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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3,646 Holiday homes

(2) Very Good 

27

San Gusme holiday villa rental

Castelnuovo Berardenga / San Gusme

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Private garden
“wonderful and peaceful place” San Donato is very quiet, a very beautiful place, the garden and all the Villa Arceno aera are amazing, the house is simple but comfortable, and with a soul, as if you ever know this place, I will return one day, for sure
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from £187 / night

£1308 - £1746 / week

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from £187 / night

(5) Excellent 

31

Murlo holiday apartment rental

Province of Siena / Murlo

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £71 / night

£425 - £504 / week

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Responds fast!
avg. 3 hours 38 minutes

from £71 / night

(3) Excellent 

28

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 £48 / night

£334 - £498 / week

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from £48 / night

(4) Excellent 

18

Apartment rental in Siena with shared pool

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
“Heaven on Earth” This Villa Apartment was absolutely awesome! The own was the most kind and gentle man you could ever meet! The apartment was huge and way more than we expected. The furnishings were beautiful and all the rooms were very large. Absolut
…see more

from £79 / night

£527 - £965 / week

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from £79 / night

(12) Excellent 

Certificate of Excellence

26

Holiday home in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

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

Certificate of Excellence

from £71 / night

£553 - £755 / week

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from £71 / 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
“Wonderful, Wonderful, Highly Recommended.” My wife and I stayed 23rd. June - 5th. July 2013, and had a wonderful holiday. So relaxing and no hassle whatsoever. The farmhouse has three one bedroomed apartments available and a fourth which Elena (the
…see more

from £79 / night

£492 - £553 / week

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Responds fast!
avg. 1 hour 41 minutes

from £79 / night

(1) Excellent 

20

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

from £163 / night

£1141 - £1799 / week

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from £163 / 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
“Very good appartment, with great views” We stayed in Podere Le Monache 4 for one week in August. It was more then we expected from the pictures and the description. The appartment was very clean and spacious, with two large bedrooms and enough furnitu
…see more

from £66 / night

£439 - £904 / week

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Responds fast!
avg. 3 hours 1 minutes

from £66 / night

(1) Excellent 

29

Holiday farmhouse in Montepulciano

Province of Siena / Montepulciano

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £255 / night

£1404 - £2018 / week

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from £255 / 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 £106 / night

£615 - £965 / week

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from £106 / night

(6) Excellent 

35

Holiday farmhouse in Monticiano

Monticiano / Tocchi

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 50 km
  • Child friendly
  • Pet friendly

from £62 / night

£404 - £851 / week

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from £62 / night

(9) Very Good 

41

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“Stunning Views” We had a most enjoyable time at this house and would recommend it for its location and closeness to Montepulciano. The house was delightful and the views across the valley and surrounding countryside were excellent. We can recommend
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from £100 / night

£625 - £895 / week

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from £100 / night

12

Holiday apartment in San Quirico d'Orcia

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

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

from £69 / night

£470 - £680 / week

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from £69 / night

(3) Very Good 

24

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
“Well-located and roomy house” We were 10 adults and two children (three generations) spending one week at the house in May of 2014. We found the house very suitable (for five couples) since it had five large bedrooms. It was very convenient that each
…see more

from £239 / night

£1667 - £2544 / week

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from £239 / night

9

Colle di Val d'Elsa holiday farmhouse rental

Province of Siena / Colle di Val d'Elsa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £101 / night

£693 - £1500 / week

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from £101 / 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 £799 / night

£5593 - £7128 / week

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from £799 / night

(47) 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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Responds fast!
avg. 3 hours 48 minutes

from £90 / night

18

Villa rental in Gaiole in Chianti with swimming pool

Province of Siena / Gaiole in Chianti

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

from £170 / night

£1404 - £2461 / week

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Responds fast!
avg. 2 hours 52 minutes

from £170 / night

19

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 £79 / night

£483 - £667 / week

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Responds fast!
avg. 1 hour 55 minutes

from £79 / night

(1) Very Good 

35

Villa accommodation in San Gimignano with swimming pool

Province of Siena / San Gimignano

7 10 Min stay varies

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

from £189 / night

£1316 - £2106 / week

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from £189 / night

(4) Excellent 

17

Holiday apartment rental

Province of Siena / Torre A Castello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £49 / night

