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Province of Siena

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419 Holiday homes

Filters applied: Cot available

(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 £412 / night

£2883 - £4435 / week

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from £412 / night

(21) Excellent 

Certificate of Excellence

43

Holiday apartment in Monticchiello

Pienza / Monticchiello

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

Certificate of Excellence

from £66 / night

£322 - £785 / week

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from £66 / 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
…see more

Certificate of Excellence

from £140 / night

£914 - £1983 / week

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from £140 / night

(1) Excellent 

7

Farmhouse rental in Montepulciano with shared pool

Province of Siena / Montepulciano

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £61 / night

£261 - £453 / week

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from £61 / night

(13) Excellent 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect and plaisant location to explore Tuscany” We were 4 people staying in this very nice apartment : comfortable, clean, modern, well equipped. We loved the location. I never heard of Gaiole before, but it was a nice discovery. Quiet village, but
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from £175 / night

£1100 - £1600 / week

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from £175 / night

(1) Excellent 

27

Holiday barn with swimming pool in Quercegrossa

Monteriggioni / Quercegrossa

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £82 / night

£574 - £879 / week

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from £82 / night

9

Colle di Val d'Elsa holiday farmhouse rental

Province of Siena / Colle di Val d'Elsa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £100 / night

£687 - £1487 / week

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from £100 / night

(15) Excellent 

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Very comfortable home away from home” Casacorvo Minore is a very comfortable apartment well located in the heart of Chianti. It has great views from its veranda which fostered perfect starts for each day as we had breakfast sitting in the morning sun.
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from £100 / night

£560 - £760 / week

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from £100 / night

(12) Excellent 

21

Gracciano holiday cottage rental

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Really worth staying!” My partner and I spent a glorious week this spring at agriturismo Il Salarco surrounded by vineyards and idyllic rolling countryside. The owner, an English lady called Laura, made us both feel really welcome, was fabulously know
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from £70 / night

£383 - £1792 / week

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from £70 / 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

12

Holiday apartment in Sarteano

Province of Siena / Sarteano

3 11 3 nights min

  • 3 bedrooms
  • Sleeps 11
  • 3 nights min
  • Child friendly
  • Pet friendly

from £174 / night

£1044 / week

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from £174 / 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 £70 / night

£418 - £583 / week

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from £70 / night

20

Holiday villa with swimming pool in Chiusdino

Province of Siena / Chiusdino

6 12 2 nights min

  • 6 bedrooms
  • Sleeps 12
  • 2 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £696 / night

£3305 / week

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from £696 / 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
…see more

from £494 / night

£3460 - £4509 / week

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from £494 / night

(33) Excellent 

Certificate of Excellence

32

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Great apartment. Fantastic Tuscan hospitality.” My wife and I chose Casa Gelsomino because we were travelling with our 18-month old daughter and wanted to be in a location with amenities within walking distance. The hamlet of Castel San Gimignano itse
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Certificate of Excellence

from £105 / night

£566 - £740 / week

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from £105 / night

36

Holiday villa in Siena

Province of Siena / Siena

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly

from £479 / night

£2609 - £4348 / week

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from £479 / night

60

Holiday villa with swimming pool in Bettolle

Sinalunga / Bettolle

11 22 7 nights min

  • 11 bedrooms
  • Sleeps 22
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £792 / night

£5544 - £7066 / week

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from £792 / night

(15) Very Good 

17

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 55 km
  • Swimming pool
“Beautiful apartment in stunning Tuscan landscape” If you want a base in Tuscany that seems in the middle of nowhere, but is less than an hour from all of the famous Tuscan towns/villages, and a lovely apartment that is in the middle of stunning countr
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from £82 / night

