Holiday Rentals in Province of Siena - Holiday Lettings - Villas

Close

View larger map

Also consider

Europe Holidays
429187 properties
Italy Holidays
100351 properties
Tuscany Holidays
22745 properties
Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Villas San Gimignano
465 properties
Villas Siena
414 properties
Villas Montepulciano
282 properties
Casole d'Elsa
196 properties
Castelnuovo Berardenga
183 properties
Gaiole in Chianti
164 properties
Colle di Val d'Elsa
159 properties
Villas Castellina In Chianti
152 properties
Poggibonsi
149 properties
Villas Pienza
143 properties
Rapolano Terme
127 properties
Villas Montalcino
113 properties
Sinalunga
113 properties
Asciano
99 properties

Province of Siena

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

739 Holiday homes

10

Province of Siena / Siena

3 6 2 nights min

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

from £84 / night

£582 / week

Book View

from £84 / night

(6) Excellent 

36

Holiday villa with indoor pool in Radicondoli

Province of Siena / Radicondoli

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 79 km
  • Swimming pool
  • Child friendly

from £255 / night

£1780 / week

Book View

Responds fast!
avg. 28 minutes

from £255 / night

18

Holiday farmhouse accommodation

Province of Siena / San Casciano dei Bagni

3 6 Min stay varies

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

from £178 / night

£619 - £1026 / week

Enquire View

Responds fast!
avg. 42 minutes

from £178 / 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 £77 / night

£475 - £534 / week

Book View

Responds fast!
avg. 1 hour 20 minutes

from £77 / night

(1) Very Good 

18

B&b letting in Montepulciano with shared pool

Province of Siena / Montepulciano

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“nice place, nice people” Living for a bit in an old fashioned atmosphere. It is a confortable and friendly place to stay with your family , friends or alone both relaxing in a wonderful Tuscany landscape and travelling around to explore Reinassance
…see more

from £30 / night

£208 / week

Book View

Responds fast!
avg. 1 hour 50 minutes

from £30 / night

(7) Very Good 

39

Holiday villa rental

Province of Siena / Chianciano Terme

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £170 / night

£907 - £2289 / week

Book View

from £170 / night

(11) Very Good 

32

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Excellent value Tuscan villa in a lovely setting” We stayed in the Agrifolo apartment at Le Fontanelle in May 2015. I was visited with my partner and my parents as we treated them to a Tuscan trip to start the summer. The villa was lovely - simple
…see more

from £60 / night

£450 - £801 / week

Book View

Responds fast!
avg. 2 hours 24 minutes

from £60 / night

(12) Excellent 

69

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

Province of Siena / Gaiole in Chianti

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“A hidden gem.” We stayed at Villa LisiDor at the end of May with family. We made the trip to Tuscany by train to Florence from the UK and hired a car from there. We arrived during an unseasonably chilly spell and in torrential rain after a very l
…see more

from £322 / night

£2248 - £4323 / week

Book View

from £322 / night

(11) 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 £77 / night

£475 - £534 / week

Book View

Responds fast!
avg. 1 hour 20 minutes

from £77 / night

14

Holiday farmhouse rental

Province of Siena / San Casciano dei Bagni

2 4 7 nights min

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

from £86 / night

£597 - £841 / week

Enquire View

Responds fast!
avg. 42 minutes

from £86 / night

(20) Excellent 

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

from £64 / night

£314 - £765 / week

Book View

from £64 / night

12

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 £67 / night

£454 - £657 / week

Book View

from £67 / night

(4) Excellent 

31

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 £68 / night

£411 - £487 / week

Book View

Responds fast!
avg. 3 hours 33 minutes

from £68 / night

(6) Very Good 

43

Gaiole in Chianti holiday home accommodation

Gaiole in Chianti / Montefienali

3 6 Min stay varies

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

from £46 / night

£265 - £594 / week

Book View

Responds fast!
avg. 1 hour 42 minutes

from £46 / night

(8) Excellent 

33

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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
…see more

from £60 / night

£416 / week

Book View

Responds fast!
avg. 1 hour 50 minutes

from £60 / night

(8) Excellent 

24

Rapolano Terme / Serre di Rapolano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £81 / night

