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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6,188 Holiday homes

(3) Very Good 

10

Chianciano Terme holiday condo rental

Province of Siena / Chianciano Terme

2 3 2 nights min

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

from £39 / night

£246 / week

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Responds fast!
avg. 2 hours 50 minutes

from £39 / 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 £237 / night

£1,580 / week

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Responds fast!
avg. 1 hour 17 minutes

from £237 / night

(1) Excellent 

20

Holiday home in Monticchiello

Pienza / Monticchiello

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Private garden

from £176 / night

£992 / week

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from £176 / night

(7) Very Good 

13

Holiday apartment in Monticchiello

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 80 km
  • Child friendly
  • Pet friendly

from £75 / night

£492 / week

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Responds fast!
avg. 1 hour 27 minutes

from £75 / night

(56) 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
“Montepulciano House” Three of us stayed at the house and we found it to be an ideal location to walk to town and as a base to explore Tuscany. Great view of the valley from master bedroom. Well equipped cozy kitchen. The house has oodles of charm and is very clean throughout. Davide is extremely helpful and attentive. It is a god value and we would stay there again.

Certificate of Excellence

from £88 / night

£527 - £614 / week

Book View

Responds fast!
avg. 3 hours 39 minutes

from £88 / night

(2) Very Good 

12

Holiday condo in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Car not necessary

from £62 / night

£430 / week

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Responds fast!
avg. 41 minutes

from £62 / night

(3) Excellent 

26

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
  • Ask about pets

from £80 / night

£493 - £589 / week

Book View

Responds fast!
avg. 1 hour 42 minutes

from £80 / 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

£369 / week

Book View

Responds fast!
avg. 35 minutes

from £53 / night

(4) Excellent 

26

Castiglione D'Orcia holiday apartment rental

Province of Siena / Castiglione D'Orcia

2 4 2 nights min

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

from £62 / night

£308 / week

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from £62 / night

6

Holiday b&b in Monteriggioni

Province of Siena / Monteriggioni

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets

from £132 / night

£878 / week

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from £132 / night

(3) Excellent 

24

Holiday villa rental

Province of Siena / Le Piazze

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £226 / night

£1,579 - £2,106 / week

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from £226 / night

9

Holiday townhouse in Celle sul Rigo

San Casciano dei Bagni / Celle sul Rigo

2 6 7 nights min

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

from £57 / night

£396 / week

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from £57 / night

(49) 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 modern Tuscan beauty - FANTASTIC accommodation” Azzurra is as beautiful as the name suggests. The photos on line are accurate as the villa is modern, extremely well equipped, furnished and decorated. Beds are comfortable, both showers and bathrooms modern and complete. All appliances are new and easy to use. Our week was over too quickly as none of us wanted to leave and all of us (we were two couples) rushed back to Azzurra in the evening to make supper in the gourmet kitchen and share wine on the private patio and watch the sun set. There are two private seating areas at the villa joined by a third giving a panoramic view. The gardens surrounding the villa were in full bloom in late June and made the accommodation both pleasing to the eye and private. The owner has thought of every possible need you could have, you don't need to bring anything except your groceries and wine...and you will want to buy some local wine. A car is a must and the driving instructions provided are detailed and simple to follow. It is an easy drive to San Gimignano, Volterra (20 minutes) as well as Sienna, Pisa, Lucca, Livorno, Florence or Montepuliciano (Florence being the furthest at a little over an hour). The villa on a private Tuscan hilltop even has WiFi but who wants to spend time on an iPad when the views are so breathtaking!

from £174 / night

£905 - £1,432 / week

Book View

Responds fast!
avg. 2 hours 2 minutes

from £174 / 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 £97 / night

£614 / week

Book View

Responds fast!
avg. 3 hours 30 minutes

from £97 / night

(6) Excellent 

28

Tower rental in Monticchiello

Pienza / Monticchiello

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask owner if suitable for children
  • Private garden

from £132 / night

£921 / week

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from £132 / night

10

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 £79 / night

£500 / week

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from £79 / 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 £40 / night

£277 / week

Book View

from £40 / night

(1) Excellent 

21

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

2 4 Min stay varies

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

from £97 / night

£677 / week

Book View

Responds fast!
avg. 2 hours 10 minutes

from £97 / night

(14) Very Good 

37

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £145 / night

£1,011 - £2,110 / week

Book View

from £145 / 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

from £80 / night

£493 - £580 / week

Book View

Responds fast!
avg. 1 hour 42 minutes

from £80 / night

(8) Very Good 

11

Montepulciano holiday apartment let

Province of Siena / Montepulciano

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Ask about pets

from £62 / night

£421 - £1,035 / week

Book View

from £62 / 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 £79 / night

£351 / week

Book View

Responds fast!
avg. 3 hours 29 minutes

from £79 / night

20

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £69 / night

£474 - £829 / week

Enquire View

from £69 / night

(13) Excellent 

20

Holiday apartment with golf nearby in Sant'Angelo in Colle

Montalcino / Sant'Angelo in Colle

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 68 km
  • Child friendly
  • Private garden

from £66 / night

£413 - £875 / week

Book View

from £66 / night

(1) Excellent 

18

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 £71 / night

£457 - £667 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £71 / night

17

Villa rental in Petroio

Province of Siena / Petroio

4 8 2 nights min

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

from £439 / night

£2,634 / week

Book View

from £439 / night

(2) Excellent 

22

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £351 / night

£2,457 - £2,720 / week

Book View

from £351 / night

(1) Excellent 

49

Siena holiday villa rental

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £308 / night

£1,975 - £3,731 / week

Book View

from £308 / 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 £88 / night

£616 / week

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from £88 / night

19

Castiglione D'Orcia holiday home rental

Province of Siena / Castiglione D'Orcia

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £145 / night

£411 - £871 / week

Book View

Responds fast!
avg. 3 hours 29 minutes

from £145 / night

(2) 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 £176 / night

£1,141 - £2,018 / week

Book View

from £176 / 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 £79 / night

£421 / week

Book View

Responds fast!
avg. 1 hour 51 minutes

from £79 / night

(2) Excellent 

20

Apartment rental in Piancastagnaio

Province of Siena / Piancastagnaio

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
  • Pet friendly

from £87 / night

£483 / week

Book View

from £87 / night

(31) Excellent 

26

Holiday farmhouse with swimming pool in Val d'Orcia

Montalcino / Val d'Orcia

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly

from £106 / night

£737 / week

Book View

from £106 / 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

£351 - £527 / week

Book View

from £62 / night

4

Holiday farmhouse in Cetona

Province of Siena / Cetona

2 5 2 nights min

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

from £62 / night

£431 / week

Book View

from £62 / night

25

Holiday apartment rental

Province of Siena / Colle di Val d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from £53 / night

£369 / week

Book View

from £53 / night

(11) Excellent 

32

Colle di Val d'Elsa holiday home rental

Province of Siena / Colle di Val d'Elsa

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 93 km
  • Child friendly
  • Pet friendly

from £79 / night

£500 - £599 / week

Book View

Responds fast!
avg. 3 hours 26 minutes

from £79 / night

21

Holiday b&b in Acquaviva di Montepulciano

Montepulciano / Acquaviva di Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £35 / night

£246 / week

Book View

Responds fast!
avg. 3 hours 20 minutes

from £35 / night

(1) Excellent 

20

Holiday farmhouse in San Gimignano

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly

from £71 / night

£483 - £922 / week

Book View

Responds fast!
avg. 3 hours 23 minutes

from £71 / night