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

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Province of Siena

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4,312 Holiday homes

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

9

Province of Siena / Torrita di Siena

8 20 1 night min

  • 8 bedrooms
  • Sleeps 20
  • 1 night min
  • Air conditioning
  • Ask about pets
  • Private garden

 …see more

from £77 / night

£522 / week

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from £77 / night

(7) Excellent 

24

Province of Siena / Radicondoli

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Child friendly

 …see more

from £150 / night

£1048 / week

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from £150 / night

10

Province of Siena / Montepulciano

13 27 2 nights min

  • 13 bedrooms
  • Sleeps 27
  • 2 nights min
  • Swimming pool
  • Air conditioning

 …see more

from £112 / night

£642 / week

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from £112 / night

Featured properties

15

Holiday farmhouse rental

Province of Siena / Radicofani

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
We offer hospitality in two delightful double rooms, each with private bath, elegantly furnished exclusively with antique furniture. Each room is accessed directly from the garden with a separate entrance to ensure complete privacy.From the private garden and decora  …see more

from £60 / night

£334 - £445 / week

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from £60 / night

(3) Very Good 

4

Province of Siena / Bagni di San Filippo

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £77 / night

£428 / week

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from £77 / night

100

Apartment rental in San Gimignano with shared pool

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
These apartments can host from 2 to 6 guests in apartments fitted with living/dining room, kitchen and 1 to 3 bedrooms. These apartments with views share a restaurant and a swimming pool.  …see more

from £149 / night

£1039 - £1787 / week

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from £149 / night

13

Holiday cottage with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Private garden
Beautiful cottage with private garden and access to pool with amazing sunset views  …see more

from £129 / night

£770 / week

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from £129 / night

(1) Excellent 

17

Province of Siena / Trequanda

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly

 …see more

from £86 / night

£599 / week

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from £86 / night

(8) Very Good 

11

Montepulciano holiday apartment let

Province of Siena / Montepulciano

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Ask about pets
The large apartment (116 sqm) is situated in the historical centre of Montepulciano. Inside the house the guests will appreciate its peaceful and warm atmosphere.<br />The apartment has been recently restored with the intention of giving its guests the best comfor  …see more

from £60 / night

£411 - £1009 / week

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from £60 / night

6

Province of Siena / Montepulciano

1 2 Min stay varies

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

 …see more

from £60 / night

£377 - £659 / week

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from £60 / night

18

Holiday farmhouse in Poggibonsi

Province of Siena / Poggibonsi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The TUSCAN COUNTRYSIDE with its aligned vineyards, the olive trees that cover the hills, groves, the cypresses... It is a landscape that takes your breath away and gives you peace and quiet. And so dawns the realization that the most beautiful things in life are  …see more

from £82 / night

£530 - £837 / week

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from £82 / night

(1) Excellent 

7

Province of Siena / Murlo

8 13 2 nights min

  • 8 bedrooms
  • Sleeps 13
  • 2 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

 …see more

from £513 / night

£3077 / week

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from £513 / night

20

Rapolano Terme holiday b&b rental

Province of Siena / Rapolano Terme

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
Orange triple bedroom with queen size bed, single bed, bathroom with shower, toilet, hairdryer, courtesy set, air conditioning, Wi-Fi, TV in room upon request.  …see more

from £66 / night

£461 / week

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from £66 / night

(1) Excellent 

15

Province of Siena / Siena

2 4 1 night min

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

 …see more

from £60 / night

£770 - £1189 / week

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from £60 / night

24

Province of Siena / Castellina In Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 85 km
  • Child friendly
  • Private garden

 …see more

from £60 / night

£419 / week

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from £60 / 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 £129 / night

£513 - £599 / week

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from £129 / night

(1) Excellent 

6

Province of Siena / Montalcino

1 2 Min stay varies

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

 …see more

from £52 / night

£359 / week

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from £52 / night

45

Province of Siena / Siena

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

 …see more

from £180 / night

£847 - £1453 / week

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from £180 / night

24

Siena / Sant Andrea a Montecchio

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £90 / night

£629 / week

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from £90 / night

23

Province of Siena / Radicondoli

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Private garden

 …see more

from £60 / night

£385 - £595 / week

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from £60 / night

65

Holiday villa letting

Province of Siena / Monteroni d'Arbia

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
<p>Large air conditioned villa near Siena - Villa Santa Caterina is an imposing fully restored 13th-century monastery, subsequently used as a farmhouse, which has been transformed into an elegant country holiday house.</p>  …see more

from £1612 / night

£11280 - £16940 / week

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from £1612 / night

100

Holiday villa with swimming pool, tennis court in San Gimignano

Province of Siena / San Gimignano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Villa Gaia is a stunning villa for 14 people, conveniently located in the heart of Tuscany, within easy reach of the region’s main cities, such as Florence, Lucca, Pisa, and Siena.  …see more

