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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5,381 Holiday homes

(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

£577 - £1,320 / week

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from £83 / night

(10) Excellent 

Certificate of Excellence

37

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“Excellent with children or groups” We had very enjoyable stay in a peaceful location with stunning views around. Olimpia was very helpful and everything worked as foreseen. We were trying to find a place with a scent of a history and what would suit b
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Certificate of Excellence

from £45 / night

£310 / week

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Responds fast!
avg. 3 hours 18 minutes

from £45 / night

(1) Excellent 

45

Montalcino holiday farmhouse accommodation

Province of Siena / Montalcino

3 8 3 nights min

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

from £292 / night

£2,045 / week

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from £292 / night

(16) Excellent 

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Charming accommodations and beautiful surroundings!” My husband and I stayed for four nights in this wonderful and clean apartment in the heart of Chianti. Phil was extremely responsive and helpful throughout the booking process and our stay even goin
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from £100 / night

£560 - £760 / week

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from £100 / night

(2) Excellent 

22

Holiday apartment in Monticchiello

Pienza / Monticchiello

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £45 / night

£301 - £425 / week

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Responds fast!
avg. 1 hour 48 minutes

from £45 / night

(54) 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 £62 / night

£354 - £620 / week

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from £62 / night

(33) Excellent 

20

Holiday apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 50 km
  • Child friendly
  • Pet friendly

from £71 / night

£443 - £602 / week

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Responds fast!
avg. 2 hours 42 minutes

from £71 / night

48

Fort letting in Montisi with shared pool

Province of Siena / Montisi

1 3 Min stay varies

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

from £110 / night

£759 - £843 / week

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from £110 / night

(1) Excellent 

18

Holiday apartment in Rapolano Terme

Province of Siena / Rapolano Terme

1 4 2 nights min

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

from £49 / night

£531 - £866 / week

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from £49 / night

24

Holiday home in Celle sul Rigo

San Casciano dei Bagni / Celle sul Rigo

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask owner if suitable for children
  • Air conditioning
  • Pet friendly

from £71 / night

£310 / week

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from £71 / night

(2) Excellent 

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 £57 / night

£291 / week

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Responds fast!
avg. 2 hours 28 minutes

from £57 / night

16

Farmhouse letting in Pienza with shared pool

Province of Siena / Pienza

2 4 4 nights min

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

from £57 / night

£399 - £698 / week

Enquire View

from £57 / night

44

Holiday villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

6 13 1 night min

  • 6 bedrooms
  • Sleeps 13
  • 1 night min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £493 / night

£3,452 - £5,266 / week

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from £493 / night

(16) Very Good 

17

San Gimignano holiday villa accommodation

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly
“Brilliant weeks holiday” We have had a great family holiday, two couples enjoying your fabulous house and views. Such a lot to see and do in the area, particularly enjoyed San Gimignano and Volterra, although sitting on your terrace takes a lot to bea
…see more

from £71 / night

£500 - £950 / week

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from £71 / night

15

Holiday home in Bagni di San Filippo

Province of Siena / Bagni di San Filippo

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £57 / night

£291 - £425 / week

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Responds fast!
avg. 2 hours 28 minutes

from £57 / night

23

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £55 / night

£354 - £797 / week

Enquire View

from £55 / night

14

Apartment rental in Castellina In Chianti

Province of Siena / Castellina In Chianti

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly

from £70 / night

£442 - £659 / week

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from £70 / night

(1) Excellent 

22

Townhouse rental in Castelnuovo Berardenga with shared pool

Province of Siena / Castelnuovo Berardenga

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £40 / night

£279 - £527 / week

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from £40 / night

12

Holiday townhouse in Crete Senesi

Asciano / Crete Senesi

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 60 km
  • Child friendly
  • Pet friendly

from £62 / night

£434 / week

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from £62 / night

(1) Excellent 

99

Holiday villa with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

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

from £111 / night

£700 - £1,045 / week

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from £111 / 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

