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

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Pieve di Chio
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18 properties
Castroncello
7 properties

Castiglion Fiorentino

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4,306 Vacation rentals

(5) Excellent 

43

Vacation farmhouse in Brolio

Castiglion Fiorentino / Brolio

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
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 comf …see more

from $222 / night

$1,172 - $1,850 / week

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from $222 / night

11

Vacation townhouse with shared pool in Orzale

Castiglion Fiorentino / Orzale

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
"La Fenice" is located in the lovely Valley of Chios, which with the opposite Valley of Chiana frames Castiglion Fiorentino, typical Tuscan hill country rich in architectural beauty and corners to discover. The "Phoenix" is located on a hill about 300 metres above sea l …see more

from $222 / night

$839 - $1,048 / week

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from $222 / night

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
  • 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 $370 / night

$1,973 - $3,699 / week

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Responds fast!
avg. 2 hours 4 minutes

from $370 / night

(6) Excellent 

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 $176 / night

$1,227 / week

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Responds fast!
avg. 1 hour 15 minutes

from $176 / night

14

Vacation condo with shared pool in Montecchio Vesponi

Castiglion Fiorentino / Montecchio Vesponi

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Our beautiful apartment is located on our vegetable farm, on which we grow organically and harvest. Lots of nature and hardly any noise invite you to relax. There is a nice natural pool (chlorine free, 5x10m), a play and Tobe lawn, and a volleyball and a football field …see more

from $84 / night

$587 - $777 / week

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Responds fast!
avg. 2 hours 31 minutes

from $84 / night

(2) Excellent 

24

Vacation home with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in the Tuscan countryside, a 15-minute drive from Castiglione Fiorentino, Podere Ortaglia di Sopra offers a garden with outdoor pool and barbecue facilities. With free Wi-Fi in all areas and a rustic decor, the villa has 3 bedrooms, a TV, a fully equipped kitche …see more

from $247 / night

$1,726 - $3,625 / week

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from $247 / night

(7) Excellent 

12

Vacation home with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
The beautiful old stone house is quite large, incorporating 4,500 sf (400 sm). It includes a total of six bedrooms and five baths, with a sleeping capacity of 13. The property includes a lovely garden with a small vineyard and numerous olive trees. Il Ceriolo i …see more

from $617 / night

$4,315 / week

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from $617 / night

(5) Excellent 

23

Townhouse rental in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Pet friendly
The wide and bright apartment of approximately 100 square meters to 3° and last floor of an old building in the old town of Castiglion Fiorentino welcomes you with a hug that you won't forget. It consists of a large living room with dining area and relaxing area, 2 bedr …see more

from $99 / night

$555 / week

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from $99 / night

(2) Excellent 

17

Farmhouse rental in Castiglion Fiorentino with shared pool

Province of Arezzo / Castiglion Fiorentino

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
SWEET HILLS VILLAGE The beautiful lands of Tuscany, a magical place where dreams and rediscover the flavors of our hills and enjoy the tranquility and the green countryside that surrounds us ... Borgo Dolci Colline is located on a hilltop position the Val di Chio, from …see more

from $124 / night

$863 / week

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from $124 / night

4

Vacation apartment rental

Province of Arezzo / Castiglion Fiorentino

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
TIGLIO è un Monolocale composto da soggiorno con angolo cottura, stufa a legna, letto matrimoniale, bagno con doccia, soppalco con letto matrimoniale. Riscaldamento anche autonomo. L'Appartamento fa parte di un un casolare in pietra ristrutturato seguendo le car …see more

from $87 / night

$580 / week

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Responds fast!
avg. 31 minutes

from $87 / night

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 consente il m …see more

from $265 / night

$1,853 / week

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Responds fast!
avg. 31 minutes

from $265 / 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 $111 / night

$678 / week

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from $111 / night

12

Vacation villa accommodation

Province of Arezzo / Castiglion Fiorentino

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets
Halfway between the olive groves of Val di Chio and the tranquil countryside of the Val di Chiana, right at the foot of the Etruscan country Castiglion Fiorentino there is the B&B the House Sunday. The Bed and Breakfast, open & for a year, takes its name from the owner' …see more

from $99 / night

$432 / week

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from $99 / 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 $370 / night

