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

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Province of Siena

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4,210 Holiday homes

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

36

Holiday villa in Castelmuzio

Province of Siena / Castelmuzio

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
This little, two-storey, converted Tuscany farmhouse has been meticulously restored in a simple, rustic style, employing high-quality traditional materials. Set on a gentle elevation in a remote spot, it is entirely surrounded by the clay hills called “Crete Senes  …see more

from £156 / night

£906 - £1294 / week

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from £156 / night

7

Montepulciano holiday apartment rental

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Private garden
We have magnificent views, over the Val d'Orcia, Pienza, Montalcino, the Val Di Chiana Valley with its three lakes (Trasimeno, Chiusi and Montepulciano). Montepulciano is only 4 km far from here. You can easily reach the most famous cities of Tuscany and Umbria<  …see more

from £61 / night

£259 - £449 / week

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from £61 / night

(1) Excellent 

13

Province of Siena / Chianciano Terme

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £39 / night

£259 / week

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from £39 / night

Featured properties

(6) Very Good 

56

Torrita di Siena / Montefollonico

2 4 2 nights min

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

 …see more

from £164 / night

£1147 / week

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from £164 / 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 £57 / night

£345 / week

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from £57 / night

(1) Excellent 

7

Province of Siena / Castelmuzio

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly

 …see more

from £78 / night

£518 / week

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from £78 / night

(1) Excellent 

35

Holiday apartment in Radicondoli

Province of Siena / Radicondoli

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Child friendly
Il Noce is a very comfortable recently renovated apartment and is ideal for a quiet or active holiday in the idyllic countryside with splendid views and inviting walks. This attractive self contained apartment adjoins the main farmhouse where the owners live and has tw  …see more

from £87 / night

£604 / week

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from £87 / night

(11) Excellent 

25

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
In the deep core of old part of Montepulciano, quiet and in the middle of of streets of monuments, art shops, restaurants and wine shops and cellars.  …see more

from £77 / night

£362 - £457 / week

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from £77 / night

28

Holiday apartment in Quercegrossa

Monteriggioni / Quercegrossa

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The Villa is situated in a splendid 18th century mansion, with typical Sienese architecture. The property position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena (6 km away).The mansion is s  …see more

from £90 / night

£604 - £1630 / week

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from £90 / night

(5) Excellent 

24

Province of Siena / Radda in Chianti

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £82 / night

£574 - £694 / week

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from £82 / 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 £87 / night

£561 - £949 / week

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from £87 / 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 £43 / night

£259 - £380 / week

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from £43 / night

(8) Excellent 

24

Rapolano Terme / Serre di Rapolano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

 …see more

from £82 / night

£561 / week

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from £82 / night

25

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly

 …see more

from £113 / night

£785 / week

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from £113 / 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

11

Murlo / Vescovado di Murlo

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 70 km
  • Suitable for children age 5+
  • Private garden

 …see more

from £51 / night

£345 / week

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from £51 / 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 £407 / night

£2845 - £4656 / week

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from £407 / night

(5) Very Good 

15

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning

 …see more

from £51 / night

£345 - £563 / week

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from £51 / night

(1) Excellent 

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Fabulous place to stay with a group of friends or family.” My Husband and I stayed here with a group of our friends for a week. It was the perfect size and location. Great for day trips to the hill towns of Tuscany or just hanging out in the cute to  …see more

from £300 / night

£1500 - £2000 / week

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from £300 / night

(2) Very Good 

22

Villa rental in Montepulciano

Province of Siena / Montepulciano

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Nearest beach 180 km
  • Child friendly
  • Pet friendly
La Villa è situata poco fuori le mura, in prossimità del Tempio di San Biagio. Internamente si trovano due camere da letto, due bagni, uno spazioso e luminoso salone con divano letto, cucina e sala da pranzo. Esternamente gode di un meraviglioso panorama  …see more

from £87 / night

£518 / week

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from £87 / night

(7) Excellent 

35

Province of Siena / San Gimignano

2 4 Min stay varies

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

 …see more

from £87 / night

£544 - £906 / week

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from £87 / night

4

Apartment rental in Crete Senesi

Asciano / Crete Senesi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets
Siena, crete senesi, asciano, palio, appartamento la rondine, chianti, campagna senese, siena countryside  …see more

Pricing unknown

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Pricing unknown

27

Province of Siena / Casole d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool

 …see more

from £63 / night

£371 - £664 / week

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from £63 / 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 £95 / night

