HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled Family icon

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.

Cancel Clear Filters Apply Filters
More Filters

Price Per Night

£ £

Bedrooms

Bathrooms

Payment Options

Property Type

Popular Searches

Facilities

Location Type

Local Area

Property Details

Clear Filters
Use filters to narrow your search results!
Viewed 26 times in the last 48 hours
  • 3 BR House
  • 1 BA
  • 861 sq. ft.
Excellent! 4.6/5
(11 reviews)
avg/night
11
  • 5 BR Farmhouse
  • 3 BA
avg/night
4
  • 6 BR Villa
  • 6 BA
Exceptional! 5/5
(5 reviews)
avg/night
5
Viewed 5 times in the last 48 hours
  • 7 BR Villa
  • 5 BA
  • Separate Toilet
  • 2260 sq. ft.
Exceptional! 5/5
(5 reviews)
avg/night
5
  • 1 BR House
  • 1 BA
  • 452 sq. ft.
avg/night
  • 2 BR Apartment
  • 1 BA
  • 807 sq. ft.
avg/night
  • 2 BR House
  • 1 BA
  • 688 sq. ft.
avg/night
  • 2 BR Apartment
  • 1 BA
  • 645 sq. ft.
avg/night
  • 1 BR Apartment
  • 1 BA
  • 592 sq. ft.
avg/night
Premier Partner
  • 2 BR Villa
  • 2 BA
  • 1184 sq. ft.
avg/night
  • 2 BR House
  • 1 BA
  • 807 sq. ft.
avg/night
2
  • 2 BR House
  • 1 BA
avg/night
Premier Partner
  • 2 BR Apartment
  • 2 BA
  • 753 sq. ft.
avg/night
Premier Partner
Viewed 31 times in the last 48 hours
  • 2 BR Apartment
  • 1 BA
  • 957 sq. ft.
avg/night
Viewed 54 times in the last 48 hours
  • 1 BR Apartment
  • 1 BA
  • 495 sq. ft.
Wonderful! 4.8/5
(18 reviews)
avg/night
Premier Partner
18
Viewed 28 times in the last 48 hours
  • 3 BR House
  • 2 BA
avg/night
Premier Partner
Viewed 26 times in the last 48 hours
  • 2 BR Apartment
  • 2 BA
  • 645 sq. ft.
avg/night
Premier Partner
4
Viewed 19 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
Viewed 5 times in the last 48 hours
  • 2 BR Apartment
  • 2 BA
  • 968 sq. ft.
Exceptional! 5/5
(7 reviews)
avg/night
7
Viewed 13 times in the last 48 hours
  • 1 BR Apartment
  • 1 BA
  • 538 sq. ft.
Excellent! 4.7/5
(35 reviews)
avg/night
35
  • 2 BR House
  • 1 BA
  • 968 sq. ft.
Wonderful! 4.9/5
(14 reviews)
avg/night
14
Viewed 8 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
  • 2152 sq. ft.
Wonderful! 4.9/5
(17 reviews)
avg/night
17
Viewed 5 times in the last 48 hours
  • 1 BR Apartment
  • 1 BA
  • 592 sq. ft.
Excellent! 4.7/5
(13 reviews)
avg/night
13
Viewed 5 times in the last 48 hours
  • 3 BR Apartment
  • 2 BA
  • 1022 sq. ft.
Wonderful! 4.9/5
(25 reviews)
avg/night
25
Viewed 8 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
  • 2152 sq. ft.
Wonderful! 4.8/5
(12 reviews)
avg/night
12
Viewed 20 times in the last 48 hours
  • 1 BR Apartment
  • 2 BA
  • 688 sq. ft.
Wonderful! 4.9/5
(12 reviews)
avg/night
12
  • 1 BR Apartment
  • 1 BA
  • 430 sq. ft.
Wonderful! 4.8/5
(20 reviews)
avg/night
20
Viewed 17 times in the last 48 hours
  • 4 BR House
  • 2 BA
  • Separate Toilet
  • 2690 sq. ft.
Excellent! 4.7/5
(12 reviews)
avg/night
12
Viewed 12 times in the last 48 hours
  • 4 BR Villa
  • 4 BA
  • 2152 sq. ft.
Exceptional! 5/5
(19 reviews)
avg/night
19
