Short city breaks Province of Siena | Holiday Lettings UK

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Province of Siena

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573 Holiday homes

Filters applied: City breaks

(5) Excellent 

41

Holiday townhouse rental

Sinalunga / Rigomagno

5 10 2 nights min

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

from £69 / night

£483 / week

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from £69 / night

(12) Excellent 

69

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

Province of Siena / Gaiole in Chianti

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“A hidden gem.” We stayed at Villa LisiDor at the end of May with family. We made the trip to Tuscany by train to Florence from the UK and hired a car from there. We arrived during an unseasonably chilly spell and in torrential rain after a very l
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from £385 / night

£2690 - £4397 / week

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from £385 / night

(27) Excellent 

Certificate of Excellence

18

Holiday apartment in Siena

Province of Siena / Siena

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
“This is an excellent apartment in the centre of Sienna.” This is a great apartment as is shown by the photos. It is a little difficult to find the first time but once located the task was simple. We found overnight car parking 10 minutes away for a c
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Certificate of Excellence

from £138 / night

£906 - £1966 / week

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from £138 / night

(1) Very Good 

18

B&b letting in Montepulciano with shared pool

Province of Siena / Montepulciano

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • 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
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from £35 / night

£242 / week

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Responds fast!
avg. 1 hour 37 minutes

from £35 / night

(11) Very Good 

32

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Excellent value Tuscan villa in a lovely setting” We stayed in the Agrifolo apartment at Le Fontanelle in May 2015. I was visited with my partner and my parents as we treated them to a Tuscan trip to start the summer. The villa was lovely - simple
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from £61 / night

£457 - £815 / week

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Responds fast!
avg. 2 hours 4 minutes

from £61 / night

(2) Excellent 

7

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

2 4 1 night min

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

from £52 / night

£363 / week

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Responds fast!
avg. 2 hours 56 minutes

from £52 / night

(1) Excellent 

17

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

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

from £74 / night

£518 - £759 / week

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from £74 / night

(30) Excellent 

20

Holiday apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 50 km
  • Child friendly
  • Pet friendly

from £69 / night

£414 - £578 / week

Enquire View

from £69 / 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
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from £142 / night

£992 - £2069 / week

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from £142 / night

(6) Excellent 

23

Holiday apartment in Pienza

Province of Siena / Pienza

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • 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
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from £130 / night

£906 / week

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Responds fast!
avg. 2 hours 10 minutes

from £130 / night

(3) Excellent 

24

Holiday apartment in Staggia Senese

Poggibonsi / Staggia Senese

1 5 2 nights min

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

from £31 / night

£175 - £345 / week

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from £31 / night

(3) Excellent 

32

Siena holiday condo rental

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary

from £104 / night

£621 - £983 / week

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from £104 / night

(43) Excellent 

39

Holiday villa in Siena

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Perfect villa in perfect location” I need to start to say thank you to Jacopo and Fabio that made our holiday and stay absolutely perfect. They were both so helpful and such a pleasure to liaise with, even if we arrived later than expected! The
…see more

from £241 / night

£1552 - £3621 / week

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from £241 / night

(10) Excellent 

58

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
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from £490 / night

£3430 - £4470 / week

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Responds fast!
avg. 3 hours 34 minutes

from £490 / night

(3) Excellent 

26

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
  • Ask about pets
“Excellent base for chilling and siteseeing/citytrips” We had a great time at Elena's place! The appartement was clean, big, safe and modern. We used our own kitchen to cook our food. We stayed a week longer then planned. It is a very good base to go b
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from £78 / night

£483 - £544 / week

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Responds fast!
avg. 1 hour 23 minutes

from £78 / night

(8) Excellent 

Certificate of Excellence

33

Apartment rental 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
“Excellent with children or groups” We had very enjoyable stay in a peaceful location with stunning views around. Olimpia was very helpful and everything worked as foreseen. We were trying to find a place with a scent of a history and what would suit b
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Certificate of Excellence

from £61 / night

£423 / week

Book View

Responds fast!
avg. 1 hour 37 minutes

from £61 / night

(4) Very Good 

24

Apartment rental 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

from £61 / night

£423 / week

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Responds fast!
avg. 1 hour 37 minutes

from £61 / night

(6) Excellent 

35

Holiday farmhouse in Monticiano

Monticiano / Tocchi

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 50 km
  • Child friendly
  • Pet friendly

from £61 / night

£397 - £837 / week

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from £61 / night

41

Monticchiello holiday townhouse rental

Pienza / Monticchiello

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £151 / night

£1035 - £1207 / week

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from £151 / night

(6) Very Good 

39

Holiday villa rental

Province of Siena / Chianciano Terme

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £173 / night

£923 - £2328 / week

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Responds fast!
avg. 3 hours 37 minutes

from £173 / night

(12) 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
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from £78 / night

