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

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Province of Siena

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4,014 Holiday homes

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

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 £199 / night

£1389 - £2105 / week

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from £199 / 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

(6) Very Good 

24

Farmhouse rental in Caprera

Siena / Caprera

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning
Elegant Liberty farmhouse on the hills, in a quite village just ten minutes from Siena city centre. Stunning view toward the city steeples across the countryside. Olive groves and fields for walking and horse riding. Garden and farm yard for outdoor dining.  …see more

from £163 / night

£1069 / week

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from £163 / night

Featured properties

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 £106 / night

£733 - £814 / week

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from £106 / night

(1) Excellent 

28

Apartment rental in Torrita di Siena with shared pool

Province of Siena / Torrita di Siena

1 5 7 nights min

  • 1 bedroom
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

from £47 / night

£325 - £582 / week

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from £47 / 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 £103 / night

£684 - £855 / week

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from £103 / 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 £77 / night

£471 - £496 / week

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from £77 / night

(1) Excellent 

18

Sinalunga holiday apartment rental

Province of Siena / Sinalunga

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
In the heart of the countryside only 40 minutes from Siena five beautiful apartments have been made by restoring an old Tuscan country house set on a hillside with views all around. Each apartment retains its fascinating original characteristics. A courtyard around the  …see more

from £88 / night

£607 - £1069 / week

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from £88 / night

(3) Excellent 

12

Farmhouse rental in Val di Merse

Siena / Val di Merse

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
The property PODERE SORTOIANO dates back to the 14th century and for generations has been part of the property Santini, once farmers. The apartments, as well as the "hut" were once stables for livestock. It has now been restored by the Santini family with much  …see more

from £48 / night

£317 - £377 / week

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from £48 / night

(2) Excellent 

25

Holiday villa with swimming pool in Montisi

Province of Siena / Montisi

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“An undiscovered treasure” A well appointed and comfortable villa facing south overlooking beautiful Tuscan countryside with the abbey S Anna Camprena in the distance. This abbey of the film English Patient fame. Montisi is a wonderful small village w  …see more

from £123 / night

£855 - £1048 / week

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from £123 / night

20

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Apartment in Monticchiello with 2 bedrooms sleeps 5  …see more

from £79 / night

£462 - £808 / week

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from £79 / night

(2) Very Good 

18

Holiday apartment in Sarteano

Province of Siena / Sarteano

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 120 km
  • Child friendly
“good location & helpful landlord” Sarteano is a great location for seeing the rest of Tuscany and for experiencing "la dolce vita" in a small town. The people of Sarteano are very nice and helpful. The owner, Leonardo was especially helpful wit the a  …see more

from £52 / night

£248 / week

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from £52 / night

(13) Excellent 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect and plaisant location to explore Tuscany” We were 4 people staying in this very nice apartment : comfortable, clean, modern, well equipped. We loved the location. I never heard of Gaiole before, but it was a nice discovery. Quiet village, but  …see more

from £175 / night

£1100 - £1600 / week

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from £175 / night

(1) Excellent 

21

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 £257 / night

£1368 - £1710 / week

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from £257 / night

(12) Excellent 

49

Holiday villa in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“Gorgeous villa in Tuscany” This is a gorgeous villa in the tuscan countryside. The villa was beautiful, spotless and had everything we needed. It is right next to the small town of San Giovanni D'Osso. My 16-year-old loved it as well. While we day-tri  …see more

from £464 / night

£3248 - £4189 / week

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from £464 / 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

£603 - £877 / week

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from £87 / night

(5) Excellent 

24

Province of Siena / Montepulciano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly

 …see more

from £67 / night

£394 / week

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from £67 / night

100

Guazzino holiday apartment rental

Sinalunga / Guazzino

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 100 km
  • Child friendly
Lovely apartment located in Bettolle (sinalunga), the apartment is air conditoned and it offers a big living room with double sofa bed, fully equipped kitchen, double bedroom, bathroom with shower and terrace.  …see more

from £42 / night

£294 - £593 / week

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from £42 / 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 £73 / night

£530 - £736 / week

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from £73 / 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 £43 / night

£291 - £375 / week

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from £43 / 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 £82 / night

