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

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Province of Siena

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4,241 Holiday homes

(1) Average 

7

Siena holiday apartment rental

Province of Siena / Siena

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
There is a shopping area 500 meters away from the apartment: 3 supermarkets, shops, coffee, bar, bakery..  …see more

from £85 / night

£568 - £763 / week

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from £85 / 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 £255 / night

£1356 - £1695 / week

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from £255 / 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 £94 / night

£551 / week

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from £94 / night

(1) Excellent 

33

Chiusi holiday b&b accommodation

Province of Siena / Chiusi

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
B&B La Vinca is situated in Chiusi in the province of Siena, is an old farm building which dates back to the second half of 1800, adapted and expanded in order to adapt to the needs of new residents, still retains a substantial portion of its features walls in bloc  …see more

from £56 / night

£339 / week

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from £56 / night

7

Holiday apartment rental

San Gimignano / Casaglia

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Mimosa is a very nice and cozy apartment on the ground floor of the main villa, with a private entrance.Enfant bed  …see more

from £88 / night

£544 - £806 / week

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from £88 / night

(5) Very Good 

19

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly

 …see more

from £94 / night

£509 / week

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from £94 / night

(4) Excellent 

30

Holiday apartment in Siena

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Car not necessary
The apartment is a perfect base to visit Siena and its surroundings, Chianti and Florence. Rooms are romantic, silent and cosy. A roof terrace offers a fantastic view on the whole city. You can find many typical restaurants and all kind of shops near the apartment.Upon  …see more

from £71 / night

£399 - £612 / week

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from £71 / night

(7) Very Good 

20

Holiday apartment in Monticiano

Province of Siena / Monticiano

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden
“Fantastic Location, beautiful location, fantastic host. Perfecto !” we spent a fantastic 2 weeks with friends here. The location is a perfect base for exploring the area. The village pool if you want a relaxing day and to cool down is fantastic and on  …see more

from £68 / night

£475 / week

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from £68 / night

5

Province of Siena / Pienza

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £119 / night

£568 - £890 / week

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from £119 / night

(1) Excellent 

13

Province of Siena / Chianciano Terme

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £34 / night

£255 / week

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from £34 / night

20

Holiday villa in Vagliagli

Castelnuovo Berardenga / Vagliagli

7 14 2 nights min

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Solara is a beautiful, modern villa, offering spectacular views of the surrounding countryside. Set within well-kept, private grounds and with easy access to local amenities, the villa is a perfect place for family or cultural holidays.  …see more

from £558 / night

£2229 - £3790 / week

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from £558 / night

8

Holiday villa with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
Il Torrino is a wonderful 4 bedroom villa set within a small and perfectly kept Tuscan medieval village and situated atop a hill with stunning views over the Chianti vineyards. Once a Medieval watch tower, the property oozes character and charm, but has been completely  …see more

from £176 / night

£1229 - £2289 / week

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from £176 / night

(1) Excellent 

12

Holiday farmhouse rental

Province of Siena / Gaiole in Chianti

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
This is a traditional 5 bedroom villa situated between the towns of Gaiole in Chianti and Radda in Chianti. Accommodating up to 18 guests in total as additional apartments are available within the grounds, it's an ideal base for a stay with family or friends. The wonder  …see more

from £424 / night

£2967 - £4577 / week

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from £424 / night

(3) Very Good 

33

Holiday apartment with swimming pool in San Gimignano

Province of Siena / San Gimignano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Just 1800 mt from the historical centre of San Gimignano, along the Francigena road, you will find a place where you can spend beautiful Tuscany holidays. The apartment is located in the countryside of the medieval town, in the centre of Tuscany. The house is surround  …see more

from £45 / night

£339 / week

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from £45 / 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

£289 - £577 / week

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from £42 / night

7

San Gimignano holiday b&b rental

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Conveniently placed between world famous hilltop towns of San Gimignano Florence and Siena. We offer 360° views from the top of a hill surrounded by vines and olive trees. Abundant buffet breakfast and home cooked evening meals are avaialble for our guests, relax by t  …see more

from £81 / night

£534 - £712 / week

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from £81 / night

(1) Excellent 

37

Province of Siena / Siena

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly

 …see more

from £119 / night

£695 - £763 / week

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from £119 / night

(2) Very Good 

19

Montalcino holiday studio rental

Province of Siena / Montalcino

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Air conditioning
One large and cosy suite with a high ceiling with the typical wooden beams and wooden floor. There's a fully equipped kitchen, a small sitting area, a double bed with a restored big old Tuscan wardrobe. The private bathroom is with shower in travertine. The suite i  …see more

from £140 / night

£979 / week

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from £140 / 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 £165 / night

