Apartments in Province of Siena and Villas – Holiday Lettings - Holiday Rentals Province of Siena

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Province of Siena

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3,896 Holiday homes

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

from £65 / night

£432 - £552 / week

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from £65 / night

(35) Excellent 

24

Apartment rental in Val di Merse

Siena / Val di Merse

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 km
  • Child friendly
  • Pet friendly
“What you imagine when you think "Tuscany"!” We stayed in La Verbena, and it was amazing. Podere Sortoiano is about 15 minutes out of Siena, but it is so worth it to stay out of the city! It's incredibly quiet and relaxing, and the stars are unlike any
…see more

from £44 / night

£276 - £427 / week

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from £44 / night

36

Holiday home accommodation

Radicofani / Contignano

2 4 1 night min

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

from £61 / night

£432 / week

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from £61 / night

80

Farmhouse rental in Castel San Gimignano with shared pool, golf nearby

San Gimignano / Castel San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £190 / night

£1207 - £1897 / week

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from £190 / night

(1) Excellent 

24

Holiday apartment in Sarteano

Province of Siena / Sarteano

4 9 1 night min

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

from £44 / night

£302 / week

Book View

from £44 / night

(50) Excellent 

Certificate of Excellence

21

Holiday cottage in Montepulciano

Province of Siena / Montepulciano

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 158 km
  • Child friendly
  • Air conditioning
“Clean, comfortable and cozy house with privacy and convenience to Montepuciano” We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close
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Certificate of Excellence

from £74 / night

£432 - £604 / week

Book View

from £74 / night

(8) Very Good 

22

Condo rental in Siena

Province of Siena / Siena

1 2 Min stay varies

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

from £82 / night

£500 / week

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from £82 / night

(6) Very Good 

45

Montepulciano holiday home rental

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets
“Great view, great town!” The villa was wonderful and so is the family renting it out. They met us at the gate and showed us around the villa and how to work everything. The mother gave us a home baked treat too! There are beautiful views of the vin
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from £69 / night

£475 - £518 / week

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from £69 / night

7

Holiday apartment in Orgia

Province of Siena / Orgia

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min

from £86 / night

£560 / week

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from £86 / night

(4) Very Good 

16

Contignano holiday apartment rental

Radicofani / Contignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Child friendly
  • Pet friendly

from £69 / night

£345 / week

Book View

from £69 / night

(5) Very Good 

14

Holiday apartment in Siena

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly

from £48 / night

£332 / week

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from £48 / night

(1) Excellent 

28

Apartment rental in Torrita di Siena with shared pool

Province of Siena / Torrita di Siena

1 5 7 nights min

  • 1 bedroom
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly

from £47 / night

£328 - £587 / week

Book View

from £47 / night

(15) Very Good 

17

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
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from £82 / night

£574 / week

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from £82 / night

(7) Excellent 

7

Holiday apartment rental

Province of Siena / Rosia

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly

from £77 / night

£423 / week

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from £77 / night

12

Holiday apartment in Sarteano

Province of Siena / Sarteano

3 11 3 nights min

  • 3 bedrooms
  • Sleeps 11
  • 3 nights min
  • Child friendly
  • Pet friendly

from £173 / night

£1035 / week

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from £173 / night

9

Colle di Val d'Elsa holiday farmhouse rental

Province of Siena / Colle di Val d'Elsa

2 5 Min stay varies

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

from £100 / night

£682 - £1475 / week

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from £100 / night

20

Holiday villa in San Gusme

Castelnuovo Berardenga / San Gusme

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £107 / night

£746 - £1194 / week

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from £107 / 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

from £74 / night

£513 - £815 / week

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from £74 / night

(3) Excellent 

24

Holiday apartment in Staggia Senese

Poggibonsi / Staggia Senese

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets

from £31 / night

£175 - £345 / week

Book View

from £31 / night

(12) Excellent 

21

Gracciano holiday cottage rental

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Really worth staying!” My partner and I spent a glorious week this spring at agriturismo Il Salarco surrounded by vineyards and idyllic rolling countryside. The owner, an English lady called Laura, made us both feel really welcome, was fabulously know
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from £69 / night

