Vacation Rentals & Villas in Montalcino

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

2,236 Houses

(3) Very Good 

12

The Palazzetta Luca and Flavio Fanti

Montalcino / Castelnuovo dell'Abate

Castelnuovo dell'Abate apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$91

Price per night from

$91

(11) Excellent 

37

Podere Ferranino Townhouses -Brunelleschi

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso apartment

4 7 2 nights min

  • 4 bedrooms
  • sleeps 7
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Beautifully restored Villa Ferranino Townhouses-Brunelleschi” Just a few 100 meters south of San Giovanni d'Asso, you find Villa Ferrano.This beautiful old property consists of the main villa, the former carriage house Ferranino, the old farm house an
…see more

Price per night from

$399

Responds fast!
avg. 2 hours 35 minutes

Price per night from

$399

16

Cesira Palazzina

Montalcino / Val d'Orcia

Val d'Orcia b and b

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 48 mi
  • Child Friendly
  • Air conditioning

Price per night from

$131

Price per night from

$131

(5) Very Good 

37

Podere Ferranino Townhouses- Cimabue

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$301

Responds fast!
avg. 2 hours 35 minutes

Price per night from

$301

(14) Excellent 

31

Podere Ferranino Townhouses-Fra Angelico

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Absolutely Wonderful!” The Villa Ferranino Townhouses and grounds are a very special place. I can not do justice to how absolutely beautiful this place is. Spacious accommodations with a view towards keeping the historical integrity of the buildings w
…see more

Price per night from

$302

Responds fast!
avg. 2 hours 35 minutes

Price per night from

$302

(7) Very Good 

56

Minnie's Cottage: L'Olivo Gino

Province of Siena / Montalcino

Montalcino house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$106

Price per night from

$106

(6) Excellent 

49

Podere Ferranino Townhouses- Alberti

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso apartment

3 5 2 nights min

  • 3 bedrooms
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$319

Responds fast!
avg. 2 hours 35 minutes

Price per night from

$319

39

Le Due Sorelle

Montalcino / Poggio alle Mura

Poggio alle Mura villa

4 5 min stay varies

  • 4 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 86 mi
  • Swimming pool
  • Child Friendly

Price per night from

$196

Price per night from

$196

(53) Excellent 

30

Cozy Collection of Villas in Tuscany

Province of Siena / Montalcino

Montalcino villa

14 26 3 nights min

  • 14 bedrooms
  • sleeps 26
  • 3 nights min
  • Nearest beach 81 mi
  • Swimming pool
  • Child Friendly
“Great stay- we hope to return!” We truly enjoyed our stay here. Matteo was a wonderful host and even met us outside of town to make sure that we did not get lost on the way to the agriturismo. The room was clean and very comfortable, especially import
…see more

Price per night from

$103

Responds fast!
avg. 3 hours 40 minutes

Price per night from

$103

18

Lecci

Province of Siena / Montalcino

Montalcino apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 137 mi
  • Swimming pool
  • Pet Friendly

Price per night from

$330

Price per night from

$330

42

Spacious and Beautiful Tuscany Villa Near Montalcino - Villa Brunello

Montalcino / Poggio alle Mura

Poggio alle Mura villa

10 7 nights min

  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$1,153

Price per night from

$1,153

12

Casal d'Asso

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso house

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$558

Price per night from

$558

(34) Very Good 

46

Farmhouse Rental in Tuscany, Montalcino - Villa Montalcino

Province of Siena / Montalcino

Montalcino farmhouse

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet Friendly
“Nancy's review of Farmhouse Rental in Tuscany, Montalcino - Vill” The property surpassed our expectations. The rooms were quite comfortable, the view was extraordinary and the grounds were beautiful. Convenient location within walking distance of tow
…see more

Price per night from

$357

Price per night from

$357

(1) Very Good 

29

Podere Ferranino Townhouses-Duccio

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$285

Responds fast!
avg. 2 hours 35 minutes

Price per night from

$285

(1) Excellent 

29

Villa San Giuseppe

Montalcino / Castelnuovo dell'Abate

Castelnuovo dell'Abate villa

5 8 min stay varies

  • 5 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child Friendly

Price per night from

$942

Price per night from

$942

47

Alborata 10

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 94 mi
  • Swimming pool
  • Ask about children

