Cycling holiday villas and apartments Cortona | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona
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  • Bagnolo (2)
  • Capezzine (2)
  • Cegliolo (4)
  • Centoia (6)
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  • Fratta Santa Caterina (9)
  • Fratticciola (1)
  • Mercatale di Cortona (6)
  • Montalla (4)
  • Montanare (5)
  • Montecchio (10)
  • Pietraia (1)
  • Poggioni (1)
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  • Teverina (2)

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197 Holiday homes

Filters applied: Cycling holidays (197)

1 / 89

Querce/luxury. Private village. Sleeps 5 - Montecchio house sleeps 5

Cortona / Montecchio

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
QUERCE COTTAGE is one of two dwellings in a large cottage, overlooking the private village, Garden Of Eden, the hills, dales, olive groves and vineyards as the vista spirals into a haze of greens, dotted with colours, an infinity of brightly coloured patchwork, against  …see more

from £20 / night

£135 - £941 / week

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from £20 / night

1 / 13

Cortona / Montecchio

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Child friendly ; Pet friendly;
 …see more

from £127 / night

£889 - £1556 / week

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from £127 / night

(1) Very Good 

1 / 22

Villino Laura - Montecchio villa sleeps 4

Cortona / Montecchio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 155 km; Swimming pool; Child friendly ;
Villino Laura is an old mill immersed in the picturesque green Tuscan countryside only few kilometres from Cortona and has been completely restored maintaining its original charm. The furnishing of this property makes it one of a kind for its class, due to its precious  …see more

from £134 / night

£778 - £1112 / week

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from £134 / night

1 / 84

Fienile/luxury. Private village. Sleeps 5 - Montecchio house sleeps 5

Cortona / Montecchio

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Fienile Cottage is a cute detached cottage, situated in its own private garden, with sensational views of olive groves, vineyards, meadows full of sunflowers, poppies and purple cornflowers, spiralling infinitely into the valleys below. It has 1 double bedroom + 1 singl  …see more

from £116 / night

£812 - £941 / week

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from £116 / night

(12) Excellent 

1 / 21

Rustic Tuscan farmhouse in the town of Cortona with gorgeous views, swimming pool, private garden and barbecue - Cortona farmhouse sleeps 8

Province of Arezzo / Cortona

5 8 7 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 20 km; Swimming pool;
This charming Tuscan Farmhouse is set in a lovely, unspoilt region near the Etruscan hill town of Cortona, amongst olive groves and sunflower fields. Casa Al Campo has 2 acres of unfenced land including its own private vineyard, two terraces and plenty of shaded seating  …see more

from £212 / night

£1479 - £3248 / week

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from £212 / night

1 / 10

Grecale - PI2012_226 - Cortona apartment sleeps 3

Province of Arezzo / Cortona

1 3 7 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 7 nights min stay
Key info: Nearest beach 140 km; Swimming pool; Child friendly ;
Grecale is a part of the beautiful apartment complex, Poggio al Vento. The apartments are located in the same farmstead, which has been tastefully renovated to retain much of the original character and features. Ideal for a couple or a family, the apartments retain a wa  …see more

from £55 / night

£385 - £677 / week

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from £55 / night

(2) Very Good 

1 / 59

Charming 2 bedroom apartment in restored Tuscan farmhouse with pool located in historic Cortona - Centoia apartment sleeps 5

Cortona / Centoia

2 5 4 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 118 km; Swimming pool;
La Lombarda is our charmingly restored traditional 18th century Tuscan farmhouse. La Stufa is a charming two bedroom apartment with wood-beamed ceilings and terracotta floors. There is a comfortable sofa and two armchairs in the lounge, TV, DVD, books, games and videos  …see more

from £95 / night

£646 - £748 / week

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from £95 / night

1 / 21

Peschino - Teverina villa sleeps 12

Cortona / Teverina

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
Casa Peschino sits on the lower slopes of a quiet side valley, with stunning and extensive views over the green countryside of woods, vineyards, olive groves and farmland. It is reached by a short track through fields of sunflowers, wild flowers, maize and tobacco plant  …see more

from £246 / night

£1720 - £2708 / week

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from £246 / night

1 / 7

LA TESA Olivo - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Child friendly ; Air conditioning; Pet friendly;
You will find 4 spacious apartments for your stay in Cortona, bright and comfortable and an outbuilding between the olive trees.Farmhouse La Tesa is the best that a country house can give you for your holiday in the heart of Tuscany. You will experience a rejuvenating e  …see more

from £35 / night

£471 / week

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from £35 / night

1 / 18

Rustic two bedroom Tuscan apartment close to Cortona's main square, wifi and parking available - Cortona apartment sleeps 2

