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Castelfiorentino is a beautiful town located in the Tuscany region of Italy. The settlement and castle here was built along a road used by pilgrims during the middle ages, taking travellers from Northern Europe into the City of Rome. This is in fact the site where the ancient Roman town of Timignano once was. Set within the enclosure of the castle walls, on a defensive hill top was the settlement and its church. Holiday lettings in Castelfiorentino are the perfect accommodation option for tourists visiting this beautiful region of Italy and offer so much more than a hotel. Villas in Castelfiorentino are just one of the options available and many of them offer stunning views across this region of Florence.

History

With the settlement expanding a second set of ringed walls were built to house newcomers and there were many gates and towers to navigate in order to travel to the market square at the heart of the settlement. Growing in stature this settlement became an important outpost for the region of Florence, and home to the major of the region, as signified by the flag displaying a red lily. Apartments in Castelfiorentino and all of the other holiday accommodation in Castelfiorentino is perfect for families wanting to come and explore the area and the many sights and attractions of Florence.

Turbulent Times

At one point during 1521 Castelfiorentino was destroyed. This was a time of heavy attacks and constant raids, though it was rebuilt it never regained its stature as a defensive outpost. The 18th century again saw the town prosper and grow and once again became home to the mayoral offices. The town is now popular with tourists wanting to experience an authentic Italian holiday. Holiday rentals in Castelfiorentino are the perfect way to explore this beautiful region of Italy, and with the fabulous city of Florence and the region of Tuscany within easy reach it is understandable why holiday homes in Castelfiorentino are popular with travellers and tourists from all over the world.

  • Showing 1-50 of 300+
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    Wonderful! 4.8/5
    (4 reviews)
    avg/night
    Farmhouse #1943595
    • 10 BR
    • 5 BA
    • Separate Toilet
    • Sleeps 20
    4

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      Apartment #6435946
      • 2 BR
      • 1 BA
      • Sleeps 6
      6
      Viewed 6 times in the last 48 hours

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        Villa #6120038
        • Studio
        • 1 BA
        • Sleeps 5
        2
        Viewed 7 times in the last 48 hours

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          Villa #6514002
          • 1 BR
          • 1 BA
          • Sleeps 6

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            Villa #6516525
            • 2 BR
            • 2 BA
            • Sleeps 7
            2
            Viewed 10 times in the last 48 hours

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              #8083557
              • 11 BR
              • 5 BA
              • Separate Toilet
              • Sleeps 24

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                avg/night
                Villa #1682494
                • 4 BR
                • 3 BA
                • Sleeps 8
                Viewed 5 times in the last 48 hours

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                  Villa #6715114
                  • 5 BR
                  • 4 BA
                  • Sleeps 18

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                    Wonderful! 4.9/5
                    (117 reviews)
                    avg/night
                    Apartment #462238
                    • 1 BR
                    • 1 BA
                    • Sleeps 4
                    117
                    Viewed 42 times in the last 48 hours

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                      Exceptional! 5/5
                      (54 reviews)
                      avg/night
                      House #6235319
                      • 2 BR
                      • 2 BA
                      • Sleeps 4
                      54
                      Viewed 83 times in the last 48 hours

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                        Wonderful! 4.9/5
                        (96 reviews)
                        avg/night
                        Multiple rentals Apartment #420459
                        • 2 BR
                        • 1 BA
                        • Sleeps 5
                        96
                        Viewed 50 times in the last 48 hours

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                          Wonderful! 4.9/5
                          (46 reviews)
                          avg/night
                          Apartment #1688687
                          • 2 BR
                          • 2 BA
                          • Sleeps 5
                          46
                          Viewed 30 times in the last 48 hours

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                            Wonderful! 4.9/5
                            (29 reviews)
                            avg/night
                            Apartment #683977vb
                            • 1 BR
                            • 1 BA
                            • Sleeps 3
                            29
                            Viewed 36 times in the last 48 hours

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                              Wonderful! 4.8/5
                              (67 reviews)
                              avg/night
                              Multiple rentals Apartment #420459
                              • 2 BR
                              • 2 BA
                              • Sleeps 5
                              67
                              Viewed 63 times in the last 48 hours

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                                Exceptional! 5/5
                                (44 reviews)
                                avg/night
                                Multiple rentals Apartment #1691215
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                44
                                Viewed 39 times in the last 48 hours

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                                  Wonderful! 4.8/5
                                  (13 reviews)
                                  avg/night
                                  Apartment #8022189
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 5
                                  13
                                  Viewed 49 times in the last 48 hours

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                                    Exceptional! 5/5
                                    (49 reviews)
                                    avg/night
                                    Apartment #1621213
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    49
                                    Viewed 37 times in the last 48 hours

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                                      Exceptional! 5/5
                                      (48 reviews)
                                      avg/night
                                      Apartment #869430
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 2
                                      48
                                      Viewed 68 times in the last 48 hours

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                                        Wonderful! 4.9/5
                                        (8 reviews)
                                        avg/night
                                        Apartment #1322996
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        8
                                        Viewed 7 times in the last 48 hours

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                                          Wonderful! 4.9/5
                                          (81 reviews)
                                          avg/night
                                          Apartment #308890
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 4
                                          81
                                          Viewed 67 times in the last 48 hours

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                                            Apartment #884548vb
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 4
                                            3
                                            Viewed 29 times in the last 48 hours

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                                              Wonderful! 4.9/5
                                              (19 reviews)
                                              avg/night
                                              Apartment #1107906
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 4
                                              19
                                              Viewed 34 times in the last 48 hours

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                                                Exceptional! 5/5
                                                (22 reviews)
                                                avg/night
                                                Multiple rentals Apartment #1691215
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 3
                                                22
                                                Viewed 37 times in the last 48 hours

