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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.

    • Studio
    • 1 BA
    • Sleeps 5
    Villa #6120038
    3
    Viewed 11 times in the last 48 hours
      Excellent! 4.6/5
      (10 reviews)
      avg/night
      • 4 BR
      • 1 BA
      • Sleeps 8
      House #6429780
      10
      Viewed 11 times in the last 48 hours
        • 1 BR
        • 1 BA
        • Sleeps 6
        Villa #6514002
        1
          • 2 BR
          • 2 BA
          • Sleeps 7
          Villa #6516525
          2
            • 11 BR
            • 5 BA
            • Separate Toilet
            • Sleeps 24
            #8083557
              • 1 BR
              • 1 BA
              • Sleeps 5
              Apartment #6853657
                • 2 BR
                • 2 BA
                • Sleeps 7
                Apartment #6853659
                  • 1 BR
                  • 1 BA
                  • Sleeps 6
                  Apartment #6853658
                    • 2 BR
                    • 2 BA
                    • Sleeps 7
                    Apartment #6891643
                      • 1 BR
                      • 1 BA
                      • Sleeps 5
                      Apartment #6891641
                        • 1 BR
                        • 1 BA
                        • Sleeps 6
                        Apartment #6891642
                          • 2 BR
                          • 2 BA
                          • Sleeps 6
                          House #2333578
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            Apartment #2294184
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                              Apartment #2578459
                                • 2 BR
                                • 2 BA
                                • Sleeps 8
                                Apartment #2294181
                                  • 4 BR
                                  • 3 BA
                                  • Sleeps 8
                                  Villa #1682494
                                    • 5 BR
                                    • 4 BA
                                    • Sleeps 18
                                    Villa #6715114
                                    1
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Apartment #8290201
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Apartment #8270594
                                          Exceptional! 5/5
                                          (73 reviews)
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Apartment #1890144
                                          73
                                          Viewed 272 times in the last 48 hours
                                            Exceptional! 5/5
                                            (58 reviews)
                                            avg/night
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 4
                                            House #6235319
                                            58
                                            Viewed 236 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (28 reviews)
                                              avg/night
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Apartment #1849857
                                              28
                                              Viewed 55 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (26 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 5
                                                Apartment #1634738
                                                26
                                                Viewed 67 times in the last 48 hours
                                                  Exceptional! 5/5
                                                  (63 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 7
                                                  Apartment #708969vb
                                                  63
                                                  Viewed 63 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (58 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Multiple rentals Cottage #6049089
                                                    58
                                                    Viewed 140 times in the last 48 hours
                                                      Excellent! 4.6/5
                                                      (20 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Apartment #4174863
                                                      20
                                                      Viewed 68 times in the last 48 hours
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 2
                                                        Multiple rentals Apartment #479580
                                                        4
                                                        Viewed 12 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (127 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Apartment #462238
                                                          127
                                                          Viewed 38 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (47 reviews)
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                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Apartment #276627vb
                                                            47
                                                            Viewed 29 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (23 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 1 BA
                                                              • Separate Toilet
                                                              • Sleeps 4
                                                              Apartment #706279vb
                                                              23
                                                              Viewed 14 times in the last 48 hours
                                                                Exceptional! 5/5
                                                                (106 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 5
                                                                Multiple rentals Apartment #420459
                                                                106
                                                                Viewed 32 times in the last 48 hours
                                                                  Exceptional! 5/5
                                                                  (5 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 3 BA
                                                                  • Sleeps 9
                                                                  Apartment #927897vb
                                                                  5
                                                                  Viewed 52 times in the last 48 hours
                                                                    Exceptional! 5/5
                                                                    (48 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Multiple rentals Apartment #1691215
                                                                    48
                                                                    Viewed 32 times in the last 48 hours
                                                                      Excellent! 4.7/5
                                                                      (13 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Apartment #727606vb
                                                                      13
                                                                      Viewed 24 times in the last 48 hours
                                                                        Exceptional! 5/5
                                                                        (57 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Apartment #1621213
                                                                        57
                                                                        Viewed 71 times in the last 48 hours
                                                                          Excellent! 4.6/5
                                                                          (13 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 3
                                                                          Apartment #6657413
                                                                          13
                                                                          Viewed 22 times in the last 48 hours
                                                                            Exceptional! 5/5
                                                                            (18 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 11
                                                                            Villa #607748vb
                                                                            18
                                                                            Viewed 39 times in the last 48 hours
                                                                              Exceptional! 5/5
                                                                              (21 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 4
                                                                              Apartment #6015654
                                                                              21
                                                                              Viewed 36 times in the last 48 hours
                                                                                Wonderful! 4.8/5
                                                                                (37 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 3
                                                                                Apartment #683977vb
                                                                                37
                                                                                Viewed 26 times in the last 48 hours
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Apartment #884548vb
                                                                                  4
                                                                                  Viewed 144 times in the last 48 hours
                                                                                    Exceptional! 5/5
                                                                                    (26 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 6
                                                                                    Barn #1024402
                                                                                    26
                                                                                    Viewed 73 times in the last 48 hours
                                                                                      Excellent! 4.6/5
                                                                                      (17 reviews)
                                                                                      avg/night
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 3
                                                                                      Apartment #1348016
                                                                                      17
                                                                                      Viewed 5 times in the last 48 hours
                                                                                      • 1 - 50 of 300+

                                                                                      Castelfiorentino Holiday Apartments & Villas (300+)

                                                                                       

                                                                                      Recent Reviews

                                                                                      Lovely Apartment in Florence

                                                                                      5 of 5
                                                                                      This apartment is in a perfect location in the heart of Florence. The apartment has everything supplied to make your stay very pleasant indeed. The views from the terrace and balcony especially at night are stunning. There are a lot of stairs to climb but we didn't find this a problem and it meant that you were above all the hustle and bustle of the busy streets below. We look forward to returning - enjoy!
                                                                                      • Review Submitted: Jun 18, 2017
                                                                                      • Date of Stay: May 2017

                                                                                      Warm owners, beautiful Villa and exquisite breakfasts

                                                                                      5 of 5
                                                                                      The villa is located in a strategical location from which I could visit all of the "old Tuscany", medieval places like San Gimignano, Certaldo, Montaione, Volterra, are all very close, and there is also a lot of trains from there to Firenze, Siena and Pisa! If I had more time I would visit the whole of Tuscany from there, probably I will be back at Villa Tilla sooner or later!! Tiziana was an exquisite host and her hand-made cookies and cakes were very very good, and she even makes jams with the products in their garden! The place is very quiet, very relaxing, with a big garden and a beautiful swimming pool. It was a very relaxing and interesting experience!
                                                                                      • Review Submitted: May 16, 2017
                                                                                      • Date of Stay: May 2017