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

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Province of Siena

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4,240 Holiday homes

20

Villa rental in Castiglione D'Orcia with swimming pool

Province of Siena / Castiglione D'Orcia

1 21 7 nights min

  • 1 bedroom
  • Sleeps 21
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Farmhouse divided into apartments set in 10 hectares of private forest and with a large swimming pool.sjfa;sdl fjks;f as;fkl jfk;lj asfklj fklafj klfj ;fklj dfk;lj afklja sfkalsjd faklfj kldfj as;fkl ja;fkl jas  …see more

from £446 / night

£3119 - £6140 / week

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from £446 / night

16

Siena / Sant Andrea a Montecchio

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £60 / night

£416 / week

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from £60 / night

24

Holiday villa rental

Castelnuovo Berardenga / Vagliagli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Lovely house in the heart of the Chianti area, just 15 km from Siena. Situated in peaceful position, even though a secondary road passes 50 m away. The property is partly closed and the swimming pool, just below the house ground, has a lovely view over the val...  …see more

from £176 / night

£1232 - £2087 / week

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from £176 / night

(11) Excellent 

27

Holiday cottage with swimming pool, golf nearby in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“A lovely villa in beautiful surroundings.” We have recently returned from our first holiday in Tuscany with our two young sons and all agree that we will return to this area again. The villa although a short drive into Casole was situated amongst oli  …see more

from £114 / night

£678 - £975 / week

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from £114 / night

15

B&b rental in Serre di Rapolano

Rapolano Terme / Serre di Rapolano

1 1 Min stay varies

  • 1 bedroom
  • Sleeps 1
  • Min stay varies
  • Ask owner if suitable for children
  • Air conditioning
Poppy bedroom: single bed, private bathroom with shower, toilet, hairdryer, courtesy set, WiFi, Tv in room upon request, air conditioning. A stay at Antico Granaione b&b will delight You with unique and moving experiences.  …see more

from £34 / night

£238 / week

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from £34 / night

18

Holiday villa with swimming pool in Chiusi

Province of Siena / Chiusi

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Monica is a typical Tuscan, farm house from 1700, recently converted to a prestigious holiday home,is surrounded by woods, cultivated fields, olive groves and vineyards  …see more

from £290 / night

£1780 - £2628 / week

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from £290 / 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 £334 / night

£1949 - £2918 / week

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from £334 / night

41

Pienza / Monticchiello

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £149 / night

£1017 - £1187 / week

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from £149 / night

(1) Excellent 

15

Province of Siena / Siena

2 4 1 night min

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

 …see more

from £60 / night

£763 - £1178 / week

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from £60 / 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 £128 / night

£534 - £907 / week

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from £128 / night

(7) Excellent 

35

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £85 / night

£534 - £890 / week

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from £85 / night

(1) Excellent 

27

Holiday apartment with shared pool in Torrita di Siena

Province of Siena / Torrita di Siena

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
holiday lodging near Pienza. Torrita di Siena accommodation  …see more

from £50 / night

£348 - £649 / week

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from £50 / 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 £51 / night

£272 - £390 / week

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from £51 / night

(6) Excellent 

10

Pienza / Monticchiello

1 3 1 night min

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

 …see more

from £73 / night

£475 / week

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from £73 / night

39

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £113 / night

£789 / week

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from £113 / night

(1) Excellent 

24

Province of Siena / Sarteano

4 9 1 night min

  • 4 bedrooms
  • Sleeps 9
  • 1 night min
  • Nearest beach 120 km
  • Child friendly
  • Private garden

 …see more

from £43 / night

£297 / week

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from £43 / 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

£441 - £536 / week

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from £77 / night

(6) Excellent 

20

Apartment accommodation in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Comfortable new apartment in a traditional style, highly recommended.” The apartment has a lovely view over the town and the hills beyond. It's an easy walk down into the town centre which has bars, restaurants and a pizza cafe, though it's uphill (an  …see more

from £70 / night

£500 / week

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from £70 / night

24

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Air conditioning

 …see more

from £62 / night

£331 / week

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from £62 / night

(1) Excellent 

16

Province of Siena / Chianciano Terme

5 12 Min stay varies

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

 …see more

from £60 / night

£416 / week

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from £60 / 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

