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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 19 times in the last 48 hours
  • 1 BR Apartment
  • 1 BA
  • 484 sq. ft.
Exceptional! 5/5
(9 reviews)
avg/night
Premier Partner
9
  • 1 BR Apartment
  • 1 BA
  • Separate Toilet
  • 645 sq. ft.
Exceptional! 5/5
(25 reviews)
avg/night
Premier Partner
25
Viewed 32 times in the last 48 hours
  • 1 BR Apartment
  • 2 BA
  • 1022 sq. ft.
avg/night
2
Viewed 15 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
  • 2152 sq. ft.
Wonderful! 4.8/5
(13 reviews)
avg/night
13
  • 2 BR House
  • 2 BA
  • 1022 sq. ft.
Wonderful! 4.9/5
(17 reviews)
avg/night
17
  • 2 BR Apartment
  • 1 BA
  • 1453 sq. ft.
Exceptional! 5/5
(4 reviews)
avg/night
Premier Partner
4
Viewed 24 times in the last 48 hours
  • 8 BR Villa
  • 7 BA
  • Separate Toilet
  • 8600 sq ft
Exceptional! 5/5
(10 reviews)
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10
  • 2 BR Apartment
  • 2 BA
  • 1130 sq. ft.
Exceptional! 5/5
(24 reviews)
avg/night
Premier Partner
24
  • 2 BR Farmhouse
  • 1 BA
  • 699 sq. ft.
Wonderful! 4.8/5
(6 reviews)
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6
Viewed 14 times in the last 48 hours
  • 1 BR Apartment
  • 1 BA
  • 602 sq. ft.
Wonderful! 4.8/5
(41 reviews)
avg/night
Premier Partner
41
Viewed 8 times in the last 48 hours
  • 3 BR Chateau / Country House
  • 2 BA
  • 1614 sq. ft.
Wonderful! 4.9/5
(32 reviews)
avg/night
Premier Partner
32
  • 3 BR Chateau / Country House
  • 2 BA
  • 1345 sq. ft.
Wonderful! 4.9/5
(8 reviews)
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8
  • 5 BR Farmhouse
  • 3 BA
avg/night
4
Viewed 11 times in the last 48 hours
  • 8 BR Villa
  • 7 BA
Excellent! 4.5/5
(44 reviews)
avg/night
44
  • 3 BR Apartment
  • 2 BA
  • 1022 sq. ft.
Wonderful! 4.8/5
(10 reviews)
avg/night
Premier Partner
10
  • 2 BR House
  • 1 BA
  • 645 sq. ft.
avg/night
1
Viewed 5 times in the last 48 hours
  • 2 BR Chateau / Country House
  • 1 BA
  • 861 sq. ft.
Exceptional! 5/5
(8 reviews)
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8
Viewed 10 times in the last 48 hours
  • 1 BR Chateau / Country House
  • 2 BA
  • 957 sq. ft.
Wonderful! 4.9/5
(14 reviews)
avg/night
Premier Partner
14
  • 2 BR Farmhouse
  • 1 BA
  • 753 sq. ft.
Wonderful! 4.8/5
(20 reviews)
avg/night
20
  • 2 BR Chateau / Country House
  • 2 BA
  • 861 sq. ft.
Exceptional! 5/5
(23 reviews)
avg/night
Premier Partner
23
Viewed 10 times in the last 48 hours
  • 6 BR Villa
  • 5 BA
  • Separate Toilet
  • 4305 sq. ft.
avg/night
3
  • 7 BR Villa
  • 5 BA
  • Separate Toilet
  • 2260 sq. ft.
Exceptional! 5/5
(5 reviews)
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5
Viewed 5 times in the last 48 hours
  • 2 BR Apartment
  • 1 BA
  • 861 sq. ft.
Excellent! 4.6/5
(7 reviews)
avg/night
7
  • 9 BR Villa
  • 10 BA
  • 5166 sq. ft.
avg/night
4
Viewed 18 times in the last 48 hours
  • 2 BR Cottage
  • 1 BA
  • 861 sq. ft.
Exceptional! 5/5
(6 reviews)
avg/night
6
Viewed 5 times in the last 48 hours
  • 3 BR Villa
  • 3 BA
  • 1291 sq. ft.
Exceptional! 5/5
(43 reviews)
avg/night
43
Viewed 9 times in the last 48 hours
  • 2 BR House
  • 1 BA
  • 968 sq. ft.
Wonderful! 4.9/5
(7 reviews)
avg/night
7
Viewed 17 times in the last 48 hours
  • 3 BR House
  • 1 BA
  • 861 sq. ft.
Excellent! 4.6/5
(11 reviews)
avg/night
11
Viewed 15 times in the last 48 hours
  • 2 BR Villa
  • 2 BA
  • 1076 sq. ft.
avg/night
2
  • 6 BR Villa
  • 6 BA
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2
Viewed 8 times in the last 48 hours
  • 2 BR Apartment
  • 2 BA
  • 1076 sq. ft.
Excellent! 4.7/5
(14 reviews)
avg/night
14
  • 2 BR Apartment
  • 1 BA
  • 645 sq. ft.
Excellent! 4.7/5
(9 reviews)
avg/night
9
  • 2 BR Apartment
  • 1 BA
  • 1237 sq. ft.
avg/night
1
Viewed 5 times in the last 48 hours
  • 1 BR Apartment
  • 1 BA
  • Separate Toilet
  • 538 sq. ft.
Exceptional! 5/5
(50 reviews)
avg/night
50
  • 1 BR Apartment
  • 1 BA
  • 592 sq. ft.
Excellent! 4.7/5
(13 reviews)
avg/night
13
Viewed 20 times in the last 48 hours
  • 11 BR House
  • 5 BA
  • 2960 sq. ft.
avg/night
Premier Partner
Viewed 6 times in the last 48 hours
  • 3 BR Apartment
  • 3 BA
avg/night
1
  • 2 BR Chateau / Country House
  • 1 BA
  • 947 sq. ft.
avg/night
4
  • 2 BR Apartment
  • 2 BA
avg/night
4
  • 1 BR Apartment
  • 1 BA
  • 516 sq. ft.
avg/night
2
  • 3 BR House
  • 3 BA
avg/night
Premier Partner
2
  • 3 BR Farmhouse
  • 2 BA
  • 1377 sq. ft.
Wonderful! 4.9/5
(7 reviews)
avg/night
7
  • 2 BR Apartment
  • 3 BA
  • 1119 sq. ft.
Very Good! 4.2/5
(6 reviews)
avg/night
6
Viewed 5 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
  • Separate Toilet
  • 3767 sq. ft.
Excellent! 4.5/5
(6 reviews)
avg/night
6
  • 2 BR Villa
  • 3 BA
  • 1528 sq. ft.
Wonderful! 4.9/5
(13 reviews)
avg/night
13
Viewed 8 times in the last 48 hours
  • 2 BR Apartment
  • 1 BA
  • 1076 sq. ft.
Excellent! 4.6/5
(15 reviews)
avg/night
15
  • 2 BR Apartment
  • 1 BA
View details for price
  • 3 BR Villa
  • 2 BA
  • 2152 sq. ft.
Wonderful! 4.9/5
(17 reviews)
avg/night
17
  • 3 BR Villa
  • 2 BA
  • 1937 sq. ft.
Wonderful! 4.9/5
(18 reviews)
avg/night
18
  • 8 BR Villa
  • 7 BA
  • Separate Toilet
  • 3229 sq. ft.
Wonderful! 4.9/5
(18 reviews)
avg/night
Premier Partner
18

