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36 Holiday homes

Filters applied: Pets allowed (36)

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

(9) Excellent 

1 / 27

Borgo Tranquiitta - Le Stella - Castiglion Fiorentino cottage sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 25 km; Swimming pool; Suitable for children age 5+;
* Early Bird Saver * Via Holiday-lettings.. 8% saving for reservations made for summer 2016 made before january 30. (Mention this offer) The charming estate of Borgo Tranquiitta is surrounded by wooded hills of olives and bucolic charm that surround it like a natura  …see more

from £99 / night

£692 - £736 / week

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from £99 / night

(13) Excellent 

1 / 24

Borgo Tranquiitta - Il Sole - Castiglion Fiorentino cottage sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 27 km; 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 cottages  …see more

from £97 / night

£677 - £723 / week

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from £97 / night

1 / 14

Villa Sant Antonio - Castiglion Fiorentino villa sleeps 6

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: 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 £302 / night

£2112 / week

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from £302 / night

Featured properties

1 / 18

Santa Lucia - Castiglion Fiorentino house sleeps 11

Province of Arezzo / Castiglion Fiorentino

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Swimming pool; Child friendly ; 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 £278 / night

£1945 - £2522 / week

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from £278 / night

(9) Very Good 

1 / 24

Borgo Tranquiitta - La Luna - Castiglion Fiorentino cottage sleeps 5

Province of Arezzo / Castiglion Fiorentino

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 26 km; Swimming pool; Suitable for children age 5+;
Great Family holiday home. 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 thre  …see more

from £82 / night

£639 - £749 / week

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from £82 / night

(1) Excellent 

1 / 15

Castiglion Fiorentino / Montecchio Vesponi

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 150 km; Child friendly ; Car advised;
 …see more

Pricing unknown

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Pricing unknown

(2) Excellent 

1 / 14

La Capannina di Romani Rinaldo - Castiglion Fiorentino b&b sleeps 2

Province of Arezzo / Castiglion Fiorentino

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Not suitable for children; Car essential; 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 £77 / night

£471 / week

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from £77 / night

(1) Very Good 

1 / 21

Casa Matilde, Private Pool Cosy Tuscan Family Home - Castiglion Fiorentino cottage sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Swimming pool; Suitable for children age 5+; Ask about pets;
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 £85 / night

£595 / week

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from £85 / night

(2) Very Good 

1 / 16

Villa Maria - ALVINI Apartment - Castiglion Fiorentino apartment sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Tucked away in a quiet corner of Tuscany lies Villa Maria and Apartment Alvini, offering great value family holidays.The villa offers two lovely independent apartments which are perfect for family and friends offering a huge pool with water fall along with unspoilt vis  …see more

from £84 / night

£586 - £842 / week

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from £84 / night

1 / 8

Province of Arezzo / Castiglion Fiorentino

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £30 / night

£257 / week

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from £30 / night

1 / 18

Villa Nonna, Garden Apartment - Castiglion Fiorentino house sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 23 km; 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 £85 / night

£590 - £671 / week

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from £85 / night

(6) Excellent 

1 / 12

Villa Il Ceriolo - Castiglion Fiorentino house sleeps 13

Province of Arezzo / Castiglion Fiorentino

6 13 7 nights min stay

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
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 is locate  …see more

from £428 / night

£2992 / week

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from £428 / night

1 / 11

Castiglion Fiorentino / Orzale

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

Pricing unknown

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Pricing unknown

(5) Excellent 

1 / 15

Villa Maria. Nonna, Tuscany - Castiglion Fiorentino apartment sleeps 5

Province of Arezzo / Castiglion Fiorentino

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Nearest beach 25 km; Swimming pool; Child friendly ;
Tucked away in a quiet corner of Tuscany lies Villa Maria offering great value family vacations.The villa offers two lovely independent apartments which are perfect for family and friends offering a huge pool with water fall and unspoilt vistas of the historic valley of  …see more

from £81 / night

£567 - £790 / week

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from £81 / night

1 / 12

Casa Del Cuore - with courtyard & Free wifi - Castiglion Fiorentino guest house sleeps 3

Province of Arezzo / Castiglion Fiorentino

1 3 3 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Child friendly ; Ask about pets; Private garden;
Situated in the historic center of one of Tuscany's most beautiful walled medieval villages, this independent home is nestled in the historic center of the once fortified village of Castiglion Fiorentino. Offering privacy and serenity with views of the Valdichiana  …see more

from £52 / night

£342 / week

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from £52 / night

1 / 11

Coppa di Sopra - Castiglion Fiorentino villa sleeps 6

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 25 km; Child friendly ; Car essential;
Coppa di Sopra 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!  …see more

from £167 / night

£1167 - £1300 / week

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from £167 / night

(7) Very Good 

1 / 18

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

Province of Arezzo / Castiglion Fiorentino

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: 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 £171 / night

