Holiday houses for rent in Province of Siena

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Province of Siena

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905 Holiday homes

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

(6) Very Good 

43

Gaiole in Chianti holiday home accommodation

Gaiole in Chianti / Montefienali

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence. Moreover, you can go trekking in the beautiful trails and na  …see more

from £46 / night

£265 - £594 / week

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from £46 / night

(1) Excellent 

26

Holiday home in Rigomagno

Sinalunga / Rigomagno

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 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 £79 / night

£551 - £1263 / week

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from £79 / 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

Featured properties

(46) Excellent 

25

Holiday home with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Perfection in rural Tuscany” From the outset we knew that this place would be special. From reviewing the property on TripAdvisor, looking at the pictures, reading other travellers reviews right through to the wonderful prompt and attentive service r  …see more

from £90 / night

£625 - £900 / week

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from £90 / night

(5) Excellent 

14

Holiday home in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Ask about pets
Elegant and bright apartment is located in the heart of Siena. The street is full of restaurants, cafes and shops. The apartment is in a historic building and can comfortably accommodate four people. Very close to bus and train station.<br />The apartment is locat  …see more

from £82 / night

£556 / week

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from £82 / night

(6) Excellent 

32

Holiday home with swimming pool in Radicondoli

Province of Siena / Radicondoli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Fabulous house in glorious location” Lovely welcome from Elsa - an fantastic traditional meal mid week. The house was beautiful and spacious with everything you could need. Children - 8, 10, 12, 13 loved house and garden - especially the tortoise!  …see more

from £98 / night

£684 - £1069 / week

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from £98 / night

(1) Excellent 

11

Province of Siena / Castiglione D'Orcia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from £51 / night

£272 / week

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from £51 / night

20

Holiday home in Buonconvento

Province of Siena / Buonconvento

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautifully restored 14th century farmhouse sits within a farming estate on a hilltop with magnificent views over the soft hills of the Arbia river valley.  …see more

from £950 / night

£3799 - £6135 / week

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from £950 / night

30

Province of Siena / Casole d'Elsa

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

 …see more

from £77 / night

£509 - £653 / week

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from £77 / 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 £81 / night

£551 - £1272 / week

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from £81 / night

15

Casole d'Elsa holiday home rental

Province of Siena / Casole d'Elsa

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 64 km
  • Swimming pool
  • Child friendly
Situated between San Gimignano and Siena, Villa San Giovanni is a beautiful renovated villa for an extended family or group of friends. The ancient medieval village of Casole d’Elsa is only 3 kilometres away and there are several interesting places within 35 Km. (  …see more

from £116 / night

£806 - £2162 / week

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from £116 / 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

£526 - £729 / week

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from £73 / 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

(3) Excellent 

25

Province of Siena / Vivo d'Orcia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 70 km
  • Ski
  • Child friendly

 …see more

from £60 / night

£382 / week

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from £60 / night

(1) Very Good 

11

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from £68 / night

£407 - £814 / week

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from £68 / night

36

Radicofani / Contignano

2 4 1 night min

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

 …see more

from £60 / night

£424 / week

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from £60 / night

(1) Excellent 

32

Holiday home in Le Piazze

Province of Siena / Le Piazze

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
The nature of the Val di Chiana, where the village is situated, is gorgeous.  …see more

from £42 / night

£255 - £373 / week

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from £42 / night

14

Province of Siena / Montepulciano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £64 / night

£424 - £500 / week

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from £64 / night

(3) Very Good 

15

Siena holiday home rental

Province of Siena / Siena

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The apartment is located just 5 minutes drive from the walls surrounding the old town (10 min by bus) and its location also allows you to quickly reach the surroundings of the Sienese countryside. Supermarket and shops nearby.<br />Being a one bedroom apartment of  …see more

from £64 / night

£424 / week

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from £64 / night

23

Province of Siena / Radicondoli

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Nearest beach 56 km
  • Swimming pool
  • Child friendly

 …see more

from £303 / night

£2119 / week

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from £303 / night

(2) Very Good 

37

Province of Siena / Siena

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from £140 / night

£695 / week

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from £140 / night

24

San Casciano dei Bagni / Celle sul Rigo

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask owner if suitable for children
  • Air conditioning
  • Pet friendly

