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

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Province of Siena

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4,194 Holiday homes

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

29

Siena holiday apartment rental

Province of Siena / Siena

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
TinaiaGround Floor – large dining-living room, built-in kitchen, bathroom with shower, box room. First Floor – 1 master bedroom, 2 bedrooms with twin beds, 1 bathroom with bath, 1 bathroom with shower (one extra bed in the living room) area equipped for eati  …see more

from £115 / night

£801 / week

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from £115 / night

47

Province of Siena / San Gimignano

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 50 km
  • Child friendly
  • Private garden

 …see more

from £59 / night

£331 / week

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from £59 / night

(9) Excellent 

52

Province of Siena / Montepulciano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

 …see more

from £119 / night

£721 / week

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from £119 / night

Featured properties

100

Cetona holiday villa rental

Province of Siena / Cetona

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
This private villa in rural Siena is particularly recommended to large families or groups of up to 12 looking for a relaxing holiday in Tuscany. This exclusive property has 6 en suite double bedrooms, ample living space, a beautiful pool and garden  …see more

from £382 / night

£2543 - £4746 / week

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from £382 / night

4

San Casciano dei Bagni / Celle sul Rigo

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool

 …see more

from £61 / night

£424 / week

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from £61 / night

(6) Excellent 

36

Holiday guest house in Siena

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 100 km
  • Child friendly
  • Private garden
My Cottage is situated on top of a hill in a forest where peace and quiet of the Tuscan countryside are the characteristics. If you love the nature you will definitely love my cottage. If you prefer to rent my cottage for private use let me know and I'll arrange  …see more

from £47 / night

£424 - £638 / week

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from £47 / 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 £101 / night

£593 - £1008 / week

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from £101 / night

(6) Very Good 

24

Cottage rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Peace and tranquility” My wife and I stayed here in June 2012. On arrival we were stuned by how beautiful the house, the grounds and the surrounding valleys were. The gardens are well maintained as with the house. There are numerous sitting areas outs  …see more

from £73 / night

£509 - £1484 / week

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from £73 / 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 £111 / night

£746 - £2204 / week

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from £111 / night

100

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

Province of Siena / Monteroni d'Arbia

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in Tuscany Italy, this stunning accommodation is the perfect place for your holidays. The accommodation offers: a swimming Pool, air Conditioning, a pet friendly space .  …see more

from £1556 / night

£10897 - £15739 / week

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from £1556 / 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

£416 / week

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from £60 / 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 £94 / night

£351 - £678 / week

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from £94 / night

17

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

 …see more

from £81 / night

£416 - £967 / week

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from £81 / night

(15) Very Good 

16

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 55 km
  • Swimming pool
“Beautiful apartment in stunning Tuscan landscape” If you want a base in Tuscany that seems in the middle of nowhere, but is less than an hour from all of the famous Tuscan towns/villages, and a lovely apartment that is in the middle of stunning countr  …see more

from £82 / night

£574 / week

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from £82 / 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

£2230 - £3769 / week

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from £558 / night

36

Holiday villa in Siena

Province of Siena / Siena

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Beautiful Tuscan Villa with swimming pool, not far from Siena. It sleeps up to 22 guests. It is an ideal place for families to spend a relaxing holiday far from town noises, among the peace of the countrside.<br />A heaven of peace in the heart of the Montagnola  …see more

from £467 / night

£2543 - £4238 / week

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from £467 / night

(1) Very Good 

12

Province of Siena / Colle di Val d'Elsa

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min

 …see more

from £43 / night

£297 / week

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from £43 / 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

£467 - £492 / week

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from £77 / night

24

Holiday farmhouse in Siena

Province of Siena / Siena

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANYVilla Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city  …see more

from £115 / night

£801 / week

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from £115 / 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

Pricing unknown

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Pricing unknown

(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

100

Villa accommodation in San Gimignano with swimming pool

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Set in the heart of the Tuscan countryside, offering full privacy and a warm atmosphere in its interiors, this lovely villa is ready to welcome guests. It is fitted with modern comforts, and it sleeps up to six people.  …see more

from £128 / night

£848 - £1950 / week

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from £128 / night

(1) Very Good 

5

Province of Siena / San Quirico d'Orcia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

 …see more

from £81 / night

£424 / week

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from £81 / 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 £60 / night

£382 - £407 / week

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from £60 / 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

(7) Excellent 

24

Val d'Orcia holiday villa rental

Montalcino / Val d'Orcia

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
One of three unique and charming apartments in a XVI century villa situated in the wonderful senese countryside a few km's from Montalcino, in the natural park of the Val d' Orcia, a precious architectural and natural context.Here you will feel embraced by  …see more

from £231 / night

£1611 - £2039 / week

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from £231 / night

55

Province of Siena / Cetona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £102 / night

£594 - £721 / week

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from £102 / night

100

Holiday villa with swimming pool 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 70 km
  • Swimming pool
  • Child friendly
Villa Fiordaliso is perfect for those looking to spend their holiday in a home away from home with stunning views of the Tuscan landscape. Perfect for families and large groups of friends.  …see more

from £424 / night

£2967 - £4026 / week

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from £424 / night

34

Sant'Albino holiday villa rental

Montepulciano / Sant'Albino

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves. It has been turned into a residence of refined charm that retains an atmosphere of informal welcome. The landscape and environment of Montepulciano ar  …see more

from £388 / night

£2712 - £5255 / week

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from £388 / 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 £73 / night

£508 - £941 / week

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from £73 / 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 £60 / night

£416 / week

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from £60 / night

(3) Very Good 

35

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £89 / night

£623 / week

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from £89 / night

24

Holiday villa with swimming pool in Castiglione D'Orcia

Province of Siena / Castiglione D'Orcia

8 21 Min stay varies

  • 8 bedrooms
  • Sleeps 21
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful holiday home in the Val d'Orcia, surrounded by gently rolling hills, is near Castiglione d'Orcia (12km), just a few kilometres from the famous spa waters at Bagno Vignoni (10km) and Bagni San Filippo (7km). Surrounded by peace and quiet  …see more

from £467 / night

£1780 - £3534 / week

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from £467 / night

100

Holiday apartment with shared pool in Chiusdino

Province of Siena / Chiusdino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • 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 £85 / night

£551 - £933 / week

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from £85 / night

15

Province of Siena / Radicofani

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £68 / night

£382 / week

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from £68 / night

(7) Very Good 

22

Province of Siena / Montepulciano

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly

 …see more

from £77 / night

£450 / week

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from £77 / night

35

Radicofani / Contignano

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from £64 / night

£441 - £619 / week

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from £64 / night

(3) Excellent 

13

Poggibonsi / Staggia Senese

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 74 km
  • Child friendly
  • Pet friendly

 …see more

from £60 / night

£399 / week

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from £60 / night

32

Farnetella holiday villa rental

Sinalunga / Farnetella

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Beautiful and characteristic villa made of stone and bricks and completely restored to be a welcoming holiday home, situated on the green hills of the Siena countryside, 6 km far from the village of Sinalunga endowed with every kind of shops and services.  …see more

from £170 / night

£1187 - £2204 / week

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from £170 / night

100

Villa rental in San Gimignano with swimming pool

Province of Siena / San Gimignano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
This Tuscan villa can host up to 14 guests in 7 double bedrooms. It has a fully equipped kitchen with its own dining area, formal dining room, 2 living rooms, 6 bathrooms and an outdoor swimming pool.  …see more

from £448 / night

£3136 - £4068 / week

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from £448 / night