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270 Holiday homes in Cortona

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270 Results  |  
19 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £63 /night

£440 - £956 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

15 Photos

Guest house | 2 Bedrooms | sleeps 3

Short stays welcome

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from £56 /night

£388 - £646 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
This place and the atmosphere will be the ideal ingredients to spend a peaceful and relaxing holiday immersed in the Tuscan countryside and at the same time to visit the most beautiful cities of historical and cultural interest and gastronomic center of Italy.  …see more

7 Photos

Villa | 9 Bedrooms | sleeps 18

Min stay varies

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from £700 /night

£4900 - £5880 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Private Villa in Cortona Area, Near Montepulciano, Tuscany, Italy. Private Swimming Pool, sleeps 18. Beautiful gardens, green grass all year. Multiple family accommodation. Broadband, TV, DVD, iPod docks, table-tennis, bikes.  …see more

Featured properties

12 Photos

Hotel apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £173 /night

£1210 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Appartamento in Leopoldina nel cuore della Valdichiana - Cortona AR con giardino privato, piscina privata campi da tennis e calcetto  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 3

Min stay varies

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from £52 /night

£363 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
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

18 Photos

Farmhouse | 3 Bedrooms | sleeps 6

Min stay varies

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from £46 /night

£322 / week

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Key info:

  • Great 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

21 Photos

Hotel apartment | 9 Bedrooms | sleeps 25

Min stay varies

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from £58 /night

£404 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great 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

5 Photos

Apartment | 2 Bedrooms | sleeps 4

Min stay varies

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from £47 /night

£323 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Sito nel centro storico di cortona 2camere matrimoniali Assisi siena perugiafirenze lago trasimeno  …see more

24 Photos

Villa | 10 Bedrooms | sleeps 20

Min stay varies

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from £741 /night

£5184 / 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

9 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £259 /night

£1807 / week

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Key info:

  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner
Loft esclusivo, situato nel centro storico di Cortona. Il lusso e la cura dei dettagli offerti, faranno vivere la vacanza in completo relax.  …see more

24 Photos

House | 1 Bedroom | sleeps 2

3 Nights min stay

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from £182 /night

£1271 / week

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Key info:

  • Nearest beach 25 km
  • Swimming pool
  • Ask owner if suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa et jardin de style contemporain idéalement situés.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

Min stay varies

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from £173 /night

£1210 - £2420 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
La posizione è ideale per chi desidera visitare, con brevi spostamenti, le due regioni dell'Italia centrale Toscana ed Umbria trovandosi Cortona sulla linea principale delle strade a scorrimento veloce come l'Autostrada A1 e la superstrada Siena-Perugia. tranquillità e pace sono le principali prerogative di una vacanza nella nostra casa  …see more

19 Photos

House | 1 Bedroom | sleeps 3

Min stay varies

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from £57 /night

£396 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Appartamento in agriturismo: casa unica appena ristrutturata con comodi servizi, immersa nel parco e adiacente alla piscina. ortaggi, olio extra vergine e vinsanto di produzione della casa  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £202 /night

£1412 / week

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Key info:

  • Ask owner if suitable for children
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
Per trascorrere la tua vacanza con stile, nelle meravigliose colline toscane, questa proprietà offre 2 camere da letto e ogni servizio che può rendere unico il soggiorno. I principali servizi a pagamento sono: personal chef service, chauffeur service.  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 15

Short stays welcome

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from £343 /night

£2400 - £2900 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Beautiful farmhouse at the foot of Cortona,surrounded by 7000sqm of land cultivated with olive and fruit trees. Located in the village of Pergo, famous for its prestigious villas and farmhouses of which is scattered and of which it is part.  …see more

5 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £58 /night

£404 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
agriturismo cortona teccognano beppe toscana cucina tipica Wi fi piscina  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £381 /night

£2662 - £4194 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
An unforgettable vacation in Cortona, in a splendid luxury villa with all comforts and facilieties. Luxury villa with swimming pool and air conditioned in Corton  …see more

25 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £319 /night

£2228 - £3428 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The Villa is placed in the beautiful and striking Tuscan countryside, surrounded by olive trees and vineyard:the perfect setting to indulge in the colours and scents of our valley for a complete relaxation and comfort with breathtaking views, only 400mt far from Cortona  …see more

16 Photos

Apartment | 1 Bedroom | sleeps 2

Very Good 4.5/5 

5 Nights min stay

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from £50 /night

£350 / week

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Key info:

