50 Best Vacation Rentals in Province of Arezzo - Holiday Lettings - Cabins

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Province of Arezzo

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3,744 Vacation rentals

(1) Excellent 

24

Vacation apartment in Loro Ciuffenna

Province of Arezzo / Loro Ciuffenna

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
These holiday homes in Tuscany are in the hamlet of Poggio di Loro, on the Tuscan Apennines, in the centre of the region, which stretches itself out around a castle and a beautiful church whose origins are lost in the mists of time. Documents of 1247 attest to the exist …see more

from $55 / night

$384 - $669 / week

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Responds fast!
avg. 1 hour 31 minutes

from $55 / 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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Responds fast!
avg. 3 hours 37 minutes

from $356 / night

27

Cortona Vacation apartment rental

Province of Arezzo / Cortona

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
The main apartment is spread over three floors linked by a modern crystal and steel staircase. On the first floor, the open space living area consists of a large well-equipped kitchen (with oven, fridge and dishwasher) and a bright large dining/living room with old ston …see more

from $236 / night

$1,363 - $1,611 / week

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from $236 / night

(4) Excellent 

35

Lucignano Vacation home rental

Province of Arezzo / Lucignano

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
The house lies in a top hill location with a beautiful panorama only 2 kms from the small charming village of Rigomagno, between Siena and Arezzo (both cities are around 30 Kms far away). It's a very quiet location. The house has a large garden with pool (13,5x5), whole …see more

from $149 / night

$992 - $2,478 / week

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Responds fast!
avg. 3 hours 40 minutes

from $149 / night

5

Capolona Vacation villa rental

Arezzo / Capolona

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
Immersed in the Tuscan countryside, near Arezzo, the Relais Santa Margherita offers its guests unforgettable holidays in an environment rich in charm and history.The large park surrounding the villa is composed of grass and pine trees and has a swimming pool, a large pe …see more

from $112 / night

$533 / week

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from $112 / 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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Responds fast!
avg. 3 hours 0 minutes

from $93 / night

(26) Excellent 

33

Vacation villa with swimming pool in Poppi

Province of Arezzo / Poppi

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 130 mi
  • Swimming pool
  • Child friendly
Five bedrooms, 4 double bedrooms and one bedroom with two single beds, 3 full bathrooms each with a shower. Large living room with stereo, CD, SAT TV and a large fireplace. Many outdoor eating areas - overlooking the castle, overlooking the pool and overlooking the su …see more

from $248 / night

$1,239 - $3,469 / week

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from $248 / night

(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

35

Vacation home in Levane

Province of Arezzo / Levane

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Private garden
A delightful residence just a short walk from the center complete with everything needed for every guest just in case. The village is situated a few kilometers from Arezzo, Siena and Florence. Feature housing is also the discovery of wall paintings of the early '900. Gu …see more

from $47 / night

$310 - $622 / week

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from $47 / night

20

Casentino Vacation farmhouse rental

Bibbiena / Casentino

5 6 3 nights min

  • 5 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful stone house in the Tuscan countryside between Florence and Arezzo offers elegant spaces and landscapes. The House is divided into two apartments, one for 4-5 persons (' News ') on the ground floor and one for 6-7 persons (' Raoul ') on the first floor. …see more

from $248 / night

$1,735 / week

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from $248 / night

(2) Excellent 

24

Vacation home with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in the Tuscan countryside, a 15-minute drive from Castiglione Fiorentino, Podere Ortaglia di Sopra offers a garden with outdoor pool and barbecue facilities. With free Wi-Fi in all areas and a rustic decor, the villa has 3 bedrooms, a TV, a fully equipped kitche …see more

from $248 / night

$1,735 - $3,643 / week

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from $248 / night

10

Poppi Vacation apartment rental

Province of Arezzo / Poppi

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 80 mi
  • Child friendly
  • Pet friendly
In the National Park of Casentino in Tuscany diArezzo province town of Poppi, at 50 km from Florence, at 100 km from Siena, 200 km from Rome and close to the monasteries of Camaldoli and La Verna and Vallombrosa, rental apartment in farmhouse for 2 or 4 people. Wide ope …see more

from $174 / night

$992 / week

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from $174 / night

(7) Excellent 

28

Castiglion Fibocchi Vacation home rental

Province of Arezzo / Castiglion Fibocchi

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly
 House built around 1450 basis of justice and prison tower. Remained intact in the structure with its 140cm wide walls, vaulted ceilings and terracotta stone floors and parquet, revives special atmosphere far from our time. The house overlooks the main square living roo …see more

