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Holidaymakers searching for holiday rentals in Castelfiorentino also enquired about villas in Castelnuovo Berardenga, villas in Cortona and villas in Vinci

Make a holiday rental home or villa in Castelfiorentino, Italy your home away from home

The town of Castelfiorentino lies in the heart of the Valdelsa Valley in the Chianti region of Tuscany, Italy. Ideally located between the natural landscapes of the Chianti Hills and the famous art centres of Tuscany’s cities, a holiday rental property in Castelfiorentino is an ideal base for a full exploration of Chianti. Castelfiorentino is a wonderfully ornate, historical city, with wide, clean streets that are a pleasure to wander along.

Things to do in Castelfiorentino, Italy

A gentle stroll through the streets of Castelfiorentino will almost certainly surprise you. There are a delightful range of attractions within the town, which boasts one of the most laidback, peaceful atmospheres of any town in Tuscany. The fortified castle on the hillside above the town and the defensive walls, interspersed with five large gates and towers are unmissable sights within Castelfiorentino, but there are a couple of more hidden attractions worth seeking out from a holiday rental apartment in Castelfiorentino, including the Raccolta Comunale art gallery.

The Valdesa Valley is a magnificent destination for exploring the beautiful Chianti Hills. The Valdesa River is a fantastic fishing river, and there is plenty of walking, cycling and horse riding to be done. The beautiful array of colour that washes over the Tuscan countryside are particularly vivid in the Chianti Hills, which makes exploration a wonderful adventure, but make sure you have a few spare rolls of film in your camera. Landscape painting holidays are particularly popular from Castelfiorentino villas.

As with many of the town and villages in the area, the Castelfiorentino calendar is splashed with events. The Canti & Banchi festival in May sees the town centre returned to its medieval glory, with performances of street theatre and many little stalls serving traditional dishes. The People’s Theatre Festival and the Cinema Under the Stars Festival, both in August, the Choral Festival in November and the Valdelsa Summer Festival from July until September are all fantastic times to be staying in Castelfiorentino accommodation, providing endless entertainment, night and day.

Places to visit on holiday to Castelfiorentino, Italy

The historic town of Barberino Val d’Elsa makes a perfect day trip from a Castelfiorentino property. The town has changed little since its creation as a military base, and many of the original buildings still stand. The ancient defensive walls offer a great circuit for walking around the town.

Weather in Castelfiorentino, Italy

Castelfiorentino’s climate is magnificent. Walking and cycling holidays are wonderful at any time from the end of April until late September, as average monthly temperatures remain above 22˚C, with daily peaks reaching up to 34˚C in July and August.

Travel to Castelfiorentino, Italy

Pisa Airport (PSA) is just 35km from a holiday rental property in Castelfiorentino. There are regular flights to Pisa from the UK, provided by Ryanair and easyJet.

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  • Showing 1-50 of 300+
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    • 5 BR
    • 3 BA
    • Sleeps 10
    Multiple rentals House #530011
    11
      • 2 BR
      • 1 BA
      • Sleeps 4
      Multiple rentals Apartment #530011
      3
        • 1 BR
        • 1 BA
        • Sleeps 3
        Multiple rentals Apartment #530011
        2
          • 2 BR
          • 1 BA
          • Sleeps 5
          Multiple rentals Apartment #27374
          4
            • 3 BR
            • 2 BA
            • Sleeps 6
            Multiple rentals Apartment #27374
            8
              • 3 BR
              • 1 BA
              • Sleeps 5
              Multiple rentals Apartment #27374
              4
                • 2 BR
                • 2 BA
                • Sleeps 4
                Multiple rentals Apartment #27374
                4
                  • 4 BR
                  • 2 BA
                  • Sleeps 8
                  Multiple rentals House #27374
                  8
                    • 4 BR
                    • 3 BA
                    • Sleeps 8
                    Villa #1682494
                      • 10 BR
                      • 5 BA
                      • Separate Toilet
                      • Sleeps 20
                      Farmhouse #1943595
                      4
                        • 2 BR
                        • 1 BA
                        • Sleeps 4
                        Multiple rentals Chateau / Country House #6366214
                        7
                          • 1 BR
                          • 1 BA
                          • Sleeps 4
                          Multiple rentals Chateau / Country House #6366214
                          33
                            Exceptional! 5.0/5
                            (21 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Separate Toilet
                            • Sleeps 2
                            Apartment #6252928
                            21
                              Very Good! 4.2/5
                              (5 reviews)
                              avg/night
                              • 4 BR
                              • 1 BA
                              • Sleeps 7
                              House #6429780
                              5
                                • 1 BR
                                • 1 BA
                                • Sleeps 4
                                Apartment #6576492
                                2
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 6
                                  House #6245886
                                  79
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 4
                                    Apartment #174892vb
                                    3
                                      Wonderful! 4.8/5
                                      (13 reviews)
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 3
                                      Apartment #1619686
                                      13
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • Separate Toilet
                                        • Sleeps 4
                                        House #779115
                                        3
                                        Viewed 7 times in the last 48 hours
                                          • 3 BR
                                          • 3 BA
                                          • Sleeps 6
                                          Chateau / Country House #1686266
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 6
                                            Apartment #6361651
                                            3
                                              • 1 BR
                                              • 2 BA
                                              • Sleeps 4
                                              Apartment #729398vb
                                              2
                                                Excellent! 4.7/5
                                                (7 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 4
                                                Castle #1618971
                                                7
                                                Viewed 14 times in the last 48 hours
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  House #2537557
                                                  1
                                                  Viewed 7 times in the last 48 hours
                                                    Excellent! 4.7/5
                                                    (6 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Apartment #2152308
                                                    6
                                                    Viewed 10 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (5 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 5
                                                      Apartment #1754264
                                                      5
                                                      Viewed 5 times in the last 48 hours
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 6
                                                        Apartment #6481979
                                                        1
                                                          Wonderful! 4.8/5
                                                          (13 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 5
                                                          Apartment #8022189
                                                          13
                                                          Viewed 6 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (54 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Cottage #6049089
                                                            54
                                                            Viewed 31 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (31 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 6
                                                              Cottage #602572a
                                                              31
                                                              Viewed 6 times in the last 48 hours
                                                                • 3 BR
                                                                • 3 BA
                                                                • Sleeps 6
                                                                Apartment #6481946
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Apartment #6777316
                                                                  2
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 4
                                                                    Apartment #6481976
                                                                    1
                                                                      • 6 BR
                                                                      • 6 BA
                                                                      • Sleeps 12
                                                                      Villa #6482134
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 4
                                                                        Castle #1618982
                                                                        2
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          Apartment #1645841
                                                                          3
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 5
                                                                            Apartment #8019595
                                                                            2
                                                                              • 8 BR
                                                                              • 6 BA
                                                                              • Sleeps 16
                                                                              Villa #6482365
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 9
                                                                                Villa #8038986
                                                                                4
                                                                                Viewed 5 times in the last 48 hours
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Apartment #1107906
                                                                                  19
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 7
                                                                                    Villa #1363507
                                                                                    4
                                                                                    Viewed 7 times in the last 48 hours
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      Apartment #1953239
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Apartment #1628893
                                                                                        4
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Apartment #769138vb
                                                                                          1
                                                                                            • 6 BR
                                                                                            • 5 BA
                                                                                            • Sleeps 12
                                                                                            Villa #6482309
                                                                                              Excellent! 4.5/5
                                                                                              (11 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Apartment #70444
                                                                                              11
                                                                                              Viewed 10 times in the last 48 hours
                                                                                              • 1 - 50 of 300+

