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)
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  • Casole d'Elsa (32)
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  • Colle di Val d'Elsa (18)
  • Gaiole in Chianti (14)
  • Montalcino (8)
  • Montepulciano (49)
  • Monteriggioni (19)
  • Monteroni d'Arbia (5)
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  • Pienza (23)
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  • 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 (130)
  • Sinalunga (17)
  • Sovicille (25)
  • Torrita di Siena (4)
  • Trequanda (3)
  • Vivo d'Orcia (1)

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643 Holiday homes

Filters applied: City breaks (643)

(5) Excellent 

1 / 52

Province of Siena / Montepulciano

2 bedroomsSleeps 52 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Great for children of all ages ; Car not necessary; Some pets are welcome - please contact the owner;
 …see more

from £118 / night

£673 - £757 / week

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from £118 / night

(14) Excellent 

1 / 49

Lovely detached cottage with view of San Gimignano

Province of Siena / San Gimignano

2 bedroomsSleeps 56 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min stay
Key info: Nearest beach 75 km; Great for children of all ages ; Car essential;
Surrounded by idyllic countryside, this pretty holiday home contains flat-screen TV, free Wi-Fi and a barbeque. Parking is available onsite as is gas central heating. Decorated in a typical country-style using rustic furniture and bright terracotta floors, the airy hom  …see more

from £51 / night

£353 / week

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from £51 / night

(3) Excellent 

1 / 13

Poggibonsi / Staggia Senese

2 bedroomsSleeps 31 night min stay

  • 2 bedrooms
  • Sleeps 3
  • 1 night min stay
Key info: Nearest beach 74 km; Great for children of all ages ; Car advised;
 …see more

from £59 / night

£395 / week

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from £59 / night

(2) Excellent 

1 / 11

Apartment "Foriporta" in Siena - Siena apartment sleeps 4

Province of Siena / Siena

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
A spacious and luminous two roomed unit (55sqm) in Siena. The apartment is situated on the 1st floor of my historical palace (a splendid aristocratic Villa from the first part of the C17th - just 1.6 km from the pedestrian historical centre of Siena) and can accommodat  …see more

from £110 / night

£715 - £757 / week

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from £110 / night

(8) Excellent 

1 / 24

Delightful 2 bedroom farmhouse with beautiful private grounds and pool

Province of Siena / Sarteano

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
The Agriturismo Sferracavalli is the best way to enjoy Italian genuine food, which can be gathered in the back garden, and to feel compleatly plunged in peace and relax among Tuscany nature. Medieval villages complete the perfect Tuscany atmosphere all around, so that w  …see more

from £106 / night

£631 - £925 / week

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from £106 / night

(1) Very Good 

1 / 17

Province of Siena / Sovicille

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 £51 / night

£320 / week

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from £51 / night

1 / 19

Gaiole in Chianti / Lecchi

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Some pets are welcome - please contact the owner;
 …see more

from £61 / night

£429 - £874 / week

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from £61 / night

(5) Very Good 

1 / 15

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 / 11

Holiday Home Casa Ciliano - Montepulciano apartment sleeps 5

Province of Siena / Montepulciano

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Great for children of all ages ; Car advised; Pets welcome;
Casa Ciliano is an holiday house in Montepulciano, 60 Km far from Siena, it is inside the medieval wall, nearby Porta al Prato, that is the main gate to the historical centre with its Renaissance monuments. 50M far from Casa Ciliano you can see the Etruscan inscriptions  …see more

from £67 / night

£434 - £542 / week

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from £67 / night

(1) Very Good 

1 / 30

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
 …see more

from £58 / night

£462 - £1438 / week

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from £58 / night

1 / 18

galassia 18 - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 bedroomSleeps 32 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 £67 / night

