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

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Montalcino

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1,985 Holiday homes

(4) 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 £89 / night

£620 / week

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from £89 / 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

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

(12) Excellent 

40

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 £220 / night

£1,540 - £2,230 / week

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Responds fast!
avg. 3 hours 9 minutes

from £220 / night

(4) Excellent 

21

Holiday apartment in Val d'Orcia

Montalcino / Val d'Orcia

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
“Fantastic experience in a gorgeous setting that exceeded all expectations.” My wife and I spent a week here with our three teenage boys and all of us loved the place. The reality of the home is even better than the photos and we hated to leave. Hosts
…see more

from £203 / night

£1,416 - £2,080 / week

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from £203 / night

(13) Excellent 

20

Holiday apartment with golf nearby in Sant'Angelo in Colle

Montalcino / Sant'Angelo in Colle

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 68 km
  • Suitable for children age 5+
  • Private garden

from £67 / night

£399 - £770 / week

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from £67 / 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

(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
“Perfect cottage for two” Loved everything about our stay here. Alexandra was so helpful, with directions, shopping, restaurants and her love of the wine industry. She met us on the road when we got lost. Lives next door but the property is so big
…see more

from £107 / night

£744 / week

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from £107 / night

(2) Excellent 

41

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 £273 / night

£1,912 - £2,677 / week

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Responds fast!
avg. 3 hours 9 minutes

from £273 / 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 £204 / night

£1,425 / week

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from £204 / night

(7) Excellent 

24

Val d'Orcia holiday villa rental

Montalcino / Val d'Orcia

4 9 7 nights min

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

from £201 / night

£1,404 - £2,110 / week

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from £201 / night

22

Villa rental in San Giovanni d'Asso with swimming pool

Montalcino / San Giovanni d'Asso

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £718 / night

£5,020 - £6,120 / week

Enquire View

from £718 / night

21

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
  • Swimming pool
  • Child friendly
  • Pet friendly

from £738 / night

£5,165 - £8,496 / week

Enquire View

from £738 / night

(1) Excellent 

25

San Giovanni d'Asso holiday home rental

Montalcino / San Giovanni d'Asso

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £106 / night

£737 / week

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Responds fast!
avg. 1 hour 38 minutes

from £106 / night

(2) Excellent 

17

Holiday farmhouse in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

2 4 Min stay varies

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

from £123 / night

£571 / week

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from £123 / night

(3) Excellent 

57

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 £310 / night

£2,169 / week

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from £310 / night

26

Home rental in San Giovanni d'Asso with shared pool

Montalcino / San Giovanni d'Asso

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £107 / night

£744 / week

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from £107 / night

23

San Giovanni d'Asso holiday home rental

Montalcino / San Giovanni d'Asso

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £58 / night

£403 - £620 / week

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from £58 / 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 £177 / night

£1,239 / week

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from £177 / 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 £89 / night

£620 / week

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Responds fast!
avg. 3 hours 31 minutes

from £89 / night

(2) Excellent 

21

Holiday villa in Montalcino

Province of Siena / Montalcino

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly

from £452 / night

£3,160 - £3,531 / week

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from £452 / night

(3) Excellent 

15

Holiday farmhouse in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

2 4 Min stay varies

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

from £123 / night

£571 / week

Book View

from £123 / night

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 £102 / night

£660 - £1,195 / week

Book View

Responds fast!
avg. 1 hour 38 minutes

from £102 / night

(1) Excellent 

22

San Giovanni d'Asso holiday villa rental

Montalcino / San Giovanni d'Asso

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £264 / night

£1,845 - £2,570 / week

Enquire View

from £264 / night

24

San Giovanni d'Asso holiday apartment rental

Montalcino / San Giovanni d'Asso

2 4 2 nights min

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

from £274 / night

£1,915 / week

Book View

Responds fast!
avg. 1 hour 47 minutes

from £274 / 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 £89 / night

£620 / week

Book View

from £89 / night

(12) Excellent 

66

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 120 km
  • Swimming pool
  • Child friendly
“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-tri
…see more

from £470 / night

£3,292 - £4,461 / week

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Responds fast!
avg. 3 hours 9 minutes

from £470 / night

20

Holiday villa with swimming pool in Montalcino

Province of Siena / Montalcino

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £517 / night

£3,617 - £3,992 / week

Enquire View

from £517 / night

(1) Very Good 

47

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 £1,186 / night

£6,195 / week

Enquire View

from £1,186 / 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 £337 / night

£2,213 / week

Book View

from £337 / night

12

Montalcino holiday b&b rental

Province of Siena / Montalcino

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min

from £142 / night

£992 / week

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from £142 / night

21

Apartment rental in Val d'Orcia with swimming pool

Montalcino / Val d'Orcia

4 9 7 nights min

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

from £170 / night

£1,185 - £1,579 / week

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from £170 / 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 £107 / night

£708 / week

Book View

from £107 / night

22

Holiday villa with swimming pool in Montalcino

Province of Siena / Montalcino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £180 / night

£1,254 - £2,369 / week

Enquire View

from £180 / night

(11) Excellent 

80

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
“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 £567 / night

£4,248 - £5,523 / week

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Responds fast!
avg. 3 hours 9 minutes

from £567 / night

(1) Very Good 

22

B&b rental in Montalcino

Province of Siena / Montalcino

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Ask about pets

from £186 / night

£1,115 / week

Book View

from £186 / night

21

San Giovanni d'Asso holiday apartment rental

Montalcino / San Giovanni d'Asso

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £247 / night

£1,729 / week

Book View

Responds fast!
avg. 1 hour 47 minutes

from £247 / night

12

B&b rental in Montalcino

Province of Siena / Montalcino

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

from £107 / night

£708 / week

Book View

from £107 / night

12

B&b rental in Montalcino

Province of Siena / Montalcino

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

from £107 / night

£708 / week

Book View

from £107 / night

22

Holiday apartment with shared pool in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

2 4 2 nights min

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

from £274 / night

£1,915 / week

Book View

Responds fast!
avg. 1 hour 47 minutes

from £274 / 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
I MELOGRANI II: 3BDR Tuscan villa,view,pool,WiFi
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
wonderful hamlet apartments -Clementina
Great scenary, wonderful cool place with friendly staff service

Came at a right time to see and feel the cooling surroundings. We do like so much the friendly service by Ms Erena. Good guidance from her on where to visits or recommended restaurants for our meals. We might come again next year! … see more