$2,466 / week

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from $370 / night

(1) Excellent 

13

Castiglion Fiorentino Vacation apartment rental

Province of Arezzo / Castiglion Fiorentino

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
Appartamento a Castiglion Fiorentino, completamente ristrutturato in tipico stile toscano, mantenuta la pietra a vista originale. Composto da ampia cucina/soggiorno completamente attrezzata con divanetto, 1 camera matrimoniale, 1 cameretta con due lettini con possibilit …see more

from $87 / night

$605 / week

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from $87 / night

16

Castiglion Fiorentino Vacation home rental

Province of Arezzo / Castiglion Fiorentino

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
At the foot of Castiglione Fiorentino country at 2 km from the historic center is t rova ​​Guido's House lovely apartment on the first floor of a rustic country house with a large garden free parking space and wifi The house can accommodate 4 people in two rooms with do …see more

from $62 / night

$432 / week

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Responds fast!
avg. 32 minutes

from $62 / 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 $148 / night

$863 / week

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Responds fast!
avg. 31 minutes

from $148 / night

8

Vacation farmhouse with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

13 5 Min stay varies

  • 13 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Der Biohof IL MORO ist ein Familienbetrieb reiner geführt von Roberta und Alberto mit Hilfe ihres Sohnes Sandro und Tochter Guia. Hier werden nach zertifizierten biologischen Richtlinien saisonales Gemüse, Rotwein und Oliven für Olivenöl angebaut. Unsere Hühner laufen t …see more

from $74 / night

$470 - $840 / week

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from $74 / night

21

Vacation villa rental

Castiglion Fiorentino / Pieve di Chio

5 14 4 nights min

  • 5 bedrooms
  • Sleeps 14
  • 4 nights min
  • Child friendly
  • Pet friendly
The house is equipped with all comforts for a pleasant holiday in peace and relaxation. Great pool to cool off on summer days and a large heated jacuzzi located outside overlooking the hills of Castiglione Fiorentino. In the garden, with stone barbecue for cooking grill …see more

from $168 / night

$1,172 / week

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from $168 / night

(1) Excellent 

10

Vacation apartment in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
Large and bright apartment on the 3rd floor of a building in the historic center of the city. Convenient, comfortable, offers an unforgettable view over the valleys surrounding the town. Located halfway between Cortona and Arezzo is a perfect base for visiting the medie …see more

from $99 / night

$617 / week

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from $99 / night

33

Vacation farmhouse rental

Province of Arezzo / Castiglion Fiorentino

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 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

$1,062 - $2,330 / week

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from $152 / night

49

Castiglion Fiorentino Vacation villa rental

Province of Arezzo / Castiglion Fiorentino

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Villa del Colle is an antique Tuscan farmhouse recently reconstructed situated in a beautiful hilly position. The painstaking reconstruction of the farmhouse has kept the fascination of the antique Tuscan residence with terracotta tiled floors, visible stones and visibl …see more

from $335 / night

$2,343 - $5,548 / week

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from $335 / night

(3) Excellent 

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 $212 / night

$1,478 - $2,712 / week

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from $212 / night

(2) Excellent 

37

Vacation farmhouse 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
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 $222 / night

$1,554 - $2,934 / week

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from $222 / night

(19) Excellent 

42

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 $376 / night

$1,788 - $3,797 / week

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from $376 / night

(4) Excellent 

Certificate of Excellence

20

Vacation apartment rental

Province of Arezzo / Castiglion Fiorentino

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
La casa del Rigattiere is situated in the historical centre of one of Tuscany's delightful walled medieval villages, this beautifully appointed apartment is positioned in the historic centre of the once fortified village of Castiglion Fiorentino. It was built on the tow …see more

Certificate of Excellence

from $111 / night

$709 - $882 / week

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Responds fast!
avg. 3 hours 10 minutes

from $111 / night

23

Brolio Vacation villa rental

Castiglion Fiorentino / Brolio

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa De' Michelangioli is a beautiful vacation rental (800 sq m) with air conditioning, private pool and WiFi internet. The property can sleep up to 18 guests comfortably in nine bedrooms with 11 bathrooms. Conveniently located in Fattoria, Italy in the tourist area " …see more

from $837 / night

$5,856 - $9,061 / week

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from $837 / night

36

Vacation apartment rental

Province of Arezzo / Castiglion Fiorentino

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 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 $153 / night