£337 / week

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from £67 / night

(1) Very Good 

1 / 19

Province of Siena / Bagni di San Filippo

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Ski; Great for children of all ages ; Car essential;
 …see more

from £68 / night

£0 / week

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from £68 / night

1 / 12

Province of Siena / Poggibonsi

1 bedroomSleeps 41 night min stay

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

from £49 / night

£337 - £547 / week

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from £49 / night

1 / 24

Poggibonsi / Staggia Senese

1 bedroomSleeps 5Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
Key info: Great for children of all ages ; Car advised; Some pets are welcome - please contact the owner;
 …see more

from £27 / night

£169 - £320 / week

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from £27 / night

(9) Excellent 

1 / 48

Glorious historic Tuscan villa , pool,WIFI,AC

Province of Siena / San Giovanni d'Asso

8 bedroomsSleeps 16Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
A beautiful old historic family house with a large hanging garden and swimming pool (6x12) nestled in the middle of a tiny village, San Giovanni d'Asso, in the Siennese countryside: the comfort to be in a village and the privacy of a place hidden at the sight. Becoming  …see more

from £532 / night

£3933 - £5127 / week

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from £532 / night

1 / 16

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 £72 / night

£433 - £488 / week

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from £72 / night

1 / 12

Province of Siena / Poggibonsi

2 bedroomsSleeps 51 night min stay

  • 2 bedrooms
  • Sleeps 5
  • 1 night min stay
Key info: Swimming pool; Suitable for children age 5+; Pets welcome;
 …see more

from £55 / night

£379 - £589 / week

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from £55 / night

(1) Excellent 

1 / 25

Restored Barn - country home - Siena barn sleeps 3

Province of Siena / Siena

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
Splendid 18th century mansion with typical Sienese architecture. It is situated next to the historical village of Basciano. The house position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena.  …see more

from £92 / night

£550 - £842 / week

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from £92 / night

(11) Excellent 

1 / 19

Agriturismo Casanova di Lucignano (Lavanda)

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 £72 / night

£442 - £471 / week

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from £72 / night

1 / 19

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

£253 / week

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from £38 / night

1 / 12

Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Not suitable for children; Car essential; Some pets are welcome - please contact the owner;
 …see more

from £58 / night

£505 - £715 / week

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from £58 / night

1 / 28

Province of Siena / San Gimignano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 70 km; Great for children of all ages ; Car advised;
 …see more

from £100 / night

£584 - £750 / week

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from £100 / night

(4) Very Good 

1 / 12

Sienahomeandsailing-Red apartment - Siena apartment sleeps 5

Province of Siena / Siena

1 bedroomSleeps 53 nights min stay

  • 1 bedroom
  • Sleeps 5
  • 3 nights min stay
Key info: Great for children of all ages ; 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 £42 / night

£0 / week

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from £42 / night

1 / 13

Piccolo Cottage San Gimignano - San Gimignano cottage sleeps 4

Province of Siena / San Gimignano

1 bedroomSleeps 44 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay
Key info: Great for children of all ages ; Pets welcome; Private garden;
Surrounded by idyllic countryside, this pretty holiday home contains flat-screen TV, free Wi-Fi and a barbeque. Parking is available onsite as is gas central heating. Decorated in modern-style using and bright terracotta floors, the airy home contains 1 double bedroom.  …see more

from £40 / night

£0 / week

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from £40 / night

(8) Excellent 

1 / 20

Three bedroom apartment in stunning villa

Province of Siena / San Gimignano

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Car advised;
Osservatorio is a stunning villa for up to 11guests divided into two independent units. Orione apartment for up to 6 guests.The property is extraordinarily cool and pleasant throughout the summer, thanks to its location on a higher altitude (about 500 AMSL) and the beau  …see more

from £180 / night

£1261 - £1933 / week

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from £180 / night

(3) Very Good 

1 / 24

Great place for a Tuscan family holiday, 2 bedroom countryside apartments with shared pool

