Castiglion Fiorentino apartment or villa with a private pool area | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Castiglion Fiorentino

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  • Brolio (6)
  • Montecchio Vesponi (2)
  • Orzale (1)
  • Pieve di Chio (3)

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60 Holiday homes

Filters applied: Private pool (60)

Travellers going to Castiglion Fiorentino are booking August dates now. Secure your holiday home today and have the perfect trip.

(2) Excellent 

1 / 22

Tuscany cottage with Private Pool, BBQ, & Parking

Castiglion Fiorentino / Pieve di Chio

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
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 £124 / night

£864 - £1296 / week

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from £124 / night

1 / 21

Villa with pool near Cortona - Castiglion Fiorentino villa sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
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

£1345 - £2522 / week

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from £253 / night

(4) Excellent 

1 / 18

Province of Arezzo / Castiglion Fiorentino

5 bedroomsSleeps 127 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
 …see more

from £109 / night

£757 - £1614 / week

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from £109 / night

Featured properties

1 / 44

Farmhouse,private pool, hudge park,panoramic view

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
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 + 2 c  …see more

from £127 / night

£925 - £1261 / week

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from £127 / night

(2) Excellent 

1 / 79

Province of Arezzo / Castiglion Fiorentino

5 bedroomsSleeps 117 nights min stay

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
 …see more

from £192 / night

£1341 - £2479 / week

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from £192 / night

(4) Excellent 

1 / 19

Casa Dei Sogni, Tuscan Villa, Private Pool, A/C

Castiglion Fiorentino / Pieve di Chio

4 bedroomsSleeps 6Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 25 km; Swimming pool; Great for children of all ages ;
A place to feel at home in Tuscany.... Lovely air conditioned stone farmhouse situated within a small Tuscan borgo. The house offers high quality accommodation with outstanding views of the Val di Chio and Castiglion Fiorentino from the bedrooms, private pool and te  …see more

from £225 / night

£1680 - £1950 / week

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from £225 / night

1 / 40

Castello di Ginevra - Castiglion Fiorentino villa sleeps 12

Province of Arezzo / Castiglion Fiorentino

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; No pets allowed;
<br>Castello di Ginevra – Castel Fiorentino – Tuscany<br><br>6 Bedrooms - Pool<br><br>Nestling in the heart of the world-famous Chianti Valley, just thirty minutes from Florence, stands Castello  di Ginevra. This graceful country r  …see more

from £985 / night

£6891 - £10337 / week

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from £985 / night

(1) Excellent 

1 / 23

Capuchi Cottage - Orzale condo sleeps 2

Castiglion Fiorentino / Orzale

1 bedroomSleeps 27 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £75 / night

£524 - £638 / week

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from £75 / night

1 / 25

Villa Magnifica - Brolio villa sleeps 18

Castiglion Fiorentino / Brolio

9 bedroomsSleeps 187 nights min stay

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min stay
Key info: Nearest beach 125 km; Swimming pool; Great for children of all ages ;
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 £781 / night

£5463 - £7479 / week

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from £781 / night

(4) Excellent 

1 / 50

Villa Principe, Tuscany 210 sqm - Castiglion Fiorentino villa sleeps 10

Province of Arezzo / Castiglion Fiorentino

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
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 £211 / night

£1177 - £2353 / week

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from £211 / night

(3) Very Good 

1 / 48

Province of Arezzo / Castiglion Fiorentino

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
 …see more

from £101 / night

£631 - £1177 / week

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from £101 / night

(3) Very Good 

1 / 65

Province of Arezzo / Castiglion Fiorentino

2 bedroomsSleeps 44 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £248 / night

£1085 / week

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from £248 / night

(11) Excellent 

1 / 25

Villa Senaia - Castiglion Fiorentino villa sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
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

(4) Excellent 

1 / 13

Impressive stone built Tuscan holiday villa with private grounds and swimminig pool, sleeps 10

Province of Arezzo / Castiglion Fiorentino

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 27 km; Swimming pool; Great for children of all ages ;
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. The villa sits in one  …see more

from £186 / night

£1296 - £2197 / week

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from £186 / night

(1) Excellent 

1 / 33

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
 …see more

from £169 / night

£1009 - £2185 / week

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from £169 / night

1 / 16

Villa Rossi - Castiglion Fiorentino villa sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
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 £253 / night

£1681 - £2774 / week

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from £253 / night

(1) Excellent 

1 / 38

La Madonnina - Castiglion Fiorentino villa sleeps 9

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 97 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
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 splendid vi  …see more

from £172 / night

£1202 - £2765 / week

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from £172 / night

1 / 25

Castiglion Fiorentino / Brolio

9 bedroomsSleeps 247 nights min stay

  • 9 bedrooms
  • Sleeps 24
  • 7 nights min stay
Key info: Nearest beach 201 km; Swimming pool; Great for children of all ages ;
 …see more

from £781 / night

£5463 - £7479 / week

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from £781 / night

1 / 22

Province of Arezzo / Castiglion Fiorentino

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Car essential;
 …see more

from £121 / night

£841 - £1555 / week

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from £121 / night

1 / 100

Celeste - Brolio villa sleeps 18

Castiglion Fiorentino / Brolio

9 bedroomsSleeps 18Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Nearest beach 150 km; Swimming pool; Great for children of all ages ;
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 £782 / night

