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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5,523 Holiday homes

(4) Excellent 

19

Torrita di Siena holiday apartment rental

Province of Siena / Torrita di Siena

2 4 2 nights min

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

from £80 / night

£514 / week

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from £80 / night

(35) Excellent 

Certificate of Excellence

32

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Great apartment. Fantastic Tuscan hospitality.” My wife and I chose Casa Gelsomino because we were travelling with our 18-month old daughter and wanted to be in a location with amenities within walking distance. The hamlet of Castel San Gimignano itse
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Certificate of Excellence

from £89 / night

£443 - £664 / week

Book View

Responds fast!
avg. 50 minutes

from £89 / 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

£217 / week

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from £31 / night

(1) Excellent 

33

Chiusi holiday b&b accommodation

Province of Siena / Chiusi

1 4 1 night min

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

from £58 / night

£310 / week

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from £58 / night

13

Holiday cottage with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Private garden

from £133 / night

£810 - £983 / week

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from £133 / night

(4) Excellent 

17

Holiday villa rental

Province of Siena / Gaiole in Chianti

2 6 1 night min

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

from £107 / night

£531 / week

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Responds fast!
avg. 1 hour 56 minutes

from £107 / night

(22) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from £53 / night

£372 / week

Book View

Responds fast!
avg. 36 minutes

from £53 / night

(17) Excellent 

24

Holiday villa in San Gimignano

Province of Siena / San Gimignano

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“If only we could live here!” We spent the 1st 2 weeks of June here with 7 of us in total, 6 adults 1 child. The property is fantastic, it has all the facilities you want with huge rooms. We didn't realise that 2 of the rooms were adjoining which was a
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from £354 / night

£1,593 - £4,071 / week

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from £354 / night

(4) Excellent 

30

Holiday apartment in Siena

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Car not necessary

from £74 / night

£416 - £639 / week

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from £74 / night

16

Gaiole in Chianti holiday farmhouse rental

Province of Siena / Gaiole in Chianti

9 22 1 night min

  • 9 bedrooms
  • Sleeps 22
  • 1 night min
  • Child friendly
  • Private garden

from £67 / night

£465 / week

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from £67 / night

5

Montalcinello holiday apartment rental

Chiusdino / Montalcinello

2 4 7 nights min

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

from £107 / night

£744 / week

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from £107 / night

(2) Excellent 

20

Holiday farmhouse in Castellina In Chianti

Province of Siena / Castellina In Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
“An excellent slice of Tuscan beauty” The week spent at Casa del Fico was most delightful. A perfect location atop a hill with 360 degree views of Tuscany reminiscent of any da Vinci painting. Ideally located to either explore the local region or just
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from £183 / night

£1,275 / week

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from £183 / night

(2) Excellent 

16

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 3 3 nights min

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

from £67 / night

£399 / week

Book View

Responds fast!
avg. 41 minutes

from £67 / night

(19) Very Good 

Certificate of Excellence

17

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night 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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Certificate of Excellence

from £85 / night

£595 / week

Book View

Responds fast!
avg. 3 hours 49 minutes

from £85 / night

13

Holiday private room rental

Sinalunga / Bettolle

1 2 1 night min

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

from £76 / night

£443 / week

Book View

from £76 / night

(19) Excellent 

19

Apartment rental in San Gimignano

Province of Siena / San Gimignano

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 72 km
  • Child friendly
  • Private garden
“An all round fantastic experience...we have great memories...” My partner and I stayed here for a week in July, and count ourselves lucky to have discovered this place. About 8kms from San Gimignano (an easy jaunt in a car, the latter being vital)
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from £55 / night

£319 - £394 / week

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from £55 / night

16

Holiday villa rental

Province of Siena / Cetona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Pet friendly
  • Private garden

from £283 / night

£1,975 - £3,955 / week

Enquire View

from £283 / night

(12) Excellent 

24

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
“Into the bliss!” The moment we arrived at the Autostazione di Montepulciano, Luca greeted us with a big smile and and an open heart that made this trip so particularly memorable. His flat on up on the edge of the hill was as described and better. It c
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from £102 / night

