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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6,183 Holiday homes

(6) Excellent 

16

Farmhouse rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £219 / night

£1,530 / week

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from £219 / night

(5) Excellent 

36

Holiday apartment in Pienza

Province of Siena / Pienza

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 100 km
  • Ask owner if suitable for children
  • Pet friendly

from £57 / night

£398 / week

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from £57 / night

25

Siena holiday villa rental

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £219 / night

£1,311 - £2,971 / week

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from £219 / night

(1) Very Good 

24

Apartment rental in Sant Andrea a Montecchio with shared pool

Siena / Sant Andrea a Montecchio

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £62 / night

£455 - £481 / week

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Responds fast!
avg. 3 hours 45 minutes

from £62 / night

(12) Excellent 

19

Holiday apartment with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Pet friendly
“Beautiful apartment in a stunning location!” Myself and my boyfriend spent 10 relaxing days at this apartment and enjoyed every moment! The photos seriously don't do it justice! The pool overlooks the stunning Tuscan countryside and we spent many even

from £79 / night

£491 - £578 / week

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Responds fast!
avg. 1 hour 42 minutes

from £79 / night

(2) Excellent 

34

Contignano holiday home rental

Radicofani / Contignano

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £62 / night

£350 / week

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Responds fast!
avg. 3 hours 0 minutes

from £62 / night

18

Asciano holiday apartment let

Province of Siena / Asciano

2 4 2 nights min

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

from £35 / night

£219 - £305 / week

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Responds fast!
avg. 55 minutes

from £35 / night

44

Montalcino holiday home rental

Province of Siena / Montalcino

12 26 7 nights min

  • 12 bedrooms
  • Sleeps 26
  • 7 nights min
  • Child friendly
  • Pet friendly

from £562 / night

£3,934 - £5,419 / week

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from £562 / night

19

San Donato in Siena holiday farmhouse rental

San Gimignano / San Donato in Siena

2 4 Min stay varies

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

from £56 / night

£394 - £717 / week

Enquire View

from £56 / night

(19) Very Good 

17

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 55 km
  • Swimming pool
“Tranquility personified” This is a gem of a villa, beautifully furnished and with every conceivable range of utensils, etc. Added to that is the lovely pool, fantastic scenery, tranquillity and of course those gorgeous sunsets.

from £85 / night

£595 / week

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Responds fast!
avg. 1 hour 48 minutes

from £85 / night

(19) Very Good 

27

Holiday apartment in Sant Andrea a Montecchio

Siena / Sant Andrea a Montecchio

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 km
  • Child friendly
  • Car not necessary

from £62 / night

£350 - £525 / week

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from £62 / night

(1) Excellent 

22

Townhouse rental in Castelnuovo Berardenga with shared pool

Province of Siena / Castelnuovo Berardenga

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £40 / night

£276 - £520 / week

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from £40 / night

10

Valiano holiday apartment rental

Montepulciano / Valiano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £88 / night

£612 / week

Book View

from £88 / night

(2) Very Good 

27

Holiday barn with swimming pool in Quercegrossa

Monteriggioni / Quercegrossa

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £83 / night

£582 - £890 / week

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from £83 / night

(5) Very Good 

29

Castellina In Chianti holiday villa rental

Province of Siena / Castellina In Chianti

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £88 / night

£1,573 - £2,622 / week

Book View

Responds fast!
avg. 2 hours 43 minutes

from £88 / night

34

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £57 / night

£368 - £673 / week

Book View

from £57 / night

24

Holiday apartment rental

Province of Siena / Sovicille

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

from £76 / night

£542 / week

Book View

from £76 / night

(2) Very Good 

12

Holiday apartment accommodation

Province of Siena / Radicofani

3 6 1 night min

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

from £184 / night

£1,285 / week

Book View

from £184 / night

(2) Excellent 

26

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 3 nights min

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

from £105 / night

£612 / week

Book View

from £105 / night

(5) Excellent 

41

Holiday townhouse rental

Sinalunga / Rigomagno

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly

from £70 / night

£490 / week

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from £70 / night

(23) Excellent 

26

Holiday cottage in San Gimignano

Province of Siena / San Gimignano

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Nearest beach 75 km
  • Child friendly
  • Pet friendly

