50 Best Cortona Apartments on Holiday Lettings - Vacation rentals

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Cortona

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4,259 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 $317 / night

$2,216 / week

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from $317 / 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 $233 / night

$1,630 - $2,450 / week

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from $233 / night

22

Vacation apartment in Montecchio

Cortona / Montecchio

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 15 mi
  • Child friendly
  • Pet friendly
Large apartment near Cortona. New construction equipped with all major comforts. Dishwasher, convection oven, refrigerator with freezer, Fireplace. two bathrooms, one inside the large main chamber. E 'available Wi-Fi, gratutito, accessible from all rooms. The rooms are …see more

from $59 / night

$352 / week

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from $59 / night

(35) 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 $106 / night

$610 - $950 / week

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avg. 2 hours 7 minutes

from $106 / night

(3) Very Good 

6

Cortona Vacation guest house rental

Province of Arezzo / Cortona

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
Lovely cottage in the historic center of Cortona. Always our family's property was an ancient horse change station. in one of the walls is preserved the Manger hence the name.Restored with love is a typical Tuscan House: terracotta and wooden beams, brick arches and war …see more

from $118 / night

$649 / week

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from $118 / night

(2) Excellent 

25

Mercatale di Cortona Vacation home rental

Cortona / Mercatale di Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 22 mi
  • Swimming pool
  • Child friendly
Casa Gorgacce is an old stone farmhouse with lots of character beautifully converted with all modern comforts. It has a private garden and pool, complete privacy yet with great access and only a few kilometres from 2 lively villages; Meratale di Cortona and Lisciano Nic …see more

from $178 / night

$1,245 - $2,088 / week

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Responds fast!
avg. 1 hour 32 minutes

from $178 / 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 $98 / night

$645 - $792 / week

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Responds fast!
avg. 2 hours 46 minutes

from $98 / night

(3) Excellent 

23

Cottage rental in Cortona

Province of Arezzo / Cortona

1 6 5 nights min

  • 1 bedroom
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Pet friendly
  • Private garden
We rent occasionally and only for short periods, nice apartment with private garden area old town Cortona. Our house is spacious and full of light - a perfect cool retreat after a warm summer day's exploration in Tuscany. Great for two love birds or a couple with a chil …see more

from $71 / night

$493 / week

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Responds fast!
avg. 3 hours 14 minutes

from $71 / night

36

Vacation villa with swimming pool in Pietraia

Cortona / Pietraia

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The farm houses Sant'Anna offers its guests a recently renovated (2017), ideal for families and groups of friends. During the renovation special attention it was given to respect the architectural characteristics of the Tuscan houses, but will not sacrifice modern as th …see more

from $556 / night

$3,892 / week

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from $556 / 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 $118 / night

$821 - $1,436 / week

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from $118 / night

(2) Good 

37

Cortona Vacation apartment rental

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Garibaldi is a finely furnished and welcoming apartment, located on the first floor of a historic building having the same name of the Piazza that leads into the promenade in the centre of Cortona. The architecture of each area is enhanced by the choice of tones and fur …see more

from $118 / night

$879 - $1,173 / week

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from $118 / night

(6) Very Good 

51

Apartment accommodation in Montalla with shared pool

Cortona / Montalla

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 200 mi
  • Swimming pool
  • Child friendly
THE HOUSE IS SPLIT IN 2 INDEPENDENT APARTMENT OF THE SAME SIZE, BOT WITH A PRIVATE GARDEN, ENTRANCE AND PARKING, WE CAN RENT ONE OF THEM FOR 6+1 OR THE ENTIRE HOUSE FOR 12+2. THE DESCRIPTION BELOW REFERS TO Il Bozzino, the ground floor oneBUT APPLY TO BOTH. PLEASE READ …see more

from $180 / night

$969 - $1,614 / week

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avg. 2 hours 45 minutes

from $180 / night

(9) 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 $134 / night

$937 - $1,171 / week

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from $134 / night

29

Cottage rental in Pietraia with swimming pool

Cortona / Pietraia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Nestled in the colourful Tuscan countryside, just 8km away from the old town of Cortona, Il Nido is a lovely small villa recently restored and finely appointed with a contemporary country-chic style. The skillful ability in matching the soft tones and the tasteful reca …see more

from $143 / night

$997 - $2,345 / week

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from $143 / night

(1) Excellent 

20

Vacation apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 …see more

from $78 / night

$576 - $763 / week

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from $78 / night

42

Vacation cottage rental

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The search for a warm and welcoming Tuscan abode is over. Luigina cottage Cortona 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 $152 / night

$1,059 / week

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Responds fast!
avg. 1 hour 48 minutes

from $152 / night

21

Vacation apartment with shared pool in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Il Casone lies in the open countryside, a few minutes from Cortona towards Farneta. Immersed in a large garden, among the green olive trees and the delicate scent of the roses that frame the swimming pool area, this ancient farmhouse has been painstakingly restored and …see more

from $126 / night

$879 - $1,114 / week

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from $126 / night

(1) Excellent 

19

Vacation apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 …see more

from $81 / night

$603 - $803 / week

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from $81 / night

(5) Excellent 

24

Vacation home with shared pool in Cegliolo

Cortona / Cegliolo

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 140 mi
  • Swimming pool
  • Child friendly
It is situated at the foot of Cortona Etruscan city famous. It is immersed in the green countryside and close to the archaeological etruschi Melone I and Melone II of Sodo. Major cities nearby include: Arezzo Montepulciano Siena Perugia Assisi Montalcino Pienza San Gim …see more

