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In one of the oldest towns in Tuscany, holiday rental accommodation in Montalcino will give you the chance to investigate a part of the region that has been inhabited since Etruscan times, so if you have an interest in Italian history, you'll find plenty to investigate in this fascinating rural town, and even more if you tour round the other cities, towns and villages that are scattered throughout the province of Siena. Villa and apartment rentals in Montalcino can be found in situations that afford spectacular views across the hills and valleys that are so characteristic of the Tuscan countryside - landscapes as well-known for their breathtaking scenic beauty as they are for their vineyards and olive groves, as the hillside upon which this town is perched is where the grapes are grown to produce the famous Brunello di Montalcino wine and where the local olive oil proves a popular choice in kitchens right across Siena Province. Holiday accommodation in Montalcino is, unsurprisingly, often chosen by those for whom a culinary voyage of discovery is their sole reason for wanting to visit this charmingly traditional hill-town nestling amongst some of the finest rural scenery in Tuscany - apartment and villa rentals in Montalcino therefore making the perfect base for a truly relaxing and self-indulgent break in a location that is, for many, a welcome alternative to the hectic urban environment of home. But when you'll never be too far away from opportunities for recreation, sport and leisure that would suit people of all ages and interests, you'll be sure to find holiday accommodation in Montalcino offers the ideal solution to a fun-packed vacation to suit the whole family.

    Villa #1893413
    • 6 BR
    • 3 BA
    • Sleeps 12
    4
    Viewed 23 times in the last 48 hours

    Confirmation within 24 hours

    Your booking request will be confirmed or denied within 24 hours.

      Exceptional! 5/5
      (10 reviews)
      avg/night
      Apartment #479613vb
      • 3 BR
      • 2 BA
      • Sleeps 6
      10
      Viewed 5 times in the last 48 hours

      Confirmation within 24 hours

      Your booking request will be confirmed or denied within 24 hours.

        Excellent! 4.6/5
        (19 reviews)
        avg/night
        Villa #734706
        • 3 BR
        • 2 BA
        • Sleeps 6
        19
        Viewed 21 times in the last 48 hours

        Confirmation within 24 hours

        Your booking request will be confirmed or denied within 24 hours.

          Exceptional! 5/5
          (5 reviews)
          avg/night
          Chateau / Country House #1688510
          • 3 BR
          • 3 BA
          • Sleeps 8
          5
          Viewed 6 times in the last 48 hours

          Confirmation within 24 hours

          Your booking request will be confirmed or denied within 24 hours.

            Exceptional! 5/5
            (49 reviews)
            avg/night
            Multiple rentals Farmhouse #6131291
            • 2 BR
            • 2 BA
            • Sleeps 6
            49
            Viewed 9 times in the last 48 hours

            Confirmation within 24 hours

            Your booking request will be confirmed or denied within 24 hours.

              Wonderful! 4.8/5
              (5 reviews)
              avg/night
              Apartment #835349vb
              • 1 BR
              • 1 BA
              • Sleeps 4
              5
              Viewed 11 times in the last 48 hours

              Instant confirmation

              Your booking request will be confirmed immediately.

                Chateau / Country House #6726973
                • 4 BR
                • 4 BA
                • Sleeps 8
                1

                Confirmation within 24 hours

                Your booking request will be confirmed or denied within 24 hours.

                  House #6915681
                  • 3 BR
                  • 3 BA
                  • Sleeps 6

                  Confirmation within 24 hours

                  Your booking request will be confirmed or denied within 24 hours.

                    avg/night
                    Villa #4136122
                    • 14 BR
                    • 9 BA
                    • Sleeps 26
                    Viewed 8 times in the last 48 hours

                    Confirmation within 24 hours

                    Your booking request will be confirmed or denied within 24 hours.

                      Exceptional! 5/5
                      (9 reviews)
                      avg/night
                      Multiple rentals Farmhouse #6131291
                      • 1 BR
                      • 1 BA
                      • Sleeps 8
                      9
                      Viewed 8 times in the last 48 hours

                      Confirmation within 24 hours

                      Your booking request will be confirmed or denied within 24 hours.

                        Wonderful! 4.9/5
                        (10 reviews)
                        avg/night
                        Multiple rentals Farmhouse #6131291
                        • Studio
                        • 1 BA
                        • Sleeps 4
                        10
                        Viewed 6 times in the last 48 hours

                        Confirmation within 24 hours

                        Your booking request will be confirmed or denied within 24 hours.

                          House #6856276
                          • 2 BR
                          • 2 BA
                          • Sleeps 6

                          Confirmation within 24 hours

                          Your booking request will be confirmed or denied within 24 hours.

                            avg/night
                            House #6856274
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            Viewed 5 times in the last 48 hours

                            Confirmation within 24 hours

                            Your booking request will be confirmed or denied within 24 hours.

