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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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Viewed 22 times in the last 48 hours
  • 1 BR Apartment
  • 1 BA
  • 484 sq. ft.
Exceptional! 5/5
(10 reviews)
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Premier Partner
10
  • 2 BR Apartment
  • 1 BA
  • 1345 sq. ft.
Wonderful! 4.8/5
(4 reviews)
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Premier Partner
4
  • 2 BR House
  • 2 BA
  • 1022 sq. ft.
Wonderful! 4.9/5
(18 reviews)
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18
  • 1 BR Apartment
  • 1 BA
  • 430 sq. ft.
Wonderful! 4.8/5
(24 reviews)
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24
  • 1 BR Apartment
  • 1 BA
  • Separate Toilet
  • 645 sq. ft.
Exceptional! 5/5
(26 reviews)
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Premier Partner
26
  • 1 BR Apartment
  • 1 BA
  • 592 sq. ft.
Wonderful! 4.8/5
(9 reviews)
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9
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  • 1 BA
  • 699 sq. ft.
Wonderful! 4.8/5
(6 reviews)
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6
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  • 893 sq. ft.
Excellent! 4.6/5
(18 reviews)
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Premier Partner
18
  • 1 BR Apartment
  • 1 BA
  • 430 sq. ft.
Exceptional! 5/5
(51 reviews)
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51
Viewed 5 times in the last 48 hours
  • 2 BR House
  • 1 BA
  • 1076 sq. ft.
Wonderful! 4.9/5
(77 reviews)
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77
  • 2 BR Apartment
  • 2 BA
  • 645 sq. ft.
Excellent! 4.3/5
(6 reviews)
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Premier Partner
6
  • 2 BR Apartment
  • 1 BA
  • 1453 sq. ft.
Wonderful! 4.8/5
(5 reviews)
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Premier Partner
5
  • 1 BR Apartment
  • 1 BA
  • 602 sq. ft.
Wonderful! 4.8/5
(42 reviews)
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Premier Partner
42
Viewed 5 times in the last 48 hours
  • 2 BR Apartment
  • 2 BA
  • 882 sq. ft.
Exceptional! 5/5
(24 reviews)
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24
  • 2 BR Apartment
  • 1 BA
  • 516 sq. ft.
Wonderful! 4.9/5
(30 reviews)
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30
  • 1 BR Apartment
  • 2 BA
  • 1022 sq. ft.
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4
  • 1 BR Apartment
  • 1 BA
  • 538 sq. ft.
Exceptional! 5/5
(25 reviews)
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Premier Partner
25
  • 1 BR House
  • 1 BA
  • 1076 sq. ft.
Wonderful! 4.9/5
(10 reviews)
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10
  • 2 BR House
  • 1 BA
  • 645 sq. ft.
Wonderful! 4.8/5
(8 reviews)
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8
Viewed 6 times in the last 48 hours
  • 6 BR Villa
  • 5 BA
  • Separate Toilet
  • 3875 sq. ft.
Wonderful! 4.8/5
(8 reviews)
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8
  • 1 BR Apartment
  • 1 BA
  • 495 sq. ft.
Wonderful! 4.9/5
(20 reviews)
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Premier Partner
20
  • 2 BR Apartment
  • 1 BA
  • 645 sq. ft.
Wonderful! 4.8/5
(26 reviews)
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26
  • 2 BR Chateau / Country House
  • 1 BA
  • 861 sq. ft.
Exceptional! 5/5
(8 reviews)
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8
Viewed 7 times in the last 48 hours
  • 2 BR Barn
  • 2 BA
  • 807 sq. ft.
Wonderful! 4.8/5
(14 reviews)
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Premier Partner
14
  • 3 BR Chateau / Country House
  • 2 BA
  • 1345 sq. ft.
Wonderful! 4.9/5
(8 reviews)
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8
  • 5 BR Chateau / Country House
  • 2 BA
  • 2152 sq. ft.
Wonderful! 4.9/5
(21 reviews)
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21
  • 2 BR House
  • 1 BA
  • 968 sq. ft.
Wonderful! 4.9/5
(16 reviews)
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16
  • 3 BR Apartment
  • 2 BA
  • 1022 sq. ft.