£297 - £551 / week

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from £43 / night

(1) Excellent 

36

Province of Siena / Buonconvento

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £100 / night

£695 - £1009 / week

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from £100 / night

33

Holiday apartment with shared pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
These holiday apartments in Tuscany are part of an estate situated in the Chianti Classico area, just 13 km from Siena, surrounded by vineyards and olive groves, in a peaceful place far from the traffic and bustle.  …see more

from £64 / night

£356 - £585 / week

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from £64 / night

(1) Excellent 

24

Montepulciano holiday villa rental

Province of Siena / Montepulciano

6 12 4 nights min

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
“Fantastic” A great villa in a great location. Because of a minor error in the booking the owner treated us all to a meal by personal chefs Dorians Ottaviana and Claudio from Cooking for You. They came to the villa and prepared a sumptuous 4 course mea  …see more

from £212 / night

£2077 / week

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from £212 / night

15

Province of Siena / Pienza

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £187 / night

£695 - £1102 / week

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from £187 / night

22

Chiusi holiday villa accommodation

Province of Siena / Chiusi

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Villa Baiocco is a typical Tuscan, historic farm house from 1700, recently converted to a prestigious holiday home - without losing its unique character and charm. Surrounded by 20'000m2 of well kept gardens, for your private use only, it offers all the peace and t  …see more

from £242 / night

£1695 - £3814 / week

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from £242 / 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 £246 / night

£1687 - £8899 / week

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from £246 / night

18

Holiday farmhouse in Poggibonsi

Province of Siena / Poggibonsi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The TUSCAN COUNTRYSIDE with its aligned vineyards, the olive trees that cover the hills, groves, the cypresses... It is a landscape that takes your breath away and gives you peace and quiet. And so dawns the realization that the most beautiful things in life are  …see more

from £81 / night

£525 - £830 / week

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from £81 / night

27

Montepulciano holiday villa rental

Province of Siena / Montepulciano

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
Villa Ardene provides its guests with high level services in a magical, peaceful and unforgettable atmosphere. All the suites and apartments are equipped with whirlpool bath, air conditioning, satellite TV, internet connection.The interior space in “arte pover  …see more

from £545 / night

£3814 - £6645 / week

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from £545 / 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

from £145 / night

£1009 - £1187 / week

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from £145 / night

15

Montalcino / Val d'Orcia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 80 km

 …see more

from £85 / night

£594 / week

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from £85 / night

(15) Very Good 

9

Province of Siena / Chianciano Terme

4 11 1 night min

  • 4 bedrooms
  • Sleeps 11
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £128 / night

£890 / week

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from £128 / night

(1) Excellent 

14

Holiday apartment in Monticiano

Province of Siena / Monticiano

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets
This apartment is in the historical center of a beautiful town near Siena. Its name is Monticiano. It's composed by 2 bedrooms (for 4 gests), 1 bathroom (with a shower box), 1 indipendent kitchen and a great dining room. The apartment is 75 mq. In the centre of this vi  …see more

from £51 / night

£339 - £382 / week

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from £51 / 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 £55 / night

£382 - £500 / week

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from £55 / night

(8) Excellent 

24

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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 £106 / night

£636 - £933 / week

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from £106 / night

28

Sinalunga holiday villa rental

Province of Siena / Sinalunga

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Agriturismo La Casetta nel Bosco is a beautiful, stone villa divided into two separate units which is part of an agritouristic Farm including olive groves, woods, several crops and a small-scale breeding of horses and ponies.  …see more

from £120 / night

£839 - £1628 / week

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from £120 / night

(12) Excellent 

78

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 £402 / night

£2810 - £4323 / week

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from £402 / night

(2) Very Good 

49

Province of Siena / Montepulciano

2 4 2 nights min

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

 …see more

from £128 / night

£594 / week

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from £128 / night

25

Apartment rental in Siena with shared pool

Province of Siena / Siena

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Beautiful Tuscan apartment with shared swimming pool, not far from Siena. It sleeps up to 10. It is an ideal place for families to spend a relaxing holiday far from town noises, among the peace of the countrside.A heaven of peace in the heart of the Montagnola Senese,  …see more

from £204 / night

£1187 - £1950 / week

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from £204 / night

(1) Excellent 

16

Holiday home letting

Province of Siena / Monteriggioni

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Il Casale è parte della proprietà denominata Molino Bianco, un antico mulino in pietra documentato fin dall’XI secolo come possedimento della famiglia Lambardi, signori di Staggia. Come annesso del fortilizio di Castiglionalto, il Molino fu abitato da una comunità  …see more

from £111 / night

£695 - £890 / week

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from £111 / night