Villas in Montalcino and Apartments - Holiday Lettings - Holiday Rentals Montalcino

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2,224 Holiday homes

(11) Excellent 

40

Holiday villa rental

Montalcino / San Giovanni d'Asso

8 16 min stay varies

  • 8 bedrooms
  • sleeps 16
  • min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £809 / night

£5,662 - £7,207 / week

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Responds fast!
avg. 3 hours 34 minutes

from £809 / night

(1) Excellent 

18

Holiday villa with shared pool in Val d'Orcia

Montalcino / Val d'Orcia

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 25 km
  • Swimming pool
  • Child friendly

from £103 / night

£664 - £1,384 / week

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Responds fast!
avg. 1 hour 49 minutes

from £103 / 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 £124 / night

£865 / week

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from £124 / night

(4) Excellent 

8

Castelnuovo dell'Abate holiday apartment rental

Montalcino / Castelnuovo dell'Abate

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning

from £88 / night

£613 / week

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from £88 / night

(5) Excellent 

51

Holiday villa with swimming pool in Montalcino

Province of Siena / Montalcino

4 11 min stay varies

  • 4 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £412 / night

£2,883 / week

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from £412 / night

27

Villa rental in Poggio alle Mura with swimming pool

Montalcino / Poggio alle Mura

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 66 km
  • Swimming pool

from £859 / night

£6,008 - £9,883 / week

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Responds fast!
avg. 3 hours 28 minutes

from £859 / 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 £340 / night

£2,378 / week

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from £340 / night

(5) Excellent 

18

Holiday home in Castelnuovo dell'Abate

Montalcino / Castelnuovo dell'Abate

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 50 km
  • Child friendly

from £114 / night

£793 / week

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from £114 / 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 £206 / night

£1,442 / week

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Responds fast!
avg. 2 hours 47 minutes

from £206 / night

(2) Excellent 

17

Holiday farmhouse in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Child friendly
  • Pet friendly

from £145 / night

£721 / week

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Responds fast!
avg. 3 hours 26 minutes

from £145 / night

(4) Excellent 

21

Holiday villa in Montalcino

Province of Siena / Montalcino

6 12 2 nights min

  • 6 bedrooms
  • sleeps 12
  • 2 nights min
  • Child friendly

from £525 / night

£3,672 / week

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from £525 / night

(1) Excellent 

6

Holiday b&b accommodation

Province of Siena / Montalcino

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly

from £62 / night

£433 / week

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Responds fast!
avg. 2 hours 36 minutes

from £62 / night

23

San Giovanni d'Asso holiday home rental

Montalcino / San Giovanni d'Asso

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £134 / night

£772 / week

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from £134 / night

4

Apartment rental in Montalcino

Province of Siena / Montalcino

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Pet friendly

from £98 / night

£685 / week

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from £98 / night

12

Montalcino holiday b&b rental

Province of Siena / Montalcino

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min

from £165 / night

£1,153 / week

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from £165 / night

(12) Excellent 

37

Holiday villa with swimming pool in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £281 / night

£1,969 - £2,831 / week

Book View

Responds fast!
avg. 3 hours 34 minutes

from £281 / 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 £335 / night

£2,059 - £2,574 / week

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from £335 / night

(3) Excellent 

37

Holiday villa with swimming pool in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £379 / night

£2,656 - £3,552 / week

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Responds fast!
avg. 3 hours 34 minutes

from £379 / night

(13) Excellent 

20

Holiday apartment with golf nearby in Sant'Angelo in Colle

Montalcino / Sant'Angelo in Colle

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 68 km
  • Child friendly
  • Private garden

from £78 / night

£484 - £1,205 / week

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from £78 / night

(5) Very Good 

40

Holiday farmhouse in Montalcino

Province of Siena / Montalcino

7 14 min stay varies

  • 7 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly

from £75 / night

£526 / week

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from £75 / night

20

Holiday farmhouse in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £199 / night

£1,390 / week

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from £199 / night

12

Holiday b&b rental

Montalcino / Val d'Orcia

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £124 / night

£824 / week

Book View

from £124 / night

24

Holiday apartment in Val d'Orcia

Montalcino / Val d'Orcia

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

from £237 / night

£1,656 / week

Book View

from £237 / night

(3) Excellent 

15

Holiday farmhouse in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Child friendly
  • Pet friendly

from £124 / night

£772 / week

Book View

Responds fast!
avg. 3 hours 26 minutes

from £124 / night

12

Montalcino holiday b&b rental

Province of Siena / Montalcino

1 1 1 night min

  • 1 bedroom
  • sleeps 1
  • 1 night min

from £78 / night

£540 / week

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from £78 / night

24

Holiday home in Montalcino

Province of Siena / Montalcino

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly

from £103 / night

£720 / week

Book View

from £103 / night

15

Holiday b&b in Val d'Orcia

Montalcino / Val d'Orcia

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 80 km

from £93 / night

£648 / week

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from £93 / night

16

Montalcino holiday apartment rental

Province of Siena / Montalcino

2 6 2 nights min

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

from £392 / night

£2,574 / week

Book View

from £392 / night

8

Castelnuovo dell'Abate holiday home rental

Montalcino / Castelnuovo dell'Abate

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child friendly
  • Pet friendly

from £206 / night

£1,339 / week

Book View

from £206 / night

15

Val d'Orcia holiday apartment rental

Montalcino / Val d'Orcia

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 80 km

from £103 / night

£721 / week

Book View

from £103 / night

(7) Excellent 

47

Holiday villa in Montalcino

Province of Siena / Montalcino

9 18 7 nights min

  • 9 bedrooms
  • sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £524 / night

