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

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Apartments Cortona
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Poppi
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Foiano Della Chiana
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Province of Arezzo

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3,124 Vacation rentals

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(3) Very Good 

10

Province of Arezzo / Bibbiena

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets

 …see more

from $62 / night

$636 / week

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from $62 / night

(34) Excellent 

25

Vacation villa rental

Cortona / Montanare

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • 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 $249 / night

$1748 - $3125 / week

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from $249 / night

6

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden

 …see more

Pricing unknown

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(53) Excellent 

51

Anghiari Vacation villa rental

Province of Arezzo / Anghiari

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 66 mi
  • Swimming pool
  • Child friendly
Currently offering 15% discount for the only week left in 2016. Casa Leana is over 350 years old and brimming with gorgeous original features from chunky beamed, wood ceilings and exposed stone walls to the traditional tiled kitchen. We have also lavished a whole lot  …see more

from $357 / night

$2494 - $3688 / week

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from $357 / night

17

Vacation home with shared pool in Foiano Della Chiana

Province of Arezzo / Foiano Della Chiana

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 140 mi
  • Swimming pool
  • Child friendly
Beautiful country estate situated in the vicinity of Cortona, a charming medieval town in the south of Tuscany, close to the well-known cities full of art of Siena, Arezzo and Perugia. Along with the cottage Rosa dei Venti, the other two farmsteads comprise five apartme  …see more

from $107 / night

$746 - $1452 / week

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from $107 / night

(24) Excellent 

33

Vacation villa with swimming pool in Poppi

Province of Arezzo / Poppi

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 160 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 surr  …see more

from $182 / night

$1272 - $2967 / week

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from $182 / night

(12) Excellent 

40

Vacation villa in Castel San Niccolo

Province of Arezzo / Castel San Niccolo

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 120 mi
  • Swimming pool
  • Suitable for children age 5+
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 $109 / night

$757 - $2409 / week

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from $109 / night

40

Vacation farmhouse with shared pool in San Giustino Valdarno

Province of Arezzo / San Giustino Valdarno

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
Charming stone farmhouse, equipped with every comfort, in an extraordinarily scenic location. Located in Valdarno, in front of the Chianti hills, between Florence and Arezzo is only half an hour from Siena. Due to its location, is an excellent starting point to visit th  …see more

from $154 / night

$1060 - $1907 / week

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from $154 / night

(4) Excellent 

29

Province of Arezzo / Anghiari

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from $85 / night

$530 - $668 / week

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from $85 / night

(54) Excellent 

32

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 p  …see more

from $379 / night

$2649 - $4767 / week

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from $379 / 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 $170 / night

$905 - $1726 / week

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from $170 / night

18

Vacation home with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 23 mi
  • Swimming pool
  • Child friendly
Fresh, bright and very well maintained, the villa offers a great holiday home for famiies of all ages. It is located in the lovely Val di Chio a few kilometers from the small town of ancient medieval town of Castiglion Fiorentino - rich in history, in the heart of b  …see more

from $105 / night

$735 - $921 / week

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from $105 / 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 $137 / night

$954 / week

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from $137 / night

16

Vacation apartment in Lucignano

Province of Arezzo / Lucignano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
This lovely holiday apartment in Lucignano is located in the historic centre, right on the remarkably conserved medieval walls of this beautiful hill-top village in Val di Chiana, near Arezzo. Obtained from the restoration of an old medieval building, this bright flat i  …see more

from $85 / night

$339 - $551 / week

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from $85 / night

(8) Excellent 

41

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 basketballOriginally 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 $447 / night

