50 Best Cortona Apartments on Holiday Lettings - Vacation rentals

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Cortona

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3,812 Vacation rentals

(1) Excellent 

36

Vacation villa with swimming pool in Cortona

Province of Arezzo / Cortona

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 19 mi
  • Swimming pool
  • Child friendly
General Description This luxury villa, surrounded by a gorgeous and impressive garden, has been recently restored with great care of details and with respect to Tuscan tradition. What a great location! The villa is ideally located close to village and services offering …see more

from $397 / night

$3,507 / week

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from $397 / night

(13) Excellent 

Certificate of Excellence

33

Vacation villa in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
With essential private pool and (Free) Wi-Fi, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vibrant Cortona. Couples love it, families love it. It is heaven. A two bedroom, two bathrooms, fully furnished beautiful p …see more

Certificate of Excellence

from $356 / night

$2,490 - $2,833 / week

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avg. 3 hours 37 minutes

from $356 / night

(8) Excellent 

Certificate of Excellence

46

Vacation apartment rental

Cortona / Centoia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 118 mi
  • 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 is a d …see more

Certificate of Excellence

from $93 / night

$620 - $837 / week

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avg. 3 hours 0 minutes

from $93 / night

(2) Excellent 

11

Vacation villa in Cortona

Province of Arezzo / Cortona

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Dardano is a deceptively large house, full of atmosphere. It is a simple country home, basic even, but with an elemental charm. You drive up to the house with its ancient stone well and to one side there's a little vine-covered area for shady outdoor eating. The garde …see more

from $169 / night

$1,177 - $2,590 / week

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from $169 / night

16

Bagnolo Vacation villa rental

Cortona / Bagnolo

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
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 private swi …see more

from $215 / night

$1,506 - $2,038 / week

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from $215 / night

(34) Excellent 

Certificate of Excellence

16

Cortona Vacation home rental

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 150 mi
  • Child friendly
  • Pet friendly
My cozy 3-floor house is placed on top of the Etruscan walls of Cortona, at the edge of the historic center, on a very quiet and characteristic street. It can accommodate up to 4 guests. I hope you will enjoy the stunning view on the valley beneath! Caratteristica casa …see more

Certificate of Excellence

from $93 / night

$533 - $1,004 / week

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avg. 2 hours 11 minutes

from $93 / night

(1) Excellent 

17

Vacation villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A luxury villa with private pool, Villa San Martino is set on a hill, high above the beautiful Niccone Valley on a quiet road, just 3 minutes from local village shops, restaurants and cafes. The position is a typically Tuscan, offering spectacular views from the house, …see more

from $440 / night

$3,080 / week

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from $440 / night

18

Cortona Vacation b&b rental

Province of Arezzo / Cortona

11 20 1 night min

  • 11 bedrooms
  • Sleeps 20
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
The torraiolo is a small and comfortable Bed and Breakfast with six delicious & rooms where you can sleep, rest and relax surrounded by the beautiful Tuscan countryside. Located beneath the walls of the ancient Etruscan town of Cortona – just 2 km from the Centre – the …see more

from $744 / night

$4,956 / week

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avg. 1 hour 32 minutes

from $744 / night

(3) Very Good 

60

Apartment accommodation in Centoia with shared pool

Cortona / Centoia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 118 mi
  • Swimming pool
La Lombarda is our charmingly restored traditional 18th century Tuscan farmhouse in the comune of Cortona. 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 …see more

from $137 / night

$930 - $1,487 / week

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avg. 3 hours 0 minutes

from $137 / night

30

Vacation apartment in Cortona

Province of Arezzo / Cortona

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
old stone house made from an old water mill overlooking the Tuscan countryside near Cortona. Large garden surrounding the house, quiet and renovated. Excellent starting point to visit Arezzo, Siena, Perugia and Florence. The house is on the ground floor and consists of …see more

