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

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Province of Siena

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4,295 Holiday homes

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

100

Holiday apartment with shared pool in Asciano

Province of Siena / Asciano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
These accommodations offer a swimming pool, a living room with dining area, fully equipped kitchen and one or two bathrooms with shower or bathtub. Guests are accommodated in double, twin or single bedrooms.  …see more

from £91 / night

£449 - £656 / week

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from £91 / 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

(1) Excellent 

21

Holiday apartment in Tognazza

Province of Siena / Tognazza

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
“Great location to explore Tuscany from.” Lovely apartment with everything you need to be comfortable. Location was great for exploring Tuscany. Saverio (host) was also very helpful. Would recommend highly.  …see more

from £35 / night

£242 / week

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from £35 / night

Featured properties

(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

(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 £85 / night

£569 - £1078 / week

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from £85 / night

47

Province of Siena / San Gimignano

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 50 km
  • Child friendly
  • Private garden

 …see more

from £60 / night

£337 / week

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from £60 / night

100

Holiday apartment in Guazzino

Sinalunga / Guazzino

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 0.3 km
  • Child friendly
This exclusive loft with breath taking views is the ideal reantal for a couple. The apartment Located in south of Tuscany is in a very good position to explore, Siena Area.  …see more

from £38 / night

£266 - £332 / week

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from £38 / night

35

Holiday villa rental

Province of Siena / Ville di Corsano

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
The large 800 sqm villa is an ancient historical residence. Villa Siena, an 18th century villa, rises within a se cluded parkland in the hills of Tuscany. The theme of the outdoors continues in the elegant drawing room, formerly a ballroom, whose vaulted ceiling and wal  …see more

from £585 / night

£4095 - £6250 / week

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from £585 / night

(4) Excellent 

23

Holiday apartment in Val di Merse

Siena / Val di Merse

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly
Apartment Raffaello is a warm and welcoming apartment set in a XVth century villa, recently restored by a sensitive and art historically conscious architect and designer.The very best of the Tuscan tradition where nature and culture have mingled for centuries.  …see more

from £104 / night

£690 - £863 / week

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from £104 / night

(1) Very Good 

12

Province of Siena / Colle di Val d'Elsa

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min

 …see more

from £39 / night

£242 / week

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from £39 / night

(21) Excellent 

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
“Brilliant location, fantastic views and the warmest of welcomes.” We have just returned from Casa Verbena having had a fabulous time. The accommodation is very spacious and exceptionally clean and well equipped. The pictures of the apartment do not il  …see more

from £87 / night

£475 - £733 / week

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from £87 / night

15

Colle di Val d'Elsa holiday farmhouse rental

Province of Siena / Colle di Val d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet 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

(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

25

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 £42 / night

£294 - £587 / week

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from £42 / night

(7) Excellent 

25

Province of Siena / Siena

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Child friendly

 …see more

from £82 / night

£500 - £630 / week

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from £82 / night

24

Villa rental in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
This holiday home has 3 bedrooms and 2 bathrooms and can accomodate 6 people making it ideal for families. Located in Siena, Tuscany this property is a pet friendly space .  …see more

from £74 / night

£517 - £957 / week

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from £74 / night

(4) Excellent 

53

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa / Montegabbro

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets
Casa Arianna self-cathering apartment in Montegabbro, a very little 12th century village in the hearth of Tuscany with Etruscan and Roman traces. Ideal for families seeking relaxation.<br />Private area outside to enjoy the quite of the village and the Tuscan coun  …see more

from £52 / night

£302 - £423 / week

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from £52 / night

(1) Excellent 

9

Province of Siena / Pienza

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £61 / night

£414 - £647 / week

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from £61 / night

(1) Excellent 

17

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
<p><span class="x_style25">Italian village rental - This charming historic residence with private pool is located in the village of San Giovanni d'Asso, and it is just a short stroll from your door to the castle, the truffle museum and a nice  …see more

from £250 / night

£1750 - £2460 / week

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from £250 / night

(2) Excellent 

16

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Suitable for children age 5+
nice and comfortable apartment in the old town of Montepulciano Placed in the Historical Centre, just a few steps to the most beautiful and oldest wine cellar in Montepulciano (Cantina del Redi dè Ricci) an amazing sixteenth-century structure, great-looking wit  …see more

from £65 / night

£388 / week

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from £65 / 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

