Short city breaks Province of Siena

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Province of Siena

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614 Holiday homes

Filters applied: City breaks (615)

(3) Very Good 

21

Sovicille / Torri

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £77 / night

£471 / week

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from £77 / 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

£470 - £752 / week

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from £73 / night

36

Radicofani / Contignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from £60 / night

£428 / week

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from £60 / night

(5) Excellent 

23

Holiday apartment in Pienza

Province of Siena / Pienza

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
“Fantastic place - great selection of restaurants” Truly a maginificent apartment exceeding our expectations - really nice to cool down in the jacuzzi overlooking Montalcino when the weather was at its hottest ! Also very convenient with regards to  …see more

from £120 / night

£838 / week

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from £120 / 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 £25 / night

£171 / week

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from £25 / night

(2) Excellent 

39

Holiday villa with swimming pool in Siena

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“A charming Tuscan farmhouse villa” We stayed here for a most enjoyable week in September 2016. It is all that the owner Giada describes and she is a charming and helpful host. The villa, a converted stone farmhouse, is located on the outskirts of Sien  …see more

from £112 / night

£753 - £2206 / week

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from £112 / night

(16) Excellent 

22

Casole d'Elsa holiday cottage rental

Casole d'Elsa / Monteguidi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly
“Everything we wanted: excellent villa with lovely pool, beautiful countryside views and welcoming owners.” La Casa Dei Nonni was above and beyond our expectations. The location within the Tuscan hillside village of Monteguidi was easy to find from the  …see more

from £129 / night

£770 - £1154 / week

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from £129 / night

(6) Very Good 

56

Torrita di Siena / Montefollonico

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £189 / night

£1317 / week

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from £189 / night

22

Holiday villa rental

Colle di Val d'Elsa / Campiglia dei Foci

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
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  …see more

from £159 / night

£1112 / week

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from £159 / night

22

Chiusi holiday villa accommodation

Province of Siena / Chiusi

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Villa Baiocco is a typical Tuscan, historic farm house from 1700, recently converted to a prestigious holiday home - without losing its unique character and charm. Surrounded by 20'000m2 of well kept gardens, for your private use only, it offers all the peace and t  …see more

from £244 / night

£1710 - £3847 / week

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from £244 / night

(17) Excellent 

10

Apartment rental in San Gimignano

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 72 km
  • Child friendly
  • Private garden
“An all round fantastic experience...we have great memories...” My partner and I stayed here for a week in July, and count ourselves lucky to have discovered this place. About 8kms from San Gimignano (an easy jaunt in a car, the latter being vital)  …see more

from £49 / night

£287 - £317 / week

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from £49 / night

(1) Very Good 

8

Province of Siena / San Gimignano

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Air conditioning

 …see more

from £118 / night

£659 / week

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from £118 / night

(30) Excellent 

26

Holiday farmhouse with swimming pool in Val d'Orcia

Montalcino / Val d'Orcia

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
“Perfect cottage for two” Loved everything about our stay here. Alexandra was so helpful, with directions, shopping, restaurants and her love of the wine industry. She met us on the road when we got lost. Lives next door but the property is so big  …see more

from £116 / night

£808 / week

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from £116 / night

15

Sarteano holiday villa rental

Province of Siena / Sarteano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 120 km
  • Child friendly
  • Air conditioning
The home is part of a two family Villa located in a spacious garden near Sarteano, in the heart of Tuscany. The home has 4 bedrooms and offers hospitality to up to 8 guests. The house is fully equipped for a pleasant country retreat, with a fully equipped kitchen to ex  …see more

from £80 / night

£556 - £1445 / week

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from £80 / night

(1) Excellent 

99

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £107 / night

£659 - £983 / week

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from £107 / night

(1)  

19

Province of Siena / Cetona

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £43 / night

£257 / week

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from £43 / night

(2) Very Good 

12

Holiday farmhouse letting

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 fa  …see more

from £77 / night

£513 / week

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from £77 / night

(7) Excellent 

24

Province of Siena / Radicondoli

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Child friendly

 …see more

from £150 / night

£1048 / week

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from £150 / night

83

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

3 6 1 night min

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

24

Sinalunga holiday b&b rental

Province of Siena / Sinalunga

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Very spacious and elegant rooms in a b&b with restaurant. Air conditioning, wi-fi, private bathroom with shower, swimming pool. Breakfast is included. The enviroment is a historic country estate, it is a great location for visiting the most beautiful places in Tuscany.G  …see more

from £82 / night

£505 - £676 / week

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from £82 / night

13

Holiday cottage in San Gimignano

Province of Siena / San Gimignano

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Cottage country house countryside  …see more

from £41 / night

£282 / week

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from £41 / night

(10) Excellent 

48

Holiday villa rental

Province of Siena / San Giovanni d'Asso

8 16 3 nights min

  • 8 bedrooms
  • Sleeps 16
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“unforgettable tuscan paradise” Wonderful historic house, charming atmosphere, you feel at home. We were a group of 16 friends, the house was perfect, nothing was missing. Nice accommodations very clean, housekeeping every day. Unforgettable breakfa  …see more

from £571 / night

£4000 - £5214 / week

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from £571 / 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 £180 / night

