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Province of Siena

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588 Holiday homes

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

(30) Excellent 

20

Holiday apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 50 km
  • Child friendly
  • Pet friendly
The medieval atmosphere and typically Sienese welcome are just a part of our fully-renovated holiday home that has maintained unaltered the rustic Tuscan details.<br />Dietro Le Mura is in the very heart of Colle di Val d'Elsa, renowned for its artisan Crysta  …see more

from £69 / night

£414 - £578 / week

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from £69 / night

(13) Excellent 

20

Montalcino / Sant'Angelo in Colle

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 68 km
  • Suitable for children age 5+
  • Private garden

 …see more

from £65 / night

£388 - £750 / week

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from £65 / night

(6) Very Good 

25

Province of Siena / Monteriggioni

1 3 3 nights min

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

 …see more

from £48 / night

£311 - £505 / week

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from £48 / night

Featured properties

(2) Excellent 

16

Province of Siena / Siena

2 4 2 nights min

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

 …see more

from £250 / night

£1716 - £9052 / week

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from £250 / night

35

Holiday villa with swimming pool in Castelmuzio

Province of Siena / Castelmuzio

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
When Eric and Kathy decided they wanted to settle in Tuscany and provide people with the sort of holidays they themselves had always dreamed of - but had rarely been able to find - they knew they had found the ideal property in Castelmuzio for many reasons, amongst whic  …see more

from £432 / night

£3018 - £4095 / week

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from £432 / night

(48) 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
“Wish we could have stayed longer!!!” What a lovely stay we had at La Casina Toscana! Davide met us on our arrival date and gave us a very thorough tour of the property explaining where everything was and important information about the house. He was e  …see more

from £61 / night

£345 - £604 / week

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from £61 / night

(20) Excellent 

49

Holiday cottage in San Gimignano

Province of Siena / San Gimignano

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Nearest beach 75 km
  • Child friendly
  • Pet friendly
Cottage view on San Gimignano country house countryside<br />The cottage is provided with baby bed and bay chair.Pets: maximum 2 (small)  …see more

from £52 / night

£363 / week

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from £52 / night

(8) Excellent 

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  …see more

from £61 / night

£423 / week

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from £61 / night

(6) Excellent 

27

Apartment rental in San Gimignano

Province of Siena / San Gimignano

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Ask about pets
Holiday in San Gimignano ... a journey into the heart of Tuscany.Dear Guests, we are the sisters Stefania and Margherita and we are the owners of Appartamento Margherita. We decided to rent the apartment where we were born about 15 years ago, when we underst  …see more

from £87 / night

£518 / week

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from £87 / night

(5) Excellent 

14

Holiday home in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Ask about pets
Elegant and bright apartment is located in the heart of Siena. The street is full of restaurants, cafes and shops. The apartment is in a historic building and can comfortably accommodate four people. Very close to bus and train station.<br />The apartment is locat  …see more

from £82 / night

£561 / week

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from £82 / night

(6) Excellent 

35

Monticiano / Tocchi

2 6 Min stay varies

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

 …see more

from £61 / night

£397 - £837 / week

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from £61 / night

48

Fort letting in Montisi with shared pool

Province of Siena / Montisi

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 £107 / night

£739 - £821 / week

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from £107 / night

(4) Excellent 

28

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
'Podere Collinella' has been re-built to a high standard, retaining the charm of a Tuscan farmhouse.The walls are of the old stone, chestnut beams support the ceiling, and positioned on a slight hill has wonderful views of the surrounding countryside. Podere C  …see more

from £69 / night

£475 - £595 / week

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from £69 / night

(25) Excellent 

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

from £134 / night

£871 - £1962 / week

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from £134 / night

(8) Excellent 

12

Province of Siena / Monteriggioni

2 4 3 nights min

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

 …see more

from £52 / night

£345 / week

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from £52 / 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 £76 / night

£525 / week

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from £76 / night

(1) Excellent 

45

Province of Siena / Montalcino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £225 / night