from $62 / night

$434 / week

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from $62 / night

20

Penna Vacation apartment rental

Province of Arezzo / Penna

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
In the heart of the Balze is the property "IL CASOLARE", an independent apartment in a farmhouse situated in a valley between the green hills of the Arno Valley. View of the countryside, 30 m from the main road. Exclusive private garden in front of the house with a perg …see more

from $150 / night

$1,053 - $1,735 / week

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from $150 / night

20

Badia a Ruoti Vacation farmhouse rental

Bucine / Badia a Ruoti

10 22 7 nights min

  • 10 bedrooms
  • Sleeps 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful farmhouse in “Leopoldino” style with outbuilding and private swimming-pool situated on the hills surrounding Bucine, a short distance away from Arezzo and Siena. This property has been carefully restored and turned into a charming country house offering tastef …see more

from $1,062 / night

$7,434 - $8,053 / week

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from $1,062 / 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

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

12

Terranuova Bracciolini Vacation townhouse rental

Province of Arezzo / Terranuova Bracciolini

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
Lovely Studio apartment in Valdarno, Chianti and Florence. There is a small dirt road to reach us but although we are in the silence of the countryside, we are just 800 m from the town centre, easily accessible on foot. Unfortunately we are not served by public transp …see more

from $44 / night

$273 - $403 / week

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from $44 / night

9

Bucine Vacation apartment rental

Province of Arezzo / Bucine

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
House with independent entrance with private fenced garden. In front of the abitazionevi is a small courtyard equipped with table and chairs for outdoor dining. Direct access to the living room/kitchen, characterized by beautiful corner fireplace with satellite TV, sofa …see more

from $87 / night

$558 / week

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from $87 / night

16

Vacation apartment with shared pool in Arezzo

Province of Arezzo / Arezzo

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
For lovers of the great outdoors, who don't want to be too far from the next town, hike in the hills, a bio pool for swims, a trampoline and table tennis for kids, Tuscan views... The road winds higher from Arezzo through the village of Pieve san Giovanni to an olive fa …see more

from $155 / night

$1,084 / week

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from $155 / 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

13

Vacation guest house in Marciano della Chiana

Province of Arezzo / Marciano della Chiana

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Ask about pets
Typical medieval holiday house in the castle of Marciano della Chiana in Tuscany. The house consists of 2 bedrooms, bathroom, living room, kitchen and panoramic terrace in the roof. Total number of places 5 people. The house is situated in a strategic position as reg …see more

from $69 / night

$310 / week

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from $69 / night

(1) Excellent 

19

Vacation home in Anghiari

Province of Arezzo / Anghiari

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
At 5 minutes from Anghiari, La Breccia is ideal for relaxation in nature and visit the surrounding small villages that are home to jewelry art and gastronomy. Residence of the early 1900s, now renovated, is composed of independent and functional adjacent apartments that …see more

from $124 / night

$682 / week

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from $124 / night

(4) Excellent 

25

Home rental in Anghiari with swimming pool

Province of Arezzo / Anghiari

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Superb stone house in Tuscany, with a hectare of fenced park. exclusively for rent! Total privacy, unspoiled nature, infinity pool, stunning panorama, private dog park with swimming. Quiet Country House a lovely place that offers and gives peace and comfort you need. He …see more

from $137 / night

$917 - $1,314 / week

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Responds fast!
avg. 3 hours 55 minutes

from $137 / night

(9) Excellent 

46

Anghiari Vacation villa rental

Province of Arezzo / Anghiari

7 12 7 nights min

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Exceptional views. Sleeps 12. Pool, gardens, tennis court and basketball Originally a 16th century farmhouse, Villa Seccarille is situated in 57 hectares of fields and woodlands, on the lower slopes of the Appennine Mountains. The villa offers breathtaking views …see more

from $600 / night

$4,200 - $8,400 / week

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Responds fast!
avg. 3 hours 23 minutes

from $600 / night

(1) Excellent 

33

Monte San Savino Vacation b&b rental

Province of Arezzo / Monte San Savino

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Aloe House b & b is located in the heart of Tuscany. Mail foothills location, 1km. A1 exit Monte San. Savino, very central, ideal for a stopover, in a short time you can reach Florence, Siena, Grosseto a few kilometers, Cortona and Montepulciano. fenced and private prop …see more

from $81 / night

$564 / week

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from $81 / 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

