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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5,849 Holiday homes

(2) Very Good 

16

Holiday b&b in Chiusi

Province of Siena / Chiusi

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly

from £57 / night

£305 / week

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from £57 / night

16

Chiusi holiday home rental

Province of Siena / Chiusi

2 6 1 night min

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

from £52 / night

£345 - £635 / week

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from £52 / night

(7) Very Good 

Certificate of Excellence

43

Montefienali 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

Certificate of Excellence

from £47 / night

£269 - £647 / week

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Responds fast!
avg. 1 hour 18 minutes

from £47 / night

(8) Very Good 

20

Holiday apartment in Monticiano

Province of Siena / Monticiano

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden

from £69 / night

£483 / week

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Responds fast!
avg. 3 hours 28 minutes

from £69 / night

37

Holiday apartment with shared pool in Vagliagli

Castelnuovo Berardenga / Vagliagli

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Pet friendly

from £62 / night

£319 - £539 / week

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Responds fast!
avg. 2 hours 7 minutes

from £62 / night

(1) Excellent 

16

Casole d'Elsa holiday townhouse rental

Province of Siena / Casole d'Elsa

2 6 2 nights min

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

from £100 / night

£535 / week

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from £100 / night

25

Pienza holiday lodge rental

Province of Siena / Pienza

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Air conditioning

from £84 / night

£586 - £906 / week

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from £84 / 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

from £81 / night

£562 - £1,286 / week

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from £81 / night

23

Holiday farmhouse with swimming pool in Monteriggioni

Province of Siena / Monteriggioni

1 24 2 nights min

  • 1 bedroom
  • Sleeps 24
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £112 / night

£785 / week

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from £112 / night

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

from £138 / night

£966 / week

Enquire View

from £138 / night

11

Apartment letting in Colle di Val d'Elsa with shared pool

Province of Siena / Colle di Val d'Elsa

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £113 / night

£783 / week

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Responds fast!
avg. 3 hours 58 minutes

from £113 / night

24

Holiday apartment in Asciano

Province of Siena / Asciano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 117 km
  • Child friendly

from £56 / night

£259 - £345 / week

Book View

from £56 / night

(14) Excellent 

Certificate of Excellence

34

Holiday home in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 120 km
  • Child friendly
  • Air conditioning

Certificate of Excellence

from £69 / night

£518 - £681 / week

Book View

from £69 / night

11

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 £62 / night

£207 - £436 / week

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Responds fast!
avg. 2 hours 7 minutes

from £62 / night

9

Holiday home in San Gimignano

Province of Siena / San Gimignano

2 4 2 nights min

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

from £87 / night

£380 / week

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from £87 / night

(8) Excellent 

24

Serre di Rapolano holiday cottage rental

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

from £82 / night

£561 / week

Book View

from £82 / night

14

Ski home to rent in Abbadia San Salvatore

Province of Siena / Abbadia San Salvatore

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Ski
  • Child friendly
  • Pet friendly

from £87 / night

£604 / week

Book View

from £87 / night

28

Holiday villa rental

Colle di Val d'Elsa / Campiglia dei Foci

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £138 / night

£966 - £2,294 / week

Book View

from £138 / night

(2) Very Good 

28

Holiday apartment with shared pool in Ulignano

San Gimignano / Ulignano

2 6 Min stay varies

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

from £104 / night

£604 - £949 / week

Book View

Responds fast!
avg. 3 hours 48 minutes

from £104 / night

9

Holiday apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

1 4 2 nights min

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

from £95 / night

£604 / week

Book View

from £95 / night

15

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

2 4 3 nights min

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

from £82 / night

£574 / week

Book View

from £82 / night

(3) Excellent 

6

Apartment rental in Monteriggioni

Province of Siena / Monteriggioni

3 4 1 night min

  • 3 bedrooms
  • Sleeps 4
  • 1 night min

from £87 / night

£582 / week

Book View

from £87 / night

(48) Excellent 

19

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
“A wonderful holiday home” Stayed at Azzurra in June and had the most wonderful holiday. We were a group of 3 couples, the home was spotlessly clean, very well furnished and the views, well.. they are just amazing, better than the photos show!! The o
…see more

