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

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Province of Siena

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4,313 Holiday homes

5

Holiday apartment in San Fabiano

Monteroni d'Arbia / San Fabiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The Il Pino apartment is located in the villa Podernovo at San Fabiano farmestate. It offers stunning views on the Arbia valleys and the skyline of Montalcino, and an authenitc athmosphere of a Tuscan home.The furnitures ,the air conditioning, the TV satellite with Sky  …see more

from £112 / night

£642 - £855 / week

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from £112 / night

(8) Excellent 

31

Province of Siena / Siena

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £103 / night

£718 - £983 / week

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from £103 / night

7

Province of Siena / Casole d'Elsa

1 4 2 nights min

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

 …see more

from £73 / night

£471 / week

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from £73 / night

25

Pienza holiday lodge rental

Province of Siena / Pienza

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Air conditioning
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £55 / night

£385 - £808 / week

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from £55 / night

(1) Excellent 

24

Holiday apartment with shared pool in Casole d'Elsa

Province of Siena / Casole d'Elsa

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
On two floors, this apartment of 96 qm, on the ground floor has an entrance, a sitting room with a double divan bed, a dining room with fully equipped kitchenette and a small bedroom with two single beds..  …see more

from £103 / night

£684 - £1795 / week

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from £103 / 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 £137 / night

£727 / week

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from £137 / 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.Being a one bedroom apartment of about 45 sq  …see more

from £65 / night

£428 / week

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from £65 / 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 £121 / night

£847 - £1642 / week

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from £121 / 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

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 £74 / night

£512 - £949 / week

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from £74 / night

(8) Excellent 

24

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic Villa and location shame about the weather” The villa was fantastic with extremely hospitable hosts. Grandma provided us with her fantastic home made cake and olive oil. Grandad provided us with home grown beans and lettuce. The Villa is sit  …see more

from £107 / night

£642 - £941 / week

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from £107 / night

(5) Excellent 

24

Province of Siena / Radda in Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £82 / night

£569 - £689 / week

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from £82 / night

(1) Excellent 

22

Holiday farmhouse with shared pool in Torrita di Siena

Province of Siena / Torrita di Siena

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Swimming pool
  • Child friendly
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

from £35 / night

£240 - £505 / week

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from £35 / night

(1) Very Good 

17

Province of Siena / Sovicille

2 4 2 nights min

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

 …see more

from £52 / night

£325 / week

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from £52 / night

(4) Excellent 

28

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
'Podere Collinella' has been re-built to a high standard, retaining the charm of a Tuscan farmhouse.The walls are of the old stone, chestnut beams support the ceiling, and positioned on a slight hill has wonderful views of the surrounding countryside. Podere C  …see more

from £69 / night

£471 - £590 / week

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from £69 / night

(1) Excellent 

16

Holiday home letting

Province of Siena / Monteriggioni

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Il Casale è parte della proprietà denominata Molino Bianco, un antico mulino in pietra documentato fin dall’XI secolo come possedimento della famiglia Lambardi, signori di Staggia. Come annesso del fortilizio di Castiglionalto, il Molino fu abitato da una comunità  …see more

from £112 / night

£701 - £898 / week

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from £112 / night

6

Province of Siena / Montepulciano

2 4 Min stay varies

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

 …see more

from £52 / night

£257 / week

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from £52 / night

(9) Excellent 

57

Holiday lodge in Pienza

Province of Siena / Pienza

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £169 / night

£1180 - £2783 / week

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from £169 / night

13

Province of Siena / San Gimignano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £171 / night

£983 - £2821 / week

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from £171 / night

(3) Very Good 

24

Holiday farmhouse with shared pool in Buonconvento

Province of Siena / Buonconvento

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“A unique and enchanting place” We have been going to Tuscany every summer for a while, and are used to renting houses in beautiful properties… We were not expecting to be surprised and overwelmed again by the beauty of a new place. However, Casanova (  …see more

from £257 / night

£1795 / week

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from £257 / night

4

Holiday apartment in San Fabiano

Monteroni d'Arbia / San Fabiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The villa Podernovo offers a nice apartment called Il Forno, with stunning view on the sunflowers fields, with all comforts such air conditioning and heated swimming pool. The apartment Il Forno is at first floor of the villa, with a master bedroom with king size bed,  …see more

from £112 / night

£642 - £855 / week

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from £112 / night

31

Siena / Val di Merse

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 50 km
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £52 / night

