Holiday Rentals in Province of Siena - Holiday Lettings - Villas

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Province of Siena

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456 Holiday homes

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

(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
“So good we came back in 2013 - Terrific Villa, Pool, Views & Airconditioning” A lovely traditional style Villa, extremely well appointed with the luxury of Airconditioned bedrooms - which meant a comfortable nights sleep for all. With two young childr  …see more

from £90 / night

£625 - £900 / week

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from £90 / 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 £78 / night

£475 - £500 / week

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from £78 / 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 £81 / night

£561 - £1285 / week

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from £81 / night

Featured properties

(4) Excellent 

17

Holiday home in Cetona

Province of Siena / Cetona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about pets
“A real tase of Tuscany” If you're looking for an authentic old town stay then you'll be very happy. Great location in the old town and so close to lots small towns to explore. Train to Florence as a day trip. Large rooms cumfy beds and amazing views f  …see more

from £61 / night

£423 / week

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from £61 / 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 £61 / night

£388 / week

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from £61 / 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 £74 / night

£535 - £742 / week

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from £74 / 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
“A well appointed villa, convenient location and hospitable owner.” The villa is clean, has one very large bedroom and a smaller bedroom which is still adequate. The kitchen is functional with a small fridge , two ring electric hob, small electric oven  …see more

from £74 / night

£513 / week

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from £74 / night

(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 £47 / night

£269 - £604 / week

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from £47 / 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 £60 / night

£337 / week

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from £60 / night

(1) Very Good 

30

Holiday home in Siena

Province of Siena / Siena

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 100 km
  • Child friendly
  • Private garden
Only 20km outside the charming city of Siena, my cottage is emerging in a forest on top of a hill. Ideal for biking and hiking. My cottage is exclusive for you! Perfect for enjoyable holidays or for a working context. WiFi-connection. A picturesque mosaic of fields an  …see more

from £62 / night

£432 - £649 / week

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from £62 / night

18

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £82 / night

£526 - £630 / week

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from £82 / 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

£432 - £552 / week

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from £65 / night

12

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about pets

 …see more

Pricing unknown

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Pricing unknown

18

Province of Siena / Montepulciano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £91 / night

£604 - £725 / week

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from £91 / night

44

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £115 / night

£802 - £1194 / week

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from £115 / night

14

Province of Siena / Casole d'Elsa

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £75 / night

£457 - £837 / week

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from £75 / 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

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

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 £65 / night

£432 - £509 / week

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from £65 / 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

£101 / week

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from £15 / night

45

Holiday home in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

6 13 3 nights min

  • 6 bedrooms
  • Sleeps 13
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Nestled in the lush nature of the Chianti region, this charming manor built in the early 1900s lovingly embraces and preserves the romance of bygone times. It is an ideal place for relaxing in the surrounding nature while enjoying the area’s superb foods and wines  …see more

from £285 / night

£1794 - £2763 / week

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from £285 / 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 £69 / night

£414 - £828 / week

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from £69 / night

(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..E' situato ad 1 Km dall'uscita dell'autostr  …see more

from £50 / night

£350 / week

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from £50 / 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 £69 / night

£302 / week

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from £69 / night

(2) Excellent 

32

Holiday home in Radicofani

Province of Siena / Radicofani

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Swimming pool
Sun in summer, snow in winter, hiking, culture and charm of nature nothing is missing for a wonderful holiday in the comfortable house Contignano.<br />The price is guaranteed. There are no additional charges. Utilities are included in the price.  …see more

from £52 / night

£345 - £694 / week

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from £52 / 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 £65 / night

£432 / week

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from £65 / 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 £63 / night

£371 - £664 / week

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from £63 / night

(1) Very Good 

20

Province of Siena / Pienza

2 4 2 nights min

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

 …see more

from £113 / night

£604 / week

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from £113 / 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 £69 / night

£449 - £850 / week

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from £69 / night

16

Montepulciano / Sant'Albino

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £69 / night

£432 - £613 / week

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from £69 / 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 £118 / night

£819 - £2199 / week

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from £118 / night

19

Province of Siena / Colle di Val d'Elsa

3 4 2 nights min

  • 3 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning

 …see more

from £57 / night

£393 / week

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from £57 / night

(8) Excellent 

18

Province of Siena / Colle di Val d'Elsa

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 93 km
  • Child friendly
  • Pet friendly

 …see more

from £65 / night

£423 / week

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from £65 / night

22

Holiday home with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Homelidays "Casa Guia " is immersed in the most idyllic Chiantishire: surrounded by vineyards producing world-class red wine, overlooking the rolling hills of Tuscany and is located in the village of San Vincenti, with its stone houses and clay roof tiles. The  …see more

from £108 / night

£755 / week

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from £108 / night

34

Province of Siena / Siena

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £173 / night

£1035 / week

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from £173 / 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  …see more

from £113 / night

£707 - £906 / week

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from £113 / 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 £95 / night

£561 - £1294 / week

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from £95 / night

(5) Excellent 

21

Castelnuovo Berardenga / Pianella

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £65 / night

£453 / week

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from £65 / 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

£345 - £454 / week

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from £52 / night