Castiglion Fiorentino Rentals

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1,586 Houses

Price per night from

$645

4 bedroom, Restored Farmhouse, Modern Amenities

Castiglion Fiorentino cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Some Fantastic Views, Welcoming Hosts and a Great Place for our” Driving up through the valley from the local town of Castiglion, you realize how lucky the locals are to live in a place as rich in natural beauty as here. We spent two wonderful weeks here enjoying our lovely cottage which was perfect for the 4 of us. Very rustic and a real taste of Tuscany. The large pool is a quiet haven, surrounded by well maintained grass and perfect to sit, swim, relax and admire the views - and sunsets. Our hosts, Massimo and Eva were very helpful and welcoming. It was they and Massimo's mother who restored the village and, kept all the little details alive. Certainly, nothing was too much trouble although it is the other end of the valley, it was easy enough to go off on day trips. We used the rail station in Castiglion for a trip to Florence and arezzo, but the rest of the time we enjoyed some of the country drives suggested by Eva - including a visit to avignonesi winery over in montepulcano . A good family restaurant in the valley along with others in the town. We (I) even found a small (9 hole) golf course - about 40 minutes from here a long way to come, but we would love to come back one day.

Price per night from

$169

Agriturismo Le Maceie Tuscan Vacation Rental

Castiglion Fiorentino house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$82

Holiday House Traquandi

Castiglion Fiorentino house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$123

Villa Michelangelo

Brolio villa

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 18

Price per night from

$640

Villa MIchelangelo promoted by WeekHomes com

Brolio house

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 18

Price per night from

$741

Villa Angelisa D

Castiglion Fiorentino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 1 hour 35 minutes

Price per night from

$169

Villa Angelisa C

Castiglion Fiorentino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 35 minutes

Price per night from

$169

Villa Angelisa A

Castiglion Fiorentino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 35 minutes

Price per night from

$142

Villa Angelisa B

Castiglion Fiorentino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 35 minutes

Price per night from

$142

House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$125

La casa del Rigattiere - Close to Cortona WiFi A/C

Castiglion Fiorentino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$113

Farm House La Fenice

Castiglion Fiorentino townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$438

Price per night from

$645

VILLA CECILIA

Castiglion Fiorentino farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$235

Holiday House ' The House of the Sun '

Castiglion Fiorentino villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$100

Dolci Colline village hut

Castiglion Fiorentino apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 8 minutes

Price per night from

$132

CASALE IL TRECENTO

Castiglion Fiorentino farmhouse

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$376

Borgo Rolling Hills Lodge

Castiglion Fiorentino apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 8 minutes

Price per night from

$175

Borgo Sweets Cypress Hills

Castiglion Fiorentino apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 8 minutes

Price per night from

$150

Borgo Sweets Barn Hills

Castiglion Fiorentino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 8 minutes

Price per night from

$250

Superior apartment with use of 2 hours of private spa for the couple only.

Castiglion Fiorentino apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 8 minutes

Price per night from

$307

VILLA DEGLI OLIVI

Castiglion Fiorentino villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Price per night from

$588

NEW!!! Fenice, Tuscan Villa, Private pool, stunning scenery, WIFI, chef option

Castiglion Fiorentino villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$394

My Tuscan Getaway - Free WiFi

Montecchio Vesponi studio

  • Studio
  • 1 bathroom
  • sleeps 3

Price per night from

Inquire for Rates

FLOWER HILL 6

Castiglion Fiorentino villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$290

Luxury Villa with indoor and outdoor swimming pool, Hot Tub and Sauna

Brolio villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 18

Responds fast! avg. 3 hours 37 minutes

Price per night from

$893

VILLA POZZONOVO

Castiglion Fiorentino villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$257

Villa in Castiglion Fiorentino

Castiglion Fiorentino villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$381

Borgo Orzale

Pieve di Chio house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$125

Borgo Sant'Andrea al Pozzo

Castiglion Fiorentino apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$100

BORGO CAPRILE

Pieve di Chio villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

Price per night from

$225

The Garden of Jars

Pieve di Chio villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$162

Villa Brolio Quinto,exclusive use,secluded with large park and pool.

