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

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Province of Siena

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4,342 Holiday homes

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

7

Holiday home in Santa Maria, San Gimignano

San Gimignano / Santa Maria, San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 km
  • Child friendly
  • Pet friendly
Un' abitazione in pieno relax..  …see more

Pricing unknown

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Pricing unknown

(1) Very Good 

7

Castelnuovo Berardenga / Pianella

6 20 Min stay varies

  • 6 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

7

Apartment accommodation in Casole d'Elsa

Province of Siena / Casole d'Elsa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
TWO-ROOM Apt 3/5 people (63 sq m.) - first floor  …see more

from £82 / night

£459 - £894 / week

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from £82 / night

Featured properties

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly
Casa Lecchi is a spacious two bedroom apartment facing on to the main piazza of Montefiorile which is a small hamlet of 14 villas situated in a quiet position in the heart of the Chianti Classico wine producing area. The hamlet is on a hillside and the houses enjoy st  …see more

from £73 / night

£509 - £966 / week

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from £73 / night

33

Murlo / Casciano di Murlo

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning

 …see more

from £52 / night

£311 / week

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from £52 / night

23

Villa rental in Asciano with swimming pool

Province of Siena / Asciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This superb villa with pool in Tuscany is located at 8 km from the pretty medieval village of Asciano, 30 km east of Siena. Surrounded by a private garden full of olive trees, this holiday home has been renovated to an extremely high standard  …see more

from £228 / night

£1595 - £3621 / week

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from £228 / night

100

Holiday apartment with shared pool in Siena

Province of Siena / Siena

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
This spectacular farm complex near the Tuscan town of Siena is set in the rolling hills of Chianti. It has a large swimming pool and many great facilities.  …see more

from £123 / night

£815 - £1449 / week

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from £123 / night

16

Contignano holiday villa rental

Radicofani / Contignano

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful Tuscan property located in Contignano. The spacious villa sleeps up to 19 guests in the main house and annex. It is surrounded by breathtaking views over the Italian countryside  …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

24

Buonconvento holiday farmhouse rental

Province of Siena / Buonconvento

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Excellent countryside villa for those wanting to get away from it all” We travelled with 3 kids aged under 10. There was plenty of space for them to run about outside and to relax inside the villa which has one bedroom set aside as a play room. The vi  …see more

from £276 / night

£1725 / week

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from £276 / night

6

Castelnuovo Berardenga / San Gusme

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

Pricing unknown

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Pricing unknown

20

Holiday apartment in Murlo

Murlo / Casciano di Murlo

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 40 km
  • Suitable for children age 5+
  • Ask about pets
app.100 mq. sudd.: piano terra ingresso-sala-cucina mq 35 (in tutto) attrezzatissima con camino aria calda , 1piano ( 10 scalini circa si accede dalla cucina ) disimpegno , 1 camera mq. 28 letto matrimoniale con bagno-doccia , 1 camera mq.18 letto matrimoniale alla  …see more

from £199 / night

£1388 / week

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from £199 / night

(1) Excellent 

13

Province of Siena / San Quirico d'Orcia

2 4 2 nights min

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

 …see more

from £65 / night

£407 - £709 / week

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from £65 / night

13

Province of Siena / Casole d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £44 / night

£345 / week

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from £44 / night

13

Sinalunga / Bettolle

1 2 1 night min

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

 …see more

from £74 / night

£432 / week

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from £74 / night

100

Holiday villa with swimming pool in Siena

Province of Siena / Siena

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
This villa is the ideal holiday accommodation for a family or large group with its five bedrooms and bathrooms, lovely gardens and swimming pool, and best of all, its fabulous location just 3km from Siena. Also ideal for weddings and special events.  …see more

from £272 / night

£1897 - £3621 / week

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from £272 / night

100

Holiday villa with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
This exclusive and luxurious villa in Chianti affords 5 bedrooms, dining room, 2 sitting rooms, kitchen, gym, games room and a fabulous infinity swimming pool.  …see more

from £1170 / night

£8190 - £10345 / week

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from £1170 / night

24

Province of Siena / Murlo

4 10 Min stay varies

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

 …see more

Pricing unknown

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Pricing unknown

20

Province of Siena / Siena

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £113 / night

£785 / week

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from £113 / night

7

Holiday apartment in Bettolle

Sinalunga / Bettolle

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Ideally located between Montepulciano and Cortona in the small town of Bettolle, this holiday apartment is the perfect location to venture out and explore Tuscany.  …see more