from £53 / night

£367 / week

Book View

Responds fast!
avg. 35 minutes

from £53 / night

(2) Excellent 

16

Holiday townhouse in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets

from £324 / night

£2,142 - £13,111 / week

Book View

from £324 / night

18

Holiday home in Montepulciano

Province of Siena / Montepulciano

3 6 3 nights min

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

from £101 / night

£704 / week

Book View

from £101 / night

25

Holiday apartment with shared pool in San Quirico d'Orcia

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

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

from £64 / night

£385 - £656 / week

Book View

Responds fast!
avg. 1 hour 29 minutes

from £64 / night

(27) Excellent 

Certificate of Excellence

43

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Nicely located, clean and comfortable apartment” Apartment is located 70 meters from the road between Volterra and Colle val d'Elza on a hill side. A very central location for visits to the highlights in Tuscany. The building has 3 apartments and is s

Certificate of Excellence

from £88 / night

£482 - £657 / week

Book View

Responds fast!
avg. 1 hour 22 minutes

from £88 / night

(10) Excellent 

34

Radicondoli holiday villa rental

Province of Siena / Radicondoli

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly

from £324 / night

£1,443 - £2,491 / week

Book View

from £324 / night

20

Holiday farmhouse rental

Buonconvento / Chiusure

2 6 Min stay varies

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

from £113 / night

£787 - £1,311 / week

Enquire View

from £113 / night

36

Holiday home accommodation

Radicofani / Contignano

2 4 1 night min

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

from £62 / night

£438 / week

Book View

Responds fast!
avg. 3 hours 0 minutes

from £62 / night

(2) Excellent 

41

Holiday villa with swimming pool in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

3 6 Min stay varies

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

from £270 / night

£1,888 - £2,643 / week

Book View

Responds fast!
avg. 3 hours 9 minutes

from £270 / night

(2) Very Good 

5

Chianciano Terme holiday apartment rental

Province of Siena / Chianciano Terme

1 3 2 nights min

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

from £40 / night

£276 / week

Book View

Responds fast!
avg. 1 hour 32 minutes

from £40 / night

(2) Very Good 

18

Holiday farmhouse with shared pool in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £97 / night

£612 / week

Book View

from £97 / night

50

Holiday apartment in Montalcino

Province of Siena / Montalcino

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Suitable for children age 5+

from £284 / night

£1,748 - £2,448 / week

Book View

from £284 / 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 £57 / night

£398 / week

Book View

Responds fast!
avg. 3 hours 20 minutes

from £57 / night

(3) Very Good 

22

Holiday apartment in Monticchiello

Pienza / Monticchiello

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £44 / night

£298 - £420 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £44 / night

20

Ulignano holiday villa rental

San Gimignano / Ulignano

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children age 5+

from £369 / night

£2,579 / week

Book View

from £369 / 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 £236 / night

£1,574 / week

Book View

Responds fast!
avg. 1 hour 17 minutes

from £236 / night

38

Holiday villa rental

Montepulciano / Bivio di San Biagio

4 9 3 nights min

  • 4 bedrooms
  • Sleeps 9
  • 3 nights min
  • Child friendly
  • Pet friendly

from £114 / night

£797 / week

Book View

from £114 / 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

from £75 / night

£521 / week

Book View

from £75 / night

39

Siena holiday apartment rental

Province of Siena / Siena

2 4 2 nights min

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

from £75 / night

£350 / week

Book View

from £75 / night

8

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £75 / night

£520 / week

Book View

Responds fast!
avg. 3 hours 41 minutes

from £75 / night