  • Nearest beach 7 km
  • Not suitable for children
  • Car essential
  • No pets allowed
  • Private garden
Fifteen minutes walk to Cortona on a private path with exceptional views, the stone-house is secluded, and restored and furnished with taste. Surrounded by garden terraces on various levels, and well provided with garden furniture for outdoor meals and relaxation. SEPTEMBER OFFER: £250 for 5 or 7 nights. Gourmet-meals under request.  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

7 Nights min stay

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from £196 /night

£1372 - £1847 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Le Contesse sleeps 6+2 people in three bedrooms with three bathrooms and another four people in two annexes (Serenella & Limonaia), each with it's own living room, kitchenette bathroom and bedroom.  …see more

21 Photos

Villa | 1 Bedroom | sleeps 2

Excellent 5/5 

7 Nights min stay

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from £115 /night

£805 - £1059 / week

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Key info:

  • Nearest beach 14 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Why have so many people fallen in love with the charm of Cortona? Although the central area of this lovely and ancient city is well known to many, there remains the secret and ever-so-charming quarter where this hidden gem will inspire and charm you.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 16

Excellent 5/5 

4 Nights min stay

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from £300 /night

£2100 - £3700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Ruffignano is a luxury property, recently reconstructed respecting the traditional characteristics combined with the necessities of modern life.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

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from £97 /night

£678 - £721 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Casa Astrale is a lovely apartment providing a perfect base to explore southern Tuscany and Umbria. With its exclusive pool, very large gardens and , the ability to walk or cycle along the lake Trasimeno -  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £142 /night

£992 - £1815 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Your very own piece of medieval Cortona! Gracious living in this superbly equipped, spacious "home from home" at the pedestianised heart of town. Enjoy a welcome retreat from the rigours of your day's sightseeing, before an evening of fine dining and quality shopping. Cortona continues to host immunerable weddings in its medieval town hall, with the famous photogenic steps!  …see more

21 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £98 /night

£686 - £1412 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
A tranquil haven in which to recharge your batteries. Poolside relaxation with cultural visits. Great hill walking at the summit of Tuscany's toughest cycling hill climb. All this from our family friendly cottage-style apartment set high above the Tiber valley. Good sightseeing and great restaurants at nearby Cortona. An hour's drive from Perugia, Arezzo and Assisi.  …see more

18 Photos

Villa | 6 Bedrooms | sleeps 16

Excellent 5/5 

4 Nights min stay

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from £108 /night

£750 - £2218 / week

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Key info:

  • Swimming pool
  • Great 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 | 4 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £100 /night

£699 - £2199 / week

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Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautiful 800 year-old hilltop villa with stunning views , 4 bedrooms (sleeps 10) and private 12m x 6m pool. On border of Tuscany and Umbria, perfect for exploring local area. Fully restored, the house exudes character. ideal for large groups and families.  …see more

24 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £64 /night

£444 - £621 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
"Il Villino di Cortona", is a cozy house nestled in the heart of val di chiana: in an area rich in history and cultural attractions. Tuscany holiday house. (exclusive use property, house, pool, garden). The veranda is ideal to enjoy a rich and tasty breakfast, or to immerse yourself in the reading a good book.  …see more

14 Photos

Villa | 7 Bedrooms | sleeps 24

Excellent 5/5 

3 Nights min stay

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from £53 /night

£371 / week

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Key info:

  • Nearest beach 250 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Nobile is a stunning 19th Century classical villa recently restored farmhouse authentically and with artistic charm, with a private pool 13 m x 6 m. Sitting in 4 acres of natural Tuscan rural land & a private avenue of young cypresses bringing you to our doorstep. Private, Tranquil, Perfect for large get togethers or for small families. Perfect for Children of all ages  …see more

22 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

1 night min stay

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from £242 /night

£1694 - £2259 / week

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Key info:

  • Nearest beach 180 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Tuscany property in a old village with swimming pool and garden close to Cortona , Montepulciano and the Wine valley. one hour from Florence and two hours from Rome. 30 minutes from the highway and 10 from the train station.  …see more

21 Photos

Farmhouse | 5 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £196 /night

£1371 - £2783 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This charming Tuscan Farmhouse with a new salt water pool is ideal for family holidays as it is tucked away in a large garden in lovely, unspoilt Southern Tuscany near the Etruscan hill town of Cortona, amongst olive groves and sunflower fields.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £104 /night

