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

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Province of Siena

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4,394 Holiday homes

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

(5) Excellent 

46

Holiday farmhouse rental

San Gimignano / Montauto

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
A typical stone barn immersed in the Tuscan countryside of San Gimignano. A large garden overlooks the hills and surrounding countryside. Up to 7 people in a both modern and rustic atmosphere.  …see more

from £214 / night

£1492 / week

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from £214 / night

(1) Excellent 

32

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect.” The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arri  …see more

from £286 / night

£2000 - £2579 / week

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from £286 / night

(1) Excellent 

24

Holiday apartment with shared pool in Casole d'Elsa

Province of Siena / Casole d'Elsa

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
On two floors, this apartment of 96 qm, on the ground floor has an entrance, a sitting room with a double divan bed, a dining room with fully equipped kitchenette and a small bedroom with two single beds..  …see more

from £158 / night

£992 - £1878 / week

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from £158 / night

34

Holiday villa in Pienza

Province of Siena / Pienza

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
it is the ideal place if you are looking to relax, private pool and beautiful view  …see more

from £206 / night

£1439 - £2351 / week

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from £206 / 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 £43 / night

£299 - £597 / week

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from £43 / night

19

Apartment rental in Montalcino with shared pool

Province of Siena / Montalcino

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
All the charm and comfort for an artistic stay in the heart of Tuscany. Montalcino has remained quite untouched and therefore has kept it's charming atmosphere. Moreover, if you love food and wine, especially Brunello, you cannot go wrong around here, come and enjo  …see more

from £154 / night

£1075 / week

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from £154 / night

24

Poggibonsi holiday villa rental

Province of Siena / Poggibonsi

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
This beautiful villa in Tuscany, Italy, sleeps 2 people, so it is perfect for honeymoons. The accommodation offers a perfect holiday stay.  …see more

from £56 / night

£386 - £623 / week

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from £56 / night

12

Province of Siena / San Quirico d'Orcia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min

 …see more

from £75 / night

£500 / week

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from £75 / night

(1) Average 

25

Province of Siena / San Quirico d'Orcia

1 2 Min stay varies

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

 …see more

from £106 / night

£737 / week

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from £106 / night

(2) Excellent 

19

Holiday apartment in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Child friendly
  • Air conditioning
Staying here will make your holiday unique: wake up in the shadow of the majestic Torre del Mangia is a feeling that isn't easily forgotten.I would like an unforgettable vacation, so I've taken care of all the details of the apartment where I want to welcome g  …see more

from £255 / night

£1667 - £2193 / week

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from £255 / night

(12) Excellent 

69

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 £416 / night

£2908 - £4474 / week

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from £416 / night

(5) Excellent 

35

Farmhouse rental in Radda in Chianti

Province of Siena / Radda in Chianti

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • 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 £62 / night

£343 - £483 / week

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from £62 / 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 £106 / night

£527 - £746 / week

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from £106 / night

(18) Excellent 

24

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 170 km
  • Child friendly
  • Car not necessary
“Well maintained apartment and very helpful owner” Elias iwas most helpful meeting us on arrival and going through everything with us and all places to visit in the area even giving us a map with this all marked on The apartment is beautifully kept and  …see more

from £105 / night

£614 - £1043 / week

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from £105 / 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 £41 / night

£286 - £544 / week

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from £41 / 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 £395 / night

£2413 / week

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from £395 / 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 £109 / night

£752 - £836 / week

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from £109 / night

(14) Excellent 

24

Holiday villa in San Gimignano

Province of Siena / San Gimignano

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“If only we could live here!” We spent the 1st 2 weeks of June here with 7 of us in total, 6 adults 1 child. The property is fantastic, it has all the facilities you want with huge rooms. We didn't realise that 2 of the rooms were adjoining which was a  …see more

from £176 / night

£1579 - £2808 / week

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from £176 / 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 £76 / night

£526 - £974 / week

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from £76 / night

100

Holiday apartment with shared pool in Chiusdino

Province of Siena / Chiusdino

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
The property is a hamlet in Tuscany with six apartments for two or four people, with an outdoor pool  …see more

from £84 / night

£439 - £746 / week

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from £84 / night

(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 £211 / night

£702 - £1965 / week

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from £211 / 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 £31 / night

