Short city breaks Province of Siena

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Province of Siena

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589 Holiday homes

Filters applied: City breaks

Travellers going to Province of Siena are booking June dates now. Secure your holiday home today and have the perfect trip.

11

Holiday apartment with golf nearby in San Rocco a Pilli

Sovicille / San Rocco a Pilli

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
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 £119 / night

£831 / week

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from £119 / night

9

Province of Siena / Siena

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Ask about pets

 …see more

from £60 / night

£382 / week

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from £60 / night

(1) Excellent 

17

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 109 km
  • Swimming pool
  • Child friendly

 …see more

from £94 / night

£636 / week

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from £94 / night

Featured properties

(2) Excellent 

36

Radda in Chianti holiday farmhouse rental

Province of Siena / Radda in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 120 km
  • Child friendly
  • Pet friendly
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 £59 / night

£323 - £382 / week

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from £59 / night

24

Province of Siena / Sarteano

20 48 Min stay varies

  • 20 bedrooms
  • Sleeps 48
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

Pricing unknown

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Pricing unknown

(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 £43 / night

£297 / week

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from £43 / night

(1) Very Good 

18

B&b letting in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“nice place, nice people” Living for a bit in an old fashioned atmosphere. It is a confortable and friendly place to stay with your family , friends or alone both relaxing in a wonderful Tuscany landscape and travelling around to explore Reinassance  …see more

from £34 / night

£238 / week

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from £34 / night

(3) Excellent 

24

Poggibonsi / Staggia Senese

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £30 / night

£173 - £339 / week

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from £30 / night

17

Holiday apartment in Siena

Province of Siena / Siena

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
La Coroncina is situated just 2 km from the historical center, 2.7 km from Piazza del Campo, 2.9 km from Piazza del Duomo and 2.6 km from National Picture Gallery Siena. The structure is in a peaceful but very central location in the south of Siena with bus stops at few  …see more

from £50 / night

£350 / week

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from £50 / night

(1) Excellent 

22

Province of Siena / Montepulciano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 116 km
  • Child friendly
  • Pet friendly

 …see more

from £119 / night

£509 - £636 / week

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from £119 / night

(3) Very Good 

20

Holiday farmhouse with shared pool in Cedda

Poggibonsi / Cedda

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Quiet and beautiful” We spent a week in an apartment on this property. The place is very quiet and relaxing and the view is stunning. The apartment has a private patio overlooking a small valley and this patio was our living room: every night we settl  …see more

from £73 / night

£466 - £745 / week

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from £73 / night

27

Holiday villa in Monteriggioni

Province of Siena / Monteriggioni

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
Near to Siena (8 km), in the Chianti region, apartment in farmhouse (size: 170 m2) for max.6 persons. Swimming pool complex and park 3 km far away.Splendid farm house (18 th century) located on the top of a hill. The property apartment offers you the unique and rare  …see more

from £96 / night

£670 - £1034 / week

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from £96 / night

(3) Very Good 

28

Province of Siena / Castelnuovo Berardenga

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Air conditioning

 …see more

from £59 / night

£410 / week

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from £59 / night

19

Gaiole in Chianti / Lecchi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £62 / night

£433 - £882 / week

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from £62 / night

(2) Excellent 

19

Holiday apartment rental

Province of Siena / Radicondoli

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 64 km
  • Swimming pool
  • Pet friendly
Your dream holiday near Siena with swimming pool and garden, quiet area with beautiful view of the Tuscan country. Wine and olive oil tasting.  …see more

from £36 / night

£250 / week

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from £36 / night

(1) Average 

28

San Gimignano / Castel San Gimignano

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

 …see more

from £77 / night

£551 / week

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from £77 / night

(2) Excellent 

24

Province of Siena / Palazzone

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Private garden

 …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

20

Caprera holiday apartment rental

Siena / Caprera

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning
Suite Le Camelie has all the comfort you would find in a hotel. It is at the same time a real Tuscany home with a local decor and feeling, surrounded by luxurius gardens and olive trees. Ideal location for visiting both Siena and the country side.  …see more

from £68 / night

£424 - £467 / week

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from £68 / night

(1) Excellent 

20

Farmhouse rental in San Gimignano with swimming pool

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
Self catering Farmhouse with 4 luxury apartments in rural Tuscany with swimming pool spectacular views ,nearby golf, walking, trekking, fishing, biking. San Gimignano, and Certaldo, 20 minutes drive, Florence, Siena and Pisa one hour from the house.  …see more

