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

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Province of Siena

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4,256 Holiday homes

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

11

Holiday apartment in Torrita di Siena

Province of Siena / Torrita di Siena

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
This beautiful holiday home is located at 200 mt from the pretty medieval village of Torrita di Siena, only 15 km from Pienza and Montepulciano, in the heart of Val di Chiana, an attractive valley in the south-east of the region. The farmhouse faces on a side the villag  …see more

from £63 / night

£207 - £436 / week

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from £63 / night

24

Monteriggioni holiday villa rental

Province of Siena / Monteriggioni

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
<span class="x_style25">Villa near Monteriggioni : Located in the heart of Tuscany, to the south of Florence, Villa Gianni is an attractive, small property, recently renovated and well furnished throughout. There are classic Tuscan views of vineyards and  …see more

from £219 / night

£1530 - £2410 / week

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from £219 / night

(2) Excellent 

21

Holiday guest house in Radicondoli

Province of Siena / Radicondoli

3 5 4 nights min

  • 3 bedrooms
  • Sleeps 5
  • 4 nights min
  • Nearest beach 60 km
  • Suitable for children age 5+
  • Ask about pets
“Paradise in Radicondoli” We absolutely loved our stay at Casa Sulle Mura. Radicondoli is a beautiful town. We enjoyed the people there and especially enjoyed the evenings when people sit out and enjoy. The house is wonderful, clean and spacious.  …see more

from £138 / night

£690 / week

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from £138 / 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

(3) Excellent 

32

Holiday farmhouse in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic. We restored the farmhouse of the 15th century and Giovanni has personally followed all the wor  …see more

from £95 / night

£561 / week

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from £95 / 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 

23

Holiday villa with shared pool in Montepulciano

Province of Siena / Montepulciano

4 2 Min stay varies

  • 4 bedrooms
  • Sleeps 2
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Ask owner if suitable for children
“Old-world Italian charm in a beautiful Tuscan setting” It's a job to find it it, but once you do, you'll want to stay longer than you've booked for. The house has been in the family since 1812 - they produce their own wine - and Olimpia is a charming  …see more

from £44 / night

£302 / week

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from £44 / night

50

Holiday apartment in Montalcino

Province of Siena / Montalcino

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Suitable for children age 5+
The views from the terrace, the convenience of being right in the middle of things without needing a car to get food, lunch or dinner, and the beautifully renovated 17th century apartment.  …see more

from £281 / night

£1725 - £2414 / week

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from £281 / 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

(4) Excellent 

17

Holiday home in Cetona

Province of Siena / Cetona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about pets
“A real tase of Tuscany” If you're looking for an authentic old town stay then you'll be very happy. Great location in the old town and so close to lots small towns to explore. Train to Florence as a day trip. Large rooms cumfy beds and amazing views f  …see more

from £61 / night

£423 / week

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from £61 / night

(3) Excellent 

31

Holiday farmhouse with swimming pool in Monteriggioni

Province of Siena / Monteriggioni

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Beautiful apartment in glorious country setting in easy reach of Florence, Sienna and other picturesque Tuscan towns” Our host, Grazia, was spot on, really lovely. We were able to communicate in a hilarious mixture of English and Italian. She was fri  …see more

from £65 / night

£453 / week

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from £65 / night

(5) Very Good 

49

Montisi holiday fort rental

Province of Siena / Montisi

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
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

(1) Very Good 

24

San Gimignano holiday cottage rental

Province of Siena / San Gimignano

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Self-catering Tuscany cottage with stunning views over the Chianti hills, half way (35 km) between Florence and Siena.  …see more

from £87 / night

£604 - £1682 / week

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from £87 / night

27

Radicondoli holiday home rental

Province of Siena / Radicondoli

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
This typical stone house is situated in a panoramic position about 200 m. from Radicondoli, a characteristic and attractive mediaeval village (population 1.000) situated in a hilly position about 45 km from Siena. Guests can therefore avail of all the facilities availa  …see more

from £95 / night

£561 - £1294 / week

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from £95 / night

18

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This stone house was originally inhabited by a large family of farmers who worked for the monks of the nearby Abbey of Spineto. Excellent furnishing.Ground floor: large kitchen, with wood fired oven, opening directly onto the garden, spacious dining room, study  …see more

from £392 / night

£2742 - £3871 / week

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from £392 / 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 £518 / night

