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

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Castiglion Fiorentino

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186 Vacation rentals

(5) Excellent 

39

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 $169 / night

$1401 - $1794 / week

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from $169 / 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 $62 / night

$393 - $729 / week

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from $62 / night

(2) Excellent 

45

Vacation villa in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 25 mi
  • Child friendly
  • Ask about pets
Villa Coppa. 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!” Although no p …see more

from $438 / night

$1289 - $2072 / week

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from $438 / 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 train S …see more

from $161 / night

$1124 / week

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from $161 / 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 $193 / night

$1345 - $2533 / week

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from $193 / 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 $140 / night

$975 - $1480 / week

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from $140 / 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 $337 / night

$1850 - $3363 / week

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from $337 / night

(1) Excellent 

60

Pieve di Chio Vacation villa rental

Castiglion Fiorentino / Pieve di Chio

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 23 mi
  • Swimming pool
  • Child 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 $342 / night

$1625 - $3194 / week

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from $342 / 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 $90 / night

$393 / week

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from $90 / night

(3) Excellent 

59

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 160 mi
  • Swimming pool
  • Child friendly
In the shade of a cypress grove, between the warm colors of ancient stone and the restful green of the olive trees, you will discover an ideal place to spend your holidays in absolute tranquility in Tuscany! Villa Panichi is an old stone villa surrounded by olive trees …see more

from $273 / night

$1907 / week

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from $273 / 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 $289 / night

$2018 - $3026 / week

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from $289 / night

(6) 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 $561 / night

$3923 / week

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from $561 / night

14

Vacation condo with shared pool in Montecchio Vesponi

Castiglion Fiorentino / Montecchio Vesponi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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 $73 / night

$449 - $707 / week

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from $73 / 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 $79 / night

$550 / week

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from $79 / night

(18) 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 $342 / night

$1625 - $3340 / week

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from $342 / night

(4) Excellent 

26

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Nearest beach 27 mi
  • Swimming pool
  • Child friendly
This villa has outstanding space for everyone.. Offering Five bedrooms and Three bathrooms, 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 …see more

from $256 / night

$1792 - $3281 / week

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from $256 / 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 $229 / night

$1603 - $3923 / week

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from $229 / night

(3) Excellent 

37

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 $233 / night

$1625 - $3206 / week

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from $233 / 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 $90 / night

$561 / week

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from $90 / night

(3) Excellent 

Certificate of Excellence

20

Vacation apartment rental

Province of Arezzo / Castiglion Fiorentino

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night 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 $101 / night

$645 - $802 / week

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from $101 / 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+
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 cottag …see more

from $141 / night

$617 - $958 / week

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from $141 / 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 $202 / night

$1009 / week

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from $202 / night

17

Farmhouse rental in Castiglion Fiorentino with shared pool

Province of Arezzo / Castiglion Fiorentino

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 $90 / night

$606 - $785 / week

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from $90 / 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 $159 / night

$1110 - $2119 / week

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from $159 / 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 $103 / night

$721 - $894 / week

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from $103 / night

(1) Excellent 

24

Vacation villa in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 23 mi
  • Swimming pool
  • Suitable for children age 5+
his exceptional, luxurious and impeccable private villa in Castiglion Fiorentino offers seamless indoor-outdoor living in absolute comfort. Timeless views of the charming Val di Chio and beynd can be enjoyed from the terraces of the villa and the villa's poolside. f …see more

from $1170 / night

$8190 / week

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from $1170 / night

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 Fiorentino …see more

Pricing unknown

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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 $241 / night

$1682 / week

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from $241 / 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 $90 / night

$572 / week

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from $90 / 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 $101 / night

$617 / week

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from $101 / night

15

Vacation barn rental

Province of Arezzo / Castiglion Fiorentino

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Manciano is a very typical old stone Holiday House that was supposed to be also an elementary school about 100 years ago, for the kids of the rural Manciano area. The property is more than 3 acres (12.000 sq. meters) located in the strategical area of the Chiana V …see more

from $202 / night

$1401 / week

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from $202 / night

(1) Excellent 

8

Vacation home with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
A few kilometres from Castiglion Fiorentino and Cortona, going up to the foot of colle della Montanina, popping up at the top of the vegetation, the remains of an ancient castle, was recently renovated a typical farmhouse that preserves intact its original architectural …see more

from $101 / night

$505 - $863 / week

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from $101 / 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 $111 / night

$777 - $974 / week

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from $111 / night

(1) Excellent 

15

Vacation studio in Montecchio Vesponi

Castiglion Fiorentino / Montecchio Vesponi

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Nearest beach 150 mi
  • Child friendly
  • Ask about pets
Big and bright studio apartment in Castiglion Fiorentino Montecchio Vesponi, provence of Arezzo in the midst of the Tuscan Hills consisting of double bedroom with ensuite bathroom including toilet, basin and large spacious shower, eating area with table and chairs, bar …see more

Pricing unknown

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Pricing unknown

4

Vacation apartment in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Air conditioning
NESTLED in the QUIET unspoilt VALLEY of CHIOS 180 SQM APARTMENT with BIG TERRACE are EASILY ACCESSIBLE by car and train art Cities LIKE SIENA, FLORENCE, ROME, PERUGIA, Città DI CASTELLO and NEIGHBORING VILLAGES with CHARACTERISTIC FESTIVALS. Possibility Of BREAKFAST …see more

Pricing unknown

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Pricing unknown

23

Vacation apartment with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
ROLLING HILLS is a small hamlet dating back to 1600, once a farm. The perfect ristrutturaziine gave birth to 7 different apartments along with Manor House form this beautiful structure on a hill dominating the Valley of Chios. La Limonaia, so named because it was onc …see more

Pricing unknown

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Pricing unknown

16

Vacation apartment with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly
Villa Manciano is a very typical old stone Holiday House that was supposed to be also an elementary school about 100 years ago, for the kids of the rural Manciano area. The property is more than 3 acres (12.000 sq. meters) located in the strategical area of the Chiana V …see more

from $152 / night

$1065 / week

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from $152 / 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 $57 / night

$393 / week

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from $57 / 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 $761 / night

$5324 - $8238 / week

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from $761 / 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 $561 / night

$2242 - $4808 / week

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from $561 / night

1