Short city breaks Province of Siena

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  • Italy
  • Tuscany
  • Province of Siena

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  • Abbadia San Salvatore (1)
  • Asciano (23)
  • Bagni di San Filippo (1)
  • Bagno Vignoni (3)
  • Buonconvento (1)
  • Casciano (1)
  • Casole d'Elsa (32)
  • Castellina In Chianti (18)
  • Castelmuzio (2)
  • Castelnuovo Berardenga (14)
  • Castiglione D'Orcia (7)
  • Cetona (10)
  • Chianciano Terme (6)
  • Chiusdino (7)
  • Chiusi (4)
  • Colle di Val d'Elsa (18)
  • Gaiole in Chianti (13)
  • Montalcino (8)
  • Montepulciano (49)
  • Monteriggioni (19)
  • Monteroni d'Arbia (5)
  • Monticiano (6)
  • Montisi (6)
  • Murlo (6)
  • Palazzone (6)
  • Piancastagnaio (6)
  • Pienza (23)
  • Pievescola (3)
  • Poggibonsi (21)
  • Radda in Chianti (5)
  • Radicofani (19)
  • Radicondoli (24)
  • Rapolano Terme (18)
  • Rocca d'Orcia (2)
  • San Casciano dei Bagni (9)
  • San Gimignano (53)
  • San Giovanni d'Asso (5)
  • San Quirico d'Orcia (1)
  • Sarteano (7)
  • Siena (128)
  • Sinalunga (17)
  • Sovicille (25)
  • Torrita di Siena (4)
  • Trequanda (3)
  • Vivo d'Orcia (1)

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640 Holiday homes

Filters applied: City breaks (640)

(1) Excellent 

1 / 16

Tuscany / Province of Siena / Siena

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Nearest beach 80 km; Ask owner if suitable for children; Car not necessary;
 …see more

from £160 / night

£958 / week

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from £160 / night

(5) Very Good 

1 / 15

Tuscany / Province of Siena / Siena

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
 …see more

from £50 / night

£334 - £1109 / week

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from £50 / night

1 / 25

Tuscany / Province of Siena / Trequanda

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
 …see more

from £91 / night

£636 - £992 / week

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from £91 / night

1 / 16

Tuscany / Province of Siena / Siena / Sant Andrea a Montecchio

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £71 / night

£430 - £484 / week

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from £71 / night

1 / 99

Tuscany / Province of Siena / San Gimignano

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £100 / night

£625 - £825 / week

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from £100 / night

(7) Excellent 

1 / 16

OCABIANCA - Casole d'Elsa villa sleeps 4

Tuscany / Province of Siena / Casole d'Elsa

4 bedroomsSleeps 43 nights min stay

  • 4 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Great for children of all ages ; Pets welcome; 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 £67 / night

£0 / week

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from £67 / night

(2) Very Good 

1 / 18

Medioeval apartment - Sarteano apartment sleeps 4

Tuscany / Province of Siena / Sarteano

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 120 km; Great for children of all ages ; Car advised;
Maximum 4 persons: 3 rooms, of which 1 bedroom with 1 bathroom, independent kitchen, tavern with a double sofa bed and fireplace. Bedding : 1 double bed, 1 double sofa bed (totally 4 persons).Excellently furnished! Near at the 'Parco delle piscine' (beautiful  …see more

from £50 / night

£234 - £250 / week

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from £50 / night

1 / 35

Tuscany / Province of Siena / Murlo / Casciano di Murlo

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 50 km; Swimming pool; Great for children of all ages ;
 …see more

from £59 / night

£300 - £413 / week

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from £59 / night

1 / 5

Pool access in rustic apt near Siena, Tuscany

Tuscany / Province of Siena / Sovicille / San Rocco a Pilli

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; No pets allowed;
A perfect place for couples seeking peace and privacy. The apartment feature a double bedroom, a fully equipped kitchen, dining area, a comfortable living room with TV and a private bathroom with Jacuzzib shower. Access to the beautiful and peaceful garden with an outdo  …see more

from £92 / night

£584 - £667 / week

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from £92 / night

1 / 19

Tuscany / Province of Siena / Monticiano

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Great for children of all ages ; Pets welcome;
 …see more

from £38 / night

£250 / week

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from £38 / night

(4) Excellent 

1 / 31

Tuscany / Province of Siena / Siena

2 bedroomsSleeps 31 night min stay

  • 2 bedrooms
  • Sleeps 3
  • 1 night min stay
Key info: Swimming pool; Ask owner if suitable for children; Pets welcome;
 …see more

from £100 / night

£700 - £959 / week

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from £100 / night

(1) Excellent 

1 / 20

Podere le Monache 1 - San Gimignano farmhouse sleeps 4

Tuscany / Province of Siena / San Gimignano

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Great for children of all ages ;
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 £55 / night