from $141 / night

$879 / week

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from $141 / night

(1) Excellent 

19

Vacation villa with swimming pool in Cortona

Province of Arezzo / Cortona

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa La Pergola is an authentic private villa in Tuscany, very close to the Etruscan town of Cortona. La Pergola is situated in a cosy village consisting of two other villas each with private swimming pool. The patio, decorated with elegant garden furniture, has a scen …see more

from $235 / night

$1,173 - $3,693 / week

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from $235 / night

35

Bagnolo Vacation villa rental

Cortona / Bagnolo

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Antica Fonte offers you the chance to live in contact with nature, immersed in the beautiful hillside setting of Cortona, a short walk from all the major tourist centers of Valdichiana, Chianti and Umbria. The property is situated on the hills around Cortona, a fe …see more

from $563 / night

$3,939 / week

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from $563 / night

28

Home rental in Cortona

Province of Arezzo / Cortona

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Elegant and comfortable 90 sqm apartment with independent access in the heart of Cortona. It is ideal for a wonderful romantic or family and can comfortably accommodate up to 5 people. It is located a short walk from the center but in a quiet street. You can avail of a …see more

from $118 / night

$821 / week

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from $118 / 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 $421 / night

$2,944 / week

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from $421 / 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 $142 / night

$991 / week

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from $142 / 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 $252 / night

$1,759 - $2,931 / week

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from $252 / 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 $147 / night

$997 - $1,407 / week

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Responds fast!
avg. 2 hours 46 minutes

from $147 / 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 $79 / night

$551 - $926 / week

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from $79 / night

(2) Excellent 

19

Vacation apartment with shared 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
The Ciliego is situated on a Tuscan hill in a very peaceful spot that enjoys a breathtaking view of the Chiana Valley. It is an 18th century sand stone farmhouse built on two floors. Ground floor: comfortably furnished sitting room , fully equipped kitchen and dining ro …see more

from $126 / night

$879 - $1,290 / week

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from $126 / night

(5) Excellent 

20

Vacation apartment in Cortona

Province of Arezzo / Cortona

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Casa Anna is just a few km from the Etruscan-Medieval town of Cortona and offers a genuine and healthy holiday. It is situated in the hills area around Cortona (only 5 km from SR71 and 10 km from Cortona), in the heart of a small rural hamlet, and ensures guests real qu …see more

from $82 / night

$469 / week

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from $82 / night

(1) Excellent 

19

Vacation apartment with shared pool in Cortona

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The country house "I Nidi di Cortona" is situated in the countryside, in the small rural village of San Marco in Villa (sec. XIV), at the foot of the hill where the Etruscan village of Cortona. Its strategic location allows guests to fully relish the quiet of country li …see more

from $94 / night

$657 - $698 / week

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Responds fast!
avg. 2 hours 31 minutes

from $94 / 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 $163 / night

$1,136 - $2,941 / week

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from $163 / night

(14) Excellent 

Certificate of Excellence

32

Vacation home 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
Your holiday to Tuscany is special. You want a home that will provide you with the essential pool and of course the internet. You want to be close to the amenities but far enough away for privacy, seclusion and relaxation. We would love to welcome you to Villa Rosa w …see more

Certificate of Excellence

from $340 / night

$2,380 - $2,707 / week

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Responds fast!
avg. 3 hours 7 minutes

from $340 / night

5

Vacation apartment with shared pool in Pietraia

Cortona / Pietraia

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Bright and spacious apartment of 110 square meters consisting of 2 beautiful and spacious double bedrooms, a large living room with fireplace and fully equipped kitchen; It has a large loft with tv-reading room and double bedroom, where you can enjoy moments of total re …see more

from $164 / night

$1,149 / week

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Responds fast!
avg. 1 hour 14 minutes

from $164 / 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 $340 / night

$2,380 - $2,707 / week

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Responds fast!
avg. 3 hours 7 minutes

from $340 / 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 $82 / night

$528 - $563 / week

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from $82 / night

(22) Excellent 

58

Vacation home in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Charming small villa in pretty medieval village about 25 minutes from Cortona. The house is set in large gardens and olive grove with views of the surrounding hills. A/C and Wi-Fi throughout. Very comfortable and really fully equipped. Mint condition. Lovely Garde …see more

from $147 / night

$821 - $1,243 / week

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Responds fast!
avg. 1 hour 48 minutes

from $147 / night

(1) Very Good 

27

Lodge rental in Cortona with shared pool

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 $93 / night

$645 - $762 / week

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Responds fast!
avg. 1 hour 22 minutes

from $93 / 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 $340 / night

$2,378 - $2,705 / week

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Responds fast!
avg. 3 hours 7 minutes

from $340 / 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 $138 / night

$962 - $1,524 / week

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Responds fast!
avg. 3 hours 19 minutes

from $138 / night

(2) Excellent 

27

Vacation farmhouse with swimming pool in Farinaio

Cortona / Farinaio

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Casa le Celle Le Celle stands next to a small church which dates back to the 1500’s. Part of the house also dates back to that period. It is in a hillside position with various places for sitting and eating outside and the pool area with a lovely view. The property is j …see more

from $176 / night

$704 - $1,524 / week

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Responds fast!
avg. 1 hour 6 minutes

from $176 / night