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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.

Additional service fee may apply.
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    Multiple rentals Apartment #530011
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      Multiple rentals House #530011
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        Multiple rentals Apartment #530011
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          Multiple rentals Apartment #530011
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                    Exceptional! 5/5
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                    Multiple rentals Chateau / Country House #6366214
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                      Exceptional! 5/5
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                      Multiple rentals Chateau / Country House #6366214
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                        Wonderful! 4.8/5
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                        Farmhouse #1943595
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                          Villa #1092698
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                            House #6429780
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                              Wonderful! 4.8/5
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                              Villa #3748185
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                                • 11 BR
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                                    Apartment #6891642
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                                      Chateau / Country House #1686266
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                                        Apartment #6891641
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                                          Apartment #6891643
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                                            Villa #1682494
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                                              Apartment #6853658
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                                                Apartment #4346008
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                                                  Apartment #6853659
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                                                    House #6357138
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                                                          Apartment #4341500
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                                                            Villa #4025424
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                                                              Villa #1810050
                                                                Exceptional! 5/5
                                                                (4 reviews)
                                                                View details for price
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                                                                Farmhouse #3476315
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                                                                  Apartment #6854886
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                                                                    Villa #6489948
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                                                                      Villa #6488838
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                                                                        Apartment #4346004
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                                                                          Apartment #6854448
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                                                                            Apartment #1975488
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                                                                              House #2333578
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                                                                                Apartment #6848630
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                                                                                  Apartment #6489986
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                                                                                    Apartment #1953485
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                                                                                      Apartment #6862520
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                                                                                        Apartment #6941342
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                                                                                          Apartment #6941127
                                                                                            • 1 BR
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                                                                                            Apartment #6941258
                                                                                              • 6 BR
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                                                                                              Villa #1810509
                                                                                                • 4 BR
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                                                                                                Villa #6488837
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                                                                                                  Apartment #2578459
                                                                                                  Viewed 6 times in the last 48 hours
                                                                                                  • 1 - 50 of 300+

                                                                                                  Castelfiorentino Holiday Apartments & Villas (300+)

                                                                                                   

                                                                                                  Recent Reviews

                                                                                                  Amazing. ...

                                                                                                  5 of 5
                                                                                                  Overall: Amazing. Enjoyed Most: The views. Surrounding Area: The different towns with local restaurants. Nearby Events or Locales: The nearest small town is about 10-15 minutes. The town was was not within walking distance. Tips or Restaurants: Definitely use Yelp to help find the local restaurants. There are many incredible restaurants within 20-45 minutes away. Directions: We used the cars GPS. After arriving at the villa we saved the location so it was easier to get there. Check In Out: Everything went very smoothly.
                                                                                                  • Review Submitted: 14-Sep-2016
                                                                                                  • Date of Stay: Aug 2016

                                                                                                  Beautiful setting, well managed by a very attentive owner. Great time!

                                                                                                  5 of 5
                                                                                                  This was a great family vacation for us. The view was incomparable.The villa is comfortable and spacious. The owner was very concerned about our vacation experience and we celebrated some very special occasions. Though rural the surrounding area provides a host of opportunities for touring and relaxation. This is a real find in private vacation rentals.
                                                                                                  • Review Submitted: 08-Aug-2016
                                                                                                  • Date of Stay: Jul 2016

                                                                                                  Excellent location, lovely hosts

                                                                                                  5 of 5
                                                                                                  Lovely villa in an excellent location. Easy access to Florence, Siena, San Gimignano and many other lovely towns. TIziana and her husband mad every effort to ensure we had a lovely vacation. Our daughters particularly loved the superb home made breakfasts!
                                                                                                  • Review Submitted: 28-Jun-2016
                                                                                                  • Date of Stay: May 2016