50 Best Vacation Rentals in Castiglion Fiorentino - Holiday Lettings - Cabins

Close

View larger map

Also consider

Pieve di Chio
10 properties
Brolio
10 properties
Castroncello
6 properties

Castiglion Fiorentino

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

187 Vacation rentals

(3) Very Good 

22

Cottage accommodation in Pieve di Chio

Castiglion Fiorentino / Pieve di Chio

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Charming Restored character stone cottage with beautiful views across the Val Di Chio. Private swimming pool with Stone BBQ. Ideal location for day trips across Tuscany & Umbria, Siena, Montepulciano, Cortona, Perugia & Assisi. 15 minutes to Medieval town with train S  …see more

from $157 / night

$1098 / week

Book View

from $157 / night

(5) Excellent 

1

Vacation villa with swimming pool in Pieve di Chio

Castiglion Fiorentino / Pieve di Chio

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly
A place to feel at home in Tuscany.... 3 bedrooms, 4 bathrooms, Air Conditioning, Private Pool... and Easy access Lovely air conditioned stone farmhouse situated within a small Tuscan borgo. The house offers high quality accommodation with outstanding views of the V  …see more

from $286 / night

$2134 - $2601 / week

Inquire View

from $286 / night

21

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely stone villa is located on the hills between Arezzo (18km) and Cortona (12km), only few minutes from Castiglion Fiorentino (3km), a lovely medieval village dominating the green valleys of the Val di Chio and the Val di Chiana. This strategic position offers  …see more

from $321 / night

$1601 - $3202 / week

Book View

from $321 / night

(1) Excellent 

22

Villa rental in Castiglion Fiorentino with shared pool

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
This beautiful Tuscan holiday home is situated near Castiglion Fiorentino (AR). The villa has 3 double beds, so it can comfortably host a family or group of 6 people. There are also 4 bathrooms for individual comfort and privacy. Guests can relax and enjoy the tranquil  …see more

from $113 / night

$790 - $1654 / week

Inquire View

from $113 / night

(4) Excellent 

13

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 27 mi
  • Swimming pool
  • Child friendly
Just a short distance from the medieval town of Castiglion Fiorentino is "Casa Usignoli". This very old manor house dates back to 1759. It has been fully renovated to provide a stylish family home with 5 large bedrooms and two bathrooms. The villa sits in  …see more

from $236 / night

$1646 / week

Inquire View

from $236 / night

(3) Excellent 

20

Province of Arezzo / Castiglion Fiorentino

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $75 / night

$481 - $860 / week

Book View

from $75 / night

(13) Excellent 

21

Vacation cottage in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 27 mi
  • Swimming pool
  • Suitable for children age 5+
The charming estate of Borgo Tranquiitta is surrounded by wooded hills of olives and bucolic charm that surround it like a natural garden enclosing the village in beautiful countryside with extended views of the valley and beyond.Here are three, lovely detached  …see more

from $134 / night

$769 - $849 / week

Inquire View

from $134 / night

(9) Very Good 

33

Vacation cottage with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 26 mi
  • Swimming pool
  • Suitable for children age 5+
Great Family holiday home. The charming estate of Borgo Tranquiitta is surrounded by wooded hills of olives and bucolic charm that surround it like a natural garden enclosing the village in beautiful countryside with extended views of the valley and beyond.Here  …see more

from $145 / night

$798 - $902 / week

Inquire View

from $145 / night

(3) Excellent 

4

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The sweeping vista across the valley to Cortona and Castiglion Fiorention with the wonderful castle of Montecchio makes the perfect base for a friends and family home in Tuscany. Recently renovated with great care and - attention to detail, Casa Sophia is a four bedro  …see more

from $222 / night

$1548 - $2970 / week

Inquire View

from $222 / night

44

Vacation farmhouse in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Brolio Quinto is the ideal location for a peaceful holiday in the warm atmosphere of an old country farmhouse, beautifully preserved in its original architectural style. You can rent the top floor of this historic farmhouse with its independent access. It sleeps 8 +  …see more

from $161 / night

$1441 - $1655 / week

Book View

from $161 / night

28

Villa rental in Castiglion Fiorentino with swimming pool

Province of Arezzo / Castiglion Fiorentino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
Immersed in the green of the olive trees and woods in the peaceful hills of Tuscany, the ideal destination for those seeking a healthy and peaceful stay of relaxation and comfort, Villa Il Castello is located between the cities of Arezzo and the quiet Etruscan town of C  …see more

from $513 / night

$3522 / week

Book View

from $513 / night

(1) Excellent 

23

Vacation condo with swimming pool in Orzale

Castiglion Fiorentino / Orzale

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This romantic garden cottage, sits in the sleepy hamlet of Orzale and provides the perfect place to unwind and enjoy Tuscany. Simple, but charming accommodation - and a private pool. Capuchi cottage is immersed in the beautiful Tuscan country side. It provides an ine  …see more