£367 - £792 / week

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from £55 / night

(5) Excellent 

1 / 22

Apartment "Casa Laura" - Monteriggioni apartment sleeps 5

Tuscany / Province of Siena / Monteriggioni

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
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 £59 / night

£379 - £551 / week

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from £59 / night

1 / 13

Tuscany / Province of Siena / Pievescola

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Great for children of all ages ;
 …see more

from £50 / night

£334 - £375 / week

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from £50 / night

(12) Excellent 

1 / 17

La Stalla di San Lazzero, adorable house in Siena

Tuscany / Province of Siena / Siena

2 bedroomsSleeps 33 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min stay
Key info: Nearest beach 95 km; Suitable for children age 5+; Car advised;
The "Stalla di San Lazzero", adorable country house a few steps from Siena center, is the perfect starting point to discover Tuscany! The house is spacious with high ceilings, large windows, a lovely garden and a beautiful view of the countryside. One large queen size  …see more

from £71 / night

£496 / week

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from £71 / night

(2) Excellent 

1 / 32

Fonte Tuscany Holiday Apartment in Chianti Hill

Tuscany / Province of Siena / Radda in Chianti

1 bedroomSleeps 25 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 5 nights min stay
Key info: Nearest beach 120 km; Great for children of all ages ; Car advised;
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce organic Chianti Classico wine and extra virgin olive oil.We restored the farmhouse of the 15th century and Giovanni has personally followed all the work  …see more

from £55 / night

£337 - £404 / week

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from £55 / night

(1) Excellent 

1 / 11

Tuscany / Province of Siena / San Gimignano

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
 …see more

from £71 / night

£496 / week

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from £71 / night

(5) Excellent 

1 / 56

Villa di Geggiano - Siena guest house sleeps 4

Tuscany / Province of Siena / Siena

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 60 km; Great for children of all ages ; Car advised;
One of the original, charming and elegant garden pavilions, situated within the garden of Villa di Geggiano, has recently been renovated into two luxury suites which have now been opened to guests for reservation. The Pavilion has a total capacity of 4 persons but it  …see more

from £375 / night

£2292 / week

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from £375 / night

(16) Excellent 

1 / 10

Sunny 1 bedroom apartment on the Podere Magione Holiday Farm in the San Gimignano region of Tuscany

Tuscany / Province of Siena / San Gimignano

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Nearest beach 72 km; Great for children of all ages ; Car essential;
The Podere Magione Holiday Farm is capable of offering various possibilities for your stay in Tuscany, also maintaining an intimate, family atmosphere, considering its modest size.CIPRESSO APARTMENT has one bedroom with twins beds(or the possibility to have a big bed as  …see more

from £42 / night

£250 - £309 / week

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from £42 / night

(6) Excellent 

1 / 24

Tuscany / Province of Siena / Radicondoli

4 bedroomsSleeps 92 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 60 km; Great for children of all ages ;
 …see more

from £131 / night

£0 / week

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from £131 / night

1 / 27

Tuscany / Province of Siena / Siena

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Suitable for children age 5+;
 …see more

from £173 / night

£1209 - £2000 / week

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from £173 / night

1 / 24

Tuscany / Province of Siena / Asciano

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 117 km; Suitable for children age 5+; Car advised;
 …see more

from £50 / night

£250 - £292 / week

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from £50 / night

(3) Good 

1 / 5

Tuscany / Province of Siena / Montepulciano

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; Pets welcome;
 …see more

from £50 / night

£250 / week

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from £50 / night

(2) Excellent 

1 / 21

Stunning Siena villa with 5 bedrooms, amazing priv

Tuscany / Province of Siena / Siena

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
Immersed in the green countryside on the outskirts of Siena, Villa Palio offers all the quiet of its natural setting just a stone throw from the very center of the town of Siena. The villa has been restored in the last years and the result is an elegant accommodation w  …see more

from £173 / night

£1209 - £2000 / week

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from £173 / night

1 / 22

Tuscany / Province of Siena / San Gimignano

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
 …see more

from £181 / night

£1267 - £2034 / week

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from £181 / night

(4) Excellent 

1 / 19

Tuscany / Province of Siena / Torrita di Siena

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Great for children of all ages ; Car essential; Some pets are welcome - please contact the owner;
 …see more

from £75 / night

£484 / week

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from £75 / night

(7) Excellent 

1 / 6

Tuscany / Province of Siena / Montepulciano / Valiano

1 bedroomSleeps 24 nights min stay

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

from £43 / night

£295 / week

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from £43 / night

(1) Excellent 

1 / 39

Live Beautifully Five Minutes From Siena

Tuscany / Province of Siena / Siena

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Great for children of all ages ; Car not necessary; No pets allowed;
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 £84 / night

