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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!

  • Showing 1-50 of 300+
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    Wonderful! 4.9/5
    (41 reviews)
    avg/night
    Villa #6162112
    • 3 BR
    • 1 BA
    • Sleeps 5
    41
    Viewed 26 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
      (5 reviews)
      avg/night
      Corporate Apartment #6704799
      • 2 BR
      • 2 BA
      • Sleeps 5
      5
      Viewed 5 times in the last 48 hours

      Instant confirmation

      Your booking request will be confirmed immediately.

        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
          (57 reviews)
          avg/night
          House #6235319
          • 2 BR
          • 2 BA
          • Sleeps 4
          57
          Viewed 137 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
            Villa #607748vb
            • 4 BR
            • 3 BA
            • Sleeps 11
            17
            Viewed 35 times in the last 48 hours

            Confirmation within 24 hours

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

              Exceptional! 5/5
              (22 reviews)
              avg/night
              House #1053585
              • 3 BR
              • 3 BA
              • Separate Toilet
              • Sleeps 8
              22
              Viewed 36 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
                House #824486vb
                • 2 BR
                • 2 BA
                • Sleeps 4
                5
                Viewed 31 times in the last 48 hours

                Confirmation within 24 hours

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

                  Exceptional! 5/5
                  (4 reviews)
                  avg/night
                  Villa #1097226
                  • 5 BR
                  • 5 BA
                  • Separate Toilet
                  • Sleeps 10
                  4
                  Viewed 42 times in the last 48 hours

                  Confirmation within 24 hours

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

                    avg/night
                    House #582787vb
                    • 3 BR
                    • 2 BA
                    • Sleeps 6
                    3
                    Viewed 29 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
                      (22 reviews)
                      avg/night
                      Villa #421433
                      • 3 BR
                      • 3 BA
                      • Sleeps 6
                      22
                      Viewed 38 times in the last 48 hours

                      Confirmation within 24 hours

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

                        Wonderful! 4.9/5
                        (19 reviews)
                        avg/night
                        Apartment #1107906
                        • 1 BR
                        • 1 BA
                        • Sleeps 4
                        19
                        Viewed 15 times in the last 48 hours

                        Confirmation within 24 hours

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

                          Wonderful! 4.8/5
                          (13 reviews)
                          avg/night
                          Apartment #8022189
                          • 2 BR
                          • 2 BA
                          • Sleeps 5
                          13
                          Viewed 17 times in the last 48 hours

                          Confirmation within 24 hours

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

                            Wonderful! 4.9/5
                            (39 reviews)
                            avg/night
                            Multiple rentals Apartment #632967a
                            • 2 BR
                            • 2 BA
                            • Sleeps 6
                            39
                            Viewed 22 times in the last 48 hours

                            Confirmation within 24 hours

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

                              Exceptional! 5/5
                              (13 reviews)
                              avg/night
                              Apartment #1017337
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              13
                              Viewed 38 times in the last 48 hours

                              Confirmation within 24 hours

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

                                Exceptional! 5/5
                                (25 reviews)
                                avg/night
                                House #2196590
                                • 2 BR
                                • 1 BA
                                • Sleeps 5
                                25
                                Viewed 8 times in the last 48 hours

                                Confirmation within 24 hours

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

                                  Wonderful! 4.9/5
                                  (22 reviews)
                                  avg/night
                                  Multiple rentals Apartment #435134
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 3
                                  22
                                  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
                                    (20 reviews)
                                    avg/night
                                    House #403492
                                    • 3 BR
                                    • 2 BA
                                    • Separate Toilet
                                    • Sleeps 7
                                    20
                                    Viewed 37 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
                                      (33 reviews)
                                      avg/night
                                      Villa #709879vb
                                      • 3 BR
                                      • 3 BA
                                      • Separate Toilet
                                      • Sleeps 7
                                      33
                                      Viewed 37 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
                                        (31 reviews)
                                        avg/night
                                        Multiple rentals Chateau / Country House #6153067
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 5
                                        31
                                        Viewed 38 times in the last 48 hours

                                        Confirmation within 24 hours

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

                                          Wonderful! 4.9/5
                                          (20 reviews)
                                          avg/night
                                          Cottage #6078287
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 4
                                          20
                                          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
                                            (9 reviews)
                                            avg/night
                                            Villa #64607vb
                                            • 4 BR
                                            • 3 BA
                                            • Separate Toilet
                                            • Sleeps 6
                                            9
                                            Viewed 15 times in the last 48 hours

                                            Confirmation within 24 hours

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

                                              Exceptional! 5/5
                                              (57 reviews)
                                              avg/night
                                              House #6190174
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 5
                                              57
                                              Viewed 21 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
                                                1

                                                Confirmation within 24 hours

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

                                                  Wonderful! 4.8/5
                                                  (19 reviews)
                                                  avg/night
                                                  House #6225502
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  19
                                                  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
                                                    (27 reviews)
                                                    avg/night
                                                    Apartment #3880312
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 5
                                                    27
                                                    Viewed 19 times in the last 48 hours

                                                    Confirmation within 24 hours

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

                                                      Exceptional! 5/5
                                                      (39 reviews)
                                                      avg/night
                                                      Multiple rentals Chateau / Country House #6153067
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      39
                                                      Viewed 30 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
                                                        Apartment #1198165a
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        10
                                                        Viewed 43 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
                                                          Villa #6555585
                                                          • 4 BR
                                                          • 4 BA
                                                          • Sleeps 8
                                                          7
                                                          Viewed 19 times in the last 48 hours

                                                          Instant confirmation

                                                          Your booking request will be confirmed immediately.