from $95 / night

$665 - $811 / week

Inquire View

from $95 / night

(5) Excellent 

15

Vacation apartment with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly
Tucked away in a quiet corner of Tuscany lies Villa Maria offering great value family vacations.The villa offers two lovely independent apartments which are perfect for family and friends offering a huge pool with water fall and unspoilt vistas of the historic v  …see more

from $102 / night

$708 / week

Inquire View

from $102 / night

36

Vacation apartment rental

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
In a panoramic and quiet position, walking distance to the village of Castiglion Fiorentino, one of the most important villages in the Valdichiana with shops, restaurants and all kinds of facilities, we find a cottage divided into two pleasant apartments, each one with  …see more

from $133 / night

$929 - $1409 / week

Book View

from $133 / night

(4) Excellent 

48

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
San Martino is an ancient farm with three farm houses: for rent Villa Bellavista( 4 sleeps ), unique stone Villa with a relaxing atmosphere, lovingly restored and furnished.The Villa has own private pool 12mt x 5mt . The privacy is guaranted. The property consist of  …see more

from $129 / night

$801 - $1495 / week

Book View

from $129 / night

17

Province of Arezzo / Castiglion Fiorentino

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $86 / night

$577 - $748 / week

Book View

from $86 / night

100

Vacation apartment with shared pool in Brolio

Castiglion Fiorentino / Brolio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 200 mi
  • Swimming pool
  • Child friendly
4 paxThis very comfortable 80 sq-m apartment for rent in Tuscany  are situated on the ground floor. No detail as to its lovely Tuscan style has been left unattended: its terracotta tiles, wooden beams and antiques are typical of the region. This apartments is suita  …see more

from $129 / night

$897 - $1121 / week

Inquire View

from $129 / night

(7) Very Good 

18

Castiglion Fiorentino Vacation villa rental

Province of Arezzo / Castiglion Fiorentino

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The ideal destination for combining relax with culture. The unique location of the villa, the accuracy of design and all the comforts inside allow guests to fully enjoy the tuscan countryside by a unique view on it. Furthermore, the villa is situated in a strategic poin  …see more

from $214 / night

$1495 - $2882 / week

Book View

from $214 / night

(1) Excellent 

38

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
The villa, of recent reconstruction, is positioned on the hills next to the characteristic town of Castiglion Fiorentino, in the middle of the Chiana valley and Chio valley amidst nature and art. Overlooking the wide expanse of the Val di Chiana, it offers a splendi  …see more

from $219 / night

$1527 - $3736 / week

Book View

from $219 / night

58

Vacation villa with indoor pool in Brolio

Castiglion Fiorentino / Brolio

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 125 mi
  • Swimming pool
  • Child friendly
Villa Magnifica is an old country residence, skillfully restored and transformed into an exclusive private retreat. A 4 acres park, with Italian style garden and olive trees, surround the property. Large external pool with roman staircase and the bonus of the heated in  …see more

from $725 / night

$5070 - $7845 / week

Inquire View

from $725 / night

(1) Excellent 

37

Vacation farmhouse in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Property DescriptionOld farmhouse of peasant origins, where on the ground floor you can still appreciate the old stables. Located 1,5 km away from the town of Castiglion Fiorentino which can also be reached on foot. Castiglion Fiorentino is one of the most renowned town  …see more

from $173 / night

$1206 - $2412 / week

Book View

from $173 / night

18

Vacation home with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 23 mi
  • Swimming pool
  • Child friendly
Fresh, bright and very well maintained, the villa offers a great holiday home for famiies of all ages. It is located in the lovely Val di Chio a few kilometers from the small town of ancient medieval town of Castiglion Fiorentino - rich in history, in the heart of b  …see more

from $106 / night

$737 / week

Inquire View

from $106 / night

16

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The property is located in Poggio Della Coppa near Castiglion Fiorentino at about 650 meters above sea level and is situated on a hillside with amazing views of the valley below. The 2-storey stone building is contructed in typical Tuscan farmhouse style with an extern  …see more

from $534 / night

$2135 - $4579 / week

Book View

from $534 / night

(1) Excellent 

8

Province of Arezzo / Castiglion Fiorentino

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $97 / night

$481 - $822 / week

Book View

from $97 / night

100

Vacation villa with swimming pool in Brolio

Castiglion Fiorentino / Brolio

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 150 mi
  • Swimming pool
  • Child friendly
ExteriorVilla Celeste is a large villa with 9 bedrooms, all with en suite bathrooms.The property is in a perfect position for exploring wider Tucany with Arezzo and Cortona just a short distance away and other famed historical and arti  …see more