from £314 / night

£2197 - £3146 / week

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from £314 / night

100

Villa rental in Poggibonsi with swimming pool

Province of Siena / Poggibonsi

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Gorgeous country manor with swimming pool. Exquisitely decorated to a high standard and ideally located for guests to explore the wonderful region of Tuscany. Air conditioning and internet access are provided.  …see more

from £721 / night

£5044 - £6498 / week

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from £721 / night

(12) Excellent 

50

Holiday villa with indoor pool, golf nearby in Gaiole in Chianti

Gaiole in Chianti / Montefienali

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SERVICES INCLUDED • Cleaning pre-arrival and post-departure • Meet and greet by local member of staff • Daily cleaning Monday to Friday: 2 hours per day • Complete change of all sheets and towels every Saturday (a full spare set of bathroom towels i  …see more

from £693 / night

£4847 - £7150 / week

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from £693 / night

7

Province of Siena / Gaiole in Chianti

2 6 3 nights min

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

 …see more

from £86 / night

£539 / week

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from £86 / night

12

Holiday private room with golf nearby in Siena

Province of Siena / Siena

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 75 km
  • Child friendly
  • Car not necessary
ADDITIONAL SERVICES AVAILABLE ARE: CHILDREN UNDER 3 YEARS FREE in cot (from 4 years € 15 per night in an armchair bed) STROLLER € 5 a day BABYSITTING both day and night BREAKFAST housewife € 5 a day DINNER WITH THE FAMILY you can taste typical dishes of T  …see more

from £56 / night

£334 / week

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from £56 / night

24

Holiday apartment in Val di Merse

Siena / Val di Merse

6 14 3 nights min

  • 6 bedrooms
  • Sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly
Warm and welcoming, ten kilometres away from Sienna this is an ancient, XVth century villa, recently restored by a sensitive and art historically conscious architect and designer who has chosen to preserve the very best of the Tuscan tradition.  …see more

from £257 / night

£1710 / week

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from £257 / night

26

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 £120 / night

£753 - £1394 / week

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from £120 / night

(1) Excellent 

23

Province of Siena / Siena

3 10 1 night min

  • 3 bedrooms
  • Sleeps 10
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £112 / night

£778 / week

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from £112 / night

24

Province of Siena / Palazzone

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Nearest beach 106 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

Pricing unknown

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11

Farmhouse rental in Casole d'Elsa with shared pool

Casole d'Elsa / Monteguidi

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
ADATTO PER FAMIGLIE CON BAMBINI E GRUPPI DI AMICI  …see more

from £103 / night

£599 / week

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from £103 / night

15

Holiday apartment in Monticiano

Province of Siena / Monticiano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Charming and romantic hideaway in Tuscan villa with pool. Sleeps 2. All amenites in the village, an easy 3 minutes' walk. Siena 25 minutes. All Tuscan art cities and seaside are daily outings. Nature, art, peace and quiet.  …see more

from £105 / night

£723 - £744 / week

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from £105 / night

18

Montepulciano holiday villa rental

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Suite Home has two bedrooms one big bathroom and a service bath. The private entrance leads into a spacious lounge furnished with a authentic Tuscan table and chairs, a comfortable sofa set and coffee table and an open plan fire place very spacious and charming. The l  …see more

from £112 / night

£599 - £684 / week

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from £112 / night

44

Montalcino holiday home rental

Province of Siena / Montalcino

12 26 7 nights min

  • 12 bedrooms
  • Sleeps 26
  • 7 nights min
  • Child friendly
  • Pet friendly
Up to 27 guests! An enchanted place… FATTORIA PIAN DELL’ASSO is a beautiful 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  …see more

from £696 / night

£4872 - £5052 / week

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from £696 / night

45

Province of Siena / Montepulciano

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

Pricing unknown

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Pricing unknown

14

Montepulciano holiday apartment rental

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Romantic apartment ideal for couple. Located just outside Montepulciano, a delicious ancient Village well known for it's wine "Nobile di Montepulciano, you will enjoy the quiet and relax of this corner of paradise. Plenty of free parking on our 10 acres. A won  …see more

from £52 / night

£359 / week

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from £52 / night

100

Villa rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
wonderful accommodation sleeps 10 people, so it is ideal for a large group of friends and is located in Tuscany Italy. This property is perfect if you seek an unforgettable experiencie. The villa features: a swimming Pool, a pet friendly space .  …see more

Pricing unknown

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(1) Excellent 

23

Province of Siena / Poggibonsi

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £154 / night

£766 - £1412 / week

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from £154 / night

35

Province of Siena / Radicofani

6 17 7 nights min

  • 6 bedrooms
  • Sleeps 17
  • 7 nights min
  • Child friendly
  • Ask about pets

 …see more

from £269 / night

£1881 - £2838 / week

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from £269 / night

(2) Excellent 

14

Province of Siena / Monteriggioni

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask owner if suitable for children
  • Air conditioning
  • Pet friendly

 …see more

Pricing unknown

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