from £61 / night

£345 / week

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from £61 / night

(7) Very Good 

29

Province of Siena / Castelnuovo Berardenga

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £664 / night

£4647 / week

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from £664 / night

(3) Average 

27

Apartment rental in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning
The apartments have been restored preserving the typical features of country houses, though equipped with every kind of comfort.Every flat differs from the other, but each is equipped with independent entrance and is composed as follows: living room with fully equip  …see more

from £104 / night

£690 / week

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from £104 / night

101

Apartment accommodation in Siena with shared pool, tennis court

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
This beautiful estate in Tuscany includes both a b&b offering a range of lovely rooms and suites as well as fabulous apartments. These all have the outdoor swimming pool, tennis court and restaurant, and other facilities at their disposition.  …see more

from £163 / night

£1141 - £1563 / week

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from £163 / night

14

Caprera holiday farmhouse let

Siena / Caprera

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Apartment in Siena with 1 bedrooms sleeps 2  …see more

from £93 / night

£647 - £798 / week

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from £93 / night

5

Province of Siena / San Gimignano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £74 / night

£513 / week

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from £74 / night

21

Gaiole in Chianti / Lecchi

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly

 …see more

from £61 / night

£388 - £660 / week

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from £61 / night

6

Holiday apartment in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Private garden
THREE-ROOM Apt 3/5 people (50 sq m.) - ground floor  …see more

from £95 / night

£565 / week

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from £95 / night

(1) Excellent 

23

Province of Siena / Chiusdino

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 38 km
  • Swimming pool
  • Child friendly

 …see more

from £108 / night

£750 - £819 / week

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from £108 / night

(1) Excellent 

16

Province of Siena / Casole d'Elsa

2 6 Min stay varies

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

 …see more

from £100 / night

£535 - £992 / week

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from £100 / night

16

Holiday b&b rental

Gaiole in Chianti / Lecchi

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 95 km
  • Swimming pool
  • Car not necessary
Adjacent apartment with terra-cotta floors and furnished with a double Chianti iron bed (subsequently with a madonna picture above), a large armadio and an en suite bathroom. Through French doors the room leads to a 55 square meter terrace with an antique iron sofa, a f  …see more

from £95 / night

£518 / week

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from £95 / night

24

Holiday apartment with shared pool in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
This 69sqm apartment is on one floor only and consists of a sitting room with double divan bed and stone fireplace, dining area and fully equipped kitchenette, a double bedroom with bathroom fitted with shower and built-in wardrobe, a twin bedroom and another bathroom  …see more

from £198 / night

£1380 / week

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from £198 / night

(1) Excellent 

22

Holiday farmhouse in Gaiole in Chianti

Gaiole in Chianti / Montegrossi

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Le Diacce, an enchanting 18th century old farmhouse, belonging to Podere Ciona, 40 hectares of vineyards and woodland, enjoys a unique view on the surrounding hills covered with vineyards, olive groves and woods with Siena in the far distance.  …see more

from £130 / night

£3449 / week

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from £130 / night

26

Province of Siena / Siena

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 80 km
  • Child friendly
  • Air conditioning

 …see more

from £87 / night

£561 / week

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from £87 / night

14

Province of Siena / Poggibonsi

2 4 Min stay varies

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

 …see more

from £44 / night

£302 - £518 / week

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from £44 / night

(1) Very Good 

4

Province of Siena / Chiusi

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Air conditioning

 …see more

from £78 / night

£432 / week

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from £78 / night

10

Province of Siena / Casole d'Elsa

2 6 Min stay varies

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

 …see more

from £100 / night

£535 - £992 / week

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from £100 / night

27

Province of Siena / Sinalunga

2 5 Min stay varies

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

 …see more

from £130 / night

£776 - £1078 / week

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from £130 / night

4

Province of Siena / Monticiano

2 5 Min stay varies

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

 …see more

Pricing unknown

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Pricing unknown

23

Holiday tower with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
Stunning medieval tower near San Gimignano for holiday rentals  …see more

from £124 / night

£863 - £2113 / week

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from £124 / night

23

Siena / Isola d'Arbia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £107 / night

£465 - £1213 / week

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from £107 / night

100

Holiday apartment with shared pool in Montalcino

Province of Siena / Montalcino

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
A holiday at Borgo Brunello provides something for everyone: 3km from Montalcino for culture vultures and wine fans, beautiful landscape offering sporting and recreational possibilities as well as infinite calm for a romantic or family getaway.  …see more

from £294 / night

£2026 - £2328 / week

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from £294 / night