Castelfiorentino Holiday Apartments & Villas (300+)

 

Recent Reviews

Lovely old farm house villa surrounded by wine and olives. Not cheap but unique.

5 of 5
We lived for one week in Il Borghettino and really enjoyed our stay. It`s right beneath San Gimignano with a great view over the hills of Tuscany, only 10 minutes walking time from San Gimignano center. The only little manco: it was not easy to find first. The buildings can only be reached by a small, narrow farm track, starting at the right hand side of the main gate, following the city walls and then leading in the vineyards. But on the other hand, this "isolation" prevents you from the tourist hords, streaming through the medieval streets right upon the hill. Once arrived, it is really a beautiful location. The old farmhouse villa`s interieur has a rustic landlord style. The Pool is around the corner of the former stables where the owner family lives today. Very nice people. We had a very good neighborhood for the week. Il Borghettino was a good base for day trips to Florence, Siena, Volterra and the Chianti region (all reachable in about 1 hour by car). Mrs. Falchini helped us a lot with really good tips how to reach the cities, where to park and she knew some good insider spots like a local cheese manufactory in Podgibonsi. Thanks again! The rent is not cheap but worth the money. We would come back and really can recommend this lovely place.
  • Review Submitted: Jun 09, 2018
  • Date of Stay: May 2018

Spacious and convenient

4 of 5
Spacious, well equipped property in a convenient location for many Tuscan sights. The host were friendly and responsive. The property could be improved with better water pressure so that more than one person can shower/or use taps at the same time. Smaller improvements would be a microwave and some leaflets/books/maps on places of local interest. The neighbouring busy and somewhat noisy road would be a disadvantage in good weather, and this is difficult to identify in advance from the details supplied. The property was spotlessly clean and the beds were large and comfortable.
  • Review Submitted: May 25, 2018
  • Date of Stay: May 2018