£551 / week

Book View

from £81 / night

(49) Excellent 

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

from £73 / night

£424 - £594 / week

Book View

from £73 / night

34

Holiday villa in Pienza

Province of Siena / Pienza

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £199 / night

£1390 - £2272 / week

Book View

from £199 / night

(6) Very Good 

56

Torrita di Siena / Montefollonico

2 4 2 nights min

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

from £162 / night

£1128 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from £162 / night

99

Montepulciano / Abbadia di Montepulciano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Private garden

from £424 / night

£2967 / week

Book View

from £424 / night

(3) Excellent 

24

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 £46 / night

£323 - £479 / week

Book View

from £46 / 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 £102 / night

£509 - £721 / week

Book View

from £102 / night

(10) Excellent 

58

Holiday villa rental

Province of Siena / San Giovanni d'Asso

8 16 3 nights min

  • 8 bedrooms
  • Sleeps 16
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“unforgettable tuscan paradise” Wonderful historic house, charming atmosphere, you feel at home. We were a group of 16 friends, the house was perfect, nothing was missing. Nice accommodations very clean, housekeeping every day. Unforgettable breakfa
…see more

from £482 / night

£3372 - £4395 / week

Book View

Responds fast!
avg. 3 hours 22 minutes

from £482 / night

(2) Excellent 

24

Province of Siena / Colle di Val d'Elsa

3 7 3 nights min

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

from £111 / night

£653 - £975 / week

Book View

from £111 / night

(2) Excellent 

22

Pienza / Monticchiello

1 4 3 nights min

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

from £43 / night

£289 - £372 / week

Book View

Responds fast!
avg. 3 hours 22 minutes

from £43 / night

31

Murlo / Casciano di Murlo

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £68 / night

£411 - £487 / week

Book View

Responds fast!
avg. 3 hours 33 minutes

from £68 / night

(5) Excellent 

46

Holiday farmhouse rental

San Gimignano / Montauto

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £206 / night

£1441 / week

Book View

Responds fast!
avg. 59 minutes

from £206 / night

(5) Excellent 

48

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

from £102 / night

£475 - £568 / week

Book View

Responds fast!
avg. 2 hours 36 minutes

from £102 / night

(6) Excellent 

31

Holiday villa in Costalpino

Siena / Costalpino

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Private garden
“Belvedere e stupendo” After a beautifully green, bus ride from Rome, I arrived at my designated stop a few kilometer’s before Siena and waited for my transfer to Belvedere, a magical home at the end of a beautiful long winding driveway where views of
…see more

from £191 / night

£1272 - £1653 / week

Book View

Responds fast!
avg. 3 hours 10 minutes

from £191 / 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 £60 / night

£217 - £445 / week

Book View

from £60 / night

(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 £79 / night

£551 - £1263 / week

Book View

from £79 / night

(1) Excellent 

22

Province of Siena / Montepulciano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 116 km
  • Child friendly
  • Pet friendly

from £119 / night

£509 - £636 / week

Book View

from £119 / night

(46) Excellent 

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

from £90 / night

£625 - £900 / week

Book View

Responds fast!
avg. 3 hours 48 minutes

from £90 / night

(6) Very Good 

25

Province of Siena / Monteriggioni

1 3 3 nights min

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

from £47 / night

£306 - £496 / week

Book View

Responds fast!
avg. 2 hours 26 minutes

from £47 / night

(10) Excellent 

10

Province of Siena / Sovicille

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly

from £38 / night

£530 - £2206 / week

Book View

from £38 / night

(2) Excellent 

24

Holiday villa with swimming pool in Montalcinello

Chiusdino / Montalcinello

8 18 7 nights min

  • 8 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly

from £334 / night

£2331 - £3814 / week

Enquire View

from £334 / night

20

Holiday manor house rental

Province of Siena / Chiusi

8 21 7 nights min

  • 8 bedrooms
  • Sleeps 21
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Swimming pool

from £299 / night

£2093 - £3135 / week

Enquire View

from £299 / night

(13) Excellent 

41

Asciano / Crete Senesi

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £60 / night

£416 - £695 / week

Book View

Responds fast!
avg. 1 hour 54 minutes

from £60 / 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
…see more

from £100 / night

£625 - £895 / week

Book View

from £100 / night

(6) Excellent 

35

Monticiano / Tocchi

2 6 Min stay varies

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

from £60 / night

£390 - £823 / week

Book View

from £60 / night

1