(11) Very Good 

31

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • 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 £100 / night

£694 / week

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from £100 / night

(1) Very Good 

30

Holiday home in Siena

Province of Siena / Siena

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 100 km
  • Child friendly
  • Private garden
Only 20km outside the charming city of Siena, my cottage is emerging in a forest on top of a hill. Ideal for biking and hiking. My cottage is exclusive for you! Perfect for enjoyable holidays or for a working context. WiFi-connection. A picturesque mosaic of fields an  …see more

from £62 / night

£432 - £649 / week

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from £62 / night

18

Holiday apartment in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 85 km
  • Child friendly
  • Car not necessary
Brown apartment Central and cosy apartment with double bedroom, bathroom with shower, large living area with sofa bed, equipped kitchen, private equipped garden, free WIFI, TV, air conditioning.<br />Upon request as extra services: cooking classes, wine tours, e  …see more

from £52 / night

£363 / week

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from £52 / night

16

Siena / Sant Andrea a Montecchio

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £61 / night

£423 / week

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from £61 / night

12

Province of Siena / San Quirico d'Orcia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min

 …see more

from £74 / night

£492 / week

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from £74 / night

8

Province of Siena / Cetona

5 12 5 nights min

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min
  • Private garden

 …see more

from £255 / night

£1768 / week

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from £255 / night

(7) Very Good 

22

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly

 …see more

from £82 / night

£500 / week

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from £82 / 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

(4) Excellent 

20

Farmhouse rental in Radicofani with swimming pool

Province of Siena / Radicofani

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
A 17th century stone hamlet situated in one of the most wonderful position of Tuscany. The apartment is characterised by good taste and warmth, equipped with a fireplace and elegantly furnished with furniture from the era. Park, scenic swimming pool.  …see more

from £138 / night

£544 - £923 / week

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from £138 / night

(9) Excellent 

5

Province of Siena / Rapolano Terme

4 4 1 night min

  • 4 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £113 / night

£785 / week

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from £113 / night

(4) Excellent 

18

Farmhouse rental in Radicofani with shared pool

Province of Siena / Radicofani

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
A 17th century stone hamlet situated in one of the most wonderful position of Tuscany. The apartment is furnished tastefully and with exclusive period furniture, fireplace, Sky TV, independent heating, external private space. Park, scenic swimming pool.  …see more

from £104 / night

£518 - £733 / week

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from £104 / night

(1) Very Good 

31

Montisi holiday villa rental

Province of Siena / Montisi

5 6 Min stay varies

  • 5 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
We offer a relaxed holiday, You can lounge by the pool soaking up the sun or visit the many cities of intrest Siena, Florence and Rome are all very close. And of course the local places of Intrest. The spa, Pienze home of the English Patient and within view of your home  …see more

from £129 / night

£858 - £1548 / week

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from £129 / night

5

Province of Siena / Rapolano Terme

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £78 / night

£544 - £604 / week

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from £78 / 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 £184 / night

£1285 - £1716 / week

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from £184 / night

(2) Excellent 

22

Province of Siena / Castellina In Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly

 …see more

from £37 / night

£259 - £388 / week

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from £37 / 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

£449 - £932 / week

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from £82 / night

(1) Very Good 

20

Province of Siena / San Gimignano

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £200 / night

£1047 / week

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from £200 / night

24

Holiday farmhouse in Siena

Province of Siena / Siena

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANYVilla Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city  …see more

from £117 / night

£815 / week

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from £117 / night

(2) Very Good 

100

Castellina In Chianti holiday villa rental

Province of Siena / Castellina In Chianti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This grand house, with 5 bedrooms and 5 bathrooms can host 10 people, so it is ideal for large families. Located in Tuscany Italy, this house offers a swimming Pool, an internet Connection .  …see more

from £340 / night

£1982 - £2969 / week

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from £340 / night