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Responds fast!
avg. 36 minutes

from £53 / night

33

Montalcino holiday villa rental

Province of Siena / Montalcino

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £177 / night

£1,239 / week

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Responds fast!
avg. 3 hours 14 minutes

from £177 / night

(2) Excellent 

21

Holiday guest house in Radicondoli

Province of Siena / Radicondoli

3 5 4 nights min

  • 3 bedrooms
  • Sleeps 5
  • 4 nights min
  • Nearest beach 60 km
  • Suitable for children age 5+
  • Ask about pets
“Paradise in Radicondoli” We absolutely loved our stay at Casa Sulle Mura. Radicondoli is a beautiful town. We enjoyed the people there and especially enjoyed the evenings when people sit out and enjoy. The house is wonderful, clean and spacious.
…see more

from £142 / night

£708 / week

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from £142 / night

22

Home letting in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Suitable for children age 5+
  • Car not necessary
  • Air conditioning

from £107 / night

£620 / week

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from £107 / 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 £288 / night

£1,770 - £2,478 / week

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from £288 / night

(4) Very Good 

14

Poggibonsi holiday apartment rental

Province of Siena / Poggibonsi

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £53 / night

£372 - £576 / week

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Responds fast!
avg. 2 hours 54 minutes

from £53 / 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 £98 / night

£620 / week

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from £98 / 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
“Excellent base for chilling and siteseeing/citytrips” We had a great time at Elena's place! The appartement was clean, big, safe and modern. We used our own kitchen to cook our food. We stayed a week longer then planned. It is a very good base to go b
…see more

from £80 / night

£496 / week

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Responds fast!
avg. 1 hour 44 minutes

from £80 / night

16

Holiday apartment rental

Province of Siena / San Gimignano

2 6 Min stay varies

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

from £133 / night

£930 - £1,549 / week

Enquire View

from £133 / night

(4) Excellent 

19

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets

from £62 / night

£372 - £496 / week

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Responds fast!
avg. 1 hour 37 minutes

from £62 / night

(1) Excellent 

20

Castelnuovo Berardenga holiday townhouse rental

Province of Siena / Castelnuovo Berardenga

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £45 / night

£310 - £558 / week

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from £45 / night

16

Casole d'Elsa holiday apartment rental

Province of Siena / Casole d'Elsa

2 6 2 nights min

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

from £102 / night

£549 / week

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from £102 / night

(2) Excellent 

35

Holiday townhouse in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets

from £57 / night

£397 / week

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from £57 / night

9

Casole d'Elsa holiday apartment let

Province of Siena / Casole d'Elsa

2 6 2 nights min

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

from £94 / night

£531 / week

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from £94 / night

10

Holiday farmhouse in Trequanda

Province of Siena / Trequanda

2 3 2 nights min

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

from £84 / night

£514 / week

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from £84 / night

(2) Excellent 

16

Radicondoli holiday apartment rental

Province of Siena / Radicondoli

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Wonderful peaceful stay in the heart of the Tuscan countryside” The apartment at Radicondoli was wonderful. Just perfect for our requirements. It had everything you could need (except an ironing board). It was exceptionally clean, had an amazing showe
…see more

from £89 / night

£620 - £744 / week

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from £89 / night

19

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £622 / night

£4,349 / week

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Responds fast!
avg. 2 hours 25 minutes

from £622 / night

46

Holiday apartment in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 85 km
  • Child friendly
  • Private garden

from £62 / night

£434 / week

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from £62 / night

4

Holiday apartment in Rapolano Terme

Province of Siena / Rapolano Terme

3 1 2 nights min

  • 3 bedrooms
  • Sleeps 1
  • 2 nights min
  • Ask owner if suitable for children

from £124 / night

£496 / week

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from £124 / night

(7) Very Good 

49

Montisi holiday fort rental

Province of Siena / Montisi

1 3 Min stay varies

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

from £110 / night

£759 - £843 / week

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from £110 / night