Villas in Castiglion Fiorentino: Rent luxury villas in Castiglion Fiorentino

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Castiglion Fiorentino

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79 Holiday homes

Filters applied: Villa (79)

(4) Excellent 

13

Holiday 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 km
  • 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.  …see more

from £189 / night

£1318 / week

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from £189 / night

21

Holiday 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 £257 / night

£1283 - £2565 / week

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from £257 / night

(5) Excellent 

1

Holiday 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 km
  • Swimming pool
  • Child friendly
“Not to be missed” This Tuscan farmhouse has been tastefully and sympathetically restored. It is situated at the top of the valley with spectacular views of the surrounding countryside. You do need a car to stay here but most of the towns and village  …see more

from £225 / night

£1680 - £2048 / week

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from £225 / 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 lovely accommodation set in Tuscany, Italy, has 3 bedrooms and 4 bathrooms, and it is perfect for those who are looking for peace and quiet. This pet-friendly property comes with a swimming pool and an Internet connection.  …see more

from £91 / night

£633 - £1324 / week

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from £91 / night

(3) Excellent 

4

Holiday 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
Good value Tuscan Home for families or friends, Private pool, beautiful views, lots of space both inside and out. Additional facilities can be provided - A chef to prepare a lovely lunch or dinner for that special occasion, a concierge serve with local insight,  …see more

from £178 / night

£1240 - £2378 / week

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from £178 / night

(1) Excellent 

38

Holiday 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
“Magical !!” Magical large architected stone villa in a wonderful rural setting with fabulous views of Tuscany and nearby Castiglion Fiorentino hill town - topped off with a large infinity pool and large surrounding gardens / outdoor eating areas. Dedi  …see more

from £175 / night

£1223 - £2992 / week

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from £175 / night

(7) Very Good 

18

Castiglion Fiorentino holiday 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
“AMAZING!!!” I've had the most wonderful stay in this Tuscan gem! Jacopo is such a great host and was always there to answer my questions. The villa is just beautiful! Each room and corner has something unique about it. The gardner Giancarlo came to ma  …see more

from £171 / night

£1197 - £2308 / week

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from £171 / 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 owner if suitable for children
villa with pool near Cortona  …see more

from £411 / night

£2821 / week

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from £411 / night

58

Holiday villa with indoor pool in Brolio

Castiglion Fiorentino / Brolio

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 125 km
  • 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 £580 / night

£4060 - £6283 / week

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from £580 / night

(2) Excellent 

30

Holiday 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 km
  • Swimming pool
  • Child friendly
“Home in Tuscany” first, thanks to Sergio for looking after us all. We had high hopes for this place, and we were not disapointed. It is spacious, clean, bright and has just about everything anyone could want - almost if it was our "own home". Comfort  …see more

from £275 / night

£1924 / week

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from £275 / night

16

Holiday 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
Family friendly villa  …see more

from £428 / night

£1710 - £3667 / week

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from £428 / night

(5) Excellent 

50

Holiday 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 km
  • Swimming pool
  • Child friendly
Magical Villa with private pool on top of Tuscany Hills. One hour drive to Florence, Siena, Perugia. Near to Cortona, Montepulciano and Arezzo.  …see more

from £214 / night

£1197 - £2394 / week

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from £214 / night

(4) Excellent 

48

Holiday 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 km
  • Swimming pool
  • Child friendly
ENCHAINTING VILLA with private POOL on top of TUSCAN HILLS. 10 minutes drive to the town of Castiglion Fiorentino. 25 to CORTONA. One hour to FIRENZE, PERUGIA and SIENA. 30 minutes to the TRASIMENO LAKE.  …see more

from £103 / night

£642 - £1197 / week

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from £103 / night

98

Pieve di Chio holiday 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 £171 / night

£1197 - £2052 / week

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from £171 / night

11

Holiday villa in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 25 km
  • 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.  …see more

from £186 / night

£1300 / week

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from £186 / night

(17) Excellent 

25

Holiday 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 £325 / night

£1240 - £2718 / week

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from £325 / night

100

Holiday villa with swimming pool in Brolio

Castiglion Fiorentino / Brolio

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
Villa Celeste is a grand villa accommodating up to 18 and ideal for a large group or family holiday combining culture and relaxation. It boasts lovely décor, privacy and excellent facilities including both an outdoor and indoor pool.  …see more

from £580 / night

£4060 - £6283 / week

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from £580 / night

(1)  

100

Holiday 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 km
  • Swimming pool
  • Child friendly
This spacious villa boasts a very traditional Tuscan style, which mingles with many modern amenities, 4 bedrooms, full kitchen and a lovely private garden with swimming pool and splendid views of the surroundings.  …see more

from £175 / night

£1223 - £2992 / week

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from £175 / night

18

Holiday 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
Family friendly villa Luxury villas Villas in Tuscany for groups  …see more

from £794 / night

£5556 - £7607 / week

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from £794 / night

14

Holiday 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
Holiday property located in Tuscany in Castiglion Fiorentino. Close location to many touristic attractions like Cortona, Arezzo, Siena, Montepulciano, Montalcino, Chianti, Florence and many more makes it a fantastic place for family holidays.  …see more

from £302 / night

£2112 / week

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from £302 / 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 £69 / night