£1000 - £1600 / week

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from £165 / night

24

Holiday apartment with shared pool in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
On two floors, this apartment of 77sqm on the ground floor has an entrance with sitting room and a double divan bed, a dining room, a fully equipped kitchen with fireplace, a storeroom and a bathroom fitted with shower.  …see more

from £85 / night

£509 - £1356 / week

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from £85 / night

(1) Very Good 

35

Province of Siena / San Gimignano

7 10 Min stay varies

  • 7 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £246 / night

£1611 - £2289 / week

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from £246 / night

(18) Excellent 

43

Holiday apartment in Monticchiello

Pienza / Monticchiello

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden
Villa PoliFlora is a modern residence consists of two bedrooms and two bathrooms with a fully equipped kitchen. The owners husband and wife Poli and Flora built the villa in 1988 and from there they guard with love the classic environment of the house.Villa PoliFlora is  …see more

from £64 / night

£314 - £765 / week

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from £64 / night

(14) Excellent 

17

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 65 km
  • Child friendly
  • Air conditioning
“Great Tuscan apartment... but not for summer heat.” My husband and I had originally hoped to stay in Il Duca for 2 months, but because of the heat in Tuscany this summer, we had to seek other accommodations with air conditioning. Pros: The apartme  …see more

from £88 / night

£611 / week

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from £88 / night

(3) Excellent 

18

Apartment rental in Siena with shared pool

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • 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 4 guests. 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 Se  …see more

from £77 / night

£509 - £933 / week

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from £77 / night

100

Holiday villa with swimming pool, tennis court in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

9 18 3 nights min

  • 9 bedrooms
  • Sleeps 18
  • 3 nights min
  • Swimming pool
  • Child friendly
This estate offers a main villa with space to accommodate up to 14 people, and an annex with space to sleep other 4 people  …see more

from £1211 / night

£8472 / week

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from £1211 / night

(1) Excellent 

16

Apartment rental in Casole d'Elsa with shared pool

Province of Siena / Casole d'Elsa

1 7 3 nights min

  • 1 bedroom
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Apt with terrace and large shared pool in an ancient borgo nestled in the countryside between Siena, San Gimignano and Volterra. It hosts 4 people comfortably, has 7 beds. Large living room with kitchen corner and a loft, master bedroom and bathroom with shower. It ha  …see more

from £59 / night

£356 - £505 / week

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from £59 / night

(6) Very Good 

34

Radicondoli holiday villa rental

Province of Siena / Radicondoli

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly
Charming independent villa in the heart of Tuscany with panoramic pool, FREE WI FI, garden, parking, wonderful panorama, near Siena, San Gimignano, Florence.Enjoy the real tuscan experience: city tour,food & wine tasting, massage, cooking lesson,horse riding...  …see more

from £297 / night

£1009 - £2246 / week

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from £297 / night

(1) Excellent 

30

San Gimignano / Santa Maria, San Gimignano

2 4 3 nights min

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

 …see more

from £68 / night

£441 - £530 / week

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from £68 / night

22

Province of Siena / Monticiano

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

 …see more

from £150 / night

£1017 - £1060 / week

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from £150 / night

27

Province of Siena / San Gimignano

1 2 Min stay varies

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

 …see more

from £56 / night

£390 - £475 / week

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from £56 / night

(10) Excellent 

48

Holiday villa rental

Province of Siena / San Giovanni d'Asso

8 16 3 nights min

  • 8 bedrooms
  • Sleeps 16
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“unforgettable tuscan paradise” Wonderful historic house, charming atmosphere, you feel at home. We were a group of 16 friends, the house was perfect, nothing was missing. Nice accommodations very clean, housekeeping every day. Unforgettable breakfa  …see more

from £567 / night

£3967 - £5170 / week

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from £567 / night

(12) Excellent 

17

Siena holiday home rental

Province of Siena / Siena

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Nearest beach 95 km
  • Child friendly
  • Pet friendly
“A well appointed villa, convenient location and hospitable owner.” The villa is clean, has one very large bedroom and a smaller bedroom which is still adequate. The kitchen is functional with a small fridge , two ring electric hob, small electric oven  …see more

from £73 / night

£505 / week

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from £73 / night

44

Province of Siena / Monticiano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly

 …see more

from £60 / night

£407 - £467 / week

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from £60 / night

12

Apartment rental in Valiano with swimming pool

Montepulciano / Valiano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
It's composed from a stay- kitchen with read couch and fire place, two double bedrooms and a big bath with double console and Jacuzzi. In the stay-kitchen: tv sat.Guests can purchase Vino Nobile di Montepulciano and Extra Virgin Olive Oil from the farm  …see more

from £128 / night

£636 - £806 / week

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from £128 / 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 £182 / night

£1272 - £1933 / week

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from £182 / night

55

Montepulciano / Valiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £68 / night

£721 - £806 / week

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from £68 / night

(1) Excellent 

18

Province of Siena / Siena

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min

 …see more

from £60 / night

£348 / week

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from £60 / night

(2) Excellent 

26

Province of Siena / Castiglione D'Orcia

2 4 2 nights min

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

 …see more

from £60 / night

£339 / week

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from £60 / night

9

Colle di Val d'Elsa / Campiglia dei Foci

1 2 Min stay varies

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

 …see more

from £60 / night

£297 - £441 / week

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from £60 / night

(3) Very Good 

9

Rigomagno holiday apartment accommodation

Sinalunga / Rigomagno

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Splendid old farmhouse carefully restored to maintain its original structural features and divided into two apartments.  …see more

from £62 / night

£433 - £577 / week

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from £62 / night