£483 - £544 / week

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Responds fast!
avg. 1 hour 23 minutes

from £78 / night

25

Holiday tower with swimming pool in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £121 / night

£819 / week

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from £121 / night

(50) Excellent 

21

Holiday cottage in Montepulciano

Province of Siena / Montepulciano

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 158 km
  • Child friendly
  • Air conditioning
“Clean, comfortable and cozy house with privacy and convenience to Montepuciano” We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close
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from £74 / night

£432 - £604 / week

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from £74 / night

(12) Excellent 

48

Holiday villa in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“Gorgeous villa in Tuscany” This is a gorgeous villa in the tuscan countryside. The villa was beautiful, spotless and had everything we needed. It is right next to the small town of San Giovanni D'Osso. My 16-year-old loved it as well. While we day-tri
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from £468 / night

£3276 - £4225 / week

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Responds fast!
avg. 3 hours 34 minutes

from £468 / night

(15) Excellent 

Certificate of Excellence

25

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly

Certificate of Excellence

from £77 / night

£370 - £431 / week

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Responds fast!
avg. 2 hours 10 minutes

from £77 / night

(7) Excellent 

56

Holiday guest house in Siena

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning

from £388 / night

£2371 / week

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from £388 / night

(3) Excellent 

39

Holiday villa with swimming pool in Siena

Province of Siena / Siena

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • 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
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from £146 / night

£1018 - £2242 / week

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from £146 / night

(2) Excellent 

19

Holiday apartment in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Child friendly
  • Air conditioning

from £319 / night

£1897 - £2069 / week

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Responds fast!
avg. 2 hours 34 minutes

from £319 / night

(1) Excellent 

24

Holiday apartment in Sarteano

Province of Siena / Sarteano

4 9 1 night min

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

from £44 / night

£302 / week

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from £44 / night

(2) Very Good 

18

Holiday apartment in Sarteano

Province of Siena / Sarteano

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 120 km
  • Child friendly
“good location & helpful landlord” Sarteano is a great location for seeing the rest of Tuscany and for experiencing "la dolce vita" in a small town. The people of Sarteano are very nice and helpful. The owner, Leonardo was especially helpful wit the a
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from £52 / night

£250 / week

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Responds fast!
avg. 3 hours 6 minutes

from £52 / night

(6) Very Good 

25

Holiday apartment in Monteriggioni

Province of Siena / Monteriggioni

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £48 / night

£311 - £505 / week

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Responds fast!
avg. 2 hours 44 minutes

from £48 / night

15

Apartment rental in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 90 km
  • Child friendly
  • Private garden

from £48 / night

£332 / week

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from £48 / night

(2) Excellent 

24

Holiday apartment with golf nearby in Colle di Val d'Elsa

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

from £113 / night

£664 - £992 / week

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from £113 / night

6

Holiday apartment with golf nearby in San Rocco a Pilli

Sovicille / San Rocco a Pilli

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Suitable for children age 5+
  • Pet friendly

from £39 / night

£302 / week

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from £39 / 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

from £95 / night

£598 / week

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from £95 / night

(1) Excellent 

22

Holiday farmhouse in Montepulciano

Province of Siena / Montepulciano

3 5 Min stay varies

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

from £121 / night

£518 - £647 / week

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from £121 / night

(8) Excellent 

12

Holiday apartment in Monteriggioni

Province of Siena / Monteriggioni

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

from £78 / night

£544 / week

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from £78 / night

(6) Very Good 

45

Montepulciano holiday home rental

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets
“Great view, great town!” The villa was wonderful and so is the family renting it out. They met us at the gate and showed us around the villa and how to work everything. The mother gave us a home baked treat too! There are beautiful views of the vin
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from £69 / night

£475 - £518 / week

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from £69 / night

24

Holiday home in Celle sul Rigo

San Casciano dei Bagni / Celle sul Rigo

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask owner if suitable for children
  • Air conditioning
  • Pet friendly

from £69 / night

£302 / week

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from £69 / night

(9) Very Good 

41

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“Stunning Views” We had a most enjoyable time at this house and would recommend it for its location and closeness to Montepulciano. The house was delightful and the views across the valley and surrounding countryside were excellent. We can recommend
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from £100 / night

£625 - £895 / week

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from £100 / night

1