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144 Holiday homes in Cortona

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144 Results  |  
16 Photos

Villa | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £99 /night

£688 - £1260 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
This charming independent villa is situated in panoramic position in the Cortonese Mountains above the Etruscan hill town of Cortona. It's ideal location make it easy visit the most renowned historical and art cities of Tuscany and Umbria.  …see more

14 Photos

Villa | 6 Bedrooms | sleeps 12

4 Nights min stay

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from £107 /night

£744 - £2000 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Il Biancospino is a gracious property ideal for families and small groups, immersed in the greens of the cortonese mountains between oak and chestnut trees.  …see more

16 Photos

Villa | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £139 /night

£973 - £1600 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
The villa is situated within a large property and offers wonderful views on the surrounding countryside of Tuscany.  …see more

Featured properties

18 Photos

Villa | 4 Bedrooms | sleeps 12

4 Nights min stay

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from £107 /night

£744 - £1600 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Villa Neri is situated in San Lorenzo in close driving proximity to Cortona. Cortona is an antique Etruscan town which lies in the heart of the Chiana valley. You can even see the town perched on the hill in front of you  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 9

7 Nights min stay

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from £229 /night

£1600 - £2288 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Amidst the olive trees that surround the walls of the ancient city of Cortona, lies Villa Olea, a delightful recently restored property, ideal for all who search privacy and tranquility.  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 6

4 Nights min stay

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from £107 /night

£744 - £1580 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
La Farnetina is a charming independent Villa, part of a big property dating back to the first years of the 20th century, located in a beautiful position in the countryside around Cortona, at only 14 Km from the historical centre.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 9

4 Nights min stay

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from £180 /night

£1260 - £2860 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Villa le Corchie is a charming villa located in a quiet and panoramic position in one of the most scenic areas of the hills surrounding Cortona.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £246 /night

£1716 - £3200 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Villa Liliana is perfectly situated to enjoy the spectacular views of our beautiful valley. Villa Liliana sleeps up to 10 people.  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 17

7 Nights min stay

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from £458 /night

£3200 - £4000 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
The property Villa il Trebbio is an antique palace close to Cortona which dates back to the 16th century. The farmhouse in stone has been personally furnished by the owner with antique family pieces and reflects a simple and at the same time elegant atmosphere  …see more

18 Photos

Villa | 6 Bedrooms | sleeps 16

Excellent 5/5 

7 Nights min stay

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from £286 /night

£2000 - £3000 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Casale GinezzO is beautiful independent Villa, located 15 km from Cortona, in the heart of the cortonese mountains, immersed into the green woods of oak and chestnut trees. From the big garden you can enjoy the charming and unspoilt natural environment  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £180 /night

£1260 - £1716 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Villa Gloria is a quaint cottage that is set in a charming and panoramic position, with completely authentic surroundings. Immersed in the lush mountains of Cortona, near the border between Tuscany and Umbria  …see more

18 Photos

Villa | 5 Bedrooms | sleeps 10

4 Nights min stay

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from £131 /night

£916 - £2174 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
The property is situated on the hills which surround Cortona. It's a characteristic villa in rustic style which develops on two independent levels, each equipped with kitchen and comforts.  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £132 /night

£920 - £2056 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Villa Maria Laura rises in panoramic position, dipped in the green and tranquility of the cortonesian hills, ideal for all of those who wish to enjoy the beauty and tranquility which this place can offer.  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 6

4 Nights min stay

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from £99 /night

£688 - £1260 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Nice property comprising several stone buildings situated in panoramic location on the hills around Cortona, at 750 m above-sea-level. This property is surrounded by beautiful woods and valleys and offers extensive views.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £246 /night

£1716 - £3088 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Above the wood oven is engraved 1781. Villa Nello was restored in 2001. It develops on three floors, sleeping 8 people, plus a small independent single bedroom with bathroom.  …see more

18 Photos

Villa | 6 Bedrooms | sleeps 14

4 Nights min stay

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from £164 /night

£1144 - £2000 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Casa Delia is an antique villa which lies at the bottom of a green hill of Cortona in a quiet and panoramic position. The villa is surrounded by a big park, partly shaded by trees, and with its beautiful swimming pool looks onto the Chiana valley and Cortona  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 17

4 Nights min stay

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from £269 /night

£1880 - £3760 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
La Colombaia is a leopoldine house, typical residence of the 16th century of the Val di Chiana, finely restored respecting the material and original architectonic characteristics.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 11

3 Nights min stay

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from £138 /night

£960 - £1920 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Farmhouse near Cortona, in the Chiana Valley with wonderful panoramic view. Ideal solution for relaxing holidays in the Tuscan countryside. Swimming pool, barbecue, Internet connection, table-tennis table, mountain bikes. Tennis club and riding stable nearby.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £195 /night

£1361 - £1649 / week

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Key info:

  • Nearest beach 160 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
Elegant villa near the medieval town of Cortona (Arezzo). Ideal lodging for relaxing holidays in the Tuscan countryside, surrounded by pathways for bike rides and walks. Tennis club and riding stable nearby. Swimming pool, Internet connection.  …see more

22 Photos

Apartment | 3 Bedrooms | sleeps 5

2 Nights min stay

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from £51 /night

£357 - £424 / week

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Key info:

  • Suitable for over 5s only
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
La Mansarda del Sodo, a top floor apartment in a typical two storey old stone house one kilometer from the ancient Etruscan village of Cortona. We'll be happy to provide any information needed. FREE SPACIOUS PARKING LOT AVAILABLE 200 MT. FROM THE HOUSE  …see more

15 Photos

B&B | 11 Bedrooms | sleeps 20

1 night min stay

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from £60 /night

£416 - £5936 / week

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Key info:

  • Swimming pool
  • Suitable for over 5s only
  • Air conditioning
  • May take pets – please enquire
  • Private garden
bed and breakfast in toscana ,cortona ,casa vacanze ,piscina ,swimming pool ,restaurant ,ristorante ,mezza pensione ,giardino ,campagna toscana ,Montepulciano ,siena ,firenze ,arezzo ,perugia ,strada del vino ,wineries , medieval town , Il Sole del Sodo nel suo insieme, e nella semplice eleganza dei suoi dettagli, è la casa ideale per chi sceg  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 11

4 Nights min stay

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from £182 /night

£1272 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Swimming pool
  • Suitable for over 5s only
  • Car advised
  • Pets welcome
  • Private garden
A traditional stone house set in the restful landscape of the tuscan hills, provided with all comforts, very close to the main touristic destinations of central Italy. Art, culture, wine and food, Umbria jazz festival, the wonderful Trasimeno beaches, and much more...  …see more

18 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £49 /night

£340 - £526 / week

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Key info:

  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
Appartamento rustico con travi e cotto nel centro città etrusca di Cortona con complementi d'arredo e rifiniture in ceramica dipinta a mano. A due passi dalla struttura si ammira il panorama sulla Valdichiana e il lago Trasimeno raggiungibile in 15 minuti. Presente nell'appartamento la tv, il wifi, la lavatrice, lettino bebè a richiesta, ampia doccia  …see more

13 Photos

Villa | 5 Bedrooms | sleeps 12

3 Nights min stay

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from £139 /night

£971 - £2303 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Vivete un'esperienza a contatto con la natura ma con tutti i confort della vita moderna.  …see more

5 Photos

Apartment | 2 Bedrooms | sleeps 4

Short stays welcome

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from £49 /night

£340 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Sito nel centro storico di cortona 2camere matrimoniali Assisi siena perugiafirenze lago trasimeno  …see more

14 Photos

Farmhouse | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £53 /night

£365 - £458 / week

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Key info:

  • Nearest beach 10 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
I 2 appartamenti, Magnolia e Mimosa, sono l' ideale per famiglie e gruppi di amici, ideale come punto di partenza per visitare, a breve distanza, splendidi luoghi e città come: Cortona, Lago Trasimeno, Arezzo, Perugia, Assisi, Siena,Val d'orcia. tutti i servizi vicini Giardino relax ombreggiato attrezzato per giochi all'aperto (ping pong, freccette, casetta per bambini)  …see more

24 Photos

Villa | 10 Bedrooms | sleeps 20

7 Nights min stay

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from £779 /night

£5451 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Raggiungibile a piedi da Cortona. Villa per affitto settimanale a Cortona in Toscana con campo da tennis privato e piscina privata Speciale Villa a Cortona per matrimoni. Villa in Toscana per riunioni di Famiglia. Villa walking distance da cortona Piscina privata Campo da tennis privato Distanza a piedi da Cortona  …see more

21 Photos

Hotel apartment | 9 Bedrooms | sleeps 25

Short stays welcome

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from £61 /night

£424 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Borgo Elena, complesso residenziale di sette Appartamenti in collina a 5 minuti di macchina da cortona con piscina in comune ampio spazio esterno bbq, ombrelloni, sdraio, prato in piscina Appartamenti di varie grandezze da 45 metri quadrati a 90 metri quadrati, automobile necessaria  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

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from £55 /night

£382 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Casa singola appena ristrutturata, conservando le caratteristiche della casa toscana; pavimenti in cotto, soffitti con travi in legno e mattoni a vista, ampio parco fruibile con attrezzature da giardino, piscina adatta a bambini. disponibile lettino bebè; bici gratis  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £67 /night

£463 - £1005 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • No pets allowed
During the day besides going for a swim in the pool, basking in the sun and reading a good book in the shade of a nearby grove, you will be able to take a tour of a our farm consisting of woods, tilled land, lawns, ponds, olive groves, vineyards, vegetable gardens, orchards, a chicken farm and a small flock of sheep.  …see more