£620 - £769 / week

Book View

Responds fast!
avg. 3 hours 32 minutes

from £102 / night

24

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

2 2 3 nights min

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

from £191 / night

£1,332 - £2,045 / week

Enquire View

from £191 / night

(1) Excellent 

35

Holiday apartment in Radicondoli

Province of Siena / Radicondoli

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Child friendly

from £89 / night

£620 / week

Book View

from £89 / night

87

Holiday villa with swimming pool in Siena

Province of Siena / Siena

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £310 / night

£1,859 - £5,133 / week

Book View

Responds fast!
avg. 3 hours 53 minutes

from £310 / night

(8) Excellent 

31

Holiday farmhouse with shared pool in Radicondoli

Radicondoli / Belforte

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Authentic Tuscan Getaway!” This was the perfect getaway destination in the middle of the beautiful tuscan countryside. Although set right up in the hills we found the place first time thanks to the directions from the owners who greeted us with a big
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from £107 / night

£744 / week

Book View

from £107 / night

(7) Excellent 

Certificate of Excellence

30

Holiday guest house in Siena

Province of Siena / Siena

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Nearest beach 100 km
  • Child friendly
  • Private garden

Certificate of Excellence

from £53 / night

£354 - £523 / week

Book View

Responds fast!
avg. 2 hours 20 minutes

from £53 / 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 £71 / night

£354 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from £71 / night

(6) Excellent 

26

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £88 / night

£611 - £969 / week

Book View

Responds fast!
avg. 1 hour 41 minutes

from £88 / night

(1) Very Good 

5

Holiday apartment in San Quirico d'Orcia

Province of Siena / San Quirico d'Orcia

2 4 1 night min

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

from £84 / night

£443 / week

Book View

Responds fast!
avg. 1 hour 53 minutes

from £84 / night

10

Apartment rental in Casole d'Elsa with shared pool

Province of Siena / Casole d'Elsa

2 6 3 nights min

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

from £102 / night

£549 / week

Book View

from £102 / night

(11) Excellent 

27

Apartment rental in San Gimignano

Province of Siena / San Gimignano

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Ask about pets

from £89 / night

£531 / week

Book View

Responds fast!
avg. 1 hour 31 minutes

from £89 / 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 £67 / night

£465 / week

Book View

Responds fast!
avg. 2 hours 46 minutes

from £67 / night

14

Holiday villa with swimming pool in Siena

Province of Siena / Siena

5 9 Min stay varies

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

from £142 / night

£992 / week

Book View

from £142 / night

(6) Excellent 

35

Home rental in Siena

Province of Siena / Siena

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Nearest beach 110 km
  • Child friendly
  • Air conditioning

from £133 / night

£877 - £1,018 / week

Book View

Responds fast!
avg. 2 hours 57 minutes

from £133 / night

(4) Excellent 

25

Rapolano Terme holiday apartment rental

Province of Siena / Rapolano Terme

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

from £80 / night

£354 / week

Book View

from £80 / night

(2) Excellent 

29

Holiday farmhouse in Montepulciano

Province of Siena / Montepulciano

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

from £310 / night

£1,593 - £2,301 / week

Book View

from £310 / night

(3) Excellent 

23

Pienza holiday villa rental

Province of Siena / Pienza

5 10 7 nights min

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

from £430 / night

£3,009 / week

Book View

Responds fast!
avg. 3 hours 46 minutes

from £430 / night

17

Holiday farmhouse in Monticchiello

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £107 / night

£664 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from £107 / night

12

Holiday apartment with shared pool in San Quirico d'Orcia

Province of Siena / San Quirico d'Orcia

2 4 Min stay varies

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

from £77 / night

£533 / week

Book View

from £77 / night

(6) Very Good 

Certificate of Excellence

21

Holiday townhouse rental

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 77 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £111 / night

£576 - £885 / week

Book View

from £111 / night

10

Holiday finca with shared pool in San Gimignano

Province of Siena / San Gimignano

1 2 1 night min

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

from £80 / night

£487 / week

Book View

from £80 / night

36

Holiday apartment in Vagliagli

Castelnuovo Berardenga / Vagliagli

1 4 2 nights min

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

from £71 / night

£478 / week

Book View

from £71 / night

(7) Excellent 

Certificate of Excellence

14

Holiday home in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Ask about pets

Certificate of Excellence

from £84 / night

£576 / week

Book View

Responds fast!
avg. 2 hours 21 minutes

from £84 / night