from $725 / night

$5070 - $7845 / week

Inquire View

from $725 / night

33

Vacation farmhouse rental

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Property DescriptionAncient farmhouse of peasant origins, situated on the top a small hill in the heart of Valdichiana, at approx. 4 km from Castiglion Fiorentino, characteristic village with all kind of shop, restaurants and facilities. A recent and careful restoration  …see more

from $151 / night

$1057 - $2018 / week

Book View

from $151 / night

8

Province of Arezzo / Castiglion Fiorentino

13 5 Min stay varies

  • 13 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $59 / night

$374 - $694 / week

Book View

from $59 / night

(1) Excellent 

15

Castiglion Fiorentino / Montecchio Vesponi

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Nearest beach 150 mi
  • Child friendly
  • Ask about pets

 …see more

Pricing unknown

Book View

Pricing unknown

(16) Very Good 

16

Province of Arezzo / Castiglion Fiorentino

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Air conditioning

 …see more

from $73 / night

$289 / week

Book View

from $73 / night

(5) Excellent 

50

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
San Martino is an ancient farm of 9 ectars located in one of the most beatiful and strategic position of the Valle di Chio and Val di Chiana nearby the HISTORICAL TOWNS of Castiglion Fiorentino ( 10 min. ) and Cortona ( 20 min. ) Florence ( 1 hour ), Siena ( 1 hour ),  …see more

from $267 / night

$1495 - $2989 / week

Book View

from $267 / night

(2) Excellent 

30

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly
Perfect for Families and Friends, this spacious and comfortable Tuscan Villa provides more than just a place to stay... Providing absolute WOW views, this beautifully restored six bed-roomed and 5 bathroom Tuscan stone villa sleeps up to 12 guests. The villa offers pe  …see more

from $344 / night

$2402 / week

Inquire View

from $344 / night

98

Pieve di Chio Vacation villa rental

Castiglion Fiorentino / Pieve di Chio

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
The view from here is - "just stunning but wait until you see the pool..." Villa Castello Roccolo - is - "simply beautiful " Villa Castello Roccolo is for sure, a really special property for both friends and families to enjoy. Tucked away on the sleepy hillside of  …see more

from $213 / night

$1495 - $2562 / week

Inquire View

from $213 / night

(17) Excellent 

25

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villa Senaia In stunning Tuscany, along its endless artistic heritage and countryside, where stretches of silvery olive trees stand after vineyards and cypress trees, lies the Villa Senaia. An ancient stone farmhouse, located in a strategic position where it is easy t  …see more

from $406 / night

$1548 - $3394 / week

Book View

from $406 / night

(9) Excellent 

42

Vacation cottage with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 25 mi
  • Swimming pool
  • Suitable for children age 5+
* Early Bird Saver * Via Holiday-lettings.. 8% saving for reservations made for summer 2016 made before january 30. (Mention this offer) The charming estate of Borgo Tranquiitta is surrounded by wooded hills of olives and bucolic charm that surround it like a natura  …see more

from $134 / night

$774 - $881 / week

Inquire View

from $134 / night

(5) Excellent 

23

Province of Arezzo / Castiglion Fiorentino

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Pet friendly

 …see more

from $75 / night

$427 / week

Book View

from $75 / night

(2) Excellent 

79

Province of Arezzo / Castiglion Fiorentino

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $244 / night

$1703 / week

Book View

from $244 / night

11

Vacation villa in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 25 mi
  • Child friendly
  • Ask about pets
Coppa di Sopra is an elegant and enchanting villa overlooking one of Tuscany's favorite valleys - “Coppa di Sopra is a magical place. It seems like you're on top of the world. We parked our car, walked down the steps and the view - it took our breath away!  …see more

from $232 / night

$1624 / week

Inquire View

from $232 / night

11

Castiglion Fiorentino / Orzale

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

Book View

Pricing unknown

21

Vacation home with swimming pool in Montecchio Vesponi

Castiglion Fiorentino / Montecchio Vesponi

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful rural home placed on the silver hills covered with olives groves between Castiglion Fiorentino and Cortona, in a very panoramic position and a stone's throw away from the magnificent medieval castle of Montecchio Vesponi. The villages of Castiglion Fioren  …see more

from $132 / night

$918 / week

Book View

from $132 / night

(1)  

100

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 11 7 nights min

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min
  • Nearest beach 180 mi
  • Swimming pool
  • Child friendly
ExteriorsThis spacious house is in Castiglion Fiorentino, which is situated on a hill in the Valdichiana area. Its location guarantees a tranquil and relaxing stay, but not too far from the town center, which is only 3km away.There are many interesting places to visit i  …see more

from $219 / night

$1527 - $3736 / week

Inquire View

from $219 / night