                                                                                              Castelfiorentino Holiday Apartments & Villas (300+)

                                                                                               

                                                                                              Recent Reviews

                                                                                              Review for stay from 24 October 2016 to 29 October 2016

                                                                                              5 of 5
                                                                                              Sehr romantisch, nettes Personal traumhaft schön gelegen
                                                                                              • Review Submitted: 23-Nov-2016
                                                                                              • Date of Stay: Oct 2016

                                                                                              Perfect peaceful home from home.

                                                                                              5 of 5
                                                                                              Il Terazzo was absolutely perfect for the two of us. The design & layout of the property is such a great use of the space, the villa was really well equipped, the bed is very comfortable & all linen etc is as anyone would need & the spec of the property is very high. The view from the terrace is actually better than photos can show. The little hamlet in which it stands has been beautifully restored to be an excellent isolated place but near other properties. The pool was great - especially as there were not many properties occupied when we were there, in September - and Roberto, who welcomed us on arrival & checked on us occasionally through the week, was most helpful & charming. As throughout the whole booking & staying process, was Colm, the owner - even though he was actually in Dublin. It is a perfect base for what is perfect Tuscan scenery & tourist spots within an hour or so- but we enjoyed the walking too. We found the Via Francigena, which we had no idea of until we arrived. What a lovely stretch it is there between Gambassi Terme & San Gimignano. A perfect week. Many thanks. Phil
                                                                                              • Review Submitted: 04-Oct-2016
                                                                                              • Date of Stay: Sep 2016

                                                                                              Wir haben einen schönen Urlaub in unserem Ferienhaus vebracht

                                                                                              5 of 5
                                                                                              Wir haben einen schönen Urlaub in unserem Ferienhaus vebracht. Es handelt sich um eine großzügige und gepflegte Anlage mit hübschen, sehr gut ausgestatteten, Ferienhäusern und einem großem Pool, absolut ruhig gelegen. Die Anlage gehört zu einem Hotel in Montaione. Die Mitarbeiterinnen dort waren sehr freundlich und haben auch während des Aufenthalts sich mehrmals erkundigt, ob alles in Ordnung und zur Zufriedenheit ist. Der Pool ist jeden Tag gepflegt worden und wöchentlich gab es einen Wäschewechsel incl. Reinigung des Ferienhauses. Ein Gärtner war auch anwesend. Zum nächsten Ort sind es 6 Km, somit ist zwingend ein Auto erforderlich, auch für die Lebensmittelversorgung. Dafür ist die Anlage ein idealer Ausgangspunkt für Städtetouren in der Toskana (alle wichtigen Städte max. 1 Std. entfernt) und auch ideal zum Relaxen. In Montaione kann man gut essen und in Castelfiorentino sind alle Einkaufsmöglichkeiten vorhanden. Wir können diese Anlage weiterempfehlen.
                                                                                              • Review Submitted: 19-Sep-2016
                                                                                              • Date of Stay: Aug 2016