£3,669 - £7,042 / week

Book View

from £524 / night

15

Apartment rental in Montalcino with shared pool

Province of Siena / Montalcino

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £283 / night

£1,853 / week

Book View

from £283 / night

12

B&b rental in Montalcino

Province of Siena / Montalcino

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min

from £124 / night

£824 / week

Book View

from £124 / night

26

Home rental in San Giovanni d'Asso with shared pool

Montalcino / San Giovanni d'Asso

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £145 / night

£865 / week

Book View

from £145 / night

12

B&b rental in Montalcino

Province of Siena / Montalcino

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min

from £124 / night

£823 / week

Book View

from £124 / night

(1) Very Good 

29

Villa rental in Castelnuovo dell'Abate with swimming pool

Montalcino / Castelnuovo dell'Abate

5 8 min stay varies

  • 5 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £1,205 / night

£5,215 - £6,294 / week

Enquire View

from £1,205 / night

24

Holiday apartment in Val d'Orcia

Montalcino / Val d'Orcia

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

from £206 / night

£1,442 / week

Book View

from £206 / night

14

Holiday villa in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Pet friendly

from £391 / night

£2,674 - £3,497 / week

Book View

from £391 / night

12

Montalcino holiday b&b rental

Province of Siena / Montalcino

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min

from £165 / night

£1,152 / week

Book View

from £165 / night

53

Holiday villa with swimming pool in Poggio alle Mura

Montalcino / Poggio alle Mura

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 66 km
  • Swimming pool
  • Child friendly

from £697 / night

£4,872 - £8,106 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from £697 / night

Top Destination reviews

Podere Ferranino Townhouses- Cimabue
Beautifully designed and equipped townhouse in a stunning setting.

Four of us had a fantastic stay at Cimabue and were sorry to leave. The converted coach house is excellently laid out and equipped - including washing machine, micro, toaster, coffee maker, air-conditioning and high speed broadband. The grounds are beautiful and the views across the valley are utterly stunning. We were also very pleasantly surprised by the size of the pool and the fact that it had an adjacent jacuzzi. There are some lovely walks in the vicinity. If you like to run off road or to cycle the terrain and available routes in the locality are terrific. We followed the recommendations for restaurants given by our hosts and were not disappointed. We also tried another restaurant in nearby Trequanda. All the restaurants were excellent and very good value. Patricia was a wonderful host - nothing was too much trouble. We won't hesitate to return if we get the chance!see more
Bright and beautiful 4 bedroom Tuscan villa with pool, private garden and barbecue, sleeps 8
Great location, fits all types of travellers specially family reunions

The Villa is placed in a very special and beautiful area in the Tuscany region. Near (up to 1h - 1.20h) many special places and famous cities, such as Siena and Montalcino. The access to the Vila is by a not paved road, and be carefull to enter the road from Torrenieri. The house is great, comfortable and has many facilities. All new and beautiful. I really recommend this house and the hospitality we have received.see more
5BDR Casale ,view on the Crete Senesi,walking to a village,private pool,WiFi
Gorgeous villa in Tuscany

This is a gorgeous villa in the tuscan countryside. The villa was beautiful, spotless and had everything we needed. It is right next to the small town of San Giovanni D'Osso. My 16-year-old loved it as well. While we day-tripped to surrounding towns including Sienna and Florence, we always enjoyed coming back to the villa to swim and prepare dinner. I can't wait for the next time when we can return there with our friends. Great hosts as well.see more
8BDR Historic villa in the Crete Senesi walking to a village : view,pool,garden
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 breakfast on the terrace in front of the scenic, lunch in the beautiful garden and dinner by the cooker (so delicious!!) Federica, the owner , and all the staff are kind and helpful. If you need an address, do not hesitate to ask her, especially for tasting Brunello. One of the best places toto stay for visiting and appreciating Tuscany!see more
3BDR Casale Il Tribbio Il ,view on the Crete ,close to a village
Perfect.

The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arrive on a Saturday, have them bring in some groceries - everything is shut up tight on Sunday. The villa itself is lovely, the views spectacular and location convenient for touring. The highlight at the end of each day was returning to the pool and quiet evenings outside.see more
Fonte Aulente Montalcino
Great Location

We can only reiterate the excellent reviews that have gone before. Fonte Aulente is in a great location, quiet and secluded with amazing views of the Tuscan countryside and close to the beautiful town of Montalcino. The accommodation, including the extensive garden with its large fresh water pool, offered everything our family of four needed. We were close enough to visit Siena, Florence, Pisa and the beach on day trips. Our hostess Alexandra was welcoming and helpful throughout the stay without ever being intrusive, suggesting local drives and sharing her passion for the local wines. We thoroughly enjoyed our two week stay at Fonte Aulente and look forward to returning in the future.see more

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