£556 - £1283 / week

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from £82 / night

(33) Excellent 

32

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Fabulous holiday and accommodation” We stayed at this apartment in June this year. The apartment was really well fitted out and spotlessly clean, the oven looked like it had never been used !! The facilities were great and the location is lovely, it i  …see more

from £86 / night

£471 - £727 / week

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from £86 / night

20

Villa rental in Val d'Orcia with swimming pool

Montalcino / Val d'Orcia

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Villa Bandini is located only 300 meters from the hamlet of Lucignano d’Asso on top of a hill on the border between the Val d’Orcia and the Sienese clay hills. Lucignano d’Asso is a medieval ancient hamlet which, since the XV century, has belonged to t  …see more

from £401 / night

£2806 / week

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from £401 / 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

7

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets

 …see more

from £69 / night

£471 - £710 / week

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from £69 / night

16

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Apartment in Monticchiello with 3 bedrooms sleeps 6  …see more

from £100 / night

£589 - £962 / week

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from £100 / night

(1) Very Good 

39

Farmhouse rental in Castel San Gimignano with shared pool

San Gimignano / Castel San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Silence, privancy  …see more

from £171 / night

£1154 - £1881 / week

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from £171 / night

20

Holiday farmhouse rental

Province of Siena / Pienza

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Nearest beach 44 km
  • Swimming pool
  • Child friendly
Wonderful Tuscan villa with pool.  …see more

from £352 / night

£2462 - £6342 / week

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from £352 / night

(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

(5) Excellent 

23

Holiday apartment in Pienza

Province of Siena / Pienza

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
“Fantastic place - great selection of restaurants” Truly a maginificent apartment exceeding our expectations - really nice to cool down in the jacuzzi overlooking Montalcino when the weather was at its hottest ! Also very convenient with regards to  …see more

from £120 / night

£838 / week

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from £120 / 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

£354 - £684 / week

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from £95 / night

19

Holiday cottage with swimming pool in Sarteano

Province of Siena / Sarteano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Cottage with swimming pool and small lake.  …see more

from £184 / night

£1283 - £1949 / week

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from £184 / night

(32) Excellent 

24

Gaiole in Chianti holiday apartment accommodation

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
“A Little Corner of Heaven” This was our fourth visit to Gaiole in Chianti and our third stay in this apartment. The apartment is modern, well furnished and equipped and spotlessly clean. The garden is beautiful and a real bonus. It is a wonderful  …see more

from £60 / night

£420 - £665 / week

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from £60 / night

31

Asciano holiday villa let

Province of Siena / Asciano

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
This is a spectacular villa, immaculately furnished and presented in a wonderful part of Italy. The owners have imported furniture from around the world to create a unique setting for guests to enjoy their stay. Complete with private pool and beautiful gardens, it'  …see more

from £300 / night

£1667 - £3590 / week

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from £300 / night

100

Siena holiday apartment rental

Province of Siena / Siena

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
This beautiful estate in Tuscany includes both a b&b offering a range of lovely rooms and suites as well as fabulous apartments. These all have the outdoor swimming pool, tennis court and restaurant, and other facilities at their disposition.  …see more

from £85 / night

£593 - £1012 / week

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from £85 / night

(1) Very Good 

36

Province of Siena / Siena

11 20 1 night min

  • 11 bedrooms
  • Sleeps 20
  • 1 night min
  • Child friendly
  • Car not necessary

 …see more

from £77 / night

£539 / week

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from £77 / night

(1) Excellent 

14

Province of Siena / Castelnuovo Berardenga

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

 …see more

from £39 / night

£240 - £449 / week

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from £39 / night

11

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

 …see more

from £60 / night

£377 / week

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from £60 / 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 £129 / night

£770 - £1154 / week

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from £129 / night

(2) Excellent 

13

Holiday apartment in Rapolano Terme

Province of Siena / Rapolano Terme

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Private garden
L'appartamento nasce dalla ristrutturazione di un ovile al piano terra, ha spesse e antiche mura, cucina attrezzata e luminosa con porta a vetri sul giardino, una zona armadi antistante il bagno, molto curato, un ampio salone con camino e seconda porta sull'es  …see more

from £30 / night

£210 / week

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from £30 / night