£380 - £1776 / week

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from £69 / night

(30) Excellent 

20

Holiday apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 50 km
  • Child friendly
  • Pet friendly

from £69 / night

£414 - £578 / week

Enquire View

from £69 / night

100

Holiday villa with swimming pool in Castelmuzio

Province of Siena / Castelmuzio

5 10 Min stay varies

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

from £432 / night

£3018 - £4095 / week

Enquire View

from £432 / night

(4) Excellent 

18

Apartment rental in Siena with shared pool

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
“Heaven on Earth” This Villa Apartment was absolutely awesome! The own was the most kind and gentle man you could ever meet! The apartment was huge and way more than we expected. The furnishings were beautiful and all the rooms were very large. Absolut
…see more

from £78 / night

£518 - £949 / week

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from £78 / night

(3) Excellent 

28

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £35 / night

£242 - £828 / week

Book View

from £35 / night

60

Holiday villa with swimming pool in Bettolle

Sinalunga / Bettolle

11 22 7 nights min

  • 11 bedrooms
  • Sleeps 22
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £786 / night

£5496 - £7005 / week

Enquire View

from £786 / 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

from £444 / night

£3104 - £4656 / week

Book View

from £444 / night

(10) Excellent 

Certificate of Excellence

52

Apartment rental in Montepulciano

Province of Siena / Montepulciano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

Certificate of Excellence

from £121 / night

£733 / week

Book View

from £121 / night

(4) Very Good 

24

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £61 / night

£423 / week

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from £61 / night

7

Holiday apartment with shared pool in Valiano

Montepulciano / Valiano

1 4 3 nights min

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

from £130 / night

£785 / week

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from £130 / night

36

Holiday villa in Siena

Province of Siena / Siena

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly

from £475 / night

£2587 - £4311 / week

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from £475 / night

(4) Excellent 

24

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £154 / night

£1078 - £2371 / week

Enquire View

from £154 / night

(1) Excellent 

13

Holiday apartment rental

Province of Siena / Asciano

1 4 Min stay varies

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

from £95 / night

£647 - £845 / week

Book View

from £95 / night

(2) Very Good 

14

Holiday apartment in Torrita di Siena

Province of Siena / Torrita di Siena

1 3 3 nights min

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

from £61 / night

£220 - £453 / week

Book View

from £61 / night

(10) Excellent 

18

Colle di Val d'Elsa holiday home rental

Province of Siena / Colle di Val d'Elsa

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 93 km
  • Child friendly
  • Pet friendly

from £61 / night

£345 - £590 / week

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from £61 / night

21

Isola d'Arbia holiday farmhouse rental

Siena / Isola d'Arbia

1 4 Min stay varies

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

from £76 / night

£332 - £821 / week

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from £76 / night

18

Radda in Chianti holiday apartment rental

Province of Siena / Radda in Chianti

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Ask about pets

from £50 / night

£350 / week

Book View

from £50 / night

(3) Excellent 

22

Holiday apartment with shared pool, golf nearby in Buonconvento

Province of Siena / Buonconvento

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £74 / night

£518 - £845 / week

Book View

from £74 / night

10

Siena holiday home rental

Province of Siena / Siena

3 6 2 nights min

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

from £85 / night

£592 / week

Book View

from £85 / 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
“What a wonderful stay! We highly recommend this house!” We instinctively felt in love with Leonardo's house the moment we arrived! The description we received from Leonardo how to get to the house was perfect and we immediately found the correct way
…see more

from £74 / night

£513 / week

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from £74 / night

24

Holiday farmhouse letting

Castelnuovo Berardenga / San Gusme

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Ask about pets

from £802 / night

£5613 - £9742 / week

Enquire View

from £802 / night

1