£300 / week

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from £69 / night

(2) Excellent 

24

Holiday 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 km
  • Swimming pool
  • Child friendly
Opened in 2010 .Beautiful villa in panoramic position with private pool in the countryside 8/11persons.Peaceful e charming location, ideal for families or groups.4 bedroom / 6 bathroom.Only 10km from Cortona , 10 min from the village of Castiglion Fiorentino.  …see more

from £183 / night

£1283 / week

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from £183 / 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 £195 / night

£1364 / week

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from £195 / night

40

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
  • Private garden
<br>nestling in the heart of the world-famous chianti valley, just thirty minutes from florence, stands castello  di ginevra. This graceful country residence is located near the ancient town of castelfiorentino and is steeped in history. Traces of the origina  …see more

from £1002 / night

£7009 / week

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from £1002 / night

(2) Excellent 

18

Province of Arezzo / Castiglion Fiorentino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

(3) Very Good 

23

Holiday villa with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
“Amazing villa, peaceful with stunning views. Perfect location!” We stayed at this villa last Summer. Despite some confusion over our arrival day the owners and family ensured the villa was prepared for us before we settled in. I believe we were the fi  …see more

from £186 / night

£1300 / week

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from £186 / night

25

Holiday villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
it is the ideal place if you are looking to relax, private pool and beautiful view  …see more

from £88 / night

£616 - £1000 / week

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from £88 / night

26

Villa rental in Castiglion Fiorentino with swimming pool

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
It is the ideal place if you are looking to relax, private pool and beautiful view  …see more

from £86 / night

£599 - £1146 / week

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from £86 / night

24

Montecchio Vesponi holiday villa rental

Castiglion Fiorentino / Montecchio Vesponi

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Possibility to add 6 extra beds  …see more

from £794 / night

£5556 - £7607 / week

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from £794 / night

31

Province of Arezzo / Castiglion Fiorentino

7 18 7 nights min

  • 7 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £367 / night

£2565 / week

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from £367 / night

38

Castiglion Fiorentino holiday villa rental

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Podere San Martino is an ancient farm of 9 ectars located in one of the most beatiful and strategic position of the Valle di Chio nearby the Historical towns of Castiglion Fiorentino ( 10 min. ), Cortona ( 20 min. ), Florence ( 1 hour ), Siena ( 1 hour ), Perugia ( 1 h  …see more

from £103 / night

£642 - £2223 / week

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from £103 / night

(1) Excellent 

24

Holiday villa in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 23 km
  • Swimming pool
  • Suitable for children age 5+
Luxury Tuscan Villa . Villa for family reunions in Tuscany and for those looking for a stylish retreat.  …see more

from £465 / night

£3250 / week

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from £465 / night

43

Holiday villa with swimming pool in Brolio

Castiglion Fiorentino / Brolio

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Private garden
<br>Villa Colline Senesi is an old country residence, skilfully restored and transformed into an exclusive private retreat. Situated in the centre of Valdichiana, close to Arezzo and Cortona, the villa offers the possibility to quickly reach the main historical an  …see more

from £611 / night

£4274 - £6325 / week

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from £611 / 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
Villa in Castiglion Fiorentino with 3 bedrooms sleeps 8  …see more

from £201 / night

£1283 - £2992 / week

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from £201 / night

24

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
Villa in Castiglion Fiorentino with 3 bedrooms sleeps 8  …see more

from £141 / night

£855 - £2992 / week

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from £141 / night

(1) Excellent 

33

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £171 / night

£1026 - £2223 / week

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from £171 / night

56

Castiglion Fiorentino / Brolio

9 24 7 nights min

  • 9 bedrooms
  • Sleeps 24
  • 7 nights min
  • Nearest beach 201 km
  • Swimming pool
  • Child friendly

 …see more

from £580 / night

£4060 - £6283 / week

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from £580 / night

17

Province of Arezzo / Castiglion Fiorentino

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Suitable for children age 5+

 …see more

from £178 / night

£1240 - £2378 / week

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from £178 / night

(4) Excellent 

48

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £103 / night

£642 - £1197 / week

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from £103 / night

(3) Very Good 

65

Province of Arezzo / Castiglion Fiorentino

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £253 / night

£1103 / week

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from £253 / night

Top Destination reviews

Casa dei Sogni, Stefano - An attractive air conditioned stone farmhouse with Private Pool - set within a  small Tuscan borgo
Not to be missed

This Tuscan farmhouse has been tastefully and sympathetically restored. It is situated at the top of the valley with spectacular views of the surrounding countryside. You do need a car to stay here but most of the towns and villages to be explored … see more
Casa Dei Sogni, Tuscan Villa, Private Pool, A/C
Not to be missed

This Tuscan farmhouse has been tastefully and sympathetically restored. It is situated at the top of the valley with spectacular views of the surrounding countryside. You do need a car to stay here but most of the towns and villages to be explored … see more
Tuscany cottage with Private Pool, BBQ, & Parking
The Trip of a Lifetime!!

This was a beautiful experience! The house was out in the country but not too far away from all of the activities and conveniences. It was beautiful at night! A million stars and so very quiet! It was up on a hill so the view was lovely; vineyar … see more

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