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Castelfiorentino

Excellent 526 Reviews 4.8/5

Searching for the perfect villa in Castelfiorentino? Look no further! Our exclusive selection of villas offers the ideal blend of comfort, and authenticity, making your escape to Tuscany truly unforgettable. If you rent one of our Castelfiorentino villas, you will have the entire property to yourself and will not have to worry about other guests.. Find the right villa for your vacation in Italy now.

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Results 1 - 15 of 32
  • 17
  • 9
  • 6
  • 300 m2
  • Charming Tuscan country property
  • Common area with also sauna and gym
  • Perfect for organising events
from 547 $per night
  • 4
  • 2
  • 1
  • 50 m2
  • Beautiful detached house in Chianti
  • Large terrace with swimming pool
  • Basic services within walking distance
from 107 $per night
  • 6
  • 3
  • 2
  • 240 m2
  • Detached villa in the countryside
  • Hilly and panoramic position
  • Close to San Gimignano and the Via Francigena
from 278 $per night
  • 12
  • 6
  • 6
  • 350 m2
  • Luxury villa in Tuscany with heatable pool
  • Panoramic views of San Gimignano
  • Indoor spa with jacuzzi, sauna e steam room
from 2026 $per night
  • 8
  • 4
  • 3
  • 230 m2
  • Historical villa of the Buonaparte family
  • Hilly and panoramic position
  • Large park with olive grove
from 614 $per night
  • 6
  • 3
  • 3
  • 200 m2
  • Large villa with luxury furnishings
  • Enchanting view of the Tuscan countryside
  • 3 bedrooms, each with private bathroom
from 285 $per night
  • 4
  • 2
  • 1
  • 65 m2
  • Pretty house with private pool
  • Completely surrounded by greenery
  • 6 km from the medieval village of Certaldo
from 139 $per night
  • 10
  • 5
  • 3
  • 310 m2
  • Stone farmhouse in Chianti
  • Large garden with panoramic view
  • Quiet and strategic position
from 516 $per night
Someone else is currently looking at this property!
  • 6
  • 3
  • 3
  • 115 m2
  • Characteristic Tuscan country house
  • Large garden with relaxation areas
  • Good location to visit Chianti
from 236 $per night
  • 8
  • 4
  • 3
  • 130 m2
  • Beautiful property in a panoramic position
  • Large terraced garden with private pool
  • Basic services within walking distance
from 181 $per night
  • 10
  • 5
  • 4
  • 350 m2
  • Traditional Tuscan country house
  • Large and well-kept garden
  • Incredible view of the Chianti hills
from 336 $per night
  • 8
  • 4
  • 2
  • 350 m2
  • Large property on a hill
  • Pool with panoramic views of the Tuscany countryside
  • Tennis and five-a-side soccer pitch
from 215 $per night
  • 12
  • 6
  • 6
  • 270 m2
  • Beautiful villa in the Tuscan countryside
  • 6 bedrooms, each with a private bathroom
  • Magnificent panoramic views
from 1008 $per night
  • 18
  • 8
  • 8
  • 345 m2
  • Large Tuscan farmhouse in Chianti
  • Wine and oil production (cellar)
  • 8 bedrooms, each with private bathroom
from 857 $per night
  • 15
  • 8
  • 7
  • 400 m2
  • Renovated villa of 17th century
  • Panoramic position in the Chianti area
  • Suitable for events
from 365 $per night

Can't find your perfect villa here? Explore our holiday homes in Castelfiorentino with guest reviews to see what our previous guests have to say about their stay. Gain insights from real experiences and choose your ideal accommodation with confidence. You can also discover our exclusive collection of luxury villas in Castelfiorentino, designed for those seeking elegance and comfort. If you're looking for a last-minute escape, browse our last-minute villa offers in Castelfiorentino for exclusive deals on premium stays.

Still searching? Expand your options with our selection of villas all over Italy, handpicked for their unique charm, prime locations, and exceptional amenities.

Why Choose a Villa in Castelfiorentino with a Private Pool

Imagine waking up to the gentle rustle of olive trees and the golden glow of the Italian sun – all from the comfort of your own private villa. Choosing a villa in Castelfiorentino isn’t just about where to stay – it’s about how you experience Italy. With exclusive access to a private pool, you can unwind in total privacy, far from the bustle of daily life. Our handpicked collection of Castelfiorentino villas caters to every type of traveller – from intimate retreats for couples to spacious homes for families or groups. Each property is thoughtfully equipped with a full kitchen, giving you the freedom to savour local ingredients and feel truly at home. These villas offer more than just relaxation. They are the perfect base for wine tasting tours, scenic countryside walks, and exploring charming hilltop villages. And with a range of affordable options, your dream Italian escape can be both indulgent and within reach. Choose a villa in Castelfiorentino – where comfort, culture, and calm meet under the Italian sun.

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Guido Posarelli
Founder of Posarelli Villas, hand-picking all the vacation rentals in Italy we offer on our website.
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