£215 / week

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from £31 / night

(5) Excellent 

31

Holiday villa in Costalpino

Siena / Costalpino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden
“Belvedere e stupendo” After a beautifully green, bus ride from Rome, I arrived at my designated stop a few kilometer’s before Siena and waited for my transfer to Belvedere, a magical home at the end of a beautiful long winding driveway where views of  …see more

from £158 / night

£965 - £1711 / week

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from £158 / 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 £286 / night

£1755 - £2457 / week

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from £286 / night

(3) Very Good 

51

Holiday cottage in Siena

Province of Siena / Siena

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 100 km
  • Child friendly
  • Pet friendly
“Wonderful place, great location and well appointed” It was a great place to stay in central Tuscany. It is within a easy drive of Sienna, Pisa, Volterra, Florence and more. Lovely, comfortable, spacious and well appointed. Very nice, helpful owners  …see more

from £79 / night

£553 / week

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from £79 / night

(5) Excellent 

22

Apartment rental in Monteriggioni with swimming pool

Province of Siena / Monteriggioni

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Casa Laura is an independent apartment in a restored farmhouse Agriturismo la Magione that is situated on an agricultural estate on a hilltop at about 300 meters above sea level. It offers a wonderful panorama of the surrounding countryside with fields, olive groves, vi  …see more

from £62 / night

£395 - £487 / week

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from £62 / night

31

Province of Siena / Monticiano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 50 km
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £62 / night

£395 - £422 / week

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from £62 / night

14

Castelnuovo Berardenga / Montaperti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £120 / night

£834 - £1930 / week

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from £120 / night

(6) Very Good 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“Peaceful taste of Tuscany!!!!” Stayed here for a lovely, idyllic, December week. Amazing apartment with all home comforts. Loved walking through the village, stopping for pizza and fine wines :-) The views over the hills and vineyards are incredibly i  …see more

from £150 / night

£600 / week

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from £150 / night

12

Province of Siena / Montepulciano

4 6 2 nights min

  • 4 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £246 / night

£1720 / week

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from £246 / night

(30) Excellent 

26

Holiday farmhouse with swimming pool in Val d'Orcia

Montalcino / Val d'Orcia

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
“Perfect cottage for two” Loved everything about our stay here. Alexandra was so helpful, with directions, shopping, restaurants and her love of the wine industry. She met us on the road when we got lost. Lives next door but the property is so big  …see more

from £119 / night

£829 / week

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from £119 / night

22

Province of Siena / Montepulciano

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 116 km
  • Child friendly
  • Pet friendly

 …see more

from £123 / night

£860 / week

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from £123 / 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 £79 / night

£483 - £667 / week

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from £79 / night

13

Holiday apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Casa al bosco” is an elegant house restored in the second half of the 1800s. It is situated in a property of approximately 12 hectares where there are olive trees and a vineyard.  …see more

Pricing unknown

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Pricing unknown

17

Holiday apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
holiday resort located in the middle of a vine yard, few minutes from Montepulciano. Excellent wine for tasting  …see more

from £58 / night

£360 - £707 / week

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from £58 / night

26

Province of Siena / Radicofani

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly

 …see more

from £49 / night

£351 - £506 / week

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from £49 / night

(2) Excellent 

39

Holiday villa with swimming pool in Siena

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“A charming Tuscan farmhouse villa” We stayed here for a most enjoyable week in September 2016. It is all that the owner Giada describes and she is a charming and helpful host. The villa, a converted stone farmhouse, is located on the outskirts of Sien  …see more

from £115 / night

£772 - £2264 / week

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from £115 / night

(21) Excellent 

20

Holiday farmhouse with swimming pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
“Fabulous Tuscan villa experience!” Casa Bassa is a beautiful old Tuscan farmhouse and was the perfect central point for our stay in Tuscany. We were a party of 7, ranging in age from 16 to 63, and found the villa gave us ample space to gather togethe  …see more

from £250 / night

£2000 - £2750 / week

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from £250 / night

(2) Excellent 

18

Province of Siena / Gaiole in Chianti

2 2 7 nights min

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £79 / night

£553 / week

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from £79 / night

(6) Very Good 

19

Holiday villa with swimming pool in Siena

Province of Siena / Siena

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
Villa Le Tolfe is so close to Siena you can almost touch it (only 3 kilometres away). With stunning views and beautiful antique gardens this villa is perfect for relaxed stress free holidays. The house is built on top of a hill covered with olive groves and vineyards.  …see more

from £157 / night

£1097 - £2185 / week

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from £157 / night