Province of Siena / Montepulciano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
Tenuta di Argiano a Montepulciano Please ask always AVAILABILITY , we will find in one of our structures the ideal place for your holiday. CAR IS NECESSARY WE ARE IN THE MIDDLE OF COUNTRYSIDE, SURROUNDED BY NATURE. The beautiful apartment FIASCO (60square Mt) , FOR  …see more

from £68 / night

£0 / week

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from £68 / night

1 / 22

Province of Siena / Montepulciano

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 116 km; Great for children of all ages ; Car advised;
 …see more

from £118 / night

£631 / week

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from £118 / night

1 / 22

Tuscan Villa Nr. San Gimignano large gardens

Colle di Val d'Elsa / Campiglia dei Foci

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 60 km; Swimming pool; Great for children of all ages ;
Villa Nr. San Gimignano, Siena Province, Tuscany, ItalyTypical Tuscan Style Villa with Private Pool and Large Private garden.12.000 Square Metres Of Gardens, With Pine Trees, Monumental Oaks And Olive GroveWonderful stone building situated in a peaceful position with a  …see more

from £157 / night

£1093 - £2101 / week

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from £157 / night

(5) Excellent 

1 / 24

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 £66 / night

£387 / week

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from £66 / night

1 / 14

Province of Siena / Pievescola

1 bedroomSleeps 3Min 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 £59 / night

£375 - £459 / week

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from £59 / night

1 / 24

Province of Siena / San Gimignano

2 bedroomsSleeps 4Min stay varies

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

from £82 / night

£572 - £824 / week

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from £82 / night

1 / 5

Pool access in rustic apt near Siena, Tuscany

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 £93 / night

£589 - £673 / week

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from £93 / night

(3) Very Good 

1 / 24

Villa Gaiole - Gaiole in Chianti villa sleeps 8

Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 107 km; Swimming pool; Great for children of all ages ;
Beautiful Family Villa in Borgo di Gaiole, surrounded by the Chianti hills covered in vineyards and olive groves, just a 100 meters walk from the quiet village of Gaiole in Chianti, a typical Tuscan hamlet with restaurants, shops and amenities, an ideally located betwee  …see more

from £82 / night

£572 - £1370 / week

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from £82 / night

(6) Very Good 

1 / 45

Province of Siena / Montepulciano

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Great for children of all ages ; Car advised; Some pets are welcome - please contact the owner;
 …see more

from £68 / night

£446 - £505 / week

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from £68 / night

1 / 39

Province of Siena / Siena

2 bedroomsSleeps 42 nights min stay

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

from £72 / night

£337 / week

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from £72 / night

(18) Excellent 

1 / 24

The Beautiful Sun Apartment - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 bedroomsSleeps 61 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Nearest beach 170 km; Great for children of all ages ; 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 £100 / night

£588 - £1025 / week

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from £100 / night

1 / 26

San Gimignano / Castel San Gimignano

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Great for children of all ages ; Some pets are welcome - please contact the owner;
 …see more

from £43 / night

£286 - £513 / week

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from £43 / night

(3) Excellent 

1 / 35

The Notary's House - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
Small charming flat, old residence of householder's great-grandfather, Notary in Montepulciano. Recently wholly restructured, very quiet, in a very beautiful position: in the centre of town, but facing the walls of the city, in a dominant position.Two nice bedrooms, sma  …see more

from £59 / night

£337 - £505 / week

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from £59 / night

1 / 25

Cottage with view among olivetrees in Tuscany

Province of Siena / Siena

3 bedroomsSleeps 82 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Great for children of all ages ; Pets welcome; Private garden;
Independent 2 family cottage located in the outskirts of Siena in an olive tree grove at 1km from: newsstand, coffee shop, food market, hair dresser, pastry shop, butcher, pizza restaurant, discount market, gas station, free parking lot, bus stops to down town, train s  …see more

from £127 / night

£841 - £1555 / week

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from £127 / night

(3) Excellent 

1 / 32

Province of Siena / Siena

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Suitable for children age 5+; Car not necessary; No pets allowed;
 …see more

from £100 / night

£600 - £950 / week

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from £100 / night

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