

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from £71 / night

22

Province of Siena / San Gimignano

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Ask about pets

 …see more

from £189 / night

£1322 - £1768 / week

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from £189 / night

(2) Excellent 

9

Province of Siena / San Giovanni d'Asso

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly

 …see more

from £87 / night

£522 - £566 / week

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from £87 / night

(1) Excellent 

13

Your Villa in Tuscany with private garden and pool - Sovicille villa sleeps 4

Province of Siena / Sovicille

3 4 3 nights min

  • 3 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 68 km
  • Swimming pool
  • Air conditioning
The holiday home "Il Rifugio del Falconiere" offers an elegant villa of 220 square meters with a large living room, where there is a fireplace and a unique décor, a large dining room, a fully equipped kitchen with dishwasher, refrigerator that produces ice and water, a  …see more

from £435 / night

£2609 - £3044 / week

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from £435 / night

24

Province of Siena / Asciano

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 117 km
  • Suitable for children age 5+

 …see more

from £57 / night

£261 / week

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from £57 / night

(7) Excellent 

31

Province of Siena / Siena

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £105 / night

£731 - £1000 / week

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from £105 / night

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