Province of Arezzo / Cortona

2 2 1 night min stay

  • 2 bedrooms
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 20 km; Ask owner if suitable for children;
Quintani Sole - central apartmentApartment for 2 person and 1/2, compose by one bedroom + lounge with kitchen + 2 bathroom. WIFI, TV led, microwave, washing machine, toaster, kettle. Central position, near public parking and restaurants. Only 3 minute from main square a  …see more

from £69 / night

£428 / week

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from £69 / night

1 / 8

La Tesa Girasole - Farinaio apartment sleeps 4

Cortona / Farinaio

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
The apartment Girasole is situated on the ground floor and it has a separate entrance. It consists of: a living room, a kitchen, two bedrooms, two bathrooms with shower and independent heating.Apartment cleaning, detergents and waste:We use non-toxic cleaning products a  …see more

from £35 / night

£684 / week

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from £35 / night

1 / 55

Casa dei Colori - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Ask owner if suitable for children; No pets allowed;
The apartment consists of living room with a convertible sofa-bed, kitchen, bathroom with shower, bidet, sink and toilette connected to a separate room with washer machine. Bedroom with queen size bed and wardrobe/closet. The house has been completely renovated in 2011,  …see more

from £71 / night

£428 - £753 / week

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from £71 / night

1 / 12

Quintani Luna - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 20 km; Ask owner if suitable for children;
QUINTANI LUNAApartment for 2 person, compose by one bedroom + kitchen + 1 bathroom with shower. WIFI, TV, microwave, washing machine, toaster, kettle. Central position, near public parking and restaurants. Only 3 minute from main square and grocery.THE HISTORICAL BUILD  …see more

from £69 / night

£428 / week

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from £69 / night

1 / 9

Il Borgo Agritourism - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car not necessary;
The il Borgo Agritourism Complex is near the historic Etruscan city of Cortona. It is in a beautiful country setting amongst olive trees, cypresses and sunflowers in the Chiana Valley. There is a spacious garden and a communal swimming pool. The agritourism complex is e  …see more

from £171 / night

£1026 / week

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from £171 / night

1 / 12

appartment in old court yard in Cortona, Arezzo - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
nice apartment made of hall with sofa bed, kitchen with dishwasher micro wave and electric oven, washing machine, one bed-room and bathroom with shower and air conditioning system. The apartment is part of an ancient court yard among Tuscany's hills. The property i  …see more

from £52 / night

£342 / week

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from £52 / night

(11) Excellent 

1 / 35

Villa Nobile is a stunning 19th Century Villa - Cortona villa sleeps 24

Province of Arezzo / Cortona

7 24 3 nights min stay

  • 7 bedrooms
  • Sleeps 24
  • 3 nights min stay
Key info: Nearest beach 250 km; Swimming pool; Child friendly ;
Villa Nobile is a stunning 19th Century classical style villa recently restored 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. Tran  …see more

from £65 / night

£471 / week

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from £65 / night

1 / 4

Province of Arezzo / Cortona

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £60 / night

£385 / week

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from £60 / night

(1) Excellent 

1 / 24

Il Moro Novo - Montalla apartment sleeps 3

Cortona / Montalla

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Equipped with chairs, shades, and beach beds.It has been restored with respect for the original stile and all the furniture are antique, you will have a warm and relaxing feeling when you enter Il Moro Novo.The house is located just outside a small country village, so i  …see more

from £60 / night

£314 - £593 / week

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from £60 / night

1 / 27

Sopra di Brena - Teverina farmhouse sleeps 8

Cortona / Teverina

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Sopra di Brena is located in San Pietro a Dame, about 20 kms from Cortona. The villa is an old restored farmhouse which enjoys stunning, panoramic views. It is surrounded by vinyards (around 1,350 Pinot Nero vines), which have been producing a highly-prized wine since  …see more