£726 - £2017 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Charming villa with private pool near Cortona and lake Trasimeno  …see more

15 Photos

Apartment | 4 Bedrooms | sleeps 5

Excellent 5/5 

7 Nights min stay

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from £126 /night

£880 - £1012 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
This lovely apartment is available for a minimum of 4 nights. A perfect location in the heart of Cortona and, a great base to explore many of Tuscany's and Umbria's famous towns, vineyards and stunning countryside.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

7 Nights min stay

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from £167 /night

£1166 - £2279 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
For those who enjoy privacy, this beautifully restored traditional Tuscan farm house offers the opportunity experience real Tuscan living.  …see more

21 Photos

Villa | 4 Bedrooms | sleeps 7

Excellent 5/5 

7 Nights min stay

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from £220 /night

£1534 - £2156 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This is a place to enjoy an authentic Tuscan experience. Close to the historic town of Cortona and set in acres of olives and pastures - this beautiful 17th century newly renovated Mill House with private pool has been painstakingly restored.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £287 /night

£2009 - £2380 / week

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Key info:

  • Nearest beach 26 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
The Villa is set along a sun soaked hill where the garden extends into pretty olive groves and vineyards.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £135 /night

£944 - £2936 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Characteristic farmhouse near Cortona in Tuscany immersed in large private gardens, situated at the foot of the ancient town of Cortona.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

Good 3/5 

4 Nights min stay

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from £132 /night

£924 - £1730 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • 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

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £493 /night

£3445 - £4550 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden

Cortona Tuscan Villa with pool- rural views and two independent annexes within walking distance of the medieval walled town of Cortona.

 …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £67 /night

£468 - £565 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Apartment Roland is a fun and stylish and inexpensive home set in the foothills of Cortona are two individual and lovely properties with spacious gardens, magnificent private pool, tennis court and many wonderful features.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £217 /night

£1513 - £2380 / week

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Key info:

  • Nearest beach 135 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Situated on a hillside and surrounded by the vineyards of a famous local wine producing farm, Villa Al Pozzo is the ideal place to spend a holiday in complete relaxation and tranquility. Independent villa of about 400 square meters that can accommodate up to 12 people.  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £220 /night

£1540 - £1867 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 3 bedrooms sleeps 6  …see more

18 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £218 /night

£1521 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartment Gelsiminoandnbsp;is located in an antique palace near the town of Cortona build in 1600 and provides an ideal setting for a holiday in Tuscany countryside.andnbsp; The apartment can comfortable accommodateandnbsp;6 guests, it has two entries and own garden  …see more

17 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £55 /night

£380 - £450 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Casa Severina is a characteristic apartment. It sleeps four people. From Casa Severina you will have a partial view of Piazza della Repubblica (Republic Square). Casa Severina is 65 square meters (700 square feet)  …see more

20 Photos

Farmhouse | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £572 /night

£4000 - £6775 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Restored to high standard. Accommodation split in two private buildings. Ideal location between South Tuscany and Umbria. Private tennis court.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 15

7 Nights min stay

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from £169 /night

£1177 - £2452 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This secluded Cortona farmhouse for 15 people is perfect for families and friends. Situated in the Tuscan province of Arezzo, this villa boasts a magnificent swimming pool.  …see more

14 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £133 /night

£927 - £1947 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Only a few minutes from the proud and ancient hill town of Cortona, lays the tiny hamlet of Pergo. A dirt road leads you to this spacious holiday house, surrounded by well-kept lawns, olive groves and a mixed vegetation of trees and rose bushes. The living room, with...  …see more

14 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £160 /night

£1120 - £1600 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Pets welcome
  • Private garden

Tucked away in the blissful rolling countryside on the edge of Cortona, this stone cottage with its private pool is a delightful hideaway for a coupleseeking to experience the best of Tuscany and Umbria.

 …see more

13 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £80 /night

£557 - £670 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa August' provides a good value family holiday in Tuscany, Cortona. With its huge swimming pool, tennis court, barbecues and lots of space both inside and out, this is a perfect for young/teenage families to enjoy the area.  …see more

16 Photos

Villa | 5 Bedrooms | sleeps 12

4 Nights min stay

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from £300 /night

£2100 - £3954 / week

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Key info:

  • Swimming pool
  • Great 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

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