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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3,625 Holiday homes

(4) Excellent 

20

Farmhouse rental in Radicofani with swimming pool

Province of Siena / Radicofani

2 7 Min stay varies

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

from £142 / night

£602 - £947 / week

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from £142 / night

20

Holiday farmhouse rental

Province of Siena / San Gimignano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about pets

from £327 / night

£2284 - £3531 / week

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from £327 / night

34

Holiday villa in Pienza

Province of Siena / Pienza

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £208 / night

£1452 - £2372 / week

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from £208 / night

47

Home rental in San Gimignano

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

from £62 / night

£346 / week

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from £62 / 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 £136 / night

£790 - £1316 / week

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from £136 / night

5

Holiday barn in Monteriggioni

Province of Siena / Monteriggioni

1 5 2 nights min

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

from £67 / night

£465 / week

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from £67 / night

100

Tognazza holiday apartment rental

Province of Siena / Tognazza

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly

from £88 / night

£614 - £1047 / week

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from £88 / night

22

Holiday villa rental

Province of Siena / Pienza

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £301 / night

£2106 - £3422 / week

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from £301 / night

100

Holiday villa with swimming pool in Monticiano

Province of Siena / Monticiano

9 18 2 nights min

  • 9 bedrooms
  • Sleeps 18
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £974 / night

£6638 / week

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from £974 / night

(21) Excellent 

20

Holiday farmhouse with swimming pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
“Fabulous Tuscan villa experience!” Casa Bassa is a beautiful old Tuscan farmhouse and was the perfect central point for our stay in Tuscany. We were a party of 7, ranging in age from 16 to 63, and found the villa gave us ample space to gather togethe
…see more

from £250 / night

£2000 - £2750 / week

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from £250 / night

24

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about pets
  • Private garden

from £189 / night

£1158 - £2027 / week

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from £189 / night

19

Holiday cottage with swimming pool in Cetona

Province of Siena / Cetona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £347 / night

£2425 - £3416 / week

Enquire View

from £347 / night

48

Fort letting in Montisi with shared pool

Province of Siena / Montisi

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £110 / night

£759 - £843 / week

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Responds fast!
avg. 2 hours 11 minutes

from £110 / night

(11) Excellent 

39

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £177 / night

£1239 - £1985 / week

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Responds fast!
avg. 3 hours 11 minutes

from £177 / night

(1) Excellent 

23

Holiday villa with shared pool in Montepulciano

Province of Siena / Montepulciano

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Ask owner if suitable for children
“Old-world Italian charm in a beautiful Tuscan setting” It's a job to find it it, but once you do, you'll want to stay longer than you've booked for. The house has been in the family since 1812 - they produce their own wine - and Olimpia is a charming
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from £31 / night

£217 / week

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Responds fast!
avg. 2 hours 15 minutes

from £31 / night

9

Holiday apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

1 4 Min stay varies

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

from £98 / night

£620 - £753 / week

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from £98 / night

(2) Very Good 

20

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £71 / night

£447 - £837 / week

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Responds fast!
avg. 3 hours 14 minutes

from £71 / night

(1) Excellent 

24

Holiday villa with swimming pool in Poggibonsi

Province of Siena / Poggibonsi

7 18 7 nights min

  • 7 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £244 / night

£1708 - £4116 / week

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Responds fast!
avg. 3 hours 14 minutes

from £244 / night

9

Bagno Vignoni holiday apartment rental

Province of Siena / Bagno Vignoni

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Private garden

from £107 / night

£602 - £788 / week

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Responds fast!
avg. 3 hours 14 minutes

from £107 / night

6

Holiday apartment rental

Castelnuovo Berardenga / Pianella

1 2 1 night min

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

from £133 / night

£930 / week

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from £133 / 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 £824 / night

£5762 - £10000 / week

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from £824 / night

(1) Very Good 

39

Farmhouse rental in Castel San Gimignano with shared pool

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 £177 / night

£1239 - £1947 / week

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from £177 / night

(1) Very Good 

11

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

from £62 / night

£372 / week

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from £62 / night

12

San Quirico d'Orcia holiday apartment rental

Province of Siena / San Quirico d'Orcia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min

from £76 / night

£505 / week

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from £76 / night

10

Holiday condo in San Gimignano

Province of Siena / San Gimignano

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 80 km
  • Car not necessary
  • Air conditioning

from £71 / night

£496 / week

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Responds fast!
avg. 2 hours 6 minutes

from £71 / night

(1) Excellent 

14

B&b rental in Sinalunga

Province of Siena / Sinalunga

9 20 1 night min

  • 9 bedrooms
  • Sleeps 20
  • 1 night min
  • Nearest beach 200 km

from £71 / night

£443 / week

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from £71 / night

28

Radicondoli holiday farmhouse rental

Province of Siena / Radicondoli

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly

from £142 / night

£611 - £788 / week

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from £142 / night

(22) Excellent 

24

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 170 km
  • Child friendly
  • Car not necessary
“Well maintained apartment and very helpful owner” Elias iwas most helpful meeting us on arrival and going through everything with us and all places to visit in the area even giving us a map with this all marked on The apartment is beautifully kept and
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from £106 / night

£619 - £1097 / week

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Responds fast!
avg. 2 hours 27 minutes

from £106 / night

(1) Very Good 

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

from £45 / night

£354 / week

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Responds fast!
avg. 3 hours 39 minutes

from £45 / night

12

Montisi holiday home rental

Province of Siena / Montisi

2 4 2 nights min

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

from £62 / night

£310 / week

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from £62 / night

(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 £62 / night

£434 / week

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from £62 / night

19

Holiday apartment in Siena

Province of Siena / Siena

1 3 2 nights min

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

from £80 / night

£487 - £673 / week

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Responds fast!
avg. 1 hour 55 minutes

from £80 / night

16

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
  • Swimming pool
  • Child friendly
  • Air conditioning

from £62 / night

£430 / week

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from £62 / night

(2) Very Good 

20

Holiday apartment rental

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets

from £205 / night

£1075 - £1336 / week

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from £205 / night

(7) Excellent 

16

Holiday villa in Casole d'Elsa

Province of Siena / Casole d'Elsa

4 4 3 nights min

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

from £71 / night

£496 / week

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from £71 / night

(2) Excellent 

24

Castellina In Chianti holiday apartment rental

Province of Siena / Castellina In Chianti

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
  • Private garden

from £107 / night

£775 / week

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from £107 / 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 £83 / night

£576 - £1319 / week

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from £83 / 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 £62 / night

£224 - £461 / week

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Responds fast!
avg. 3 hours 14 minutes

from £62 / night

(4) Excellent 

39

Holiday villa with swimming pool in Siena

Province of Siena / Siena

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“A charming Tuscan farmhouse villa” We stayed here for a most enjoyable week in September 2016. It is all that the owner Giada describes and she is a charming and helpful host. The villa, a converted stone farmhouse, is located on the outskirts of Sien
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from £150 / night

£1045 - £2301 / week

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from £150 / night

(12) Very Good 

Certificate of Excellence

25

Holiday cottage in Siena

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 65 km
  • Air conditioning
“Peaceful cottage in isolated location” Property although in an isolated location was fairly central for accessing all of the Tuscany region. All points requiring access were never any more than 1 hours drive away. Great base for touring. Property
…see more

Certificate of Excellence

from £80 / night

£496 - £531 / week

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Responds fast!
avg. 2 hours 18 minutes

from £80 / night

1