from £175 / night

£1223 - £1590 / week

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from £175 / night

1 / 16

Tuscan hideaway: charming rural villa with pool and spectacular views, sleeps 4 - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
A special hide-away in Tuscany ! Casa Serena is a really charming little house/villa is set in the middle of olive grove and surrounded Tuscan woodland, and provides privacy and serenity for a truly relaxing vacation. During Autumn and winter, there are the spectacular  …see more

from £93 / night

£648 - £977 / week

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from £93 / night

(27) Excellent 

1 / 33

Under the Tuscan Sun - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Child friendly ; No pets allowed;
This charming apartment, made of stones, consists of bedroom with queen size bed and a big wardrobe/closet, living room with a convertible sofa-bed and a breath taking view of the Val di Chiana Valley, full kitchen with dish washer, breakfast table and the same beautifu  …see more

from £77 / night

£428 - £653 / week

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from £77 / night

(5) Very Good 

1 / 44

La Mimosa at La Lombarda - Centoia apartment sleeps 3

Cortona / Centoia

1 3 4 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 118 km; Swimming pool;
La Lombarda, our beautifully restored traditional 18th century Tuscan farmhouse is ideally placed within easy reach of Tuscany and Umbria's wealth of art and cultural centres. Cortona, nestling in its hillside just 20 minutes away, with its medieval cobbled lanes i  …see more

from £65 / night

£428 - £471 / week

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from £65 / night

1 / 24

"Il Palazzolo" casa vacanze Mercatale di Cortona - Mercatale di Cortona farmhouse sleeps 10

Cortona / Mercatale di Cortona

4 10 7 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
“Il Palazzolo” is beautifully situated on the border between Tuscany and Umbria, on the road that connects Cortona to Perugia.Originally An ancient monastry, at the end of the 16th century under the Laurenzi family it became a manor house and around about 1750 after  …see more

from £232 / night

£1624 / week

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from £232 / night

1 / 23

Cortona / Fratta Santa Caterina

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
 …see more

from £171 / night

£1283 / week

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from £171 / night

1 / 16

Province of Arezzo / Cortona

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 10 km; Child friendly ;
 …see more

from £56 / night

£368 - £428 / week

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from £56 / night

(1) Excellent 

1 / 83

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 18 km; Swimming pool; Child friendly ;
 …see more

from £86 / night

£513 - £838 / week

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from £86 / night

(1) Excellent 

1 / 10

ETRUSCA - Cortona apartment sleeps 3

Province of Arezzo / Cortona

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Child friendly ; Pet friendly;
Dopo il positivo riscontro per le Mura Etrusche, Gian Luca e Lucia hanno il piacere di proporvi una nuova struttura, Etrusca.La casa, situata nel centro storico di Cortona, lungo Via Nazionale detta "Ruga Piana", strada principale, che unisce Piazza della  …see more

from £79 / night

£556 / week

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from £79 / night

(1) Excellent 

1 / 14

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £112 / night

£389 - £569 / week

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from £112 / night

1 / 18

GLI ARCHI - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Not suitable for children; Car essential;
It 'a beautiful cottage completely restored, was once a barn and a tobacco warehouse. now has 2 bedrooms, a lounge, a kitchen, 2 bathrooms and a dining room that can become an extraordinary study. It has a swimming pool, a large garden, a bocce court, private parki  …see more

from £69 / night

£855 - £1197 / week

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from £69 / night

1 / 7

Casale del Gabbiano - large villa near Cortona - Centoia villa sleeps 18

Cortona / Centoia

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
Large villa and guest house set in one of the Tuscany's most sought after areas. Wake up each morning to some truly stunning views across Tuscany - some of the best in the region. Relax by the pool with a cool drink, looking over the valley to Montepulciano. Set am  …see more

from £700 / night

£4900 / week

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from £700 / night

(30) Excellent 

1 / 21

Tuscan Villa. Borgo Valecchie. Cortona - Montanare villa sleeps 10

Cortona / Montanare

4 10 5 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min stay
Key info: Nearest beach 180 km; Swimming pool; Child friendly ;
Our villa offers an ideal combination of elegant simplicity and historical charm which create a unique experience and can comfortably accommodate up to 10 guests. Located just five minutes away from The Hill town Cortona. Along with a private swimming pool, this holida  …see more