£1657 / week

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from £225 / night

24

Holiday villa in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
"Villa Palazzone" is a charming country house set in the heart of a large estate of 153 hectares. The property has been completely renovated and upgraded with all modern conveniences.  …see more

from £281 / night

£1716 - £2888 / week

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from £281 / night

(10) Excellent 

26

Province of Siena / Montepulciano

2 4 Min stay varies

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

 …see more

from £74 / night

£535 - £742 / week

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from £74 / night

14

Holiday farmhouse rental

Province of Siena / Colle di Val d'Elsa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Our farm is the only one with a horse on the property, offers a beautiful view, surrounded by green gardens, with a wood-burning oven in the central courtyard and have WI-FI internet access. We offer many services and activities of a different kind, for everyone.  …see more

from £80 / night

£453 - £785 / week

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from £80 / night

(6) Very Good 

45

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £78 / night

£475 - £500 / week

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from £78 / night

15

Holiday townhouse in Pienza

Province of Siena / Pienza

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 100 km
  • Child friendly
  • Car not necessary
In the very center of a lovely ancient medieval village stands Casa Marelli. Recently carefully restored preserving all the traditional Tuscan characteristics of the building such as wooden beamed ceilings and brick work arches. It was meant to become the owner's r  …see more

from £108 / night

£755 - £970 / week

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from £108 / night

(18) Excellent 

24

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 170 km
  • Child friendly
  • Car not necessary
“Well maintained apartment and very helpful owner” Elias iwas most helpful meeting us on arrival and going through everything with us and all places to visit in the area even giving us a map with this all marked on The apartment is beautifully kept and  …see more

from £103 / night

£603 - £1025 / week

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from £103 / night

15

Farmhouse rental in Colle di Val d'Elsa with shared pool

Province of Siena / Colle di Val d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Our farm is the only one with a horse on the property, offers a beautiful view, surrounded by green gardens, with a wood-burning oven in the central courtyard and have WI-FI internet access. We offer many services and activities of a different kind, for everyone.  …see more

from £69 / night

£374 - £755 / week

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from £69 / night

(3) Excellent 

25

Province of Siena / Vivo d'Orcia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 70 km
  • Ski
  • Child friendly

 …see more

from £61 / night

£388 / week

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from £61 / night

15

Province of Siena / Castellina In Chianti

1 2 3 nights min

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

 …see more

from £48 / night

£332 / week

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from £48 / night

(2) Excellent 

34

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 £52 / night

£276 - £397 / week

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from £52 / 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
“Perfect holiday location” Our family group of 8 adults spent 5 nights at Villa LisiDor - a perfect location for both relaxing & a great base for exploring the local region. The roads in Chianti can be narrow & windy but worth the drive to villages lik  …see more

from £409 / night

£2858 - £4397 / week

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from £409 / night

19

Crete Senesi holiday apartment rental

Asciano / Crete Senesi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Apartment in Tuscany , with special countryside vieuw from private terrace. At only 20 minutes from Siena. 2 km from village. Swimming pool in garden  …see more

from £95 / night

£357 - £690 / week

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from £95 / night

(1) Excellent 

27

Holiday barn with swimming pool in Quercegrossa

Monteriggioni / Quercegrossa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Restored Barn, description: this ground floor flat has an entrance with three large glass doors. The main living area has an open fireplace and is divided into a sitting room and a large kitchen. Dining table, wicker armchairs. Sofa bed for one person. From this room th  …see more

from £82 / night

£449 - £871 / week

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from £82 / night

(2) Excellent 

24

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

 …see more

from £113 / night

£664 - £992 / week

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from £113 / night

(3) Excellent 

24

Province of Siena / Castiglione D'Orcia

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
  • Pet friendly

 …see more

from £47 / night

£328 - £488 / week

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from £47 / 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 £302 / night

£2069 - £4604 / week

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from £302 / night

(16) Very Good 

27

Holiday apartment in Sant Andrea a Montecchio

Siena / Sant Andrea a Montecchio

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 km
  • Child friendly
  • Car not necessary
“Reality of a dream!” I was looking for a quiet week with a beautiful panorama not far from Siena, to enjoy after the Palio and before participating in an intensive celebration later in July within Siena. I studied the information on Sant'Andrea a Mon  …see more

from £52 / night

£302 - £518 / week

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from £52 / night

(16) Excellent 

22

Casole d'Elsa holiday cottage rental

Province of Siena / Casole d'Elsa

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 £130 / night

£776 - £1164 / week

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from £130 / 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 £44 / night

£302 / week

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from £44 / 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 £108 / night

£664 - £992 / week

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from £108 / night

(9) Excellent 

52

Province of Siena / Montepulciano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

 …see more

from £138 / night

£733 / week

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from £138 / night

(1) Very Good 

39

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £104 / night

£604 - £755 / week

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from £104 / 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 £78 / night

£544 / week

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from £78 / night