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

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Castiglion Fiorentino

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187 Vacation rentals

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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 $322 / night

$1606 - $3211 / week

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from $322 / night

(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  …see more

from $151 / night

$1055 / week

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from $151 / 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 $727 / night

$5084 - $7866 / week

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from $727 / 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 $114 / night

$792 - $1658 / week

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from $114 / 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
  • Pet friendly

 …see more

from $75 / night

$482 - $862 / week

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from $75 / 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

$899 - $1124 / week

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from $129 / 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 $727 / night

$5084 - $7866 / week

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from $727 / 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

$1392 - $1659 / week

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from $161 / 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

$578 - $750 / week

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from $86 / 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

$482 - $825 / week

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from $97 / 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 $184 / night

$1285 - $2419 / week

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from $184 / 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

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Pricing unknown

(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

$803 - $1499 / week

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from $129 / night

14

Castiglion Fiorentino / Montecchio Vesponi

2 5 Min stay varies

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

 …see more

from $70 / night

$429 - $675 / week

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from $70 / 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 $268 / night

$1499 - $2997 / week

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from $268 / night

7

Province of Arezzo / Castiglion Fiorentino

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

Pricing unknown

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Pricing unknown

17

Apartment rental in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
The house is a typical "mansarda" wonderfully furnished with original antique pieces that belonged to my grandparents and have been in the family for generations. This little gem is located in the historical center of Castiglion Fiorentino (Arezzo). Th  …see more

Pricing unknown

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Pricing unknown

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

$375 - $696 / week

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from $59 / 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 $152 / night

$1060 - $2023 / week

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from $152 / night

6

Castiglion Fiorentino Vacation apartment rental

Province of Arezzo / Castiglion Fiorentino

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
Gelsomino is a beautiful apartament entry on ground floor to a spacious sitting room with a large fireplace, and a well-equipped kitchen with a wood-burning stove; an internal stair leads to the upper floor with two rooms, each having a double bed plus optional single b  …see more

from $129 / night

$750 / week

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from $129 / 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

$1531 - $3746 / week

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from $219 / 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 $215 / night

$1499 - $2890 / week

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from $215 / 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

$429 / week

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from $75 / night

(2) Excellent 

24

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Nearest beach 128 mi
  • Swimming pool
  • Child friendly
Villa Vallibona is situated in the midst of peace and greenery in the gentle hills between Castiglion Fiorentino and Cortona, among olive groves and fruit trees, in a splendid panoramic position. The extensive property includes the main villa and the pool. Villa Vallibo  …see more

Pricing unknown

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Pricing unknown

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 $134 / night

$932 - $1413 / week

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from $134 / 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 $514 / night

$3532 / week

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from $514 / night

14

Vacation villa in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Villa Sant Antonio is a beautiful holiday property in the heart of Tuscany, in Castiglion Fiorentino, close to Cortona and Arezzo. Great location in the middle of the olive growth, recently restored and beautifully furnished, full of art and antiques, with private swimm  …see more

from $378 / night

$2644 / week

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from $378 / 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 $536 / night

$2141 - $4592 / week

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from $536 / night

18

Vacation villa with indoor pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This stunning villa is located in the heart of Valdichiana, close to Arezzo and Cortona, the relais offers the possibility to reach easily the main historical and artistic sites such as Florence, Siena, Perugia, Montepulciano, Assisi, Gubbio and lots more. Villa degli  …see more

from $727 / night

$5084 - $7866 / week

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from $727 / 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

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Pricing unknown

16

Province of Arezzo / Castiglion Fiorentino

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly

 …see more

from $54 / night

$375 / week

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from $54 / night

(1) Excellent 

10

Province of Arezzo / Castiglion Fiorentino

2 5 2 nights min

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

 …see more

from $86 / night

$536 / week

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from $86 / night

(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

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from $73 / night

40

Villa rental in Castiglion Fiorentino with swimming pool

Province of Arezzo / Castiglion Fiorentino

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Private garden
Castello di Ginevra – Castel Fiorentino – Tuscany6 Bedrooms - PoolNestling in the heart of the world-famous Chianti Valley, just thirty minutes from Florence, stands Castello  di Ginevra. This graceful country residence is located ne  …see more

from $1254 / night

$8776 - $13164 / week

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from $1254 / night

(2) Excellent 

14

Vacation b&b in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Ask about pets
A large indipendent room with bathroom. The gorgeous swimming pool sits just below the room. The sound of the gently cascading waterfall is lovely and adds to the already tranquil ambiance. Strategically placed is a shaded gazebo where guests can sit and read their favo  …see more

from $97 / night

$589 / week

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from $97 / night

21

Vacation apartment with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
The Madonnina Agriturismo is very quiet, in a very sunny location with wonderful view over the Valdichiana valley. The ideal location for those who wish to spend a holiday in a quiet area. You can walk through the olive groves or relax poolside The stone house has two v  …see more

from $193 / night

$964 / week

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from $193 / night

12

Province of Arezzo / Castiglion Fiorentino

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets

 …see more

from $86 / night

$375 / week

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from $86 / night

8

Province of Arezzo / Castiglion Fiorentino

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from $86 / night

$546 / week

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from $86 / night

(1) Excellent 

8

Province of Arezzo / Castiglion Fiorentino

14 39 Min stay varies

  • 14 bedrooms
  • Sleeps 39
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

15

Vacation cottage with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Spinabbio è un antico casale ristrutturato secondo il suo originale stile rustico toscano, situato a 700 mt. S.l.m., immerso tra il verde di secolari boschi di querce e castagni, domina sullo splendido panorama della Val di Chiana. La particolare posizione consen  …see more

from $230 / night

$1606 / week

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from $230 / night