Holiday rentals in Province of Siena: Villas, Cottages and Apartments

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Province of Siena

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4,024 Holiday homes

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(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
“Fabulous holiday!” We had an absolutely great holiday in Tuscany. La Fontanella is ideally located to everything we wanted to do. 10 mins to beautiful San Giminiano, less than an hour to Florence, Siena and Chianti. Comfortable house, lovely terrace,  …see more

from £60 / night

£453 - £808 / week

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from £60 / night

19

Holiday villa in Pienza

Province of Siena / Pienza

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful independent country house near Pienza. This villa is located few minutes driving from Pienza, in a quiet and beautiful location in the middle of the country side. Private swimming pool.<br />The villa is elegantly furnished, in a perfect combination betw  …see more

from £157 / night

£1095 - £2052 / week

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from £157 / night

(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 £69 / night

£428 - £471 / week

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from £69 / night

Featured properties

32

Farnetella holiday villa rental

Sinalunga / Farnetella

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Beautiful and characteristic villa made of stone and bricks and completely restored to be a welcoming holiday home, situated on the green hills of the Siena countryside, 6 km far from the village of Sinalunga endowed with every kind of shops and services.  …see more

from £171 / night

£1197 - £2223 / week

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from £171 / night

(1) Excellent 

9

Province of Siena / Montepulciano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 100 km
  • Child friendly

 …see more

from £52 / night

£300 / week

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from £52 / night

(1) Excellent 

8

Province of Siena / Strove

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Private garden

 …see more

from £43 / night

£300 / week

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from £43 / night

(5) Excellent 

24

Province of Siena / Radda in Chianti

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £82 / night

£569 - £689 / week

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from £82 / night

(1) Very Good 

24

Holiday apartment rental

Colle di Val d'Elsa / Campiglia dei Foci

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
These lovely rental apartments in Tuscany are located on a plateau in the heart of the Chianti countryside at only 5 km from Colle Val d'Elsa, internationally renowned for the production of crystal glassware and art.  …see more

from £72 / night

£500 - £812 / week

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from £72 / night

(3) Very Good 

24

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
“Well-located and roomy house” We were 10 adults and two children (three generations) spending one week at the house in May of 2014. We found the house very suitable (for five couples) since it had five large bedrooms. It was very convenient that each  …see more

from £232 / night

£1624 - £2906 / week

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from £232 / night

25

Pienza holiday lodge rental

Province of Siena / Pienza

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Air conditioning
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £73 / night

£509 - £808 / week

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from £73 / night

(6) 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
The Villa and its gardens are a National Heritage property and there is a great deal to see and enjoy!  …see more

from £385 / night

£2351 / week

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from £385 / night

52

Holiday villa rental

Poggibonsi / Staggia Senese

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Villa Senese is an ancient mansion dating back to the eighteenth century, located in the heart of Chianti Senese, just 17 km away from Siena and 45 Km from Florence. Villa Senese is an holiday villa in Tuscany, located in a vantage position on a hill above the old town  …see more

from £513 / night

£3590 - £4787 / week

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from £513 / night

(2) Very Good 

20

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
holiday apartments in Montepulciano. Farm stay in a wine estate in Montepulciano  …see more

from £69 / night

£432 - £808 / week

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from £69 / night

(2) Very Good 

19

Montalcino holiday studio rental

Province of Siena / Montalcino

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Air conditioning
One large and cosy suite with a high ceiling with the typical wooden beams and wooden floor. There's a fully equipped kitchen, a small sitting area, a double bed with a restored big old Tuscan wardrobe. The private bathroom is with shower in travertine. The suite i  …see more

from £142 / night

£988 / week

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from £142 / night

20

Radicondoli holiday apartment rental

Province of Siena / Radicondoli

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
On the ground floor of a 1600 Villa ,completely renovated for the maximum comfort of guests. All windows facing the valley and the natural reserve below.50 square meter private terrace with incredible view on the countryside.15x4 meter swimming pool .  …see more

Pricing unknown

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Pricing unknown

(2) Excellent 

63

Villa rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Villa Bossona is an impressive villa which dates back to the eighteenth century. Ideal for quiet and relaxing holidays it is located in the sweet Montepulciano hills few minutes from the town. A small church with an enchanting bell tower is preserved in its original for  …see more

from £513 / night

£3334 - £3676 / week

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from £513 / night

(13) Excellent 

41

Asciano / Crete Senesi

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

 …see more

from £60 / night

£419 - £727 / week

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from £60 / night

(1) Excellent 

25

Murlo / Casciano di Murlo

5 11 3 nights min

  • 5 bedrooms
  • Sleeps 11
  • 3 nights min
  • Nearest beach 70 km
  • Child friendly
  • Private garden

 …see more

from £76 / night

£530 - £693 / week

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from £76 / night

22

Villa rental in San Giovanni d'Asso with swimming pool

Province of Siena / San Giovanni d'Asso

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
<p><span class="x_style25">Centred around a pretty garden, Casa Vittorio is a notable, historic residence set over several levels and elegantly furnished. It is in a village location, just a short stroll from a restaurant, the castle and the truffl  …see more

from £686 / night

£4800 - £5850 / week

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from £686 / night

(1) Excellent 

12

Province of Siena / Cetona

5 6 Min stay varies

  • 5 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 28 km
  • Swimming pool
  • Child friendly