18 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £49 /night

£339 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
L'arredo della casa è semplice, per non alterare l'atmosfera delle antiche case di campagna, ma molto curato. Gode di due giardini privati, uno sul davanti, di circa 400 metri quadri con una pergola e un antico forno a legna, l'altro sul retro di circa 1000 metriquadri. Parcheggio privato. La struttura è adatta a famiglie con bambini ai quali possono essere forniti lettini.  …see more

12 Photos

Farmhouse | 6 Bedrooms | sleeps 16

2 Nights min stay

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from £55 /night

£382 - £1866 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Novole is a group of houses nestled in the green hills on the border between Umbria and Tuscany Novole offers easy access to the nearby towns of Arezzo, Siena, Florence, Montepulciano, San Gimignano and Perugia, and it is only 15 km away from Lake Trasimeno.  …see more

24 Photos

B&B | 2 Bedrooms | sleeps 7

Excellent 5/5 

1 night min stay

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from £55 /night

£382 - £976 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
Casa in campagna; Vacanze; Toscana; Cortona; Relax; Piscina; Agriturismo; Firenze; Siena; Umbria; Lago Trasimeno; Montepulciano; Pienza; Assisi; Valdichiana; Valdorcia; bed and breakfast; La struttura è situata a poche centinaia di metri dall'uscita della superstrada e 8 km da Cortona.  …see more

8 Photos

House | 6 Bedrooms | sleeps 6

Very Good 4/5 

Short stays welcome

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from £122 /night

£848 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • Private garden
-  …see more

7 Photos

Apartment | 1 Bedroom | sleeps 4

Min stay varies

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from £103 /night

£721 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
'Vecchio Frantoio' is only a five minute drive from the medieval hilltop town of Cortona. The main A1 motorway is a fifteen minute drive from the apartment and the mainline train station is only a five minute drive away.  …see more

13 Photos

B&B | 3 Bedrooms | sleeps 7

Min stay varies

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from £146 /night

£1018 / week

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Key info:

  • Nearest beach 15 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Per chi vuole soggiornare in mezzo al verde, ma vivere anche Cortona ( raggiungibile in tre minuti d'auto), per chi vuol sentirsi avvolti dal passato ma coi confort di oggi, per chi sceglie il rispetto per l'ambiente e l'ecosostenibilità...per chi vuol farsi coccolare. La posizione strategica del B&B vi permette di visitare Arezzo, Siena, Pienza Montepulciano, Assisi, Spello  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 2

Min stay varies

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from £50 /night

£350 - £635 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Apartment with private terrace and splendid pool with jacuzzi set in gardens with shady arbours. Lovely views across the fields to the hills. Short walk to shops, bars and restaurants. Near Cortona and Lake Trasimeno. Ideal for Assisi and Perugia as well as Tuscany.  …see more

16 Photos

Villa | 8 Bedrooms | sleeps 14

Min stay varies

Add to shortlist

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
The villa is composed of 2 buildings. Main building: ground floor: with dining room, kitchen, bathroom and 3 bedrooms. I° floor: with dining room, kitchen, bathroom and 3 bedrooms. II° building: small house with 2 bedrooms, bathrooms, dining room, living room  …see more

21 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £195 /night

£1360 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Tuscany property in a village with swimming pool and garden close to Cortona , Montepulciano and the Wine valley. one hour from Florence and two hours from Rome.  …see more

18 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £275 /night

£1920 / week

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Key info:

  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
The Sole is a beautiful farmhouse in Tuscan bricks situated in the flat Cortona countryside, within there is a property of around 5000sq. mt. with an entirely enclosed garden with its own automatic gate electric controlled.. Cortona is a small charming town in the Valdichiana, or Chiana Valley, in the province of Arezzo in southern  …see more

16 Photos

Villa | 5 Bedrooms | sleeps 12

Min stay varies

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from £354 /night

£2475 - £3765 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Villa Torre degli Elci is set in the greens of the Tuscan countryside, midst olives and cypress trees and just 4 km from Cortona. The name of the Villa derives from the old sighting tower which has testimonials from 13th and 14th century and which became a monastery  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 16

Excellent 5/5 

Min stay varies

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from £300 /night

£2100 - £3700 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Villa Ruffignano is a luxury property, recently reconstructed respecting the traditional characteristics combined with the necessities of modern life.  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

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from £307 /night

£2145 - £3860 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Lovingly restored in 2004 Villa Orlando sleeps 8 people comfortably with four bedrooms, all with en-suite bathrooms with showers. This villa is perfect for families or groups that like to spend time enjoying the outdoors.  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

Min stay varies

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from £287 /night

£2003 - £2940 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
This charming old villa inserted in the enchanting setting of the typical chiana valley Tuscan landscape, Villa Salcotto lies at the foot of the hill of Cortona, a delightful town whose Etruscan origins left it with a still very conspicuous archaeological heritage  …see more