from £201 / night

£1411 - £2522 / week

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from £201 / night

1 / 19

Wonderful traditional Tuscan a - Cortona apartment sleeps 6

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car not necessary;
'Vecchio Frantoio' is a bright and spacious air-conditioned two-bedroom apartment reconstructed from an ancient olive mill. Chestnut beams, terracotta tiles and antique stone all in the Tuscan manner add to the character of this comfortable and beautiful apart  …see more

from £120 / night

£770 - £1018 / week

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from £120 / night

1 / 16

Casina Vereno - Bagnolo villa sleeps 4

Cortona / Bagnolo

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
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. The property, with privat  …see more

from £149 / night

£1039 - £1406 / week

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from £149 / night

(1) Excellent 

1 / 12

Large Tuscan farmhouse apartment in beautiful Cortona countryside, four bedrooms, pool access - Cortona farmhouse sleeps 6

Province of Arezzo / Cortona

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
The apartment is independent, and has beautiful piece of ancient furniture own heating system, some of them has a fire-place. This has a own outside space and very well fitted out with garden furniture, all equipped with every thing necessary to be efficient and functi  …see more

Pricing unknown

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(2) Excellent 

1 / 10

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Child friendly ; No pets allowed; Private garden;
 …see more

from £77 / night

£513 - £1048 / week

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from £77 / night

(3) Very Good 

1 / 42

La Bozza , country apartment with private garden - Montalla apartment sleeps 8

Cortona / Montalla

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 200 km; Swimming pool; Child friendly ;
Started officially as a busines in 1994 but with previous experience of property rental in the precedent 10 years, Agriturismo Fontelunga is now a reference poit for those searching for a true Tuscan experience.W own same of the nicest accommodation in the traditional  …see more

from £137 / night

£730 - £1393 / week

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from £137 / night

(3) Excellent 

1 / 30

Poggiobello - Cortona cottage sleeps 5

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
The cottage is immersed in the splendid countryside with breathtaking views all around. It is surrounded by the lovelyundulating hills covered with sunflowers, olive groves and cypresses, you will find yourself totally immersed in an enchanted atmosphere frozen in time.  …see more

Pricing unknown

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1 / 17

Province of Arezzo / Cortona

2 6 3 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 10 km; Child friendly ;
 …see more

from £65 / night

£436 - £496 / week

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from £65 / night

1 / 24

Villa Margherita Tre - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
Located in a true oasis of peace and tranquillity, Villa Margherita Tre is a sweet indipendent villa with private pool offering breathtaking views over the hills surrounding the sought after town of Cortona as well as unbeatable value for money. With 2 bedrooms, 2 bathr  …see more

from £35 / night

£240 - £1036 / week

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from £35 / night

1 / 11

Beautiful four bedroom Tuscan villa with private pool and garden - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
Fonte Vecchia is a beautifully restored, spacious luxury Tuscany villa for rent with a dramatic watch tower, lying among gentle hills enjoying views unchanged for centuries. Centuries ago, when the church was the significant power in this area, most of the local nobili  …see more

from £328 / night

£2295 - £4195 / week

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from £328 / night

Top Destination reviews

To Stones
Amazing Home Away From Home

The best first impression was to be greeted late at night by Ester and her partner in the dark and in poor weather just so we could find a parking spot and get situated in the property. Ester was amazing and has gone to great lengths to ensure her ho … see more
villa ai cedri
A marvellous house with a beautiful panorama view

A beautiful house in a peaceful area with a wonderful view to the valley. There are lovely rooms with tasteful furniture. Although the owners live next door, they do not disturb at all, they are really friendly and helpful any time you need somethin … see more
Charming Cottage Near Cortona, Garden, AC,WiFI
A Gem in Tuscany

The information provided by Cesare at the time of booking was the best we've ever had! On arrival, we were greeted with a very helpful introduction to "our home for the week". It was great having a welcome gift of wine, some delicious home grown plum … see more
Stunning Tuscan villa with five bedrooms, private
A true TUSCAN experience. Better than words can describe.

It is quite a challenge to put into words a description of this place, the family and the amazing time we had at Vila Papale. The house and the entire property has so much history and character making this place a unforgettable experience. The garden … see more

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