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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.

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

    Confirmation within 24 hours

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

      avg/night
      Villa #6782825
      • 5 BR
      • 3 BA
      • Sleeps 9
      1
      Viewed 14 times in the last 48 hours

      Confirmation within 24 hours

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

        avg/night
        Apartment #1340371
        • 2 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.

          Excellent! 4.6/5
          (19 reviews)
          avg/night
          Villa #734706
          • 3 BR
          • 2 BA
          • Sleeps 6
          19
          Viewed 23 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 10 times in the last 48 hours

              Confirmation within 24 hours

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

                House #6915681
                • 3 BR
                • 3 BA
                • Sleeps 6
                Viewed 5 times in the last 48 hours

                Confirmation within 24 hours

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

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

                  Confirmation within 24 hours

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

                    House #6966902
                    • 2 BR
                    • 1 BA
                    • Sleeps 4

                    Instant confirmation

                    Your booking request will be confirmed immediately.

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

                      Confirmation within 24 hours

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

                        Wonderful! 4.9/5
                        (36 reviews)
                        avg/night
                        Villa #62257
                        • 2 BR
                        • 3 BA
                        • Sleeps 5
                        36
                        Viewed 77 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
                          Villa #1812215
                          • 5 BR
                          • 5 BA
                          • Sleeps 12
                          9
                          Viewed 26 times in the last 48 hours

                          Instant confirmation

                          Your booking request will be confirmed immediately.

                            Exceptional! 5/5
                            (9 reviews)
                            avg/night
                            Apartment #1106728
                            • 2 BR
                            • 2 BA
                            • Sleeps 4
                            9
                            Viewed 22 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
                              (42 reviews)
                              avg/night
                              Apartment #50681
                              • 1 BR
                              • 1 BA
                              • Sleeps 3
                              42
                              Viewed 7 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
                                (12 reviews)
                                avg/night
                                Multiple rentals Farmhouse #15138
                                • Studio
                                • 1 BA
                                • Sleeps 3
                                12
                                Viewed 14 times in the last 48 hours

                                Instant confirmation

                                Your booking request will be confirmed immediately.

                                  Villa #6790455
                                  • 6 BR
                                  • 4 BA
                                  • Sleeps 12
                                  Viewed 14 times in the last 48 hours

                                  Instant confirmation

                                  Your booking request will be confirmed immediately.

                                    Exceptional! 5/5
                                    (12 reviews)
                                    avg/night
                                    Multiple rentals Farmhouse #15138
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 5
                                    12
                                    Viewed 7 times in the last 48 hours

                                    Instant confirmation

                                    Your booking request will be confirmed immediately.

                                      Wonderful! 4.8/5
                                      (9 reviews)
                                      avg/night
                                      House #40344
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 6
                                      9
                                      Viewed 16 times in the last 48 hours

                                      Confirmation within 24 hours

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

                                        Excellent! 4.3/5
                                        (7 reviews)
                                        avg/night
                                        Multiple rentals House #411866
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 6
                                        7
                                        Viewed 20 times in the last 48 hours

                                        Confirmation within 24 hours

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

                                          Exceptional! 5/5
                                          (60 reviews)
                                          avg/night
                                          Villa #867633
                                          • 12 BR
                                          • 8 BA
                                          • Separate Toilet
                                          • Sleeps 26
                                          60
                                          Viewed 49 times in the last 48 hours

                                          Confirmation within 24 hours

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

                                            Exceptional! 5/5
                                            (16 reviews)
                                            avg/night
                                            Villa #1686237
                                            • 4 BR
                                            • 4 BA
                                            • Separate Toilets
                                            • Sleeps 8
                                            16
                                            Viewed 31 times in the last 48 hours

                                            Confirmation within 24 hours

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

                                              Good! 3.9/5
                                              (9 reviews)
                                              avg/night
                                              House #725313
                                              • 4 BR
                                              • 2 BA
                                              • Separate Toilet
                                              • Sleeps 8
                                              9
                                              Viewed 11 times in the last 48 hours

                                              Confirmation within 24 hours

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

                                                Exceptional! 5/5
                                                (8 reviews)
                                                avg/night
                                                House #2497551
                                                • 3 BR
                                                • 3 BA
                                                • Sleeps 6
                                                8
                                                Viewed 12 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
                                                  (8 reviews)
                                                  avg/night
                                                  Villa #70004
                                                  • 9 BR
                                                  • 9 BA
                                                  • Sleeps 17
                                                  8
                                                  Viewed 16 times in the last 48 hours

                                                  Confirmation within 24 hours

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

                                                    Exceptional! 5/5
                                                    (6 reviews)
                                                    avg/night
                                                    Apartment #883786vb
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 4
                                                    6
                                                    Viewed 10 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
                                                      Villa #578567vb
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      5
                                                      Viewed 7 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
                                                        (16 reviews)
                                                        avg/night
                                                        Multiple rentals Farmhouse #15138
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 6
                                                        16
                                                        Viewed 10 times in the last 48 hours

                                                        Instant confirmation

                                                        Your booking request will be confirmed immediately.