$3125 - $5625 / week

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from $447 / night

35

Vacation villa with swimming pool in Loro Ciuffenna

Loro Ciuffenna / Malva

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
For those who love nature and the Tuscany countryside, our country villa “Oliveta” is the ideal holiday destination in Tuscany. The villa is located on the Aretine Chianti hills, in a lovely countryside area at the foot of Pratomagno mountain and along to th  …see more

from $154 / night

$1166 / week

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from $154 / night

22

Castiglion Fibocchi Vacation apartment rental

Province of Arezzo / Castiglion Fibocchi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
A breathtaking view, an age-old sense of peace and unspoiled nature together with the high level of comfort of the three apartments make this house the ideal destination for those who wish to spend a relaxing holiday in Tuscany. The beauty of natural surroundings, the h  …see more

from $90 / night

$625 - $1081 / week

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from $90 / night

28

Vacation apartment rental

Province of Arezzo / Lucignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets
A fully self-contained apartment located in a medieval building opening onto its own garden, right in the centre of the charming central Tuscan town of Lucicnano.Appartamento Giardino is located in a a converted frantoio, olive oil mill is the centre of the medieval tow  …see more

from $88 / night

$562 - $793 / week

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from $88 / night

55

Province of Arezzo / Cavriglia

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $224 / night

$1568 - $2384 / week

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from $224 / night

11

Vacation villa with shared pool in Pian di Sco

Castelfranco Piandisco / Pian di Sco

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 140 mi
  • Swimming pool
  • Child friendly
Set in a beautiful farming estate, which has transformed its charming XVIIth century convent into an ultra stylish rural hideaway, it is the perfect retreat for discerning guests who love the countryside, art, food and wine of Italy. Besides villa La Leccina, this ancie  …see more

from $556 / night

$3888 - $5297 / week

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from $556 / night

(14) Excellent 

25

Vacation villa rental

Province of Arezzo / Poppi

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
The spacious villa, 250 square meters, can accomodate 10 + 2 people with 5 bedrooms and 3 bathrooms. It has a good level of furniture. It has modern kitchen, with stainless steel cutlery, and modern bathroom facilities, but it still gives one the feeling of stepping bac  …see more

from $35 / night

$240 - $2326 / week

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from $35 / night

(2) Excellent 

23

Farmhouse rental in Anghiari with swimming pool

Province of Arezzo / Anghiari

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 133 mi
  • Swimming pool
  • Child friendly
Set within the beautiful hamlet La Palaia, Casa Mimosa has been resurrected from a ruin to a beautiful holiday home through careful restoration and the addition of modern comforts. This home has 3 double bedrooms and 3 bathrooms and so comfortably sleeps 6. For larger  …see more

from $303 / night

$2119 / week

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from $303 / night

25

Province of Arezzo / Anghiari

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

 …see more

from $128 / night

$848 / week

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from $128 / night

100

Vacation villa with swimming pool in Lucignano

Province of Arezzo / Lucignano

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
Exteriors   Perched on a hilltop which has kept its untouched purity and surrounded by land that brings life again to stressed souls, this villa for rent in Tuscany is a great destination spot.The villa boasts its swimming pool with sweeping captivating views  …see more

from $485 / night

$3390 - $4767 / week

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from $485 / night

(5) Excellent 

1

Vacation villa with swimming pool in Pieve di Chio

Castiglion Fiorentino / Pieve di Chio

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly
A place to feel at home in Tuscany.... 3 bedrooms, 4 bathrooms, Air Conditioning, Private Pool... and Easy access Lovely air conditioned stone farmhouse situated within a small Tuscan borgo. The house offers high quality accommodation with outstanding views of the V  …see more

from $282 / night

$2100 - $2560 / week

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from $282 / night

20

Castle rental in Stia

Province of Arezzo / Stia

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Ask about pets
  • 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 $64 / night

$398 - $424 / week

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from $64 / night

44

Vacation farmhouse in Brolio

Castiglion Fiorentino / Brolio

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Brolio Quinto is the ideal location for a peaceful holiday in the warm atmosphere of an old country farmhouse, beautifully preserved in its original architectural style. You can rent the top floor of this historic farmhouse with its independent access. It sleeps 8 +  …see more

from $159 / night

$1378 - $1642 / week

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from $159 / night

(13) Excellent 

12

Vacation cottage in Moncioni

Montevarchi / Moncioni

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Air conditioning
  • Private garden
If you love walking, peaceful rusticity, organically grown olive oil and all the joys of glorious Tuscany then this cottage is for you! Podere La Rota is a delightful cottage set among peaceful olive groves, barely a ten minute stroll from the village of Moncioni, whic  …see more