from $93 / night

$484 - $657 / week

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from $93 / night

10

Cortona Vacation apartment rental

Province of Arezzo / Cortona

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 140 mi
  • Swimming pool
  • Child friendly
Grecale is a part of the beautiful apartment complex, Il Poggiolo. 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 warm, …see more

from $84 / night

$583 - $979 / week

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from $84 / night

(4) Excellent 

27

Cortona Vacation cottage rental

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The search for a warm and welcoming Tuscan abode is over. Cottage Cortona Roccaio is a stone-clad home adjoined to another occupied house on a small family estate encircled by olive groves. From here, the alluring hill towns of Tuscany and Umbria are within easy reach. …see more

from $173 / night

$1,206 / week

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avg. 2 hours 23 minutes

from $173 / night

(3) Very Good 

18

Vacation villa in Cortona

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 140 mi
  • Swimming pool
  • Child friendly
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. It nestles in the immediate out skirts of Cortona, one of the many …see more

from $266 / night

$1,859 - $2,838 / week

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from $266 / night

14

Vacation apartment in Cortona

Province of Arezzo / Cortona

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
“Le Gelosie apartments” are the natural and inviting alternative to our hospitality and combine good taste and attention for details. The materials, the colours and the spaces were studied to satisfy the esthetical pleasure along with the natural need for comfort. Th …see more

from $496 / night

$3,469 / week

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from $496 / night

(2) Excellent 

27

Vacation lodge in Cortona

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
The "Fattoria Borgonuovo" is located in an agricultural and hilly area of the Val di Chiana, very close to the beautiful and old town of Cortona, and a short distance from the most important historical and wine centers of the southern part of Tuscany, as, Montepulciano, …see more

from $81 / night

$558 - $806 / week

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avg. 3 hours 56 minutes

from $81 / night

24

Vacation home in Cortona

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Private garden
Villa Casale Girifalco, 16th century, is a charming country house, located on an extensive ground (nearly 5 hectares) with a stunning view of the Valdichiana valley. Perched on the terraced slopes of olive groves, it guarantees you complete privacy and tranquility, whil …see more

from $560 / night

$3,915 - $5,080 / week

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from $560 / night

(1) Excellent 

31

Villa rental in Cortona with swimming pool, golf nearby

Province of Arezzo / Cortona

3 11 3 nights min

  • 3 bedrooms
  • Sleeps 11
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
tipical old house, swimming pool, wifi, tv satelite,bbq, volley ball field, pétanque field, mini tennis field. beatiful wiew over the chiana valley. all the old charme of tuscany. 4bedroom, 4 bathroom Located in the village of Ossaia ( 3 km from Cortona), t …see more

from $372 / night

$2,478 / week

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from $372 / night

(7) Excellent 

Certificate of Excellence

30

Vacation home with swimming pool in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
A two bedroom, two bathrooms, fully furnished beautiful private house for your Tuscan holiday. Complete with the essential private sparkling pool and Wi-Fi connection, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vibr …see more

Certificate of Excellence

from $356 / night

$2,490 - $2,833 / week

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Responds fast!
avg. 3 hours 37 minutes

from $356 / night

(8) Excellent 

14

Vacation home in Mercatale di Cortona

Cortona / Mercatale di Cortona

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
Located in the heart of the Tuscan countryside, Borgo di Vagli is a quaint, meticulously restored 14th century Hamlet surrounded by a protected area of olive groves, fruit trees and ancient oaks. From the terraces, you can enjoy panoramic views of the breathtaking Tusca …see more

from $142 / night

$990 - $1,238 / week

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from $142 / night

35

Cortona Vacation villa rental

Province of Arezzo / Cortona

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Casa Fontelunga is a lovely country house placed in an enchanted location hillside, between our olive plantation and just a few minutes from the beautiful art city of Cortona, made famous worldwide from the book and movie 'Under the Tuscan Sun'. Privacy and quietness ar …see more