from £161 / night

£840 - £1,329 / week

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Responds fast!
avg. 2 hours 39 minutes

from £161 / night

(6) Very Good 

56

Holiday apartment rental

Torrita di Siena / Montefollonico

2 4 2 nights min

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

from £166 / night

£1,157 / week

Book View

from £166 / night

(10) Very Good 

22

Condo rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Child friendly
  • Car not necessary

from £82 / night

£561 - £802 / week

Book View

from £82 / night

(9) Excellent 

70

Holiday farmhouse in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly

from £87 / night

£561 - £690 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from £87 / night

(50) Excellent 

Certificate of Excellence

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
“Perfection in rural Tuscany” From the outset we knew that this place would be special. From reviewing the property on TripAdvisor, looking at the pictures, reading other travellers reviews right through to the wonderful prompt and attentive service r
…see more

Certificate of Excellence

from £90 / night

£625 - £900 / week

Book View

from £90 / night

(3) Excellent 

30

Holiday farmhouse in Castiglione D'Orcia

Province of Siena / Castiglione D'Orcia

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
  • Pet friendly

from £56 / night

£393 - £544 / week

Book View

Responds fast!
avg. 3 hours 8 minutes

from £56 / night

11

Holiday apartment with swimming pool in Sinalunga

Province of Siena / Sinalunga

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £87 / night

£592 / week

Book View

from £87 / night

(6) Excellent 

16

Holiday farmhouse with swimming pool in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

6 8 3 nights min

  • 6 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £233 / night

£1,552 / week

Book View

Responds fast!
avg. 1 hour 27 minutes

from £233 / night

14

Apartment rental in Castellina In Chianti

Province of Siena / Castellina In Chianti

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly

from £69 / night

£431 - £642 / week

Book View

from £69 / night

(7) Excellent 

33

Holiday farmhouse with golf nearby in Brenna

Province of Siena / Brenna

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 50 km
  • Child friendly
  • Ask about pets

from £82 / night

£518 / week

Book View

from £82 / night

(7) Excellent 

42

Holiday villa with shared pool in Monteriggioni

Province of Siena / Monteriggioni

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 76 km
  • Swimming pool
  • Child friendly

from £117 / night

£815 / week

Book View

Responds fast!
avg. 2 hours 4 minutes

from £117 / night

(3) Very Good 

20

Radicondoli holiday apartment rental

Province of Siena / Radicondoli

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Excellent Experience” Beautiful location, great apartment, friendly and helpful owners, outstanding breakfast... really nothing left to be desired.
…see more

from £78 / night

£544 - £664 / week

Book View

from £78 / night

(1) Very Good 

15

Holiday b&b in Buonconvento

Province of Siena / Buonconvento

1 2 1 night min

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

from £31 / night

£212 / week

Book View

from £31 / night

(1) Excellent 

21

Ski apartment to rent in Pienza

Province of Siena / Pienza

2 4 1 night min

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

from £121 / night

£561 / week

Book View

from £121 / night

(8) Excellent 

Certificate of Excellence

31

Holiday villa in Costalpino

Siena / Costalpino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden

Certificate of Excellence

from £194 / night

£1,380 / week

Book View

Responds fast!
avg. 3 hours 45 minutes

from £194 / night

24

Holiday villa with swimming pool in Rapolano Terme

Province of Siena / Rapolano Terme

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £204 / night

£1,423 - £2,414 / week

Book View

Responds fast!
avg. 2 hours 7 minutes

from £204 / 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

(5) Very Good 

27

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £56 / night

£393 / week

Book View

Responds fast!
avg. 3 hours 20 minutes

from £56 / night