11

Vacation townhouse with shared pool in Orzale

Castiglion Fiorentino / Orzale

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
"La Fenice" is located in the lovely Valley of Chios, which with the opposite Valley of Chiana frames Castiglion Fiorentino, typical Tuscan hill country rich in architectural beauty and corners to discover. The "Phoenix" is located on a hill about 300 metres above sea l …see more

from $223 / night

$843 - $1,053 / week

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from $223 / night

(3) Very Good 

10

Apartment rental in Bibbiena

Province of Arezzo / Bibbiena

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets
Casa Vacanze La Contessa is located in a prestigious building of the characteristic village of Bibbiena, in the heart of the Casentino, one of the most beautiful valleys of Tuscany, where you can discover the unique historical treasures, art, nature and traditions of a …see more

from $72 / night

$744 / week

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from $72 / night

(1) Excellent 

13

Castiglion Fiorentino Vacation apartment rental

Province of Arezzo / Castiglion Fiorentino

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
Appartamento a Castiglion Fiorentino, completamente ristrutturato in tipico stile toscano, mantenuta la pietra a vista originale. Composto da ampia cucina/soggiorno completamente attrezzata con divanetto, 1 camera matrimoniale, 1 cameretta con due lettini con possibilit …see more

from $87 / night

$607 / week

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from $87 / night

20

Castle rental in Stia

Province of Arezzo / Stia

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Medieval Little Guard Tower situated in a beautiful and undiscovered corner of Tuscany, the Casentino Valley, between Arezzo and Florence. Enjoy the beauty and peace of the ancient hamlet of Porciano with its stone paved walkways, centuries old church and breathtaking v …see more

from $50 / night

$372 - $434 / week

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from $50 / night

25

Anghiari Vacation farmhouse rental

Province of Arezzo / Anghiari

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
In a beautiful panoramic area of Tuscany, just over an hour from Florence, a real family farm, rent for short periods the only apartment for guests. From the brand new renovation of a rustic farmhouse adjacent to the homeowner, is a self-contained and accessible ground …see more

from $149 / night

$992 / week

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from $149 / night

(3) Excellent 

11

Vacation villa in Caprese Michelangelo

Caprese Michelangelo / Lama

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Pet friendly
Casa Cappellino nestles among the Tuscan hills and stands on 3 acres of gardens and vineyard. These grounds are lovingly landscaped with ponds, olive grove, vineyard, fruit trees and flowering plants. Your private holiday home is an independent stone house that has bee …see more

from $149 / night

$930 / week

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from $149 / 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

(1) Excellent 

19

Vacation apartment with shared pool in Capolona

Arezzo / Capolona

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
La struttura troneggia su un'altura, abbracciata dal verde rigoglioso di un bosco, a Capolona distante circa 10 km da Arezzo ai piedi del Casentino. Vecchio casolare contadino in pietra a ridosso di un piccolo centro abitato, cristallizzata nel passato, con origini risa …see more

from $130 / night

$892 / week

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from $130 / night

(14) Excellent 

35

Vacation villa in Castel San Niccolo

Province of Arezzo / Castel San Niccolo

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
We are spectacularly located in a prominent elevated position in a South facing valley which brings long hours of sunshine and a favourable micro climate. The house is approached by a lane which winds its way from the main road, crossing over a river by an ancient bridg …see more

from $174 / night

$885 - $2,263 / week

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Responds fast!
avg. 3 hours 37 minutes

from $174 / night

(2) Very Good 

32

Vacation villa with swimming pool in Capolona

Arezzo / Capolona

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Caterina is a nice villa with large garden and private swimming pool. Located in Casavecchia (Capolona) a few Km far from Arezzo on Tuscany hills, Villa Caterina enjoys a spectacular view over the city of Arezzo. Villa Caterina is equipped with 3 spaci …see more

from $160 / night

$1,115 / week

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from $160 / night

28

Vacation home in Castiglion Fibocchi

Province of Arezzo / Castiglion Fibocchi

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
stone cottage with large garden, study, living room, kitchen, utility room, stairs, 3 bedrooms, wardrobes, computer room, 2 bathrooms, large yerrazza, large outdoor area with rocking tables, near Castiglion Fibocchi small town 1500 inhabitants in the province of Arezzo, …see more

from $38 / night

$261 / week

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from $38 / night

22

Vacation villa rental

Province of Arezzo / Arezzo

14 30 7 nights min

  • 14 bedrooms
  • Sleeps 30
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Can accommodate up to 32 people. 7 apartments in a large villa (rented out as a whole). Equipped with private swimming pool, wifi internet, gazebo with barbecue, restaurant where you can taste the specialties of Tuscany. The proximity to the city you can find all the se …see more

from $1,310 / night

$9,169 / week

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from $1,310 / night

(56) Excellent 

38

Arezzo Vacation villa rental

Province of Arezzo / Arezzo

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Located on the hills that divide the Casentino valley from Chianti, the Villa is ideally positioned for those wishing to visit cities such as Florence, Arezzo or Siena.It is also the perfect base to experience and explore the Tuscan countryside. Now restored to perfect …see more

from $496 / night

$3,469 - $5,576 / week

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from $496 / night