from £50 / night

£339 - £763 / week

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from £50 / night

(3) Average 

20

Province of Siena / Montalcino

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly

 …see more

from £75 / night

£516 / week

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from £75 / night

47

Fort rental in Montisi with shared pool

Province of Siena / Montisi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Romantic and charming 14th century fortress. Very authentic medieval atmosphere. Strategically located between Val d'Orcia and Crete Senesi, close to Montalcino, Montepulciano, Pienza and Siena. Shops at walking distance. Organic wine and extra virgin olive oil.  …see more

from £154 / night

£1050 - £1146 / week

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from £154 / night

24

Holiday farmhouse in Siena

Province of Siena / Siena

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
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  …see more

from £115 / night

£801 / week

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from £115 / night

(12) Very Good 

28

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Villa PetrAlexa - excellent leisure facility” This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfec  …see more

from £175 / night

£1221 - £2034 / week

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from £175 / night

(1) Excellent 

39

Holiday apartment in Siena

Province of Siena / Siena

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
Fully furnished country style apartment 5 minutes away from the historic Medieval city of Siena. Confortable and spacious living-room, private parking, WiF, shops close. 1 hour drive from main Tuscan attractions, Florence, S. Gimignano, Chianti Vineyard, Hill Towns.<  …see more

from £85 / night

£551 / week

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from £85 / night

24

Monastero holiday farmhouse let

Siena / Monastero

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Nearest beach 100 km
  • Child friendly
  • Ask about pets
Romantic one bedroom apartment in Elegant Liberty country village close to Siena medieval city. Picturesque courtyard and garden for outdoor dining.  …see more

from £85 / night

£509 / week

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from £85 / night

19

Province of Siena / Castiglione D'Orcia

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £119 / night

£831 / week

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from £119 / night

45

Province of Siena / Siena

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

Pricing unknown

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Pricing unknown

27

Province of Siena / Sarteano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £1022 / night

£7149 / week

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from £1022 / night

(2) Excellent 

18

Province of Siena / Gaiole in Chianti

2 2 7 nights min

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £77 / night

£534 / week

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from £77 / night

(1) Excellent 

54

Province of Siena / Cetona

8 12 Min stay varies

  • 8 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 29 km
  • Swimming pool

 …see more

from £297 / night

£2034 - £4526 / week

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from £297 / night

(1) Excellent 

46

Province of Siena / Siena

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 80 km
  • Child friendly

 …see more

from £178 / night

£1068 / week

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from £178 / night

(1) Excellent 

33

Province of Siena / Chiusdino

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly

 …see more

from £170 / night

£1272 / week

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from £170 / night

13

Holiday apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Casa al bosco” is an elegant house restored in the second half of the 1800s. It is situated in a property of approximately 12 hectares where there are olive trees and a vineyard.  …see more

Pricing unknown

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Pricing unknown

(8) Excellent 

18

Province of Siena / Colle di Val d'Elsa

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 93 km
  • Child friendly
  • Pet friendly

 …see more

from £68 / night

£416 / week

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from £68 / night

(1) Excellent 

16

Apartment rental in Casole d'Elsa with shared pool

Province of Siena / Casole d'Elsa

1 7 3 nights min

  • 1 bedroom
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Apt with terrace and large shared pool in an ancient borgo nestled in the countryside between Siena, San Gimignano and Volterra. It hosts 4 people comfortably, has 7 beds. Large living room with kitchen corner and a loft, master bedroom and bathroom with shower. It ha  …see more

from £59 / night

£356 - £505 / week

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from £59 / night

20

Buonconvento / Chiusure

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Nearest beach 87 km
  • Swimming pool
  • Child friendly

 …see more

from £77 / night

£530 / week

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from £77 / night

20

Apartment rental in San Gimignano with shared pool

Province of Siena / San Gimignano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Aquario apartment for up to 5 guests. The property is extraordinarily cool and pleasant throughout the summer, thanks to its location on a higher altitude (about 500 AMSL) and the beautiful structure in heavy stones. This magnificent country home offers no compromise in  …see more

from £182 / night

£1102 - £1950 / week

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from £182 / night

(1) Excellent 

11

Holiday apartment accommodation

Province of Siena / Siena

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Siena apartment with easy access to the town centre  …see more

from £60 / night

£373 - £467 / week

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from £60 / night

14

Asciano / Crete Senesi

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £231 / night

£1611 - £2543 / week

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from £231 / night

(1) Excellent 

11

San Rocco a Pilli holiday b&b rental

Sovicille / San Rocco a Pilli

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Air conditioning
ROOMSBeautiful rooms, elegantly furnished, spacious and comfortable, with large windows which overlook the beautiful landscapes of the historic city of Siena and the green of uncontaminated nature.Each is equipped with air conditioning and a private bathroom.  …see more

from £94 / night

£588 / week

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from £94 / night