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Nestling amongst the peaceful Chianti hills south-east of Siena, holiday accommodation in Montepulciano is surrounded by countryside with an outstanding aesthetic quality that has provided inspiration to many artists through the ages, notably the painters of the Rennaissance period in Tuscany - holiday villas and apartments in Montepulciano therefore proving to be a popular choice for anyone planning a thorough investigation of the region's wealth of art, history and culture as you'll never have far to go from your villa or apartment rental in Montepulciano before you find more ancient towns and cities and magnificent architectural heritage than you thought was possible to cram into this fascinating part of Italy. Holiday rental accommodation in Montepulciano also makes the ideal base from where you can plan a voyage of gastronomical discovery through a spectacular landscape of rolling hills carpeted in the olive groves and vineyards that produce the fine wine and oil that are essential to the culinary prowess of Tuscany - holiday rental accommodation in Montepulciano being found in a destination that is sure to give you the opportunity to enjoy a truly comprehensive experience of all the diverse aspects that make this such a unique part of the country.

    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.

      Wonderful! 4.9/5
      (38 reviews)
      avg/night
      Multiple rentals Apartment #6432643
      • 1 BR
      • 1 BA
      • Sleeps 4
      38
      Viewed 34 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 15 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 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
            (21 reviews)
            avg/night
            Apartment #615969vb
            • 2 BR
            • 2 BA
            • Sleeps 6
            21
            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
              (69 reviews)
              avg/night
              Villa #97774
              • 6 BR
              • 4 BA
              • Sleeps 12
              69
              Viewed 20 times in the last 48 hours

              Confirmation within 24 hours

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

                Apartment #1017638
                • 2 BR
                • 1 BA
                • Sleeps 6
                16

                Instant confirmation

                Your booking request will be confirmed immediately.

                  Wonderful! 4.8/5
                  (48 reviews)
                  avg/night
                  Apartment #6066867
                  • 2 BR
                  • 1 BA
                  • Sleeps 7
                  48
                  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
                    (18 reviews)
                    avg/night
                    Multiple rentals Apartment #6432643
                    • 2 BR
                    • 2 BA
                    • Sleeps 6
                    18
                    Viewed 14 times in the last 48 hours

                    Confirmation within 24 hours

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

                      Farmhouse #6561116
                      • 6 BR
                      • 5 BA
                      • Sleeps 14
                      1
                      Viewed 9 times in the last 48 hours

                      Confirmation within 24 hours

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

                        avg/night
                        Barn #8123164
                        • 2 BR
                        • 2 BA
                        • Sleeps 5
                        Viewed 5 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
                          Farmhouse #1875874
                          • 4 BR
                          • 3 BA
                          • Sleeps 10
                          10
                          Viewed 13 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
                            (20 reviews)
                            avg/night
                            Apartment #515617vb
                            • 2 BR
                            • 2 BA
                            • Sleeps 4
                            20

                            Instant confirmation

                            Your booking request will be confirmed immediately.

                              Wonderful! 4.9/5
                              (29 reviews)
                              avg/night
                              Townhome #33620vb
                              • 2 BR
                              • 2 BA
                              • Sleeps 6
                              29

                              Confirmation within 24 hours

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

                                Exceptional! 5/5
                                (22 reviews)
                                avg/night
                                Chateau / Country House #25004
                                • 4 BR
                                • 2 BA
                                • Separate Toilet
                                • Sleeps 6
                                22
                                Viewed 5 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 #999940vb
                                  • 5 BR
                                  • 6 BA
                                  • Separate Toilet
                                  • Sleeps 18
                                  10
                                  Viewed 8 times in the last 48 hours

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

                                    Apartment #6961990
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    1

                                    Confirmation within 24 hours

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

                                      Confirmation within 24 hours

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                                        Villa #1639715
                                        • 6 BR
                                        • 6 BA
                                        • Sleeps 12
                                        1

                                        Confirmation within 24 hours

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                                          Apartment #6943675
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 4

                                          Confirmation within 24 hours

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                                            Apartment #706177vb
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 4
                                            2

                                            Confirmation within 24 hours

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

                                              Farmhouse #1150802
                                              • 7 BR
                                              • 7 BA
                                              • Separate Toilet
                                              • Sleeps 16
                                              1
                                              Viewed 9 times in the last 48 hours

                                              Instant confirmation

                                              Your booking request will be confirmed immediately.

