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Castiglion Fiorentino Rentals

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2,663 Houses

Tuscany Villa Bellavista

Castiglion Fiorentino villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$162

MAS THE LEADER OF HOLIDAY HOUSE

Castiglion Fiorentino villa

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 2 hours 40 minutes

Price per night from

$404

Private villa in the Cortona area for 18 persons. Pool, internal pool and A/C!

Brolio villa

9 bedrooms / 11 bathrooms / sleeps 24

Price per night from

$790

Dreamful rooms or apartments in the heart of Tuscany

Castiglion Fiorentino apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 40 minutes

Price per night from

$162

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

$182

Villa Margarita, Spacious Tuscan Family home with lovely Pool

Castiglion Fiorentino villa

6 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$749

Large Tuscan Villa, Private Pool, Gardens and views

Castiglion Fiorentino villa

5 bedrooms / 3 bathrooms / sleeps 11

“this could be heaven!” A well maintained, bright and inviting home for our two weeks in Tuscany. Beautiful views and amazing sunsets, a crystal blue pool and deep blue sky. In the evening, fireflies to entertain us as we sipped local wine and planned the next days tour. Rooms the largest we found on our recent tours of Italy, and very helpful agent too. This could be heaven! Fantastic value, fantastc place, fantastic people and fantastic vacation.

Price per night from

$505

Agriturismo Le Maceie Tuscan Vacation Rental

Castiglion Fiorentino house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$88

Big & Bright Studio in Tuscany near Cortona - WiFi

Castiglion Fiorentino apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$81

Holiday House Traquandi

Castiglion Fiorentino house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$132

Large Studio apartment in Historical Centre - WiFi

Castiglion Fiorentino apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$92

Villa Angelisa C

Castiglion Fiorentino apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 minutes

Price per night from

$154

Villa MIchelangelo

Brolio house

9 bedrooms / 11 bathrooms / sleeps 18

Price per night from

$631

Exclusive , Luxury Tuscan Vacation Home.

Castiglion Fiorentino villa

6 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$505

Villa Angelisa A

Castiglion Fiorentino apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 minutes

Price per night from

$123

Villa Michelangelo

Brolio villa

9 bedrooms / 11 bathrooms / sleeps 18

Price per night from

$632

Monolocale Borgo Santa Lucia

Castiglion Fiorentino house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$72

Villa Rustica

Castiglion Fiorentino house

9 bedrooms / 9 bathrooms / sleeps 18

Price per night from

$529

Casa Santa Lucia, Noto Barocca

Castiglion Fiorentino house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$90

Villa Angelisa D

Castiglion Fiorentino apartment

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 minutes

Price per night from

$154

Villa Angelisa B

Castiglion Fiorentino apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 minutes

Price per night from

$123

Restored Tuscan Villa with Private Studio

Pieve di Chio house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$440

Tuttomio Home & Breakfast

Castiglion Fiorentino b&b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$224

Borgo Santa Lucia, Casa Legnaia

Castiglion Fiorentino house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$156

cottage Lina

Pieve di Chio villa

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 50 minutes

Price per night from

$299

Villa Galati

Castiglion Fiorentino villa

5 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$206

House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

13 bedrooms / 1 bathroom / sleeps 5

Price per night from

$81

Tuscany cottage near Castiglion Fiorentino, with Private Pool, BBQ, & Parking

Pieve di Chio cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 32 minutes

Price per night from

$194

guido's house

Castiglion Fiorentino house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$67

Villa Sant Antonio

Castiglion Fiorentino villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$423

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

Castiglion Fiorentino apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$120

Farm House La Fenice

Castiglion Fiorentino townhouse

2 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$406

Boscatello

Castiglion Fiorentino b&b

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$108

Superb Villa with pool in Castiglion Fiorentino, Cortona, air conditioning

Castiglion Fiorentino villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 48 minutes

Price per night from

$400

La Capannina di Romani Rinaldo

Castiglion Fiorentino b&b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$121

Price per night from

$790

VILLA CECILIA

Castiglion Fiorentino farmhouse

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$174

Gaggioleto, fascinating villa with panoramic view

Castiglion Fiorentino villa

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$381

Viewing 38 of 2,663
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
Large Tuscan Villa, Private Pool, Gardens and views
Perfect family celebration in Tuscany

This review is a little late, but the experience we had is well worth taking the time to write it. My wife and I were trying to find a place to relax and enjoy our 25th anniversary with our family and we couldn't have found a better spot. The grounds and property are amazing, with a private pool enjoy all to ourselves. The pool terraces and out kitchen very cozy and had everything we needed to just relax and enjoy the real Tuscany. With everything so close including wineries and restaurants, there was plenty to keep us busy when we went sight seeing. But, the best part about it, is that some of us didn't want to leave the villa - simply relaxing by the pool and just enjoying the endless scenery and villa - a vacation in itself. For our "big Day" we arranged for a local chef to come along and prepare the most awesome lunch for us all. Everything from canapés to a fabulous cake - We were spoilt! We can easily highly recommend this vacation home if your looking to enjoy either Tuscany's countryside,go touring or, simple enjoy living in an amazing Tuscan villa that will make you want to return - before another 25 years! . Thank you Gerry for all that you did to make our trip a great experience!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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