Wonderful! 4.9/5
(29 reviews)
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29
Viewed 11 times in the last 48 hours
  • 2 BR House
  • 1 BA
  • 645 sq. ft.
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1
  • 2 BR Farmhouse
  • 1 BA
  • 753 sq. ft.
Wonderful! 4.8/5
(20 reviews)
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20
  • 1 BR Chateau / Country House
  • 1 BA
  • 473 sq. ft.
Exceptional! 5/5
(27 reviews)
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Premier Partner
27
Viewed 7 times in the last 48 hours
  • 1 BR Apartment
  • 1 BA
  • 592 sq. ft.
Excellent! 4.7/5
(14 reviews)
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14
Viewed 673 times in the last 48 hours
  • 3 BR Castle
  • 3 BA
  • 1291 sq. ft.
Wonderful! 4.9/5
(10 reviews)
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10
  • 1 BR Barn
  • 1 BA
  • 699 sq. ft.
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2
Viewed 16 times in the last 48 hours
  • 2 BR Apartment
  • 1 BA
  • 1076 sq. ft.
Excellent! 4.6/5
(15 reviews)
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15
  • 2 BR Apartment
  • 1 BA
  • 807 sq. ft.
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Premier Partner
  • 3 BR Apartment
  • 2 BA
  • 1022 sq. ft.
Wonderful! 4.8/5
(10 reviews)
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Premier Partner
10
Viewed 18 times in the last 48 hours
  • 2 BR Apartment
  • 2 BA
  • 807 sq. ft.
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4
  • 2 BR Barn
  • 2 BA
  • 764 sq. ft.
Exceptional! 5/5
(21 reviews)
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21
  • 2 BR Apartment
  • 2 BA
  • 1130 sq. ft.
Exceptional! 5/5
(24 reviews)
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Premier Partner
24
  • 3 BR Villa
  • 3 BA
  • 2475 sq. ft.
Excellent! 4.7/5
(15 reviews)
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Premier Partner
15
  • 2 BR Apartment
  • 1 BA
  • 645 sq. ft.
Excellent! 4.5/5
(8 reviews)
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8
  • 1 BR Chateau / Country House
  • 1 BA
  • 645 sq. ft.
Exceptional! 5/5
(33 reviews)
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33
  • 2 BR Chateau / Country House
  • 2 BA
  • 861 sq. ft.
Exceptional! 5/5
(23 reviews)
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Premier Partner
23
  • 3 BR Apartment
  • 1 BA
  • 1022 sq. ft.
Wonderful! 4.8/5
(4 reviews)
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Premier Partner
4
  • 2 BR Apartment
  • 1 BA
  • 807 sq. ft.
Exceptional! 5/5
(7 reviews)
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7
  • 1 BR Apartment
  • 1 BA
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  • 1 BR Apartment
  • 1 BA
  • Separate Toilet
  • 538 sq. ft.
Exceptional! 5/5
(50 reviews)
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50
  • 4 BR House
  • 2 BA
  • 1937 sq. ft.
Excellent! 4.7/5
(20 reviews)
avg/night
20
  • 2 BR Apartment
  • 1 BA
  • 645 sq. ft.
Exceptional! 5/5
(7 reviews)
avg/night
Premier Partner
7

Castelfiorentino Holiday Apartments & Villas (300+)

 

Recent Reviews

Holiday at Apt. Corbezzolo, Villa Santa Maria

5 of 5
We enjoyed our two week stay at Apt Corbezzolo. The apartment was clean and cool, and had everything we needed. We were made very welcome by Maurizio and his wife and also by Giorgio. We enjoyed making use of the pool, although we are not really swimmers!. We loved the beautiful views of the Tuscan countryside, and we enjoyed our trips to Florence (by train), Siena, Pisa, Lucca, Volterra, and some of the Chianti villages. We hope to return to Italy some day.
  • Review Submitted: Jul 13, 2018
  • Date of Stay: Jun 2018

Beautiful house and setting, great location

5 of 5
We had an amazing stay, we received a very warm welcome from Sandra and Gianni, who were very helpful showing us around. The pool area has an amazing view and wasn’t too busy. The location was great for visiting the nearby towns and Sienna and Florence, we will definitely go back. Thank you for such a lovely stay.
  • Review Submitted: Jul 01, 2018
  • Date of Stay: Jun 2018