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Holidaymakers searching for holiday rentals in Castiglion Fiorentino also enquired about villas in Cortona, apartments in Lucca and apartments in San Gimignano

Make a holiday rental home or apartment in Castiglion Fiorentino, Italy your home away from home

The walled town of Castiglion Fiorentino is a great alternative destination to Cortona when staying in this peaceful part of the Arezzo province. A visit to Castiglion Fiorentino is akin to a trip back to the Middle Ages, with strong medieval influences to be seen almost everywhere you look. The town is laid-back and friendly, and can also be used as a base for enjoying a holiday of walking and exploring in the fantastic surrounding countryside.

Things to do in Castiglion Fiorentino, Italy

The well-preserved city walls are Castiglion Fiorentino’s most recognisable feature, and date back to the 13th century. Once inside the walls you will also discover an array of historical attractions on the paved streets, including the Municipal Art Gallery (in the former church of Sant’Angelo) and the remains of the town’s 14th century fortress.

As with many Tuscan towns and cities, Castiglion Fiorentino is home to immensely proud locals who hold a number of festivals and evens throughout the year to celebrate their town and the local region in general. These are great times to visit the area, as the festivals will allow you to learn more about the town and interact with these residents – in Italian of course! Popular festivals in Castiglion Fiorentino include the Palio dei Rioni – a historic June horse race, and an Easter Sunday parade.

Castiglion Fiorentino also has a train station, which provides good links with the well-known towns and cities of the region such as Cortona, Perugia, Arezzo, Siena and Pienza, and you can alternate your days of exploring these destinations with days of walking, hiking, horse riding and cycling in the unspoilt countryside that surrounds Castiglion Fiorentino.

Places to visit on holiday in Castiglion Fiorentino, Italy

Cortona is just 12km south of Castiglion Fiorentino, and a hugely popular destination with both foreign and domestic travellers. The city has a huge number of old buildings and cultural attractions, but combines these with modern amenities and a vibrant nightlife to create an enticing destination for visitors. Also within close reach of Castiglion Fiorentino is Lucignano (18km), which boasts a hilltop position amongst dense woodland and olive groves – ‘Real Tuscany’ as some may call it.

Weather in Castiglion Fiorentino, Italy

The weather in Castiglion Fiorentino is particularly good during summer months, with June, July and August having an average daily high temperature of 28C. Spring and early autumn are also great times for a visit, with temperatures of 20C common, but winter is less popular due to increased levels of rainfall.

Flights to Castiglion Fiorentino, Italy

San Egidio Airport (PEG) is located just outside Perugia, 55km from Castiglion Fiorentino. A Ryanair flight from London Stansted to San Egidio is the easiest and cheapest way of getting to your Castiglion Fiorentino rental accommodation, but if you are intent on arriving in style you may wish to fly to Florence Peretola Airport (FLR) and make the 114km journey north instead.