$1,070 - $1,631 / week

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from $153 / night

20

Villa rental in Pieve di Chio with swimming pool

Castiglion Fiorentino / Pieve di Chio

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
HOLIDAY HOME WITH SWIMMING POOL - VILLA CASSIANO Spacious holiday home with private swimming pool located just 8km away from Castiglion Fiorentino. The property is perfectly located between the beautiful towns of Arezzo and Cortona. This is the ideal place to spend a r …see more

from $226 / night

$1,583 - $3,452 / week

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from $226 / 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 $223 / night

$1,112 / week

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from $223 / night

33

Vacation apartment with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Manciano is a very typical Tuscan home that was originally built as an elementary school for the children of the rural Manciano area over 100 years ago. The house has been fully renovated and tastefully extended and now nestles in more than 3 acres (12.000 sq. me …see more

from $247 / night

$1,726 / week

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from $247 / 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 $592 / night

$4,069 / week

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from $592 / night

12

Castiglion Fiorentino Vacation guest house rental

Province of Arezzo / Castiglion Fiorentino

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Studio located in the park in the Tuscan countryside, in Castiglione Fiorentino, near Cortona, in the province of Arezzo. 28 square meters with:> Fully equipped kitchen> Shower> Double bed> TV> WI-FI inside and outside> Veranda> Shared swimming pool> Barbecue> …see more

from $60 / night

$370 / week

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from $60 / night

8

Vacation b&b in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
B&B Boscatello is a small bed and breakfast in a family environment friendly and relaxing atmosphere. It is situated between Cortona and Arezzo, in a hilly landscape surrounded by olive trees and with an enchanting panoramic view over the Valley of Val di Chiana.La our …see more

from $99 / night

$629 / week

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from $99 / night

37

Vacation apartment in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 150 mi
  • Swimming pool
  • Child friendly
Casa Cicci is a lovely apartment located in an ancient XVIII century rural hamlet, designed by the architect Fossombroni. The complex covers approximately 7 hectares and it is situated on a hill above the Val di Chiana, surrounded by vineyards of the nearby famous wine …see more

from $179 / night

$1,202 / week

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from $179 / night

(1) Excellent 

23

Vacation apartment with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
La Limonaia is the ground floor 3 bedroom apartment in the original stone built wing of Villa Manciano. Villa Manciano itself consists of 3 homes arranged in such a way to ensure maximum privacy. Each home has it's own private entrance, private terrace and private BBQ …see more

from $247 / night

$1,726 / week

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from $247 / night

(1) Excellent 

20

Vacation cottage in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Pet friendly
Romantic detached cottage with views of the castle of Montecchio in a Tuscan style, with stone and exposed beams, terracotta floors. Limonaia takes its name from the lemon, in fact, when Borgo Dolci Colline was still a farm, this was the winter shed their groves. This o …see more

from $124 / night

$863 / week

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from $124 / night

(1) Excellent 

22

Vacation apartment in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Pet friendly
Apartment with separate entrance for 2 people overlooking the medieval town of Castiglione Fiorentino with private garden with furniture. Comprising a double bedroom, sitting room, bathroom and kitchenette with a characteristic vaulted ceiling in bricks. Carefully decor …see more

from $136 / night

$950 / week

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from $136 / night

(1) Excellent 

20

Apartment rental in Castiglion Fiorentino with shared pool

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
The farm holiday La Crosticcia is an old farmhouse that has been carefully and expertly restored and divided into three apartments. Immersed in the gentle hills of the Appenines and the green plains of the Valdichiana, and very near to Castiglion Fiorentino, it is ideal …see more

from $73 / night

$510 - $846 / week

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from $73 / night

17

Vacation apartment with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
The farm holiday La Crosticcia is an old farmhouse that has been carefully and expertly restored and divided into three apartments. Immersed in the gentle hills of the Appenines and the green plains of the Valdichiana, and very near to Castiglion Fiorentino, it is ideal …see more

from $73 / night

$510 - $908 / week

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from $73 / night