£574 / week

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from £82 / night

19

Holiday apartment in Siena

Province of Siena / Siena

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Air conditioning

from £79 / night

£479 - £661 / week

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from £79 / night

(15) Excellent 

23

Castelnuovo Berardenga holiday apartment rental

Province of Siena / Castelnuovo Berardenga

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“We enjoyed our holidays in this beautiful agriturismo” We have spent two weeks in Fernando Mattii's agriturismo. The site is very clean and very well maintained. Fernando Mattii was always helpful when we needed anything and he even brought us some wo
…see more

from £131 / night

£914 / week

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from £131 / night

(21) Excellent 

Certificate of Excellence

43

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Perfect location with delightful owners” This is such a beautiful spot and ideal for exploring as very close to everything we wanted to see: Siena, San Gimignano, Volterra and many other less well known medieval towns and villages. The pool has a stu
…see more

Certificate of Excellence

from £105 / night

£566 - £740 / week

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from £105 / night

(5) Excellent 

Certificate of Excellence

30

Farmhouse letting in Radda in Chianti

Province of Siena / Radda in Chianti

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly

Certificate of Excellence

from £66 / night

£392 - £427 / week

Book View

from £66 / night

20

Holiday villa in San Gusme

Castelnuovo Berardenga / San Gusme

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £107 / night

£746 - £1194 / week

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from £107 / night

(4) Excellent 

18

Apartment rental in Siena with shared pool

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
“Heaven on Earth” This Villa Apartment was absolutely awesome! The own was the most kind and gentle man you could ever meet! The apartment was huge and way more than we expected. The furnishings were beautiful and all the rooms were very large. Absolut
…see more

from £79 / night

£522 - £957 / week

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from £79 / 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 £174 / night

£1244 - £2348 / week

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from £174 / night

(11) Excellent 

39

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £174 / night

£1218 - £1696 / week

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from £174 / 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 £131 / night

£914 / week

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from £131 / night

(32) Excellent 

24

Gaiole in Chianti holiday apartment accommodation

Province of Siena / Gaiole in Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden
“A Little Corner of Heaven” This was our fourth visit to Gaiole in Chianti and our third stay in this apartment. The apartment is modern, well furnished and equipped and spotlessly clean. The garden is beautiful and a real bonus. It is a wonderful
…see more

from £85 / night

£595 - £665 / week

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from £85 / night

(50) Excellent 

Certificate of Excellence

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
…see more

Certificate of Excellence

from £61 / night

£348 - £609 / week

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from £61 / night

(1) Excellent 

18

Holiday apartment rental

Province of Siena / Montepulciano

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £57 / night

£374 - £679 / week

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from £57 / night

(4) Excellent 

24

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £156 / night

£1087 - £2392 / week

Enquire View

from £156 / night

(1) Excellent 

20

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

from £162 / night

£1131 - £1783 / week

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from £162 / night

(1) Excellent 

54

Cetona holiday farmhouse rental

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

from £305 / night

£2087 - £4644 / week

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from £305 / 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 £147 / night

£1027 - £2261 / week

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from £147 / night

(5) Excellent 

31

Murlo holiday apartment rental

Province of Siena / Murlo

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £70 / night

£421 - £500 / week

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from £70 / night

(7) Excellent 

24

Val d'Orcia holiday villa rental

Montalcino / Val d'Orcia

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £274 / night

£1914 - £2092 / week

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from £274 / night

(1) Excellent 

24

Buonconvento holiday farmhouse rental

Province of Siena / Buonconvento

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Excellent countryside villa for those wanting to get away from it all” We travelled with 3 kids aged under 10. There was plenty of space for them to run about outside and to relax inside the villa which has one bedroom set aside as a play room. The vi
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from £248 / night

£1653 - £1740 / week

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from £248 / night

(9) Excellent 

57

Holiday lodge in Pienza

Province of Siena / Pienza

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £222 / night

£1553 - £2831 / week

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from £222 / night

(4) Very Good 

19

Barn rental in Sovicille with shared pool

Province of Siena / Sovicille

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £61 / night

£423 / week

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from £61 / night

(5) Excellent 

24

Barn rental in Radda in Chianti

Province of Siena / Radda in Chianti

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Child friendly
  • Pet friendly
  • Private garden
“Living the Dream!” Val delle Corti was the quintessential Tuscan experience. Lis and Roberto treated us like family during our stay on their vineyard and their local recommendations were invaluable. The beautifully restored barn that became our home
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from £87 / night

£609 - £700 / week

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from £87 / night

1