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                                                  Wonderful! 4.9/5
                                                  (22 reviews)
                                                  avg/night
                                                  Apartment #435134
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 3
                                                  22
                                                  Viewed 22 times in the last 48 hours

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                                                    Excellent! 4.6/5
                                                    (11 reviews)
                                                    View details for price
                                                    Apartment #6023090
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    11

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                                                      Excellent! 4.7/5
                                                      (24 reviews)
                                                      avg/night
                                                      Apartment #1686314
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      24
                                                      Viewed 14 times in the last 48 hours

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                                                        Exceptional! 5/5
                                                        (37 reviews)
                                                        avg/night
                                                        Villa #1137514
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 10
                                                        37
                                                        Viewed 51 times in the last 48 hours

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                                                          Wonderful! 4.8/5
                                                          (6 reviews)
                                                          avg/night
                                                          House #1973366
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 5
                                                          6
                                                          Viewed 20 times in the last 48 hours

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                                                            Wonderful! 4.8/5
                                                            (19 reviews)
                                                            avg/night
                                                            Apartment #3929069
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 5
                                                            19
                                                            Viewed 34 times in the last 48 hours

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                                                              Excellent! 4.4/5
                                                              (36 reviews)
                                                              avg/night
                                                              Apartment #8114
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              36
                                                              Viewed 26 times in the last 48 hours

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                                                                Exceptional! 5/5
                                                                (12 reviews)
                                                                avg/night
                                                                Apartment #1017337
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 4
                                                                12
                                                                Viewed 19 times in the last 48 hours

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                                                                  Wonderful! 4.9/5
                                                                  (18 reviews)
                                                                  avg/night
                                                                  Apartment #6468924
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  18
                                                                  Viewed 25 times in the last 48 hours

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                                                                    Wonderful! 4.9/5
                                                                    (53 reviews)
                                                                    avg/night
                                                                    Apartment #437934
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 5
                                                                    53
                                                                    Viewed 32 times in the last 48 hours

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                                                                      avg/night
                                                                      House #1980329
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 4
                                                                      3
                                                                      Viewed 17 times in the last 48 hours

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                                                                        Excellent! 4.7/5
                                                                        (13 reviews)
                                                                        avg/night
                                                                        Farmhouse #89525
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        13
                                                                        Viewed 14 times in the last 48 hours

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                                                                          Exceptional! 5/5
                                                                          (10 reviews)
                                                                          avg/night
                                                                          Multiple rentals Apartment #734524
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 5
                                                                          10
                                                                          Viewed 26 times in the last 48 hours

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                                                                            Wonderful! 4.9/5
                                                                            (56 reviews)
                                                                            avg/night
                                                                            Multiple rentals House #420494
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            56
                                                                            Viewed 7 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 #699409vb
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 4
                                                                              21
                                                                              Viewed 24 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 23 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
                                                                                  (14 reviews)
                                                                                  avg/night
                                                                                  Multiple rentals House #734524
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 4
                                                                                  14
                                                                                  Viewed 35 times in the last 48 hours

                                                                                  Confirmation within 24 hours

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                                                                                    Exceptional! 5/5
                                                                                    (46 reviews)
                                                                                    avg/night
                                                                                    Apartment #6196463
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 5
                                                                                    46
                                                                                    Viewed 24 times in the last 48 hours

                                                                                    Confirmation within 24 hours

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

                                                                                      Excellent! 4.4/5
                                                                                      (7 reviews)
                                                                                      avg/night
                                                                                      House #1992424
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 4
                                                                                      7
                                                                                      Viewed 25 times in the last 48 hours

                                                                                      Confirmation within 24 hours

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                                                                                        Wonderful! 4.9/5
                                                                                        (70 reviews)
                                                                                        avg/night
                                                                                        Multiple rentals Farmhouse #6126982
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 5
                                                                                        70
                                                                                        Viewed 24 times in the last 48 hours

                                                                                        Confirmation within 24 hours

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

                                                                                          Wonderful! 4.9/5
                                                                                          (15 reviews)
                                                                                          avg/night
                                                                                          Apartment #827364vb
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          15
                                                                                          Viewed 40 times in the last 48 hours

                                                                                          Instant confirmation

                                                                                          Your booking request will be confirmed immediately.

                                                                                            Wonderful! 4.8/5
                                                                                            (21 reviews)
                                                                                            avg/night
                                                                                            Farmhouse #5491
                                                                                            • 5 BR
                                                                                            • 4 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 12
                                                                                            21
                                                                                            Viewed 16 times in the last 48 hours

                                                                                            Confirmation within 24 hours

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                                                                                              Exceptional! 5/5
                                                                                              (13 reviews)
                                                                                              avg/night
                                                                                              Villa #6433993
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 5
                                                                                              13
                                                                                              Viewed 10 times in the last 48 hours

                                                                                              Confirmation within 24 hours

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                                                                                                Farmhouse #2554049
                                                                                                • 3 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                3
                                                                                                Viewed 32 times in the last 48 hours

                                                                                                Confirmation within 24 hours

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                                                                                                  Excellent! 4.4/5
                                                                                                  (12 reviews)
                                                                                                  avg/night
                                                                                                  Apartment #680568vb
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  12
                                                                                                  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
                                                                                                    (10 reviews)
                                                                                                    avg/night
                                                                                                    Apartment #1409521
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    10
                                                                                                    Viewed 19 times in the last 48 hours

                                                                                                    Confirmation within 24 hours

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

                                                                                                      Exceptional! 5/5
                                                                                                      (9 reviews)
                                                                                                      avg/night
                                                                                                      Apartment #395024vb
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 3
                                                                                                      9
                                                                                                      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 Castelfiorentino (300+)