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

Price per night from

$501

CASOLARE IL CONDOTTIERO

Montecchio Vesponi house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Price per night from

Inquire for Rates

Villa Luisella

Castiglion Fiorentino villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Responds fast! avg. 2 hours 30 minutes

Price per night from

$288

BROLIO GALLERY

Brolio villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$232

POZZONOVO - THE CHERRY

Castiglion Fiorentino apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$89

Viewing 38 of 1,586
rentals in Castiglion Fiorentino

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About Castiglion Fiorentino

Millions of people come to visit Tuscany every year, but a stay in the quiet village of Castiglion Fiorentino, where beautiful countryside and mountains surround you everywhere you turn, is a great way to get the Tuscan experience without enduring throngs of visitors. You'll find most of the top restaurants in town and trendy boutique shopping along Via Nazionale, the main street in Castiglion Fiorentino. Several stunning old buildings can also be found on the street known as Via Vecchie Ciminiere.

Here are some of the other must-see attractions and activities in the area:

  • Castello di Fiorentina: This nearby village is surrounded by great architecture and offers picturesque views of the countryside.
  • Try the Cuisine: The food in this part of Tuscany is simple, yet full of flavor. Try the Panzanella, a delicate ravioli made in a rich truffle sauce.
  • Apennine Mountains: These mountains offer walking and hiking trails that take you past the olive trees that the area is famous for.
  • Church of Saint Angelo: The most popular church in Castiglion Fiorentino dates back to the 12th century and is one of the many ancient structures in the middle of the historical center.
  • Play Golf: Several golf courses for all levels of players have sprung up in recent years throughout the area. Casentino Golf Club is the most popular amongst the locals.

It doesn't matter when you decide to Castiglion Fiorentino because the Fiera Antiquaria is one of the many events that take place year-round. Held on the first Sunday of every month, people from all over Italy come to look at clothing and locally made food and crafts from over 500 vendors. Some of the other major events in the area include the horse race in June known as the Palio dei Rioni and Giostra del Sacarino an equestrian competition in nearby Arezzo that has been held every June for over 400 years.

The Tuscan region is one of the most popular vacation spots in the world, which means that there is no shortage of vacation rentals available year-round. Book a condo that overlooks the vineyards and beautiful countryside, or rent a property downtown near the restaurants and shopping.

A vacation to Castiglion Fiorentino wouldn't be complete without visiting some of the nearby cities and towns that make this area so popular. If you have some extra time to explore, plan a day trip to the world-renowned art on display in the town of Arezzo or the canals and historical attractions of Florence, both which can be reached within 30 minutes by car.

Top Destination reviews

4 bedroom, Restored Farmhouse, Modern Amenities
Lovely time at Castiglion Fiorentino

We stayed in the ground floor apartment, which was very clean and tastefully decorated. There was a swimming pool, which we had virtually to ourselves, but would have been shared by others in the adjacent barn conversion. There was lots of wildlife in the nearby field (tiny ghekos and lizzards on the patio, wild boar, etc) to view from our balcony, overlooking the field. This provided endless entertainment for our two boys (7 and 8 years old). We will probably return next year. The only draw-back was the location was not so easy to find, so check-in was not straight-forward, bit of an adventure.see more
Villa la Foce: breathtaking panoramic view
Perfection

Villa la Foce is amazing! And I am very fussy! This home is immaculate and the gardens and pool area are superb. We arrived via the newer part of the village and were initially concerned that it did not have the charm we were after... A drive through the old village and up the hill put our concerns to rest! The view is breathtaking and sipping prosecco while cooking homemade pizza in the wood fired oven while the children swam and laughed in the balmy twilight will never be forgotten! We spotted wild boar in the olive grove below the house, pheasant, badgers, squirrels and even a scorpion scurried out of the pizza oven when lit! All a novelty for this australian family! The restaurant at the top of the hill "la Foce" was recommended by our helpful key holder Enrico... Fabulous food - try the Chianina Bistecca and wonderful service. The famous Palio was on in the village during our stay and was wildly entertaining. We were well positioned to explore Tuscany and loved being out of the village but not too far away. We would return in a heartbeat and thank both the owners for sharing such a beautiful property and terretrushe for the excellent service! We hope to return one day. Bellisimo ! The Foster Family.see more
Villa del Colle ideal location for family reunion
Wonderful stay with friends

Nice site, great hospitality, wonderful holiday with our friends. Great pool also for night swimming. … see more

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