£1077 / week

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from £180 / night

(1) Excellent 

16

Villa rental in Chiusi with swimming pool

Province of Siena / Chiusi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Casa Baiocco is a typical Tuscan home, newly built in the traditional farmhouse style, perfectly blending with the Italian countryside. Surrounded by a well kept park, for your private use only, it offers all the peace and tranquility that you look for during your holid  …see more

from £62 / night

£428 - £1325 / week

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from £62 / night

(4) Very Good 

14

Apartment rental in Siena

Province of Siena / Siena

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
“nice stay, central, clean” property was as advertised, very clean, easy access, central and very near to the central bus stop, owner came to pick us up at the bus station, we were very happy with our choice  …see more

from £42 / night

£294 / week

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from £42 / night

(2) Excellent 

12

Farmhouse rental in Val di Merse

Siena / Val di Merse

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
For couple, family or group of friends that want to taste the Tuscan countryside with small budget. The property is close to Siena, San Gimignano, Monteriggioni and others famous places !Country house , 1 room, kitchen , 1 bathroom with private terrace and garden .REED  …see more

from £40 / night

£250 - £370 / week

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from £40 / night

36

Sovicille holiday chateau rental

Province of Siena / Sovicille

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Historical house, but comfortable; pool 50 m3; 7000 m2 green and wood around, garden funiture; very peacefull; historical area: 34 castels, churches, ecc. at Sovicille; central to visit Siena(10-15 mins drive), San Gimignano, Volterra, Montalcino (40-60 mins drive).Tusc  …see more

from £107 / night

£753 - £1676 / week

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from £107 / night

(4) Excellent 

19

Province of Siena / San Gimignano

2 4 3 nights min

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

 …see more

from £60 / night

£359 - £479 / week

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from £60 / 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 £43 / night

£300 / week

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from £43 / 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

£359 - £509 / week

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from £59 / night

(5) Excellent 

41

Sinalunga / Rigomagno

5 10 2 nights min

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

 …see more

from £22 / night

£150 / week

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from £22 / night

(4) Very Good 

16

Radicofani / Contignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Child friendly
  • Pet friendly

 …see more

from £69 / night

£342 / week

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from £69 / night

(11) Excellent 

19

Holiday apartment with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Pet friendly
“Wonderful, Wonderful, Highly Recommended.” My wife and I stayed 23rd. June - 5th. July 2013, and had a wonderful holiday. So relaxing and no hassle whatsoever. The farmhouse has three one bedroomed apartments available and a fourth which Elena (the  …see more

from £73 / night

£449 - £479 / week

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from £73 / night

(12) Excellent 

17

Siena holiday home rental

Province of Siena / Siena

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Nearest beach 95 km
  • Child friendly
  • Pet friendly
“A well appointed villa, convenient location and hospitable owner.” The villa is clean, has one very large bedroom and a smaller bedroom which is still adequate. The kitchen is functional with a small fridge , two ring electric hob, small electric oven  …see more

from £73 / night

£509 / week

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from £73 / 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 £30 / night

£35 - £753 / week

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from £30 / night

(15) Very Good 

97

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

7 16 1 night min

  • 7 bedrooms
  • Sleeps 16
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
“Wonderful place, we'll come back!” Everything was first class: the rooms, the pool, breakfast, the countryside. We enjoyed a walk in the countryside and had an archery session with a very patient instructor. Staff is very friendly and helpful.  …see more

from £513 / night

£2992 / week

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from £513 / night

(1) Excellent 

27

Province of Siena / Poggibonsi

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

 …see more

from £60 / night

£359 - £590 / week

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from £60 / night

(1) Excellent 

29

Province of Siena / Montepulciano

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £231 / night

£1283 - £1881 / week

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from £231 / night

5

Province of Siena / Pienza

2 4 Min stay varies

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

 …see more

from £120 / night

£573 - £898 / week

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from £120 / night

(2) Very Good 

31

San Gimignano / Larniano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 69 km
  • Swimming pool
  • Child friendly

 …see more

from £95 / night

£599 / week

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from £95 / night

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