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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5,855 Holiday homes

20

Villa rental in Castiglione D'Orcia with swimming pool

Province of Siena / Castiglione D'Orcia

1 21 7 nights min

  • 1 bedroom
  • Sleeps 21
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £709 / night

£4,957 - £6,854 / week

Enquire View

from £709 / night

(1) Average 

10

Colle di Val d'Elsa holiday apartment rental

Province of Siena / Colle di Val d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask owner if suitable for children
  • Ask about pets

from £121 / night

£845 / week

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from £121 / night

33

Holiday apartment with shared pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £69 / night

£388 - £595 / week

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Responds fast!
avg. 2 hours 4 minutes

from £69 / night

(13) 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
…see more

from £100 / night

£609 - £755 / week

Book View

Responds fast!
avg. 3 hours 44 minutes

from £100 / night

(20) Excellent 

Certificate of Excellence

25

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning

Certificate of Excellence

from £78 / night

£339 - £417 / week

Book View

Responds fast!
avg. 1 hour 39 minutes

from £78 / night

(19) Very Good 

Certificate of Excellence

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
“Cosy and comfortable lodgings minutes from historic centre — excellent value” The Sant'Andrea residence is located on the outskirts of Siena, 10 minutes from the historic centre. The cosy apartment has all the amenities a visitor needs. Located in a
…see more

Certificate of Excellence

from £61 / night

£345 - £518 / week

Book View

from £61 / night

(3) Excellent 

16

Townhouse rental in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 80 km
  • Child friendly

from £39 / night

£272 / week

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from £39 / night

(3) Excellent 

22

Villa rental in Siena with swimming pool

Province of Siena / Siena

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly

from £345 / night

£1,983 - £3,449 / week

Book View

from £345 / night

(3) Very Good 

15

Holiday home in Bagni di San Filippo

Province of Siena / Bagni di San Filippo

1 4 1 night min

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

from £56 / night

£283 / week

Book View

Responds fast!
avg. 3 hours 5 minutes

from £56 / 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
  • Pet friendly

from £31 / night

£175 - £296 / week

Book View

from £31 / night

(11) 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 - £914 / week

Book View

Responds fast!
avg. 2 hours 47 minutes

from £121 / 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
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from £74 / night

£513 / week

Book View

from £74 / night

(4) Excellent 

18

B&b rental in Chianciano Terme

Province of Siena / Chianciano Terme

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

from £86 / night

£598 / week

Book View

from £86 / night

(1) Excellent 

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 £156 / night

£1,035 - £1,983 / week

Book View

from £156 / night

19

Holiday farmhouse with swimming pool in Palazzone

San Casciano dei Bagni / Palazzone

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £968 / night

£6,775 - £9,854 / week

Enquire View

from £968 / night

(12) Excellent 

17

Holiday farmhouse in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £63 / night

£785 / week

Book View

from £63 / night

(11) Excellent 

77

Holiday villa rental

Montalcino / San Giovanni d'Asso

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £552 / night

£4,138 - £5,380 / week

Book View

Responds fast!
avg. 3 hours 9 minutes

from £552 / night

36

Holiday villa in Castelmuzio

Province of Siena / Castelmuzio

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £130 / night

£906 - £1,294 / week

Enquire View

from £130 / night

(1) Excellent 

21

Holiday farmhouse with swimming pool in Sarteano

Province of Siena / Sarteano

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £142 / night

£992 - £1,552 / week

Book View

from £142 / night

(3) Excellent 

57

Holiday villa with swimming pool in Montalcino

Province of Siena / Montalcino

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £345 / night

£2,414 / week

Book View

from £345 / night

(55) 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
“Wish we could have stayed longer!!!” What a lovely stay we had at La Casina Toscana! Davide met us on our arrival date and gave us a very thorough tour of the property explaining where everything was and important information about the house. He was e
…see more

Certificate of Excellence

from £74 / night

£431 - £604 / week

Book View

from £74 / night

(1) Excellent 

22

Holiday farmhouse with shared pool in Torrita di Siena

Province of Siena / Torrita di Siena

1 3 7 nights min

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

from £35 / night

£246 - £509 / week

Book View

Responds fast!
avg. 2 hours 4 minutes

from £35 / night

25

B&b rental in San Quirico d'Orcia with shared pool

Province of Siena / San Quirico d'Orcia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly

from £112 / night

£785 / week

Book View

from £112 / night

22

Holiday apartment with swimming pool in Crete Senesi

Asciano / Crete Senesi

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £105 / night

£731 / week

Book View

from £105 / night

12

Holiday apartment rental

Province of Siena / Pienza

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £112 / night

£604 / week

Book View

from £112 / night

(9) Excellent 

132

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £776 / night

£2,766 - £4,287 / week

Book View

from £776 / night

(5) Very Good 

42

Siena holiday apartment rental

Province of Siena / Siena

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

from £87 / night

£431 / week

Book View

from £87 / 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

Book View

Responds fast!
avg. 3 hours 28 minutes

from £69 / night

100

Gaiole in Chianti holiday villa rental

Province of Siena / Gaiole in Chianti

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly

from £394 / night

£2,759 - £4,052 / week

Enquire View

from £394 / night

20

Holiday apartment with shared pool in Crete Senesi

Asciano / Crete Senesi

3 6 Min stay varies

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

from £173 / night

£949 - £1,121 / week

Book View

from £173 / night

(2) 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

Responds fast!
avg. 2 hours 4 minutes

from £47 / night

8

San Gusme holiday apartment rental

Castelnuovo Berardenga / San Gusme

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

from £51 / night

£356 / week

Book View

from £51 / night

(2) Excellent 

17

Holiday farmhouse in Montepulciano

Province of Siena / Montepulciano

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 106 km
  • Child friendly
  • Car not necessary

from £123 / night

£862 / week

Book View

from £123 / night

11

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Car not necessary

from £61 / night

£380 / week

Book View

from £61 / night

(5) Excellent 

23

Holiday apartment with shared pool, golf nearby in Buonconvento

Province of Siena / Buonconvento

2 4 4 nights min

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

from £74 / night

£487 - £853 / week

Book View

Responds fast!
avg. 3 hours 33 minutes

from £74 / night

(1) Very Good 

39

Farmhouse rental in Castel San Gimignano with shared pool

San Gimignano / Castel San Gimignano

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £173 / night

£3,276 - £6,423 / week

Book View

from £173 / night

7

Holiday apartment in San Rocco a Pilli

Sovicille / San Rocco a Pilli

2 6 3 nights min

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

from £138 / night

£966 / week

Book View

from £138 / night

(2) Excellent 

24

Holiday apartment with shared pool in Monticchiello

Pienza / Monticchiello

3 7 5 nights min

  • 3 bedrooms
  • Sleeps 7
  • 5 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £242 / night

£1,681 / week

Enquire View

from £242 / night

(1) Excellent 

11

Ski apartment to rent in Pienza

Province of Siena / Pienza

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Ski
  • Child friendly
  • Pet friendly

from £78 / night

£302 / week

Book View

from £78 / night

(1) Excellent 

22

Apartment rental in Castiglione D'Orcia with shared pool

Province of Siena / Castiglione D'Orcia

2 6 1 night min

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

from £156 / night

£1,087 / week

Book View

from £156 / night