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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3,892 Holiday homes

(8) Very Good 

16

Apartment rental in Siena

Province of Siena / Siena

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Car not necessary

from £113 / night

£966 / week

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from £113 / 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 £281 / night

£1725 - £2414 / week

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from £281 / night

60

Holiday villa with swimming pool in Bettolle

Sinalunga / Bettolle

11 22 7 nights min

  • 11 bedrooms
  • Sleeps 22
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £786 / night

£5496 - £7005 / week

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from £786 / night

(5) Excellent 

24

Barn rental in Radda in Chianti

Province of Siena / Radda in Chianti

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Child friendly
  • Pet friendly
  • Private garden
“Living the Dream!” Val delle Corti was the quintessential Tuscan experience. Lis and Roberto treated us like family during our stay on their vineyard and their local recommendations were invaluable. The beautifully restored barn that became our home
…see more

from £87 / night

£604 - £694 / week

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from £87 / night

14

Holiday villa letting

Province of Siena / Montisi

6 14 4 nights min

  • 6 bedrooms
  • Sleeps 14
  • 4 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £475 / night

£1725 / week

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from £475 / night

(1) Excellent 

32

Holiday home in Le Piazze

Province of Siena / Le Piazze

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £43 / night

£259 - £423 / week

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from £43 / night

(3) Excellent 

22

Holiday apartment with shared pool, golf nearby in Buonconvento

Province of Siena / Buonconvento

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £74 / night

£518 - £845 / week

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from £74 / 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 £69 / night

£345 / week

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from £69 / night

(15) Very Good 

17

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights 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
…see more

from £82 / night

£574 / week

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from £82 / night

(3) Very Good 

26

Holiday apartment rental

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £82 / night

£569 - £932 / week

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from £82 / night

(4) Excellent 

18

Farmhouse rental in Radicofani with shared pool

Province of Siena / Radicofani

2 4 Min stay varies

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

from £104 / night

£518 - £733 / week

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from £104 / night

(9) Very Good 

6

Valiano holiday home rental

Montepulciano / Valiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Pet friendly

from £44 / night

£302 / week

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from £44 / night

(5) Excellent 

Certificate of Excellence

30

Farmhouse letting in Radda in Chianti

Province of Siena / Radda in Chianti

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly

Certificate of Excellence

from £65 / night

£388 - £423 / week

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from £65 / 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 £44 / night

£345 / week

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from £44 / night

(1) Excellent 

54

Cetona holiday farmhouse rental

Province of Siena / Cetona

8 12 Min stay varies

  • 8 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 29 km
  • Swimming pool

from £302 / night

£2069 - £4604 / week

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from £302 / 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

£212 / week

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from £31 / night

(8) Excellent 

56

Holiday apartment rental

Province of Siena / Siena

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

from £99 / night

£647 - £1100 / week

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from £99 / night

36

Holiday villa in Siena

Province of Siena / Siena

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly

from £475 / night

£2587 - £4311 / week

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from £475 / night

(6) Excellent 

32

Holiday home with swimming pool in Radicondoli

Province of Siena / Radicondoli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Fabulous house in glorious location” Lovely welcome from Elsa - an fantastic traditional meal mid week. The house was beautiful and spacious with everything you could need. Children - 8, 10, 12, 13 loved house and garden - especially the tortoise!
…see more

from £99 / night

£690 - £1078 / week

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from £99 / night

(4) Excellent 

11

Pienza holiday apartment rental

Province of Siena / Pienza

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Ask about pets

Pricing unknown

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Pricing unknown

(46) Excellent 

Certificate of Excellence

25

Holiday home with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Perfection in rural Tuscany” From the outset we knew that this place would be special. From reviewing the property on TripAdvisor, looking at the pictures, reading other travellers reviews right through to the wonderful prompt and attentive service r
…see more

Certificate of Excellence

from £90 / night

£625 - £900 / week

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from £90 / night

(1) Excellent 

13

Holiday apartment rental

Province of Siena / Asciano

1 4 Min stay varies

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

from £95 / night

£647 - £845 / week

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from £95 / night

(50) 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
“Clean, comfortable and cozy house with privacy and convenience to Montepuciano” We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close
…see more

Certificate of Excellence

from £61 / night

£345 - £604 / week

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from £61 / night

(5) Very Good 

14

Holiday apartment in Siena

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly

from £48 / night

£332 / week

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from £48 / night

(5) Excellent 

20

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

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

Pricing unknown

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Pricing unknown

(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 £61 / night

£220 - £453 / week

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from £61 / night

19

Holiday villa in Pienza

Province of Siena / Pienza

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £158 / night

£1104 - £2069 / week

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from £158 / 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 £802 / night

£5613 - £9742 / week

Enquire View

from £802 / night

(32) Excellent 

24

Gaiole in Chianti holiday apartment accommodation

Province of Siena / Gaiole in Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden
“A Little Corner of Heaven” This was our fourth visit to Gaiole in Chianti and our third stay in this apartment. The apartment is modern, well furnished and equipped and spotlessly clean. The garden is beautiful and a real bonus. It is a wonderful
…see more

from £85 / night

£595 - £665 / week

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from £85 / night

(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 £78 / night

£500 / week

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from £78 / night

11

Apartment letting in Colle di Val d'Elsa with shared pool

Province of Siena / Colle di Val d'Elsa

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £104 / night

£604 - £949 / week

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from £104 / night

(8) Excellent 

24

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic Villa and location shame about the weather” The villa was fantastic with extremely hospitable hosts. Grandma provided us with her fantastic home made cake and olive oil. Grandad provided us with home grown beans and lettuce. The Villa is sit
…see more

from £95 / night

£604 - £949 / week

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from £95 / night

(1) Excellent 

18

Holiday apartment rental

Province of Siena / Montepulciano

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £57 / night

£371 - £673 / week

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from £57 / night

(3) Average 

19

Bagni di San Filippo ski penthouse to rent.

Province of Siena / Bagni di San Filippo

3 6 2 nights min

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

from £104 / night

£725 / week

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from £104 / night

(3) Excellent 

24

Holiday farmhouse in Castiglione D'Orcia

Province of Siena / Castiglione D'Orcia

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
  • Pet friendly

from £47 / night

£328 - £488 / week

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from £47 / night

4

Apartment rental in Crete Senesi

Asciano / Crete Senesi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets

Pricing unknown

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Pricing unknown

(6) Very Good 

23

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
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“Peaceful taste of Tuscany!!!!” Stayed here for a lovely, idyllic, December week. Amazing apartment with all home comforts. Loved walking through the village, stopping for pizza and fine wines :-) The views over the hills and vineyards are incredibly i
…see more

from £150 / night

£600 / week

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from £150 / night

(1) Excellent 

24

Buonconvento holiday farmhouse rental

Province of Siena / Buonconvento

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Excellent countryside villa for those wanting to get away from it all” We travelled with 3 kids aged under 10. There was plenty of space for them to run about outside and to relax inside the villa which has one bedroom set aside as a play room. The vi
…see more

from £246 / night

£1638 - £1725 / week

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from £246 / night

5

Holiday townhouse in Chiusdino

Province of Siena / Chiusdino

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Private garden

from £78 / night

£518 / week

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from £78 / night

(6) Very Good 

56

Holiday apartment rental

Torrita di Siena / Montefollonico

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £164 / night

£1147 / week

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from £164 / night

1