from $105 / night

$731 / week

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from $105 / night

(2) Excellent 

30

Province of Arezzo / Cortona

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly

 …see more

from $223 / night

$1558 / week

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from $223 / night

(23) Excellent 

28

Arezzo Vacation villa rental

Province of Arezzo / Arezzo

1 9 4 nights min

  • 1 bedroom
  • Sleeps 9
  • 4 nights min
  • Nearest beach 120 mi
  • Child friendly
  • Private garden
Holiday Villa of Dario on the ground and first floor of owner's house. French windows lead onto a patio with lovely views of the hilltop village of Lucignano, 2 minutes drive away. The living/dining room has a fireplace and an open, modern, kitchen. The bathroom to  …see more

from $53 / night

$339 - $2575 / week

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from $53 / night

54

Vacation home in Caprese Michelangelo

Province of Arezzo / Caprese Michelangelo

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Singerna has been converted from a 300-year-old stone barn. Although it has come a long way from its humble beginnings, original features have been retained and materials reused wherever possible to preserve its original character with chestnut beamed ceilings, ha  …see more

from $79 / night

$551 - $3390 / week

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from $79 / night

(1) Excellent 

28

Vacation farmhouse rental

Province of Arezzo / Anghiari

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
Anghiari, a beautiful hilltop medieval Tuscan town is less than 30 minutes drive from the house but when you are at Bagnolino you will feel as though you have escaped from the whole world. A local family has owned this beautifully kept farmhouse for decades and have onl  …see more

from $303 / night

$2119 / week

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from $303 / night

34

Province of Arezzo / Loro Ciuffenna

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Nearest beach 150 mi
  • Swimming pool
  • Child friendly

 …see more

from $45 / night

$308 - $530 / week

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from $45 / night

(36) Excellent 

35

Province of Arezzo / Poppi

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from $53 / night

$371 / week

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from $53 / night

(2) Excellent 

25

Mercatale di Cortona Vacation home rental

Cortona / Mercatale di Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $188 / night

$1105 - $1938 / week

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from $188 / night

(16) Excellent 

25

Vacation apartment in Sansepolcro

Province of Arezzo / Sansepolcro

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Car not necessary
  • Air conditioning
The Medieval Tower is in the center of Sansepolcro with its entrance on the main street, just 50 meters far from the central square. The Tower is the perfect place to spend an unforgettable holiday in a real medieval tower located in the heart of Sansepolcro. You ente  …see more

from $89 / night

$587 / week

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from $89 / night

23

Vacation apartment accommodation

Province of Arezzo / Lucignano

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
This charming apartment and very large apartment of 200 sqm, in Lucignano hamlet, is located on the summit of this beautiful medieval walled hill-top village, near Arezzo, famous for its unique elliptical shape and concentric streets. Right next the Museum and the old  …see more

from $106 / night

$488 - $827 / week

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from $106 / night

(1) Excellent 

8

Terranuova Bracciolini Vacation apartment rental

Province of Arezzo / Terranuova Bracciolini

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Little flat in the Valdarno area, at the gates of Chiantishire and Florence.There is a small stretch of dirt road to get here but whilst at the silence of the countryside, we are only 800m from the town center, easily reachable on foot. Unfortunately we are not serv  …see more

from $38 / night

$255 - $366 / week

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from $38 / night

21

Vacation villa in Lucignano

Province of Arezzo / Lucignano

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 15 mi
  • Swimming pool
  • Child friendly
Casa Luisa is a completely refurbished 3 bedroom property. It is located between Lucignano and Sinalunga, about 10 mins from the A1 Betolle toll. The houses in the tiny hamlet are mainly farms and the sheep one can hear in the distance have bells around their necks and  …see more

from $134 / night

$938 - $2750 / week

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from $134 / night

(3) Excellent 

4

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The sweeping vista across the valley to Cortona and Castiglion Fiorention with the wonderful castle of Montecchio makes the perfect base for a friends and family home in Tuscany. Recently renovated with great care and - attention to detail, Casa Sophia is a four bedro  …see more

from $220 / night

$1537 - $2914 / week

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from $220 / night