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In situations of peaceful seclusion amongst the Chianti hills and vineyards of Siena, holiday cottages in Monteriggioni are the kind of accommodation in Tuscany that is guaranteed to give you a truly authentic experience of country life in a part of the region renowned for its breathtaking natural beauty and fascinating cultural heritage - holiday accommodation in Monteriggioni providing bags of traditional rustic character and charm whether you need the kind of room a family-sized Tuscan villa promises or an apartment rental in Monteriggioni with just enough spacious luxury to give you and your loved one an exquisitely romantic Italian holiday. Villas and apartments in Monteriggioni can also be found in typically rural settings just a few miles away from the vibrant city of Siena and within easy reach of the magnificent city of Florence - holiday rental accommodation in Monteriggioni giving you the chance to discover yet another aspect of a region that shows an incredible diversity of history and culture as well as landscapes and lifestyles, so after a hectic day of urban excitement in some of the most famous cities in Tuscany, villa, apartment and cottage rentals in Monteriggioni offer you a haven of tranquility to return to and the perfect atmosphere in which to relax with a glass of local chianti!

    Villa #616750vb
    • Studio
    • 1 BA
    • Sleeps 18

    Confirmation within 24 hours

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

      Exceptional! 5/5
      (58 reviews)
      avg/night
      House #6235319
      • 2 BR
      • 2 BA
      • Sleeps 4
      58
      Viewed 694 times in the last 48 hours

      Instant confirmation

      Your booking request will be confirmed immediately.

        Wonderful! 4.9/5
        (7 reviews)
        avg/night
        House #824486vb
        • 2 BR
        • 2 BA
        • Sleeps 4
        7
        Viewed 76 times in the last 48 hours

        Confirmation within 24 hours

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

          Exceptional! 5/5
          (17 reviews)
          avg/night
          Apartment #1017337
          • 2 BR
          • 2 BA
          • Sleeps 4
          17
          Viewed 72 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
            Apartment #1107906
            • 1 BR
            • 1 BA
            • Sleeps 4
            23
            Viewed 55 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
              Villa #607748vb
              • 4 BR
              • 3 BA
              • Sleeps 11
              23
              Viewed 235 times in the last 48 hours

              Confirmation within 24 hours

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

                Apartment #4216056
                • 2 BR
                • 1 BA
                • Sleeps 4
                3
                Viewed 14 times in the last 48 hours

                Confirmation within 24 hours

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

                  Wonderful! 4.8/5
                  (6 reviews)
                  avg/night
                  Villa #1097226
                  • 5 BR
                  • 5 BA
                  • Separate Toilet
                  • Sleeps 10
                  6
                  Viewed 51 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
                    (63 reviews)
                    avg/night
                    House #6190174
                    • 2 BR
                    • 1 BA
                    • Sleeps 5
                    63
                    Viewed 123 times in the last 48 hours

                    Confirmation within 24 hours

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

                      Exceptional! 5/5
                      (25 reviews)
                      avg/night
                      House #1053585
                      • 3 BR
                      • 3 BA
                      • Separate Toilet
                      • Sleeps 8
                      25
                      Viewed 82 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
                        (27 reviews)
                        avg/night
                        Villa #421433
                        • 3 BR
                        • 3 BA
                        • Sleeps 6
                        27
                        Viewed 44 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
                          (10 reviews)
                          avg/night
                          House #6565474
                          • 2 BR
                          • 1 BA
                          • Sleeps 6
                          10
                          Viewed 52 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
                            House #582787vb
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            10
                            Viewed 86 times in the last 48 hours

                            Confirmation within 24 hours

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

                              Chateau / Country House #6778769
                              • 2 BR
                              • 1 BA
                              • Sleeps 6
                              3
                              Viewed 51 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
                                (24 reviews)
                                avg/night
                                House #403492
                                • 3 BR
                                • 2 BA
                                • Separate Toilet
                                • Sleeps 7
                                24
                                Viewed 38 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
                                  House #6896531
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 6
                                  5
                                  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
                                    (29 reviews)
                                    avg/night
                                    House #2196590
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 5
                                    29
                                    Viewed 16 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
                                      Multiple rentals Apartment #632967a
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 6
                                      44
                                      Viewed 55 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
                                        (35 reviews)
                                        avg/night
                                        Multiple rentals Chateau / Country House #6153067
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 5
                                        35
                                        Viewed 52 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
                                          (24 reviews)
                                          avg/night
                                          House #6225502
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 8
                                          24
                                          Viewed 71 times in the last 48 hours

                                          Confirmation within 24 hours

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

                                            Exceptional! 5/5
                                            (32 reviews)
                                            avg/night
                                            Apartment #3880312
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 5
                                            32
                                            Viewed 37 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
                                              House #6570358
                                              • 4 BR
                                              • 2 BA
                                              • Separate Toilet
                                              • Sleeps 9
                                              7
                                              Viewed 36 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 #13190
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                17
                                                Viewed 23 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
                                                  (21 reviews)
                                                  avg/night
                                                  House #6046194
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 6
                                                  21
                                                  Viewed 50 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
                                                    (24 reviews)
                                                    avg/night
                                                    Multiple rentals Apartment #809657
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    24
                                                    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
                                                      (19 reviews)
                                                      avg/night
                                                      Apartment #8022189
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 5
                                                      19
                                                      Viewed 62 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
                                                        (26 reviews)
                                                        avg/night
                                                        Multiple rentals Apartment #435134
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 3
                                                        26
                                                        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
                                                          (8 reviews)
                                                          avg/night
                                                          Barn #1697270
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 5
                                                          8
                                                          Viewed 15 times in the last 48 hours

                                                          Confirmation within 24 hours

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

                                                            Farmhouse #2554049
                                                            • 3 BR
                                                            • 1 BA
                                                            • Sleeps 6
                                                            3
                                                            Viewed 10 times in the last 48 hours

                                                            Instant confirmation

                                                            Your booking request will be confirmed immediately.