£3621 - £4828 / week

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from £518 / night

(3) Excellent 

22

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Rustic and romantic apartment for up to 7 people (5+2) with swimming pool (1 May-1 Oct), four-poster beds, rustic, classic furniture, air cond, garden, terrace, private sunbeds / umbrellas.Situated near San Gimignano with breathtaking views all the way to Volterra<b  …see more

from £36 / night

£250 - £854 / week

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from £36 / 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
Tenuta di Argiano a Montepulciano Please ask always AVAILABILITY , we will find in one of our structures the ideal place for your holiday. CAR IS NECESSARY WE ARE IN THE MIDDLE OF COUNTRYSIDE, SURROUNDED BY NATURE. The beautiful apartment FIASCO (60square Mt) , FOR  …see more

from £61 / night

£423 / week

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from £61 / night

(9) Excellent 

16

Holiday farmhouse in San Gimignano

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
House with two apartments near San Gimignano in TuscanyHoliday Apartment offers 2 flats inside an old barn that were recently restructured.Both the apartments can accommodate up to 4 people and are composed of a bedroom with bathroom, a small bedroom and a dinin  …see more

from £63 / night

£432 - £785 / week

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from £63 / night

(8) Excellent 

24

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic Villa and location shame about the weather” The villa was fantastic with extremely hospitable hosts. Grandma provided us with her fantastic home made cake and olive oil. Grandad provided us with home grown beans and lettuce. The Villa is sit  …see more

from £138 / night

£949 / week

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from £138 / night

(9) Excellent 

42

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Private garden

 …see more

from £95 / night

£604 - £785 / week

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from £95 / night

21

Holiday b&b in Acquaviva di Montepulciano

Montepulciano / Acquaviva di Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Tenuta di Argiano a Montepulciano, located near MONTEPULCIANO, is surrounded by vineyards growing grapes for the famous local wines, Vino Nobile di Montepulciano and Rosso di Montepulciano, and is peaceful and quite. swimming pool and wifi . bikes tour, spa nearby, It  …see more

from £59 / night

£411 / week

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from £59 / 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 

22

Pienza / Monticchiello

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £44 / night

£294 - £378 / week

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from £44 / night

20

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Suitable for children age 5+
  • Ask about pets

 …see more

Pricing unknown

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Pricing unknown

(4) Excellent 

19

Holiday farmhouse with swimming pool in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Farm estate living in Tuscany is pretty special, truly a unforgettable place to stay with fantastic owners” Great place to stay to truly get away and enjoy the relaxing Tuscany life. The chef at home was fantastic and the local shopping 5-10 minutes a  …see more

from £207 / night

£690 - £1932 / week

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from £207 / night

(3) Excellent 

20

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Rustic and romantic apartment for up to 6 people (4+2) with swimming pool, four-poster beds, rustic, classic furniture, air conditioning, garden, terrace, private sunbeds / umbrellas. Situated near San Gimignano with breathtaking views all the way to Volterra.<br /&  …see more

from £35 / night

£242 - £828 / week

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from £35 / 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

(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

(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

(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

(4) Excellent 

24

Cottage rental in Casole d'Elsa with swimming pool

Province of Siena / Casole d'Elsa

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly
“Beautiful location” The villa is lovely & bigger than it looks in the photos! I would recommend it although there are a couple of grumbles! The villa is definately not walking distance to the town. It is down a long, long gravel track, so beautiful  …see more

from £81 / night

£561 - £1207 / week

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from £81 / night

(1) Excellent 

16

Province of Siena / Sarteano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £259 / night

£1380 - £1725 / week

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from £259 / night

(3) Excellent 

20

Holiday apartment rental

Province of Siena / Cetona

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
The apartment is designed in a typical Italian style - it feels like a house. It offers wrought iron and marble accents, tile floors, wood beams and small yard.<br />Cetona is the ideal spot to explore southeast Tuscany and Umbria.  …see more

from £61 / night

£354 / week

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from £61 / night

36

Radicofani / Contignano

2 4 1 night min

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

 …see more

from £61 / night

£432 / week

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from £61 / night

18

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £48 / night

£311 - £371 / week

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from £48 / night

19

Province of Siena / Siena

1 3 2 nights min

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

 …see more

from £78 / night

£475 - £656 / week

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from £78 / night

(4) Very Good 

14

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly

 …see more

from £48 / night

£332 / week

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from £48 / night

21

Villa rental in Pienza

Province of Siena / Pienza

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 95 km
  • Child friendly
  • Private garden
Villa Arpicella really does offer the best of both worlds! Despite its prime location at just 10 minutes’ walking distance from Pienza, it enjoys the peace and quiet of a beautiful countryside setting with spectacular panoramic views. It is a large, traditionally  …see more

from £87 / night

£608 - £884 / week

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from £87 / night

(6) Very Good 

56

Torrita di Siena / Montefollonico

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £164 / night

£1147 / week

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from £164 / night