                                                          Exceptional! 5/5
                                                          (10 reviews)
                                                          avg/night
                                                          Villa #1674525
                                                          • 4 BR
                                                          • 4 BA
                                                          • Separate Toilet
                                                          • Sleeps 10
                                                          10
                                                          Viewed 7 times in the last 48 hours

                                                          Instant confirmation

                                                          Your booking request will be confirmed immediately.

                                                            avg/night
                                                            Farmhouse #1103983
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 9
                                                            3
                                                            Viewed 31 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
                                                              (19 reviews)
                                                              avg/night
                                                              Apartment #515617vb
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 4
                                                              19

                                                              Instant confirmation

                                                              Your booking request will be confirmed immediately.

                                                                Excellent! 4.7/5
                                                                (7 reviews)
                                                                avg/night
                                                                Multiple rentals Farmhouse #69771
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                7
                                                                Viewed 14 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
                                                                  (12 reviews)
                                                                  avg/night
                                                                  Villa #558587vb
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Separate Toilet
                                                                  • Sleeps 8
                                                                  12
                                                                  Viewed 34 times in the last 48 hours

                                                                  Instant confirmation

                                                                  Your booking request will be confirmed immediately.

                                                                    Villa #719334
                                                                    • 5 BR
                                                                    • 5 BA
                                                                    • Separate Toilet
                                                                    • Sleeps 12

                                                                    Confirmation within 24 hours

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

                                                                      Exceptional! 5/5
                                                                      (8 reviews)
                                                                      avg/night
                                                                      Farmhouse #1875874
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 10
                                                                      8
                                                                      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
                                                                        (7 reviews)
                                                                        avg/night
                                                                        Multiple rentals Apartment #89105
                                                                        • 1 BR
                                                                        • Separate Toilet
                                                                        • Sleeps 3
                                                                        7
                                                                        Viewed 6 times in the last 48 hours

                                                                        Confirmation within 24 hours

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

                                                                          avg/night
                                                                          Multiple rentals House #447800
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Separate Toilet
                                                                          • Sleeps 6
                                                                          1
                                                                          Viewed 14 times in the last 48 hours

                                                                          Confirmation within 24 hours

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

                                                                            Exceptional! 5/5
                                                                            (8 reviews)
                                                                            avg/night
                                                                            Multiple rentals Villa #89105
                                                                            • 2 BR
                                                                            • Sleeps 4
                                                                            8
                                                                            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
                                                                              (33 reviews)
                                                                              avg/night
                                                                              Apartment #204437vb
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              33
                                                                              Viewed 13 times in the last 48 hours

                                                                              Confirmation within 24 hours

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

                                                                                Exceptional! 5/5
                                                                                (21 reviews)
                                                                                avg/night
                                                                                Multiple rentals Villa #89105
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 11
                                                                                21
                                                                                Viewed 45 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
                                                                                  (6 reviews)
                                                                                  avg/night
                                                                                  Apartment #1033066
                                                                                  • 4 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 6
                                                                                  6
                                                                                  Viewed 30 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 44 times in the last 48 hours

                                                                                    Confirmation within 24 hours

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

                                                                                      Multiple rentals Apartment #414350
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 5
                                                                                      5

                                                                                      Confirmation within 24 hours

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

                                                                                        Exceptional! 5/5
                                                                                        (8 reviews)
                                                                                        avg/night
                                                                                        Apartment #1683498
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 5
                                                                                        8
                                                                                        Viewed 6 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
                                                                                          (49 reviews)
                                                                                          avg/night
                                                                                          Apartment #6059609
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 4
                                                                                          49

                                                                                          Confirmation within 24 hours

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

                                                                                            Cottage #16442
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            1

                                                                                            Confirmation within 24 hours

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

                                                                                              Multiple rentals Farmhouse #8051284
                                                                                              • 4 BR
                                                                                              • 4 BA
                                                                                              • Sleeps 10
                                                                                              4
                                                                                              Viewed 6 times in the last 48 hours

                                                                                              Confirmation within 24 hours

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

                                                                                                House #420786
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                1
                                                                                                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
                                                                                                  (10 reviews)
                                                                                                  avg/night
                                                                                                  Villa #1019868
                                                                                                  • 6 BR
                                                                                                  • 6 BA
                                                                                                  • Separate Toilet
                                                                                                  • Sleeps 12
                                                                                                  10
                                                                                                  Viewed 23 times in the last 48 hours

                                                                                                  Confirmation within 24 hours

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

                                                                                                    avg/night
                                                                                                    Villa #1058073
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 10
                                                                                                    Viewed 17 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 8 times in the last 48 hours

                                                                                                      Confirmation within 24 hours

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

                                                                                                      • 1 - 50 of 300+

                                                                                                      Holiday Accommodation Montalcino (300+)