£638 / week

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from £95 / night

(4) Excellent 

24

Cottage rental in Casole d'Elsa with swimming pool

Province of Siena / Casole d'Elsa

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly
“Beautiful location” The villa is lovely & bigger than it looks in the photos! I would recommend it although there are a couple of grumbles! The villa is definately not walking distance to the town. It is down a long, long gravel track, so beautiful  …see more

from £81 / night

£561 - £1207 / week

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from £81 / night

(1) Excellent 

23

Holiday villa with shared pool in Montepulciano

Province of Siena / Montepulciano

4 2 Min stay varies

  • 4 bedrooms
  • Sleeps 2
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Ask owner if suitable for children
“Old-world Italian charm in a beautiful Tuscan setting” It's a job to find it it, but once you do, you'll want to stay longer than you've booked for. The house has been in the family since 1812 - they produce their own wine - and Olimpia is a charming  …see more

from £44 / night

£302 / week

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from £44 / night

23

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Villa in the heart of Tuscany with private pool, stunning views!  …see more

from £173 / night

£1207 - £1811 / week

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from £173 / night

(1) Very Good 

39

Province of Siena / Siena

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

Pricing unknown

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Pricing unknown

9

Holiday apartment with shared pool in Poggibonsi

Province of Siena / Poggibonsi

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
Casale Oliveta is located in a little hamlet with a few houses up in the hills.  …see more

from £19 / night

£1916 / week

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from £19 / night

16

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

7 13 1 night min

  • 7 bedrooms
  • Sleeps 13
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
We are in a very good position, we are just 3,5 km from San Gimignano, 40 km from Firenze, 25 km from Siena, 25 km from Volterra, 15 km from Certaldo, 45 km from Pisa; you can visit a lots of thinghs and a lots of beautiful historical town.  …see more

from £121 / night

£535 / week

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from £121 / night

28

Sinalunga holiday villa rental

Province of Siena / Sinalunga

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Agriturismo La Casetta nel Bosco is a beautiful, stone villa divided into two separate units which is part of an agritouristic Farm including olive groves, woods, several crops and a small-scale breeding of horses and ponies.  …see more

from £122 / night

£854 - £1656 / week

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from £122 / night

20

Holiday manor house rental

Province of Siena / Chiusi

8 21 7 nights min

  • 8 bedrooms
  • Sleeps 21
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Swimming pool
This large country house, located in the hills between Lake Chiusi and Lake Trasimeno is an ideal property for a large family or a group of friends that which to spend their holidays together in the beautiful Tuscan countryside.This property is particular suitab  …see more

from £307 / night

£2147 - £3216 / week

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from £307 / night

20

Holiday farmhouse with swimming pool in Palazzone

Province of Siena / Palazzone

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa in San Casciano dei Bagni with 7 bedrooms sleeps 13  …see more

from £785 / night

£5489 - £7982 / week

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from £785 / night

(1) Very Good 

36

Province of Siena / Siena

11 20 1 night min

  • 11 bedrooms
  • Sleeps 20
  • 1 night min
  • Child friendly
  • Car not necessary

 …see more

from £78 / night

£544 / week

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from £78 / night

36

Radicofani / Contignano

2 4 1 night min

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

 …see more

from £61 / night

£432 / week

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from £61 / night

(1) Excellent 

20

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Apartment in San Gimignano with 1 bedrooms sleeps 3  …see more

from £75 / night

£475 - £906 / week

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from £75 / night

(2) Very Good 

41

Holiday barn with shared pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
The Piaggione of Serravalle is a lively farm that is in constant action and that brings forth its daily acti  …see more

from £98 / night

£682 - £1199 / week

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from £98 / night

100

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
This marvelous villa is located in the heart of Tuscany, near the enchanting town of Pienza, and is the ideal villa for anyone looking for a relaxing and peaceful getaway in Tuscany.  …see more

from £370 / night

£2587 - £3449 / week

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from £370 / night

(1) Very Good 

15

Holiday apartment in Siena

Province of Siena / Siena

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Federico Frati I' m a art teacher 50 years old i have three fantastic sons <br />There are two little buses each 7' minutes that bring you in 5' minutes in Piazza del Campo or in Piazza del  …see more

from £156 / night

£819 / week

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from £156 / night

(1) Excellent 

100

Holiday apartment in Siena

Province of Siena / Siena

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Nearest beach 75 km
  • Child friendly
3 attractive apartments right in the centre of Siena, a privileged location very convenient for all the sites and restaurants but still quiet and private. The apartments can accommodate up to 4 or 5 and are ideal for both couples and families.  …see more

from £69 / night

£544 - £785 / week

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from £69 / night