 …see more

from £300 / night

£2095 / week

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from £300 / night

(13) Excellent 

25

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
In the deep core of old part of Montepulciano, quiet and in the middle of of streets of monuments, art shops, restaurants and wine shops and cellars.  …see more

from £77 / night

£359 - £453 / week

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from £77 / night

(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 £248 / night

£1701 - £8975 / week

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from £248 / night

(3) Very Good 

22

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary

 …see more

from £95 / night

£582 - £821 / week

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from £95 / night

100

Siena holiday apartment rental

Province of Siena / Siena

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 75 km
  • Child friendly
3 attractive apartments right in the centre of Siena, a privileged location very convenient for all the sites and restaurants but still quiet and private. The apartments can accommodate up to 4 or 5 and are ideal for both couples and families.  …see more

from £60 / night

£419 - £718 / week

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from £60 / night

(13) Excellent 

32

Province of Siena / Poggibonsi

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £112 / night

£778 - £1616 / week

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from £112 / night

(2) Very Good 

27

San Gusme holiday villa rental

Castelnuovo Berardenga / San Gusme

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Private garden
“wonderful and peaceful place” San Donato is very quiet, a very beautiful place, the garden and all the Villa Arceno aera are amazing, the house is simple but comfortable, and with a soul, as if you ever know this place, I will return one day, for sure  …see more

from £182 / night

£1274 - £1701 / week

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from £182 / night

(1) Excellent 

100

Holiday apartment in Siena

Province of Siena / Siena

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Nearest beach 75 km
  • Child friendly
3 attractive apartments right in the centre of Siena, a privileged location very convenient for all the sites and restaurants but still quiet and private. The apartments can accommodate up to 4 or 5 and are ideal for both couples and families.  …see more

from £73 / night

£509 - £838 / week

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from £73 / night

(2) Very Good 

17

Holiday farmhouse rental

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
Self catering Farmhouse and 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 one hour .  …see more

from £63 / night

£424 - £941 / week

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from £63 / night

36

Holiday villa in Castelmuzio

Province of Siena / Castelmuzio

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
This little, two-storey, converted Tuscany farmhouse has been meticulously restored in a simple, rustic style, employing high-quality traditional materials. Set on a gentle elevation in a remote spot, it is entirely surrounded by the clay hills called “Crete Senes  …see more

from £154 / night

£898 - £1283 / week

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from £154 / 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 £60 / night

£419 / week

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from £60 / night

(9) Excellent 

18

Holiday farmhouse with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“peaceful paradise” This villa met all our expectations. The view from the bedrooms and the terrace were spectacular. Location in small village was perfect. Villa had special arragements for food delivery from local restaurants. Vila was spotless an  …see more

from £84 / night

£565 - £1069 / week

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from £84 / 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
“Comfortable base in the heart of Tuscany” Poggio Saragio is located on a quiet lane among vineyards and orchards, with beautiful views across rolling hills in central Tuscany - sitting on the back terrace taking in the amazing views and colours and l  …see more

from £100 / night

£500 - £895 / week

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from £100 / night

17

Farmhouse letting in Pienza with shared pool

Province of Siena / Pienza

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Apartment in Monticchiello with 2 bedrooms sleeps 4  …see more

from £66 / night

£385 - £674 / week

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from £66 / night

(2) Very Good 

29

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
.This charming accommodation lies in the countryside enjoying the most marvellous views of the undulating landscape and the towers of the city of San Gimignano only 3km away. It is a lovely location for enjoying country walks and relaxing<br />The pool and the gar  …see more

from £171 / night

£1197 - £1795 / week

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from £171 / night

(6) Excellent 

37

Torrita di Siena / Montefollonico

2 5 2 nights min

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

 …see more

from £103 / night

£1112 - £2009 / week

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from £103 / night

26

Holiday apartment with shared pool in Torrita di Siena

Province of Siena / Torrita di Siena

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
This lovely country house with pool in Tuscany is located at 1.5km from the beautiful medieval village of Torrita di Siena, in the heart of Val di Chiana, only 15 km from Pienza and Montepulciano, and 48 km from Siena. Situated on a knoll, the 18th-century farmhouse is  …see more

from £43 / night

£300 - £556 / week

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from £43 / night

4

Province of Siena / Orgia

1 3 30 nights min

  • 1 bedroom
  • Sleeps 3
  • 30 nights min
  • Nearest beach 80 km
  • Private garden

 …see more

from £15 / night

£100 / week

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from £15 / night

(1) Excellent 

9

Province of Siena / Pienza

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 98 km
  • Swimming pool
  • Child friendly

 …see more

from £180 / night

£607 - £983 / week

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from £180 / night

(3) Very Good 

26

Holiday apartment rental

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Just as expected!” From our first enquiry, the owners were always so helpful and our stay at the Muricce was everything we wanted it to be. This is a wonderful place to stay, and to tour from. There is something to see or to visit in all directions.  …see more

from £82 / night

£445 - £924 / week

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from £82 / night

(11) Excellent 

33

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
“Great stay!” Luca was wonderful to work with. He gave us directions on how to meet him and took us to the apartment to unload the car then helped us find a parking spot. Apartment was very nice, comfortable and close to the city center. Luca was alwa  …see more

from £77 / night

£445 - £541 / week

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from £77 / night