£1197 - £2308 / week

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from £171 / night

1 / 12

Province of Arezzo / Castiglion Fiorentino

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £69 / night

£300 / week

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from £69 / night

(1) Excellent 

1 / 38

La Madonnina - Castiglion Fiorentino villa sleeps 9

Province of Arezzo / Castiglion Fiorentino

4 9 7 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; 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 £175 / night

£1223 - £2812 / week

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from £175 / night

(4) Excellent 

1 / 18

Province of Arezzo / Castiglion Fiorentino

5 12 7 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £110 / night

£770 - £1069 / week

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from £110 / night

1 / 21

Villa with pool near Cortona - Castiglion Fiorentino villa sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Child friendly ; 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 £257 / night

£1283 - £2565 / week

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from £257 / night

1 / 44

Farmhouse,private pool, hudge park,panoramic view - Castiglion Fiorentino farmhouse sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: 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 + 2 c  …see more

from £129 / night

£941 - £1283 / week

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from £129 / night

(4) Excellent 

1 / 48

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

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Child friendly ;
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 £103 / night

£642 - £1197 / week

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from £103 / night

1 / 8

Province of Arezzo / Castiglion Fiorentino

13 28 Min stay varies

  • 13 bedrooms
  • Sleeps 28
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £48 / night

£300 - £556 / week

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from £48 / night

1 / 19

Villa Nonina, Tuscan Home - Castiglion Fiorentino apartment sleeps 5

Province of Arezzo / Castiglion Fiorentino

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car not necessary;
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 £101 / night

£704 - £765 / week

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from £101 / night

1 / 14

Cottage Grande, Lovely Home - Pieve di Chio house sleeps 6

Castiglion Fiorentino / Pieve di Chio

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 22 km; Swimming pool; Child friendly ;
A place to feel at home in Tuscany. A quiet and charming setting for you to enjoy country living. Cottage Grande is part of a working organic farm or agriturismo. It offers a real taste of the Tuscan traditions along with all the modern comforts you will appreciate for  …see more

from £121 / night

£842 - £995 / week

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from £121 / night

1 / 25

La Casa di Pino Castiglion Fiorentino - Castiglion Fiorentino villa sleeps 2

Province of Arezzo / Castiglion Fiorentino

1 2 7 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
In the heart of the Val di Chio, on the border between Tuscany and Umbria and only a few km far form the village of Castiglion Fiorentino, we find the lovely CASA DI PINO, small and ancient stone cottage dated back to the year 1200, like the beautiful "Maestà" a painte  …see more

from £88 / night

£616 - £1000 / week

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from £88 / night

1 / 20

San Lazzo, graceful apt in a special tuscan hamlet - Castiglion Fiorentino apartment sleeps 3

Province of Arezzo / Castiglion Fiorentino

2 3 3 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min stay
Key info: Ask owner if suitable for children; Ask about pets;
The picturesque Via San Lazzo, named after the characteristic small Romanesque church, winds along the massive Medieval walls surrounding the Etruscan town of Castiglion Fiorentino, once entered Porta Romana. Casa San Lazzo rises at the middle of the alley characterised  …see more

from £103 / night

£385 - £513 / week

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from £103 / night

1 / 17

Agriturismo La Crosticcia-Poggetto Castiglion Fio - Castiglion Fiorentino apartment sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
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 £54 / night

£377 - £700 / week

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from £54 / night

1 / 20

Agriturismo la Crosticcia-Oliveto Castiglion Fiore - Castiglion Fiorentino apartment sleeps 2

Province of Arezzo / Castiglion Fiorentino

1 2 7 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
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 £37 / night

£257 - £469 / week

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from £37 / night

(1) Excellent 

1 / 20

Agriturismo La Crosticcia-Rio Castiglion Fiorentin - Castiglion Fiorentino apartment sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
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 £47 / night

£325 - £614 / week

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from £47 / night

1 / 26

Casa Largnano Palazzo del Pero - Castiglion Fiorentino villa sleeps 6

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
A traditional stone farmhouse which emerges from the dense vegetation of the hills of Val Cerfone, a real oasis of peace immersed in nature, far from the noise and frenetic pace of modern day life. This house, which is in a natural park, is the ideal place for those wis  …see more

from £86 / night

£599 - £736 / week

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from £86 / night

1 / 38

VILLA PRINCIPE 8 prsns - Castiglion Fiorentino villa sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: 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 

1 / 8

Province of Arezzo / Castiglion Fiorentino

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £51 / night

£353 - £659 / week

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from £51 / night

1 / 8

Villa Giovanna - Castiglion Fiorentino villa sleeps 12

Province of Arezzo / Castiglion Fiorentino

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Car advised;
Situated on the border between Tuscany and Umbria, this lovely country villa has been recently built in perfect harmony with the surrounding territory. A welcoming property with all modern comforts, it is the perfect choice for anyone looking for a traditional feel wit  …see more

from £163 / night

£1140 - £3191 / week

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from £163 / night

1 / 8

Province of Arezzo / Castiglion Fiorentino

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
 …see more

from £354 / night

£2477 / week

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from £354 / 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, 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
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

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