Viewed 32 times in the last 48 hours
  • 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 Barn
  • 2 BA
  • 764 sq. ft.
Wonderful! 4.9/5
(19 reviews)
avg/night
19
Viewed 13 times in the last 48 hours
  • 2 BR Apartment
  • 1 BA
  • 645 sq. ft.
Excellent! 4.6/5
(8 reviews)
avg/night
8
Viewed 5 times in the last 48 hours
  • 3 BR Chateau / Country House
  • 2 BA
  • 1345 sq. ft.
Wonderful! 4.9/5
(8 reviews)
avg/night
8
Viewed 25 times in the last 48 hours
  • 1 BR Cottage
  • 1 BA
  • 409 sq. ft.
Excellent! 4.7/5
(7 reviews)
avg/night
7
Viewed 16 times in the last 48 hours
  • 2 BR House
  • 1 BA
  • 1076 sq. ft.
Wonderful! 4.9/5
(73 reviews)
avg/night
73
Viewed 23 times in the last 48 hours
  • 1 BR House
  • 1 BA
  • 1076 sq. ft.
Wonderful! 4.9/5
(10 reviews)
avg/night
10
Viewed 11 times in the last 48 hours
  • 2 BR Apartment
  • 1 BA
  • 645 sq. ft.
Exceptional! 5/5
(6 reviews)
avg/night
Premier Partner
6
  • 2 BR Chateau / Country House
  • 1 BA
  • 861 sq. ft.
Exceptional! 5/5
(8 reviews)
avg/night
8
Viewed 16 times in the last 48 hours
  • 2 BR Cottage
  • 1 BA
  • 861 sq. ft.
Exceptional! 5/5
(5 reviews)
avg/night
5
  • 1 BR Apartment
  • 1 BA
  • Separate Toilet
  • 645 sq. ft.
Exceptional! 5/5
(25 reviews)
avg/night
25
Viewed 15 times in the last 48 hours
  • 3 BR Apartment
  • 2 BA
  • 968 sq. ft.
avg/night
Viewed 23 times in the last 48 hours
  • 2 BR Chateau / Country House
  • 2 BA
  • 861 sq. ft.
Exceptional! 5/5
(20 reviews)
avg/night
Premier Partner
20
  • 3 BR Cottage
  • 2 BA
  • Separate Toilet
  • 1614 sq. ft.
Wonderful! 4.8/5
(13 reviews)
avg/night
13
  • 2 BR Apartment
  • 1 BA
  • 645 sq. ft.
Excellent! 4.5/5
(8 reviews)
avg/night
8
  • 3 BR Villa
  • 2 BA
  • 1937 sq. ft.
Wonderful! 4.9/5
(18 reviews)
avg/night
18
Viewed 14 times in the last 48 hours
  • 5 BR Villa
  • 3 BA
  • 2475 sq. ft.
avg/night
3
Viewed 21 times in the last 48 hours
  • 2 BR Cottage
  • 1 BA
  • 861 sq. ft.
avg/night
3
Viewed 8 times in the last 48 hours
  • 3 BR Apartment
  • 2 BA
  • 1022 sq. ft.
avg/night
2
Viewed 17 times in the last 48 hours
  • 2 BR Apartment
  • 2 BA
  • 1130 sq. ft.
Exceptional! 5/5
(24 reviews)
avg/night
24
Viewed 13 times in the last 48 hours
  • 4 BR Villa
  • 4 BA
  • 1614 sq. ft.
Exceptional! 5/5
(7 reviews)
avg/night
7

Castelfiorentino Holiday Apartments & Villas (300+)

 

Recent Reviews

Review for stay from 01 July 2017 to 01 July 2017

5 of 5
Sehr schön war es in dieser grossen Villa. Wir sind sehr nett empfangen worden und haben Geheimtipps für kleine Restaurants bekommen die ausgesprochen gut waren. Die Gegend ist wunderschön und Haus und Garten gut gepflegt. Wir haben uns sehr wohl gefühlt und empfehlen die Betreuung durch Posarellivillas gerne weiter.
  • Review Submitted: Mar 30, 2018
  • Date of Stay: Jul 2017

Lovely stay and very welcoming

4 of 5
This was a beautiful property and a lovely place to stay within close distance to the big towns and some lovely restaurants nearby.
  • Review Submitted: Oct 25, 2017
  • Date of Stay: Oct 2017