Apartments and villas with a garden in Castiglion Fiorentino | Holiday Lettings UK

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Castiglion Fiorentino

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102 Holiday homes

Filters applied: Garden (102)

(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
“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  …see more

from £124 / night

£864 / week

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from £124 / 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

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 £253 / night

£1261 - £2522 / week

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from £253 / night

(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 £186 / night

£1296 / week

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from £186 / night

(13) Excellent 

21

Holiday cottage in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 27 km
  • Swimming pool
  • Suitable for children age 5+
“Looking forward to next time” We thoroughly enjoyed our holiday at Borgo Tranquillita. It is the perfect place to stay whether you use it as a base for travelling the eastern part of Tuscany or just for a relaxing time at the top of picturesque hill.  …see more

from £106 / night

£606 - £669 / week

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from £106 / night

(9) Very Good 

33

Holiday 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 km
  • Swimming pool
  • Suitable for children age 5+
“Rustic charm and a five star pool with a breathtaking view” This was indeed a haven of peace high up in the hills with a lovely view across the valley to the hills on the other side. The well appointed cottages make you feel you are part of the local  …see more

from £114 / night

£628 - £711 / week

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from £114 / 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 £175 / night

£1219 - £2338 / week

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from £175 / night

44

Holiday 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 £127 / night

£1135 - £1303 / week

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from £127 / night

(1) Excellent 

23

Holiday 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
“Romantic Lovely and Memorable Honeymoon” Thank you Terry for the opportunity to stay at Orzale and the little cottage. It was wonderful. After a few days in Venice and then Modena, the little cottage was a great place for us to enjoy the last 10 days  …see more

from £75 / night

£524 - £638 / week

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from £75 / night

(5) Excellent 

15

Holiday 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 km
  • Swimming pool
  • Child friendly
“Absolutely gorgeous!” We had the best time at Maria's beautiful place! Very nice apartment with two large and bright bed rooms, fans and mosquito nets at the windows (yeah!!). The surroundings were absolutely stunning, situated among wineyards and oli  …see more

from £80 / night

£558 / week

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from £80 / night

36

Holiday 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,  …see more

from £105 / night

£732 - £1110 / week

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from £105 / 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 £101 / night

£631 - £1177 / week

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from £101 / 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 £68 / night

£454 - £589 / week

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from £68 / 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 £169 / night

£1177 - £2269 / week

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from £169 / 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 £172 / night

£1202 - £2942 / week

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from £172 / 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 £571 / night

£3992 - £6177 / week

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from £571 / night

(1) Excellent 

37

Holiday 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
Old 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.  …see more

from £136 / night

£950 - £1900 / week

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from £136 / night

18

Holiday 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 km
  • Swimming pool
  • Child friendly
The freshness of this charming garden apartment offering space and easy access to many of Tuscany's hill towns, vineyards and festivals., makes it a good choice for families (or friends) looking for something special and a lovely home in Tuscany  …see more

from £83 / night

£580 / week

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from £83 / 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 £421 / night

£1681 - £3606 / week

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from £421 / 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 £76 / night

£379 - £648 / week

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from £76 / night

33

Holiday farmhouse letting

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Ancient 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.  …see more

from £119 / night

£832 - £1589 / week

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from £119 / 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 £47 / night

£295 - £547 / week

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from £47 / night

(1) Excellent 

15

Castiglion Fiorentino / Montecchio Vesponi

Studio 3 Min stay varies

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

 …see more

Pricing unknown

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Pricing unknown

(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 £211 / night

£1177 - £2353 / week

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from £211 / 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 £271 / night

£1891 / week

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from £271 / 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 £320 / night

£1219 - £2673 / week

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from £320 / night

(9) Excellent 

42

Holiday 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 km
  • Swimming pool
  • Suitable for children age 5+
“Romantic, clean cottage, splendid view, lovely silence; unique location.” Whenever we plan a vacation we have following criteria in mind: comfortable, clean housing, privacy, far from all noise, nice view, close to cultural highlights, pleasant climat  …see more

from £106 / night

£610 - £694 / week

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from £106 / 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 £192 / night

£1341 / week

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from £192 / 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 £183 / night

£1279 / week

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from £183 / 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

21

Holiday 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
Strategic location to visit TUSCANY. Full packages available with tours (wine, food, historical, religious and many others).  …see more

from £104 / night

£723 / week

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from £104 / 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 £68 / night

£295 / week

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from £68 / night

23

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

Pricing unknown

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Pricing unknown

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

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 £297 / night

£2076 / week

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from £297 / 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 £571 / night

£3992 - £6177 / week

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from £571 / night

24

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

Pricing unknown

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Pricing unknown

(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 £180 / night

£1261 / week

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from £180 / night

(2) Very Good 

16

Holiday apartment with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
“A warm welcome and a great time for us” We are late to thank Maria and Terry for their help in making our vacation plans and for their warm welcome. Our cottage/apartment here was just what we expected -clean, comfortable and fantastic views - from  …see more

from £83 / night

£576 / week

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from £83 / night

15

Holiday 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 the ideal place to stay in Tuscany, for relax and also for daily drives into the best places of Tuscany and Umbria  …see more

from £152 / night

£1051 / week

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from £152 / 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