                              Chateau / Country House #6474017
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              1

                              Instant confirmation

                              Your booking request will be confirmed immediately.

                                Farmhouse #6401678
                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                2

                                Instant confirmation

                                Your booking request will be confirmed immediately.

                                  House #1068422vb
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 1

                                  Instant confirmation

                                  Your booking request will be confirmed immediately.

                                    Villa #6978307
                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 6

                                    Confirmation within 24 hours

                                    Your booking request will be confirmed or denied within 24 hours.

                                      Villa #8209173
                                      • 2 BR
                                      • 3 BA
                                      • Sleeps 5

                                      Confirmation within 24 hours

                                      Your booking request will be confirmed or denied within 24 hours.

                                        avg/night
                                        Apartment #6478719
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 3
                                        Viewed 7 times in the last 48 hours

                                        Confirmation within 24 hours

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                                          Villa #1150807
                                          • 6 BR
                                          • 7 BA
                                          • Sleeps 12

                                          Instant confirmation

                                          Your booking request will be confirmed immediately.

                                            House #8340150
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 4

                                            Confirmation within 24 hours

                                            Your booking request will be confirmed or denied within 24 hours.

                                              Exceptional! 5/5
                                              (15 reviews)
                                              avg/night
                                              Cottage #1760582
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                              15
                                              Viewed 377 times in the last 48 hours

                                              Confirmation within 24 hours

                                              Your booking request will be confirmed or denied within 24 hours.

                                                Wonderful! 4.9/5
                                                (39 reviews)
                                                avg/night
                                                Villa #62257
                                                • 2 BR
                                                • 3 BA
                                                • Sleeps 5
                                                39
                                                Viewed 58 times in the last 48 hours

                                                Confirmation within 24 hours

                                                Your booking request will be confirmed or denied within 24 hours.

                                                  Exceptional! 5/5
                                                  (13 reviews)
                                                  avg/night
                                                  Chateau / Country House #6115214
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 2
                                                  13
                                                  Viewed 73 times in the last 48 hours

                                                  Confirmation within 24 hours

                                                  Your booking request will be confirmed or denied within 24 hours.

                                                    Excellent! 4.7/5
                                                    (18 reviews)
                                                    avg/night
                                                    Apartment #13190
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    18
                                                    Viewed 29 times in the last 48 hours

                                                    Confirmation within 24 hours

                                                    Your booking request will be confirmed or denied within 24 hours.

                                                      Exceptional! 5/5
                                                      (15 reviews)
                                                      avg/night
                                                      Apartment #757059vb
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      15

                                                      Confirmation within 24 hours

                                                      Your booking request will be confirmed or denied within 24 hours.

                                                        Exceptional! 5/5
                                                        (14 reviews)
                                                        avg/night
                                                        Villa #1812215
                                                        • 5 BR
                                                        • 5 BA
                                                        • Sleeps 12
                                                        14
                                                        Viewed 58 times in the last 48 hours

                                                        Confirmation within 24 hours

                                                        Your booking request will be confirmed or denied within 24 hours.

                                                          Wonderful! 4.9/5
                                                          (15 reviews)
                                                          avg/night
                                                          Castle #445224
                                                          • 5 BR
                                                          • 3 BA
                                                          • Sleeps 11
                                                          15
                                                          Viewed 121 times in the last 48 hours

                                                          Confirmation within 24 hours

                                                          Your booking request will be confirmed or denied within 24 hours.

                                                            Exceptional! 5/5
                                                            (7 reviews)
                                                            avg/night
                                                            Chateau / Country House #2544354
                                                            • 4 BR
                                                            • 3 BA
                                                            • Separate Toilet
                                                            • Sleeps 9
                                                            7
                                                            Viewed 30 times in the last 48 hours

                                                            Confirmation within 24 hours

                                                            Your booking request will be confirmed or denied within 24 hours.

                                                              Exceptional! 5/5
                                                              (15 reviews)
                                                              avg/night
                                                              Farmhouse #3749715
                                                              • 3 BR
                                                              • 4 BA
                                                              • Sleeps 10
                                                              15
                                                              Viewed 21 times in the last 48 hours

                                                              Confirmation within 24 hours

                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                Wonderful! 4.9/5
                                                                (44 reviews)
                                                                avg/night
                                                                Apartment #50681
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 3
                                                                44
                                                                Viewed 9 times in the last 48 hours

                                                                Confirmation within 24 hours

                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                  Wonderful! 4.9/5
                                                                  (17 reviews)
                                                                  avg/night
                                                                  Apartment #6166856
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  17
                                                                  Viewed 8 times in the last 48 hours