£542 / week

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from £84 / night

1 / 15

Tuscany / Province of Siena / Radicofani

1 bedroomSleeps 41 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
 …see more

from £67 / night

£375 / week

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from £67 / night

1 / 21

Tuscany / Province of Siena / Radicondoli

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 48 km; Swimming pool; Great for children of all ages ;
 …see more

from £83 / night

£542 / week

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from £83 / night

1 / 27

Rocca dei Monaci 14 - Monteriggioni house sleeps 4

Tuscany / Province of Siena / Monteriggioni

1 bedroomSleeps 47 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 110 km; Swimming pool; Great for children of all ages ;
The apartment is situated in a residence which represent the perfect Tuscan style. Centuries ago it was a convent, in fact residence's name is “Rocca dei Monaci”, then it was inhabited by farmers. They improved and enlarged it in a little village absorbed in ty  …see more

from £36 / night

£250 - £375 / week

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from £36 / night

(1) Excellent 

1 / 12

Tuscany / Province of Siena / Rapolano Terme / Serre di Rapolano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 110 km; Great for children of all ages ; Car advised;
 …see more

from £50 / night

£292 - £567 / week

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from £50 / night

(5) Excellent 

1 / 24

Tuscany / Province of Siena / Montepulciano

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Great for children of all ages ; Car advised; No pets allowed;
 …see more

from £65 / night

£384 / week

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from £65 / night

(15) Excellent 

1 / 23

Farmhouse near Siena, private pool, brilliant views

Tuscany / Province of Siena / Castelnuovo Berardenga

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 90 km; Swimming pool; Great for children of all ages ;
Farmhouse "I Moraioli" is in Montebenichi in the heart of the Chianti hills. A unique panorama, a breathtaking view over a valley among the most beautiful and unspoilt ones of Tuscany and ... the view goes as far as the south of Crete Senesi with a view of the  …see more

from £75 / night

£417 - £834 / week

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from £75 / night

(4) Excellent 

1 / 19

Tuscany / Province of Siena / San Gimignano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Great for children of all ages ; Car advised; Some pets are welcome - please contact the owner;
 …see more

from £59 / night

£350 - £467 / week

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from £59 / night

(3) Very Good 

1 / 22

Agriturismo Casanova di Lucignano (Maggiorana)

Tuscany / Province of Siena / Monteroni d'Arbia

1 bedroomSleeps 2Min 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 £71 / night

£438 - £467 / week

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from £71 / night

(3) Very Good 

1 / 11

Artu' - Siena apartment sleeps 2

Tuscany / Province of Siena / Siena

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 50 km; Great for children of all ages ; Car advised;
The apartment is ideal for holiday in Siena is located in the centre of Siena, one of the most beautiful towns in Italy.The position of the flat with a splendid view on the cathedral and San Domenico church and the position in the centre of the town create a nice estate  …see more

from £80 / night

£400 / week

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from £80 / night

1 / 20

Sienahomeandsailing-Brown apartment with garden

Tuscany / Province of Siena / Siena

1 bedroomSleeps 53 nights min stay

  • 1 bedroom
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 85 km; Great for children of all ages ; Car not necessary;
Brown apartment is a typical Tuscan house and features a private fully equipped garden. Located at the first floor, completely restored, it consists of a bedroom with double bed and a bathroom with shower, toilet, hairdryer. A flight of stairs leads to the open studio  …see more

from £39 / night

£0 / week

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from £39 / night

1 / 24

Tuscany / Province of Siena / Pienza / Monticchiello

4 bedroomsSleeps 81 night min stay

  • 4 bedrooms
  • Sleeps 8
  • 1 night min stay
Key info: Great for children of all ages ; Air conditioning; Some pets are welcome - please contact the owner;
 …see more

from £75 / night

£500 - £2075 / week

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from £75 / night

(3) Very Good 

1 / 20

Vernianello "Riccio" - Cedda farmhouse sleeps 4

Tuscany / Province of Siena / Poggibonsi / Cedda

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
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 £75 / night

£458 - £716 / week

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from £75 / night

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