                                                              Exceptional! 5/5
                                                              (15 reviews)
                                                              avg/night
                                                              Farmhouse #391835vb
                                                              • 6 BR
                                                              • 5 BA
                                                              • Separate Toilet
                                                              • Sleeps 18
                                                              15
                                                              Viewed 55 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
                                                                (24 reviews)
                                                                avg/night
                                                                Cottage #6078287
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                24
                                                                Viewed 53 times in the last 48 hours

                                                                Confirmation within 24 hours

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

                                                                  Exceptional! 5/5
                                                                  (42 reviews)
                                                                  avg/night
                                                                  Multiple rentals Chateau / Country House #6153067
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  42
                                                                  Viewed 41 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
                                                                    (12 reviews)
                                                                    avg/night
                                                                    Farmhouse #8461
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 6
                                                                    12
                                                                    Viewed 22 times in the last 48 hours

                                                                    Confirmation within 24 hours

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

                                                                      Villa #1061581vb
                                                                      • 6 BR
                                                                      • 5 BA
                                                                      • Sleeps 13
                                                                      4
                                                                      Viewed 78 times in the last 48 hours

                                                                      Confirmation within 24 hours

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

                                                                        Exceptional! 5/5
                                                                        (25 reviews)
                                                                        avg/night
                                                                        Multiple rentals Chateau / Country House #27152
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 3
                                                                        25
                                                                        Viewed 35 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
                                                                          Apartment #1198165a
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          12
                                                                          Viewed 20 times in the last 48 hours

                                                                          Confirmation within 24 hours

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

                                                                            Wonderful! 4.8/5
                                                                            (31 reviews)
                                                                            avg/night
                                                                            Apartment #1803159
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 3
                                                                            31
                                                                            Viewed 27 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
                                                                              (69 reviews)
                                                                              avg/night
                                                                              House #6162521
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 5
                                                                              69
                                                                              Viewed 26 times in the last 48 hours

                                                                              Confirmation within 24 hours

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

                                                                                Exceptional! 5/5
                                                                                (40 reviews)
                                                                                avg/night
                                                                                Villa #709879vb
                                                                                • 3 BR
                                                                                • 3 BA
                                                                                • Separate Toilet
                                                                                • Sleeps 7
                                                                                40
                                                                                Viewed 123 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
                                                                                  (16 reviews)
                                                                                  avg/night
                                                                                  Multiple rentals House #734524
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 4
                                                                                  16
                                                                                  Viewed 20 times in the last 48 hours

                                                                                  Instant confirmation

                                                                                  Your booking request will be confirmed immediately.

                                                                                    Wonderful! 4.9/5
                                                                                    (18 reviews)
                                                                                    avg/night
                                                                                    Apartment #785711
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 4
                                                                                    18
                                                                                    Viewed 16 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
                                                                                      (32 reviews)
                                                                                      avg/night
                                                                                      Villa #275267
                                                                                      • 5 BR
                                                                                      • 5 BA
                                                                                      • Sleeps 10
                                                                                      32
                                                                                      Viewed 32 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
                                                                                        (21 reviews)
                                                                                        avg/night
                                                                                        Villa #90810
                                                                                        • 5 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 12
                                                                                        21
                                                                                        Viewed 17 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
                                                                                          Multiple rentals Chateau / Country House #27152
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 3
                                                                                          5
                                                                                          Viewed 17 times in the last 48 hours

                                                                                          Confirmation within 24 hours

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

                                                                                            Exceptional! 5/5
                                                                                            (20 reviews)
                                                                                            avg/night
                                                                                            Villa #443062vb
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 10
                                                                                            20
                                                                                            Viewed 35 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
                                                                                              (12 reviews)
                                                                                              avg/night
                                                                                              Chateau / Country House #1851746
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 7
                                                                                              12
                                                                                              Viewed 47 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
                                                                                                (9 reviews)
                                                                                                avg/night
                                                                                                Apartment #1870265
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                9

                                                                                                Confirmation within 24 hours

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

                                                                                                  Excellent! 4.7/5
                                                                                                  (6 reviews)
                                                                                                  avg/night
                                                                                                  Cottage #1949272
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  6
                                                                                                  Viewed 21 times in the last 48 hours

                                                                                                  Confirmation within 24 hours

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

                                                                                                    Wonderful! 4.8/5
                                                                                                    (32 reviews)
                                                                                                    avg/night
                                                                                                    Multiple rentals Apartment #450158
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    32
                                                                                                    Viewed 10 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
                                                                                                      (14 reviews)
                                                                                                      avg/night
                                                                                                      Apartment #1330072a
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 4
                                                                                                      14
                                                                                                      Viewed 16 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 Monteriggioni (300+)