Price per night from

$366

Price per night from

$366

18

Dobel

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso villa

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$837

Responds fast!
avg. 15 minutes

Price per night from

$837

15

Luxury villa Capanno

Province of Siena / Montalcino

Montalcino villa

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$407

Price per night from

$407

30

5 bedroom Villa in San Giovanni d'Asso, Tuscany, Italy: ref 5455314

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$828

Price per night from

$828

27

5 bedroom Villa in Argiano, Tuscany, Italy : ref 5239265

Montalcino / Poggio alle Mura

Poggio alle Mura villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$1,014

Price per night from

$1,014

16

Appartamento vicino a san gimignano

Province of Siena / Montalcino

Montalcino apartment

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$91

Price per night from

$91

27

4 bedroom Villa in Sant'Antimo, Tuscany, Italy : ref 5049050

Montalcino / Castelnuovo dell'Abate

Castelnuovo dell'Abate villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$492

Price per night from

$492

30

Perfect for weddings, business meetings or a quiet getaway, Villa Tolomei is on

Province of Siena / Montalcino

Montalcino house

14 30 min stay varies

  • 14 bedrooms
  • sleeps 30
  • min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$3,623

Price per night from

$3,623

(4) Very Good 

26

FOUNTAINS

Montalcino / Poggio alle Mura

Poggio alle Mura villa

5 16 min stay varies

  • 5 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet Friendly

Price per night from

$1,782

Price per night from

$1,782

30

3 bedroom Villa in San Giovanni d'Asso, Tuscany, Italy: ref 5455309

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso villa

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$403

Price per night from

$403

44

Lavacchio 16

Montalcino / Poggio alle Mura

Poggio alle Mura villa

8 16 7 nights min

  • 8 bedrooms
  • sleeps 16
  • 7 nights min
  • Nearest beach 63 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,026

Price per night from

$1,026

(3) Excellent 

25

ART-HANGAR BY TUSCAN-EXPERIENCE

Province of Siena / Montalcino

Montalcino apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 81 mi
  • Swimming pool
  • Child Friendly

Price per night from

$319

Price per night from

$319

30

4 bedroom Villa in Siena, Tuscany, Italy : ref 5455310

Province of Siena / Montalcino

Montalcino villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$527

Price per night from

$527

18

Pozzo

Province of Siena / Montalcino

Montalcino apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 137 mi
  • Swimming pool
  • Pet Friendly

Price per night from

$312

Price per night from

$312

24

Le Macine 6

Province of Siena / Montalcino

Montalcino villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$281

Price per night from

$281

16

Minnie's Cottage: Romantic Tuscany

Montalcino / Sant'Angelo in Colle

Sant'Angelo in Colle apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 40 mi
  • Child Friendly

Price per night from

$77

Price per night from

$77

25

Villa Rental in Tuscany, Castlenuovo dell'Abate - Mulino Abate

Province of Siena / Montalcino

Montalcino villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$667

Price per night from

$667

30

Montebendico 4

Province of Siena / Montalcino

Montalcino villa

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Ask about children

Price per night from

$175

Price per night from

$175

20

Archi

Province of Siena / Montalcino

Montalcino apartment

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 137 mi
  • Swimming pool
  • Pet Friendly

Price per night from

$431

Price per night from

$431

41

6 bedroom Villa in Camigliano, Tuscany, Italy : ref 5239281

Montalcino / Poggio alle Mura

Poggio alle Mura villa

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$822

Price per night from

$822

20

Villa Asso

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso villa

7 16 7 nights min

  • 7 bedrooms
  • sleeps 16
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$804

Price per night from

$804

53

Villa il Poggetto

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$261

Price per night from

$261

(2) Excellent 

59

Villa Giardinello, your dream villa in Tuscany

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso villa

6 11 min stay varies

  • 6 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$779

Price per night from

$779