£5463 - £6639 / week

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from £782 / night

1 / 100

Belladonna - Castiglion Fiorentino villa sleeps 11

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 117 nights min stay

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min stay
Key info: Nearest beach 180 km; Swimming pool; Great for children of all ages ;
ExteriorsThis spacious house is in Castiglion Fiorentino, which is situated on a hill in the Valdichiana area. Its location guarantees a tranquil and relaxing stay, but not too far from the town center, which is only 3km away.There are many interesting places to visit i  …see more

from £138 / night

£962 - £1803 / week

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from £138 / night

1 / 42

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 117 nights min stay

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £253 / night

£1681 / week

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from £253 / night

1 / 18

Villa degli Affreschi - Castiglion Fiorentino villa sleeps 18

Province of Arezzo / Castiglion Fiorentino

9 bedroomsSleeps 187 nights min stay

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
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 £781 / night

£5463 - £7479 / week

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from £781 / night

(1) Very Good 

1 / 21

Casa Matilde, Private Pool Cosy Tuscan Family Home

Province of Arezzo / Castiglion Fiorentino

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Swimming pool; Suitable for children age 5+; Some pets are welcome - please contact the owner;
Casa Matilde. Family Home for 3-4 guests. Private Pool. Cottage Matilde is an independent cottage within a small hamlet. It offers a private pool and some lovely views of the surrounding countryside. With two bedrooms, sitting room and kitchen, it offers a great opport  …see more

from £84 / night

£585 / week

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from £84 / night

1 / 36

LA PIETRAIA Castiglion Fiorentino Walking distance

Province of Arezzo / Castiglion Fiorentino

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
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 £105 / night

£732 - £1110 / week

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from £105 / night

(4) Excellent 

1 / 48

Villa Bellavista, Tuscany 180 sqm - Castiglion Fiorentino villa sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
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 9 e  …see more

from £101 / night

£631 - £1177 / week

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from £101 / night

1 / 18

Santa Lucia - Castiglion Fiorentino house sleeps 11

Province of Arezzo / Castiglion Fiorentino

5 bedroomsSleeps 117 nights min stay

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
The home is carefully decorated in a classic Tuscan style with well maintained outdoor areas.Its large lounge area with wonderful ancient brick arches, the swimming pool bordered by flowers and olive trees, and the elegant Tuscan décor create an enchanting setting for  …see more

from £355 / night

£2479 / week

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from £355 / night

(7) Very Good 

1 / 18

Luxury villa with private swimming pool - Castiglion Fiorentino villa sleeps 10

Province of Arezzo / Castiglion Fiorentino

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
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 £240 / night

£1681 - £2269 / week

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from £240 / night

(1) Excellent 

1 / 60

Province of Arezzo / Castiglion Fiorentino

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
 …see more

from £211 / night

£1177 - £2353 / week

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from £211 / night

(2) Excellent 

1 / 24

Villa Vallibona - Castiglion Fiorentino villa sleeps 11

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 11Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Nearest beach 128 km; Swimming pool; Great for children of all ages ;
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

from £180 / night

£1261 - £3026 / week

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from £180 / night

(1) Excellent 

1 / 37

CASALE IL TRECENTO Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
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 £136 / night

£950 - £1841 / week

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from £136 / night

(2) Excellent 

1 / 20

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
 …see more

from £240 / night

£1429 - £2673 / week

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from £240 / night

(3) Excellent 

1 / 4

Villa Sophia in Brolio. Tuscany Family Home & Pool

Province of Arezzo / Castiglion Fiorentino

5 bedroomsSleeps 97 nights min stay

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
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 £175 / night

£1219 - £2185 / week

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from £175 / night

1 / 33

VILLA CECILIA Castiglion Fiorentino - Castiglion Fiorentino farmhouse sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
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 £119 / night

£832 - £1589 / week

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from £119 / night

(1) Very Good 

1 / 48

Province of Arezzo / Castiglion Fiorentino

9 bedroomsSleeps 187 nights min stay

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £672 / night

£4704 - £7483 / week

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from £672 / night

(2) Excellent 

1 / 30

Villa Castalini Tuscany, Incredible Views and more

Province of Arezzo / Castiglion Fiorentino

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 25 km; Swimming pool; Great for children of all ages ;
Perfect for Families and Friends, this spacious and comfortable Tuscan Villa provides more than just a place to stay... Providing absolute WOW views, this beautifully restored six bed-roomed and 5 bathroom Tuscan stone villa sleeps up to 12 guests. The villa offers pe  …see more

from £271 / night

£1891 / week

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from £271 / night

1 / 21

CASOLARE IL CONDOTTIERO - Montecchio Vesponi house sleeps 11

Castiglion Fiorentino / Montecchio Vesponi

4 bedroomsSleeps 11Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
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 Fioren  …see more

from £104 / night

£673 - £1723 / week

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from £104 / night

1 / 13

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £261 / night

£1824 - £2748 / week

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from £261 / night

1 / 18

Province of Arezzo / Castiglion Fiorentino

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Some pets are welcome - please contact the owner;
 …see more

from £289 / night

£2017 - £2816 / week

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from £289 / night

1 / 16

Province of Arezzo / Castiglion Fiorentino

9 bedroomsSleeps 187 nights min stay

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Some pets are welcome - please contact the owner;
 …see more

from £301 / night

£2101 - £4185 / week

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from £301 / night

Top Destination reviews

Luxury villa with private swimming pool
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 make sure the … see more
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
Borgo Tranquiitta - Il Sole
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. Lots of space around the thr … see more
Borgo Tranquiitta - La Luna
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 landscape and the pool and its surroundings are delightfull … see more
Casa Matilde, Private Pool Cosy Tuscan Family Home
Peace and tranquility

We had a great time, the pool was most welcome and the peace and tranquility much appreciated (only noise was the chickens next door!). It is quite remote but the stars were great and we even saw a porcupine. … see more
Cottage maltilde - Casa Matilde. Family Home for 3-4 guests. Private Pool.
Peace and tranquility

We had a great time, the pool was most welcome and the peace and tranquility much appreciated (only noise was the chickens next door!). It is quite remote but the stars were great and we even saw a porcupine. … see more

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