£342 - £350 / week

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from £52 / night

(15) Excellent 

23

Casole d'Elsa holiday villa rental

Province of Siena / Casole d'Elsa

7 12 7 nights min

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Villa Podere Scopicciolo is located about 30 miles from Florence. It is 900 ft above sea level in the heart of Tuscany surruonded by cultivated farm land and well preserved forests. It is fully immersed in the countryside enjoying peace and tranquillity, yet convenientl  …see more

from £916 / night

£6411 - £8975 / week

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from £916 / night

(5) Excellent 

24

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Podere Torricchi is in a typical tuscan landscape characterised by hills with olive trees and mediterrenean bush. Podere Torricchi is a group of converted farm buildings. The apartment has been newly restored in a traditional Tuscan style.Gambassi Terme and San  …see more

from £60 / night

£419 - £983 / week

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from £60 / night

(43) Excellent 

39

Holiday villa in Siena

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Perfect villa in perfect location” I need to start to say thank you to Jacopo and Fabio that made our holiday and stay absolutely perfect. They were both so helpful and such a pleasure to liaise with, even if we arrived later than expected! The  …see more

from £239 / night

£1253 - £4274 / week

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from £239 / night

(1) Excellent 

16

Villa rental in Chiusi with swimming pool

Province of Siena / Chiusi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Casa Baiocco is a typical Tuscan home, newly built in the traditional farmhouse style, perfectly blending with the Italian countryside. Surrounded by a well kept park, for your private use only, it offers all the peace and tranquility that you look for during your holid  …see more

from £62 / night

£428 - £1325 / week

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from £62 / night

(1) Excellent 

15

Province of Siena / Monteroni d'Arbia

2 4 3 nights min

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

 …see more

from £56 / night

£359 - £659 / week

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from £56 / night

(12) Excellent 

24

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
“Beautiful views” An excellent, clean and very comfortable 2 bedroom apartment with two bathrooms (one with ensuite is down stairs), 3 minutes from Piazza Grande. The views are simply sensational. The owner Luca, is very attentive, showed us were to p  …see more

from £99 / night

£599 - £742 / week

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from £99 / night

(1) Excellent 

27

Holiday barn with swimming pool in Quercegrossa

Monteriggioni / Quercegrossa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Restored Barn, description: this ground floor flat has an entrance with three large glass doors. The main living area has an open fireplace and is divided into a sitting room and a large kitchen. Dining table, wicker armchairs. Sofa bed for one person. From this room th  …see more

from £82 / night

£445 - £864 / week

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from £82 / night

100

Chianciano Terme holiday apartment rental

Province of Siena / Chianciano Terme

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
cozy farmhouse in chianciano terme for a group or 10 or for two groups, swimming pool, tv, close to tennis courts and riding center  …see more

from £112 / night

£642 - £1197 / week

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from £112 / night

18

Villa rental in Gaiole in Chianti with swimming pool

Gaiole in Chianti / Montegrossi

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Our close proximi  …see more

from £110 / night

£770 - £1966 / week

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from £110 / night

(4) Excellent 

20

Farmhouse rental in Radicofani with swimming pool

Province of Siena / Radicofani

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
A 17th century stone hamlet situated in one of the most wonderful position of Tuscany. The apartment is characterised by good taste and warmth, equipped with a fireplace and elegantly furnished with furniture from the era. Park, scenic swimming pool.  …see more

from £129 / night

£539 - £915 / week

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from £129 / 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

£257 - £377 / week

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from £42 / 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

£453 / week

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from £77 / 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

£342 - £558 / week

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from £51 / night

(5) Excellent 

24

Province of Siena / Montepulciano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly

 …see more

from £67 / night

£394 / week

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from £67 / night

(1) Excellent 

24

Province of Siena / Sarteano

4 9 1 night min

  • 4 bedrooms
  • Sleeps 9
  • 1 night min
  • Nearest beach 120 km
  • Child friendly
  • Private garden

 …see more

from £43 / night

£300 / week

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from £43 / night

(14) Excellent 

24

Holiday villa in San Gimignano

Province of Siena / San Gimignano

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“If only we could live here!” We spent the 1st 2 weeks of June here with 7 of us in total, 6 adults 1 child. The property is fantastic, it has all the facilities you want with huge rooms. We didn't realise that 2 of the rooms were adjoining which was a  …see more

from £171 / night

£1539 - £2736 / week

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from £171 / 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 £52 / night

£274 / week

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from £52 / night

(9) Very Good 

34

Holiday cottage in Siena

Province of Siena / Siena

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 65 km
“Peaceful cottage in isolated location” Property although in an isolated location was fairly central for accessing all of the Tuscany region. All points requiring access were never any more than 1 hours drive away. Great base for touring. Property  …see more

from £86 / night

£599 - £659 / week

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from £86 / night

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