                                                                  Confirmation within 24 hours

                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                    Wonderful! 4.9/5
                                                                    (34 reviews)
                                                                    avg/night
                                                                    Multiple rentals Chateau / Country House #899555
                                                                    • 3 BR
                                                                    • 4 BA
                                                                    • Sleeps 11
                                                                    34
                                                                    Viewed 38 times in the last 48 hours

                                                                    Confirmation within 24 hours

                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                      Exceptional! 5/5
                                                                      (10 reviews)
                                                                      avg/night
                                                                      Apartment #1106728
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 4
                                                                      10
                                                                      Viewed 20 times in the last 48 hours

                                                                      Confirmation within 24 hours

                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                        Wonderful! 4.9/5
                                                                        (9 reviews)
                                                                        avg/night
                                                                        Apartment #883786vb
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 4
                                                                        9
                                                                        Viewed 18 times in the last 48 hours

                                                                        Confirmation within 24 hours

                                                                        Your booking request will be confirmed or denied within 24 hours.

                                                                          Exceptional! 5/5
                                                                          (23 reviews)
                                                                          avg/night
                                                                          Multiple rentals Cottage #899555
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Separate Toilet
                                                                          • Sleeps 7
                                                                          23
                                                                          Viewed 10 times in the last 48 hours

                                                                          Confirmation within 24 hours

                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                            avg/night
                                                                            Villa #1760588
                                                                            • 2 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            1
                                                                            Viewed 9 times in the last 48 hours

                                                                            Confirmation within 24 hours

                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                              Exceptional! 5/5
                                                                              (10 reviews)
                                                                              avg/night
                                                                              Apartment #1544394
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 5
                                                                              10
                                                                              Viewed 17 times in the last 48 hours

                                                                              Confirmation within 24 hours

                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                Wonderful! 4.9/5
                                                                                (11 reviews)
                                                                                avg/night
                                                                                Apartment #515580
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 3
                                                                                11
                                                                                Viewed 5 times in the last 48 hours

                                                                                Confirmation within 24 hours

                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                  Wonderful! 4.8/5
                                                                                  (13 reviews)
                                                                                  avg/night
                                                                                  Villa #6566676
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 7
                                                                                  13
                                                                                  Viewed 22 times in the last 48 hours

                                                                                  Confirmation within 24 hours

                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                    Multiple rentals Farmhouse #6054053
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 5
                                                                                    21

                                                                                    Confirmation within 24 hours

                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                      Exceptional! 5/5
                                                                                      (21 reviews)
                                                                                      avg/night
                                                                                      Apartment #615969vb
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      21
                                                                                      Viewed 8 times in the last 48 hours

                                                                                      Confirmation within 24 hours

                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                        Villa #6790455
                                                                                        • 6 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 12
                                                                                        1
                                                                                        Viewed 24 times in the last 48 hours

                                                                                        Instant confirmation

                                                                                        Your booking request will be confirmed immediately.

                                                                                          Wonderful! 4.9/5
                                                                                          (10 reviews)
                                                                                          avg/night
                                                                                          Cottage #755019
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 3
                                                                                          10
                                                                                          Viewed 19 times in the last 48 hours

                                                                                          Confirmation within 24 hours

                                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                                            Exceptional! 5/5
                                                                                            (69 reviews)
                                                                                            avg/night
                                                                                            Villa #97774
                                                                                            • 6 BR
                                                                                            • 4 BA
                                                                                            • Sleeps 12
                                                                                            69
                                                                                            Viewed 32 times in the last 48 hours

                                                                                            Confirmation within 24 hours

                                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                                              Excellent! 4.5/5
                                                                                              (4 reviews)
                                                                                              avg/night
                                                                                              Apartment #1996686
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 3
                                                                                              4
                                                                                              Viewed 21 times in the last 48 hours

                                                                                              Confirmation within 24 hours

                                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                                Multiple rentals Apartment #455240
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                1
                                                                                                Viewed 7 times in the last 48 hours

                                                                                                Confirmation within 24 hours

                                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                                  avg/night
                                                                                                  Chateau / Country House #1322795
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  3
                                                                                                  Viewed 12 times in the last 48 hours

                                                                                                  Confirmation within 24 hours

                                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                                    Exceptional! 5/5
                                                                                                    (5 reviews)
                                                                                                    avg/night
                                                                                                    Farmhouse #8026002
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 5
                                                                                                    5
                                                                                                    Viewed 10 times in the last 48 hours

                                                                                                    Instant confirmation

                                                                                                    Your booking request will be confirmed immediately.

                                                                                                      Exceptional! 5/5
                                                                                                      (34 reviews)
                                                                                                      avg/night
                                                                                                      Apartment #204437vb
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 2
                                                                                                      34
                                                                                                      Viewed 6 times in the last 48 hours

                                                                                                      Confirmation within 24 hours

                                                                                                      Your booking request will be confirmed or denied within 24 hours.

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