 …see more

from £68 / night

£297 / week

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from £68 / 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
“What a wonderful stay! We highly recommend this house!” We instinctively felt in love with Leonardo's house the moment we arrived! The description we received from Leonardo how to get to the house was perfect and we immediately found the correct way  …see more

from £73 / night

£509 / week

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from £73 / night

(9) Very Good 

6

Montepulciano / Valiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Pet friendly

 …see more

from £43 / night

£297 / week

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from £43 / night

5

Holiday home in Montisi

Province of Siena / Montisi

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 100 km
  • Child friendly
  • Private garden
La Capanna is a self-contained guest house built in local stone, perfect for a single, a couple or (for short stays) a small family. It's situated across the valley from the village of Montisi on a small rural estate, surrounded by lovely views and has a private ou  …see more

from £65 / night

£428 - £548 / week

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from £65 / 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

5

Home rental in Monteroni d'Arbia with swimming pool

Province of Siena / Monteroni d'Arbia

12 22 7 nights min

  • 12 bedrooms
  • Sleeps 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Monteroni d'Arbia: Villa Tinaio was originally the estate wine cellar. Because of its size, it can accomodate families or groups of friends up to 24 people who can enjoy moments of absolute relax, on the border of the private pool, surrounded by ancient trees.O  …see more

from £400 / night

£2797 - £4577 / week

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from £400 / night

22

Holiday home in Montalcino

Province of Siena / Montalcino

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 80 km
  • Child friendly
Stay in our beautifully restored townhouse in the historic heart of this prestigious hill town famous for Brunello wine, 30 mins south of Siena. Travertine worktops, marble bathrooms, terracotta floors and chestnut beams. Our property is a three-storey townhouse rece  …see more

from £119 / night

£649 - £995 / week

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from £119 / night

4

Montepulciano / Gracciano

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 200 km
  • Child friendly
  • Ask about pets

 …see more

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Pricing unknown

(4) Excellent 

11

Holiday home in Chiusi

Province of Siena / Chiusi

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about pets
  • Private garden
Immerso nella meravigliosa campagna toscana LA DOLCE VITA è un affittacamere all'interno di un antico casolare ristrutturato, circondato dall'atmosfera magica della natura incontaminata.  …see more

from £50 / night

£345 / week

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from £50 / night

22

Province of Siena / Colle di Val d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Air conditioning

 …see more

from £128 / night

£509 - £594 / week

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from £128 / night

4

Province of Siena / Orgia

1 3 30 nights min

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

 …see more

from £15 / night

£99 / week

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from £15 / night

17

Holiday home with shared pool in Trequanda

Province of Siena / Trequanda

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
During high season, on sunday, we are pleased to offer a dinner to the guests to taste our products.  …see more

from £94 / night

£645 / week

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from £94 / night

17

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £52 / night

£342 - £450 / week

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from £52 / night

(1) Excellent 

30

Province of Siena / San Gimignano

2 4 Min stay varies

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

 …see more

from £68 / night

£441 - £835 / week

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from £68 / night

16

Holiday home rental

Province of Siena / Siena

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
Located inside an historical grade listed palazzo, this elegant and sophisticated apartment is perfectly located on Piazza del Campo, in the heart of the UNESCO World Heritage city of Siena.Situated on the second floor, the apartment has been completed refurbished..<  …see more

from £212 / night

£1484 / week

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from £212 / night

26

Holiday home with shared pool in Casole d'Elsa

Casole d'Elsa / Monteguidi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
This charming and carefully restored Villa is privately set on the property grounds. It is spacious and elegantly furnished, whilst also retaining original features like exposed stonework and chestnut beam ceilings. It develops over 2 floors, comprising of 3 bedrooms an  …see more

from £96 / night

£667 - £1278 / week

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from £96 / night

11

Province of Siena / Castiglione D'Orcia

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from £102 / night

£543 / week

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from £102 / 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 £240 / night

£1676 / week

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from £240 / night

(1) Excellent 

12

Province of Siena / Pievescola

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 74 km
  • Child friendly
  • Pet friendly

 …see more

from £77 / night

£534 / week

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from £77 / night