                                                            Farmhouse #2554049
                                                            • 3 BR
                                                            • 1 BA
                                                            • Sleeps 6
                                                            3
                                                            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
                                                              (18 reviews)
                                                              avg/night
                                                              Villa #90810
                                                              • 5 BR
                                                              • 4 BA
                                                              • Sleeps 12
                                                              18
                                                              Viewed 19 times in the last 48 hours

                                                              Confirmation within 24 hours

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

                                                                Multiple rentals Apartment #809657
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                22

                                                                Confirmation within 24 hours

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

                                                                  Multiple rentals Apartment #6521915
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  3
                                                                  Viewed 8 times in the last 48 hours

                                                                  Confirmation within 24 hours

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

                                                                    Wonderful! 4.8/5
                                                                    (11 reviews)
                                                                    avg/night
                                                                    Castle #445224
                                                                    • 5 BR
                                                                    • 3 BA
                                                                    • Sleeps 11
                                                                    11
                                                                    Viewed 82 times in the last 48 hours

                                                                    Confirmation within 24 hours

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

                                                                      Multiple rentals Apartment #6622282
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 3
                                                                      4

                                                                      Confirmation within 24 hours

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

                                                                        Very Good! 4/5
                                                                        (5 reviews)
                                                                        avg/night
                                                                        Villa #1934854
                                                                        • 8 BR
                                                                        • 4 BA
                                                                        • Sleeps 16
                                                                        5
                                                                        Viewed 20 times in the last 48 hours

                                                                        Instant confirmation

                                                                        Your booking request will be confirmed immediately.

                                                                          Wonderful! 4.8/5
                                                                          (15 reviews)
                                                                          avg/night
                                                                          Multiple rentals House #734524
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 4
                                                                          15
                                                                          Viewed 11 times in the last 48 hours

                                                                          Instant confirmation

                                                                          Your booking request will be confirmed immediately.

                                                                            Excellent! 4.6/5
                                                                            (9 reviews)
                                                                            avg/night
                                                                            Farmhouse #8461
                                                                            • 3 BR
                                                                            • 3 BA
                                                                            • Sleeps 6
                                                                            9
                                                                            Viewed 59 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
                                                                              (67 reviews)
                                                                              avg/night
                                                                              House #6162521
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 5
                                                                              67
                                                                              Viewed 18 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
                                                                                (9 reviews)
                                                                                avg/night
                                                                                Chateau / Country House #1851746
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 7
                                                                                9

                                                                                Confirmation within 24 hours

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

                                                                                  Wonderful! 4.9/5
                                                                                  (27 reviews)
                                                                                  avg/night
                                                                                  Multiple rentals Barn #1379588
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  27
                                                                                  Viewed 23 times in the last 48 hours

                                                                                  Instant confirmation

                                                                                  Your booking request will be confirmed immediately.

                                                                                    Wonderful! 4.9/5
                                                                                    (30 reviews)
                                                                                    avg/night
                                                                                    Villa #275267
                                                                                    • 5 BR
                                                                                    • 5 BA
                                                                                    • Sleeps 10
                                                                                    30
                                                                                    Viewed 25 times in the last 48 hours

                                                                                    Confirmation within 24 hours

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

                                                                                      avg/night
                                                                                      House #6896531
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      1
                                                                                      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
                                                                                        (66 reviews)
                                                                                        avg/night
                                                                                        Apartment #6132548
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 3
                                                                                        66
                                                                                        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
                                                                                          (12 reviews)
                                                                                          avg/night
                                                                                          Multiple rentals Chateau / Country House #6368329
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          12
                                                                                          Viewed 8 times in the last 48 hours

                                                                                          Confirmation within 24 hours

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

                                                                                            Multiple rentals Apartment #809657
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                            12

                                                                                            Confirmation within 24 hours

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

                                                                                              Cottage #1949272
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              1
                                                                                              Viewed 18 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
                                                                                                (13 reviews)
                                                                                                avg/night
                                                                                                Farmhouse #89525
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                13
                                                                                                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
                                                                                                  (10 reviews)
                                                                                                  avg/night
                                                                                                  Multiple rentals Apartment #734524
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 5
                                                                                                  10
                                                                                                  Viewed 9 times in the last 48 hours

                                                                                                  Instant confirmation

                                                                                                  Your booking request will be confirmed immediately.

                                                                                                    Very Good! 4/5
                                                                                                    (5 reviews)
                                                                                                    avg/night
                                                                                                    Cottage #696005vb
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 4
                                                                                                    5
                                                                                                    Viewed 18 times in the last 48 hours

                                                                                                    Instant confirmation

                                                                                                    Your booking request will be confirmed immediately.

                                                                                                      Wonderful! 4.9/5
                                                                                                      (8 reviews)
                                                                                                      avg/night
                                                                                                      Multiple rentals House #875022
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 7
                                                                                                      8
                                                                                                      Viewed 19 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+