                                                Villa #8146333
                                                • 4 BR
                                                • 4 BA
                                                • Separate Toilet
                                                • Sleeps 8

                                                Confirmation within 24 hours

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

                                                  Villa #1372539
                                                  • 5 BR
                                                  • 4 BA
                                                  • Sleeps 10

                                                  Confirmation within 24 hours

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

                                                    Villa #6979429
                                                    • 5 BR
                                                    • 5 BA
                                                    • Separate Toilet
                                                    • Sleeps 12

                                                    Confirmation within 24 hours

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

                                                      avg/night
                                                      Chateau / Country House #6726981
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      3
                                                      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
                                                        Villa #7007459
                                                        • 10 BR
                                                        • 10 BA
                                                        • Sleeps 20
                                                        Viewed 29 times in the last 48 hours

                                                        Confirmation within 24 hours

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                                                          Exceptional! 5/5
                                                          (5 reviews)
                                                          avg/night
                                                          Villa #15196
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 4
                                                          5
                                                          Viewed 5 times in the last 48 hours

                                                          Confirmation within 24 hours

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

                                                            Farmhouse #1042221
                                                            • 3 BR
                                                            • 1 BA
                                                            • Sleeps 6
                                                            4

                                                            Instant confirmation

                                                            Your booking request will be confirmed immediately.

                                                              Farmhouse #6674194
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              1

                                                              Confirmation within 24 hours

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                                                                House #8266344
                                                                • 1 BR
                                                                • 1 BA
                                                                • Separate Toilet
                                                                • Sleeps 4

                                                                Confirmation within 24 hours

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                                                                  Villa #6543003
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  5

                                                                  Confirmation within 24 hours

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                                                                    Villa #4267132
                                                                    • 4 BR
                                                                    • 4 BA
                                                                    • Sleeps 8
                                                                    8

                                                                    Confirmation within 24 hours

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

                                                                      Villa #1845028
                                                                      • 9 BR
                                                                      • 8 BA
                                                                      • Sleeps 20
                                                                      Viewed 5 times in the last 48 hours

                                                                      Instant confirmation

                                                                      Your booking request will be confirmed immediately.

                                                                        Apartment #6796987
                                                                        • 4 BR
                                                                        • 4 BA
                                                                        • Sleeps 9

                                                                        Instant confirmation

                                                                        Your booking request will be confirmed immediately.

                                                                          Bed And Breakfast #6004249
                                                                          • 1 BR
                                                                          • 3 BA
                                                                          • Sleeps 2

                                                                          Confirmation within 24 hours

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

                                                                            Wonderful! 4.8/5
                                                                            (6 reviews)
                                                                            avg/night
                                                                            Villa #6739918
                                                                            • 5 BR
                                                                            • 4 BA
                                                                            • Sleeps 10
                                                                            6
                                                                            Viewed 5 times in the last 48 hours

                                                                            Instant confirmation

                                                                            Your booking request will be confirmed immediately.

                                                                              Apartment #6846954
                                                                              • 5 BR
                                                                              • 5 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 11

                                                                              Confirmation within 24 hours

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

                                                                                Excellent! 4.6/5
                                                                                (12 reviews)
                                                                                avg/night
                                                                                Farmhouse #397695vb
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 4
                                                                                12
                                                                                Viewed 6 times in the last 48 hours

                                                                                Confirmation within 24 hours

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

                                                                                  Farmhouse #3764391
                                                                                  • 4 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 10
                                                                                  10

                                                                                  Confirmation within 24 hours

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

                                                                                    Villa #106843vb
                                                                                    • 6 BR
                                                                                    • 8 BA
                                                                                    • Sleeps 30

                                                                                    Confirmation within 24 hours

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

                                                                                      avg/night
                                                                                      Townhome #4473797
                                                                                      • 2 BR
                                                                                      • 2 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.

                                                                                        Apartment #1131429
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        7

                                                                                        Confirmation within 24 hours

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

                                                                                          Apartment #1124628vb
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 3

                                                                                          Confirmation within 24 hours

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

                                                                                            Villa #1150741
                                                                                            • 4 BR
                                                                                            • 5 BA
                                                                                            • Sleeps 10

                                                                                            Instant confirmation

                                                                                            Your booking request will be confirmed immediately.

                                                                                              Chateau / Country House #8085484
                                                                                              • 5 BR
                                                                                              • 5 BA
                                                                                              • Sleeps 10

                                                                                              Confirmation within 24 hours

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

                                                                                                Bed And Breakfast #1115119vb
                                                                                                • 3 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 6

                                                                                                Confirmation within 24 hours

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

                                                                                                  Farmhouse #8277727
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6

                                                                                                  Confirmation within 24 hours

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

                                                                                                    Apartment #1015562vb
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4

                                                                                                    Confirmation within 24 hours

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

                                                                                                      Villa #8105337
                                                                                                      • 7 BR
                                                                                                      • 8 BA
                                                                                                      • Sleeps 14

                                                                                                      Confirmation within 24 hours

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

                                                                                                      • 1 - 50 of 300+

                                                                                                      Holiday Accommodation Montepulciano (300+)