from $273 / night

$1,673 - $2,794 / week

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avg. 2 hours 12 minutes

from $273 / night

13

Apartment rental in Cortona

Province of Arezzo / Cortona

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
Lovely and intimate two-room apartment, La Finestra sulla Piazza is a welcoming property located in the heart of the characteristic town of Cortona. The living area is composed of a dining area and a pretty and simple kitchenette, which is characterised by two large win …see more

from $137 / night

$806 - $868 / week

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from $137 / night

(8) Very Good 

20

Vacation villa in Mercatale di Cortona

Cortona / Mercatale di Cortona

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 23 mi
  • Swimming pool
  • Child friendly
Casaccia is a beautiful medieval house on a hilltop with a large private pool and gardens offering incredible views. Fully refurbished, the villa offers 4 large bedrooms (sleeping up to 10), and three bathrooms, including a delightful cottage in the garden with its own …see more

from $170 / night

$1,189 - $3,079 / week

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from $170 / night

(40) Excellent 

35

Vacation villa rental

Cortona / Montanare

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 180 mi
  • 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 $310 / night

$2,416 - $3,655 / week

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Responds fast!
avg. 36 minutes

from $310 / night

(1) Excellent 

16

Cortona Vacation villa accommodation

Province of Arezzo / Cortona

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely small villa is located at 400 m from the charming town of Cortona, one of the most beautiful and renowned towns of Tuscany. An important Etruscan settlement, Cortona today is a medieval jewel on the side of a hill dominating the Val di Chiana. The villa, 65 …see more

from $146 / night

$1,016 - $1,487 / week

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Responds fast!
avg. 1 hour 47 minutes

from $146 / night

5

Home rental in Mercatale di Cortona with shared pool

Cortona / Mercatale di Cortona

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Casa Rancacci is a renovated farmhouse set among the rolling hills of Tuscany at the border with Umbria. Our structure is divided into three apartment equipped with full kitchen for cooking, color TV, bedroom, bathroom with shower. Outside each apartment has a private t …see more

from $44 / night

$744 / week

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from $44 / night

(1) Excellent 

44

Cortona Vacation villa rental

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Wonderful and elegant villa situated in a quiet position on the green hills which surround Cortona. The villa is situated within a large property and offers wonderful views on the surrounding countryside of Tuscany. The house is tastefully furnished and is …see more

from $199 / night

$1,388 - $2,726 / week

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from $199 / night

22

Vacation villa with swimming pool in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Name: PICCOLA BRAMASOLE Accommodation: Ville Location: CORTONA Sleep: 4 Bedrooms: 2 Bathrooms: 2 Description: This charming Tuscan, rustic stone Villa has maintained many of its authentic original features without compromising modern comfort. It is surrounded by ol …see more

from $415 / night

$2,900 - $4,510 / week

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from $415 / night

(3) Very Good 

42

Vacation apartment with shared pool in Montalla

Cortona / Montalla

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 200 mi
  • 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 traditio …see more

from $202 / night

$1,058 - $1,994 / week

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Responds fast!
avg. 2 hours 12 minutes

from $202 / night

(1) Excellent 

12

Vacation apartment with swimming pool in Mercatale di Cortona

Cortona / Mercatale di Cortona

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 12 mi
  • Swimming pool
  • Child friendly
If you take the road which follows the Tuscan-Umbrian border you come to Pierle, a medieval hamlet in the hills between Cortona and Lake Trasimeno, its castle dominating the verdant valley below. Here surrounded by olive groves and woodland of oaks and chestnuts, …see more

from $149 / night

$1,041 / week

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from $149 / night

8

Vacation home in Cortona

Province of Arezzo / Cortona

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Single house attached to the sides to other houses on two floors with large private garden is about 6 km from Cortona and 10 km from Lake Trasimeno with a strategic position for excursions in the province of Arezzo Perugia and Siena are nearby cycle paths to reach arezz …see more

from $87 / night

$558 / week

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from $87 / night

(10) Excellent 

18

Vacation apartment in Cortona

Province of Arezzo / Cortona

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Car not necessary
Ground floor apartment situated in the historical centre of the city of Cortona. It is located close to the main square and a few steps from the public parking with bus stop. The apartment is a studio apartment with large kitchen, bathroom, sofa bed in living area the t …see more