£338 / week

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from £49 / night

(38) Excellent 

24

Apartment rental in Val di Merse

Siena / Val di Merse

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 km
  • Child friendly
  • Pet friendly
“What you imagine when you think "Tuscany"!” We stayed in La Verbena, and it was amazing. Podere Sortoiano is about 15 minutes out of Siena, but it is so worth it to stay out of the city! It's incredibly quiet and relaxing, and the stars are unlike any
…see more

from £43 / night

£264 - £435 / week

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from £43 / night

(21) Excellent 

Certificate of Excellence

43

Holiday apartment in Monticchiello

Pienza / Monticchiello

2 6 2 nights min

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

Certificate of Excellence

from £66 / night

£325 - £792 / week

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from £66 / night

31

Asciano holiday villa let

Province of Siena / Asciano

5 9 5 nights min

  • 5 bedrooms
  • Sleeps 9
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £308 / night

£1711 - £3685 / week

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Responds fast!
avg. 3 hours 28 minutes

from £308 / night

7

Holiday apartment in Orgia

Province of Siena / Orgia

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min

from £87 / night

£570 / week

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from £87 / night

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly

from £49 / night

£343 - £646 / week

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from £49 / night

(15) Very Good 

97

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

7 16 1 night min

  • 7 bedrooms
  • Sleeps 16
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
“Wonderful place, we'll come back!” Everything was first class: the rooms, the pool, breakfast, the countryside. We enjoyed a walk in the countryside and had an archery session with a very patient instructor. Staff is very friendly and helpful.
…see more

from £527 / night

£3071 / week

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from £527 / night

(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 £62 / night

£224 - £461 / week

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Responds fast!
avg. 2 hours 52 minutes

from £62 / night

(1) Excellent 

22

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £290 / night

£2018 / week

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from £290 / night

24

Holiday b&b in Siena

Province of Siena / Siena

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Child friendly
  • Car not necessary

from £308 / night

£1755 - £1939 / week

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Responds fast!
avg. 2 hours 36 minutes

from £308 / night

(14) Excellent 

17

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 65 km
  • Child friendly
  • Air conditioning
“Great Tuscan apartment... but not for summer heat.” My husband and I had originally hoped to stay in Il Duca for 2 months, but because of the heat in Tuscany this summer, we had to seek other accommodations with air conditioning. Pros: The apartme
…see more

from £91 / night

£632 / week

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Responds fast!
avg. 2 hours 7 minutes

from £91 / night

(6) Excellent 

37

Holiday apartment in Montefollonico

Torrita di Siena / Montefollonico

2 5 2 nights min

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

from £106 / night

£1141 - £2062 / week

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from £106 / night

(15) Excellent 

23

Castelnuovo Berardenga holiday apartment rental

Province of Siena / Castelnuovo Berardenga

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“We enjoyed our holidays in this beautiful agriturismo” We have spent two weeks in Fernando Mattii's agriturismo. The site is very clean and very well maintained. Fernando Mattii was always helpful when we needed anything and he even brought us some wo
…see more

from £132 / night

£922 / week

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Responds fast!
avg. 3 hours 29 minutes

from £132 / night

(1) Excellent 

21

Townhouse letting in Rocca d'Orcia

Province of Siena / Rocca d'Orcia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Ask about pets

from £62 / night

£439 / week

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from £62 / night

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 105 km
  • Swimming pool
  • Child friendly

from £49 / night

£343 - £720 / week

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from £49 / 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!
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from £101 / night

£702 - £1097 / week

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from £101 / night

17

Ski apartment to rent in Abbadia San Salvatore

Province of Siena / Abbadia San Salvatore

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ski
  • Child friendly
  • Private garden

from £79 / night

£439 - £527 / week

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Responds fast!
avg. 3 hours 0 minutes

from £79 / night

4

Holiday villa in Tognazza

Province of Siena / Tognazza

1 2 1 night min

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

from £27 / night

£185 / week

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from £27 / night

(5) Excellent 

48

Holiday cottage in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 150 km
  • Child friendly
  • Private garden
“Very great time” we spend a very great time in a charming house in the middle of Chianti vines the house is well-heated and pleasant
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from £106 / night

£492 - £588 / week

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Responds fast!
avg. 2 hours 19 minutes

from £106 / 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 £36 / night

£250 - £518 / week

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Responds fast!
avg. 2 hours 52 minutes

from £36 / night