  • Showing 1-50 of 300+
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    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 7
    Apartment #6560472
    3
    Viewed 13 times in the last 48 hours
      • 1 BR
      • 1 BA
      • Sleeps 4
      Multiple rentals Apartment #1676483
      4
      Viewed 7 times in the last 48 hours
        • 1 BR
        • 1 BA
        • Sleeps 3
        Multiple rentals Apartment #1676483
        Viewed 6 times in the last 48 hours
          • 1 BR
          • 1 BA
          • Sleeps 3
          Apartment #1796166
            Exceptional! 5.0/5
            (11 reviews)
            avg/night
            • 3 BR
            • 2 BA
            • Sleeps 6
            Apartment #757059vb
            11
            Viewed 19 times in the last 48 hours
              Wonderful! 4.9/5
              (28 reviews)
              avg/night
              • 2 BR
              • 2 BA
              • Sleeps 5
              Villa #463746
              28
              Viewed 37 times in the last 48 hours
                Exceptional! 5.0/5
                (28 reviews)
                avg/night
                • 1 BR
                • 1 BA
                • Sleeps 2
                Multiple rentals Cottage #65770
                28
                Viewed 85 times in the last 48 hours
                  avg/night
                  • 4 BR
                  • 2 BA
                  • Sleeps 10
                  Cottage #6742795
                  1
                  Viewed 39 times in the last 48 hours
                    Exceptional! 5.0/5
                    (12 reviews)
                    avg/night
                    • 4 BR
                    • 2 BA
                    • Sleeps 10
                    Farmhouse #91534
                    12
                    Viewed 71 times in the last 48 hours
                      • 3 BR
                      • 2 BA
                      • Sleeps 6
                      Villa #1035117
                      Viewed 15 times in the last 48 hours
                        • 2 BR
                        • 1 BA
                        • Sleeps 4
                        Cottage #1103921
                        2
                          avg/night
                          • 2 BR
                          • 2 BA
                          • Sleeps 5
                          Apartment #1038470
                          1
                          Viewed 5 times in the last 48 hours
                            • 7 BR
                            • 7 BA
                            • Sleeps 15
                            Villa #1856283
                            Viewed 10 times in the last 48 hours
                              avg/night
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                              Villa #8003714
                              4
                              Viewed 40 times in the last 48 hours
                                Exceptional! 5.0/5
                                (9 reviews)
                                avg/night
                                • 5 BR
                                • 5 BA
                                • Sleeps 12
                                Villa #1812215
                                9
                                Viewed 44 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (5 reviews)
                                  avg/night
                                  • 4 BR
                                  • 2 BA
                                  • Sleeps 9
                                  Villa #1638206
                                  5
                                  Viewed 7 times in the last 48 hours
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 8
                                    Villa #1638389
                                    7
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Villa #1623410
                                      1
                                        • 4 BR
                                        • 3 BA
                                        • Sleeps 8
                                        Villa #579997vb
                                        4
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Apartment #1796214
                                          1
                                          Viewed 7 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (5 reviews)
                                            avg/night
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 5
                                            Cottage #404807vb
                                            5
                                              avg/night
                                              • 3 BR
                                              • 4 BA
                                              • Sleeps 6
                                              Chateau / Country House #6470286
                                              Viewed 10 times in the last 48 hours
                                                Exceptional! 5.0/5
                                                (27 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 8
                                                Villa #6001627
                                                27
                                                Viewed 11 times in the last 48 hours
                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 10
                                                  House #1608948
                                                    • 4 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    Villa #6488492
                                                      • 4 BR
                                                      • 3 BA
                                                      • Sleeps 8
                                                      Villa #6090123
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 2
                                                        Villa #1623485
                                                        1
                                                          • 2 BR
                                                          • 1 BA
                                                          • Separate Toilet
                                                          • Sleeps 6
                                                          House #4334031
                                                            • 4 BR
                                                            • 3 BA
                                                            • Sleeps 10
                                                            Villa #1623552
                                                            1
                                                              avg/night
                                                              • 6 BR
                                                              • 5 BA
                                                              • Sleeps 14
                                                              Villa #1623782
                                                              2
                                                              Viewed 6 times in the last 48 hours
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Villa #1619763
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Sleeps 10
                                                                  Villa #1881600
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 8
                                                                    Villa #1623464
                                                                    3
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      House #6829656
                                                                      Viewed 7 times in the last 48 hours
                                                                        • 7 BR
                                                                        • 7 BA
                                                                        • Sleeps 15
                                                                        Villa #1623545
                                                                        1
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Chateau / Country House #1902880
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 7
                                                                            Apartment #598411vb
                                                                              • 5 BR
                                                                              • 4 BA
                                                                              • Sleeps 11
                                                                              Villa #507841vb
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Villa #1623409
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Villa #1672369
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 3
                                                                                    Villa #1623311
                                                                                      • 6 BR
                                                                                      • 6 BA
                                                                                      • Sleeps 15
                                                                                      Villa #6555639
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Villa #6853370
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 8
                                                                                          Villa #1881611
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 11
                                                                                            House #6894232
                                                                                            Viewed 5 times in the last 48 hours
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 2
                                                                                              Villa #1623408
                                                                                              • 1 - 50 of 300+

                                                                                              Castiglion Fiorentino Holiday Apartments & Villas (300+)

                                                                                               

                                                                                              Recent Reviews

                                                                                              A perfect Tuscan sunset

                                                                                              5 of 5
                                                                                              My partner and I stayed at La Casa del Rigatierre for 5 nights. It was an unforgettable experience! The house has a welcoming old world feel, with all the modern conveniences. Kristina has clearly gone that extra mile to help her guests feel more at home. Special mention must go to the window view from the master bedroom which could easily be mistaken for an Italian Renaissance artwork - stunning. We really did not want to leave this place. With an interesting history and lively population, Castiglion Fiorentino itself is the quintessential Tuscan hamlet with plenty to offer any traveller. Yes, visit Cortona but stay in Castiglion! Must try the Garden Bar and Restaurant, and Roggi at sunset. Kristina is clearly an experienced host. She has an extensive knowledge of the area and her assistance with even the simplest questions was always well received. Thank you Kristina! We would definitely stay here again.
                                                                                              • Review Submitted: 21-Jan-2017
                                                                                              • Date of Stay: Jul 2016

                                                                                              Review for stay from 23 September 2016 to 01 October 2016

                                                                                              5 of 5
                                                                                              Excellent retreat, quiet relaxing and amazing views.
                                                                                              • Review Submitted: 16-Oct-2016
                                                                                              • Date of Stay: Sep 2016

                                                                                              Review for stay from 07 September 2016 to 17 September 2016

                                                                                              5 of 5
                                                                                              Restful holiday with great location. Very welcoming, helpful owners. Hope to visit again.
                                                                                              • Review Submitted: 29-Sep-2016
                                                                                              • Date of Stay: Sep 2016