from $85 / night

$471 - $595 / week

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Responds fast!
avg. 1 hour 9 minutes

from $85 / night

30

Vacation home with swimming pool in Cortona

Province of Arezzo / Cortona

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Il Giardino di Silvana is a typical Tuscan stone house located on an evocative hilly position, a few steps away from the prestigious Santa Maria Nuova church and walk to town. The property preserves its rustic style with cotto flooring, wood beamed ceilings and Pietra …see more

from $266 / night

$1,859 - $3,098 / week

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from $266 / night

12

Vacation cottage with swimming pool in Cortona

Province of Arezzo / Cortona

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Col di Leccio is a beautiful property made up of two stone cottages which enjoy a wonderful hilly position, a few minutes from the medieval town Cortona. Each house consists of two floors which host a cosy siting room with sofa and tv, dining area, fully fitted kitchen, …see more

from $267 / night

$1,859 - $3,098 / week

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from $267 / night

24

Vacation villa rental

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Villa Fonte is located in an extraordinary panoramic position in the open countryside surrounded by olive trees and other typical Tuscan plants but within walking distance from the famous historical town of Cortona just 400 meters away. The perfect place for a holiday d …see more

from $593 / night

$4,151 - $6,443 / week

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from $593 / night

(3) Excellent 

10

Vacation apartment in Cortona

Province of Arezzo / Cortona

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Child friendly
  • Private garden
Wonderfully located only ten minutes walking from the city center of Cortona. From this property you will have one of the most beautiful views of the city, the valley and the lake Trasimeno.It is one apartment on the first floor of a villa, the owner live upstairs. The …see more

from $124 / night

$868 - $1,518 / week

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from $124 / night

(1) Excellent 

34

Vacation home in Cortona

Province of Arezzo / Cortona

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 9 mi
  • Child friendly
  • Pet friendly
House with an amazing view. You can eat outside enjoying the beauty of the Chiana Valley and Cortona, background on which stands the figure of Palazzone, princely villa of 1500 with its tower and its absolute privacy wall merlato.In, in silence, but at the same time nea …see more

from $123 / night

$859 - $1,232 / week

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from $123 / night

(14) Excellent 

Certificate of Excellence

38

Vacation cottage with swimming pool in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
A dream home just for you. We created our home in Cortona with all the essential mod cons. Music, kitchen, comfy beds, and of course with the essential pool and (Free) Wi-Fi. Villa Rosa is nestled into the Cortona (Tuscan) hillside with only a few minutes drive to …see more

Certificate of Excellence

from $356 / night

$2,490 - $2,833 / week

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Responds fast!
avg. 3 hours 37 minutes

from $356 / night

(4) Excellent 

Certificate of Excellence

34

Vacation villa with swimming pool in Cortona

Province of Arezzo / Cortona

6 15 3 nights min

  • 6 bedrooms
  • Sleeps 15
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Old Farmhouse "Agriturismo Henni" of 1800th totally renovated with antiseismic criteria in 2016, with swimming pool 6mt x 12mt, hydromassage and sauna with panoramic view. The building is situated upper the hill, around the house there is and olive grove, vineyard and w …see more

Certificate of Excellence

from $930 / night

$6,195 / week

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Responds fast!
avg. 3 hours 8 minutes

from $930 / night

(10) Excellent 

57

Vacation apartment in Centoia

Cortona / Centoia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 118 mi
  • 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 is a d …see more

from $106 / night

$682 - $899 / week

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Responds fast!
avg. 3 hours 0 minutes

from $106 / night

16

Cortona Vacation farmhouse rental

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Dive in the pool of a rental house in Tuscany! Nice villa, share of a house situated in panoramic location on the hills surrounding Cortona. The rental villa, offering extensive views over the Chiana Valley and Lake Trasimeno, has been skilfully restored and turned into …see more

from $80 / night

$558 - $977 / week

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from $80 / night