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

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Apartments Cortona
853 properties
Apartments Arezzo
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Anghiari
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Poppi
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Monte San Savino
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Loro Ciuffenna
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Foiano Della Chiana
58 properties
Castelfranco Piandisco
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Terranuova Bracciolini
49 properties
Pergine Valdarno
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Civitella in Val di Chiana
46 properties
Caprese Michelangelo
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Monterchi
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Sansepolcro
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Ambra
38 properties
Montevarchi
38 properties
Cavriglia
32 properties

Province of Arezzo

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2,753 Vacation rentals

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(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 $254 / night

$1779 - $3179 / week

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from $254 / 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

100

Vacation villa in Province of Arezzo

Tuscany / Province of Arezzo

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 180 mi
  • Swimming pool
  • Child friendly
ExteriorsA few minutes away from this historic villa lies Cortona, with its rolling hills and proximity to other Tuscan cities, such as Florence, Arezzo and Siena.The city center is only fifteen minutes away on foot, and it offers lots of cafés and restaurants. S …see more

from $693 / night

$4850 - $6927 / week

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from $693 / night

(6) Excellent 

20

Province of Arezzo / Cortona

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $54 / night

$324 - $518 / week

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from $54 / night

(12) Excellent 

45

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 $110 / night

$770 - $2451 / week

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from $110 / night

6

Province of Arezzo / Castelluccio, Arezzo

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $108 / night

$529 - $852 / week

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from $108 / night

(2) Excellent 

21

Vacation farmhouse with swimming pool in Cortona

Province of Arezzo / Cortona

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
Surrounded by olive groves and a 3000sqm private garden, the fenced-in holiday villa offers absolute peace and quiet at only 1,5 kilometres from the Etruscan Cortona, which can be easily reached on foot. The Trasimeno lake with its nice beaches and islands is at 8km and …see more

from $185 / night

$1294 - $2102 / week

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from $185 / 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 $65 / night

$405 - $432 / week

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from $65 / night

(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

from $63 / night

$647 / week

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from $63 / night

24

Vacation villa with swimming pool in Rapale

Province of Arezzo / Rapale

10 22 7 nights min

  • 10 bedrooms
  • Sleeps 22
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
This villa is an ancient tuscan villa which was once part of a larger farm in the estate of La Selva. It is a large independent villa with a charming tower and it was recently renovated and brought back to its original splendor; situated about 800 m from the main villa …see more

from $895 / night

$6260 - $7138 / week

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from $895 / 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 $87 / night

$345 - $561 / week

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from $87 / 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 $185 / night

$1294 - $3018 / week

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from $185 / night

21

Vacation villa with swimming pool in Arezzo

Province of Arezzo / Arezzo

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Lucignano holiday villa with pool to rent – Collina degli Ulivi is a charming 17th century stone farmhouse set in the verdant Tuscan countryside, known as Valdichiana, just a few miles away  from the well preserved Medieval village of Lucignano. This rustic v …see more

from $648 / night

$4532 - $6163 / week

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from $648 / night

100

Vacation villa with swimming pool in Brolio

Castiglion Fiorentino / Brolio

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 150 mi
  • Swimming pool
  • Child friendly
ExteriorVilla Celeste is a large villa with 9 bedrooms, all with en suite bathrooms.The property is in a perfect position for exploring wider Tucany with Arezzo and Cortona just a short distance away and other famed historical and arti …see more

from $732 / night

$5119 - $7921 / week

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from $732 / 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 $385 / night

$2694 - $4850 / week

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from $385 / night

(26) Excellent 

16

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly

from $97 / night

$485 - $863 / week

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from $97 / night

38

Cortona Vacation villa rental

Province of Arezzo / Cortona

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Cortona Tuscan Villa with pool – this property consists of three aristocratic 19th century villas, occupying a large estate abundant with chestnut woods and olive groves, within walking distance of the medieval walled town of Cortona, jewel of Valdichiana. The mai …see more

from $386 / night

$2700 - $4000 / week

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from $386 / night

(13) Excellent 

17

Vacation apartment rental

Province of Arezzo / Ambra

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Vepri is the perfect base for a tranquil holiday or home in the sun.It is for the discerning-a quiet and gated private luxury development comprising a small number of apartments and townhouses surrounding a communal piazza.The swimming pool is simply won …see more

from $86 / night

$599 / week

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from $86 / night

12

Province of Arezzo / Terranuova Bracciolini

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies

from $38 / night

$238 - $485 / week

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from $38 / night

(2) Very Good 

53

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Ask about pets

from $97 / night

$679 / week

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from $97 / night

55

Province of Arezzo / Cavriglia

4 8 7 nights min

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

from $228 / night

$1595 - $2425 / week

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from $228 / 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 $184 / night

$1186 / week

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from $184 / night

(2) Excellent 

18

Vacation cottage rental

Province of Arezzo / Stia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Casa Scaletta is a charming cottage situated between Arezzo and Florence, in the most beautiful, unknown and still unexplored part of Tuscany: the Casentino Valley. Enjoy the beauty and peace of the ancient hamlet of Porciano with its stone paved walkways, centuries old …see more

from $108 / night

$593 - $701 / week

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from $108 / night

(5) Very Good 

14

Province of Arezzo / Arezzo

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

from $81 / night

$485 / week

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from $81 / night

17

Vacation villa rental

Province of Arezzo / Marciano della Chiana

9 18 2 nights min

  • 9 bedrooms
  • Sleeps 18
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Poggio is set on an olive-covered hill in the heart of the Chiana Valley near Marciano della Chiana. It is an ancient medieval town of historical renown for the site of the Battle of Scannagallo.The villa enjoys stunning panoramic views over the valley, wi …see more

from $740 / night

$2959 - $5894 / week

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from $740 / night

(10) Excellent 

42

Province of Arezzo / Arezzo

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $539 / night

$3125 - $5604 / week

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from $539 / night

(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

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 $119 / night

$701 - $755 / week

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from $119 / night

34

Vacation farmhouse rental

Province of Arezzo / Foiano Della Chiana

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Property DescriptionFattoria il Salice is a farm house where guests can stay in five attractive holiday apartments, four of which (Il Salice, La Scaletta, La Cantina and Il Granaio) are built into the renovations of the old cattle byre, while the other (Il Giardino) occ …see more

from $73 / night

$507 - $884 / week

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from $73 / night

12

Province of Arezzo / Arezzo

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

from $76 / night

$432 / week

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from $76 / night

(3) Excellent 

31

Province of Arezzo / Badia Agnano

9 22 Min stay varies

  • 9 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from $248 / night

$1735 - $4300 / week

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from $248 / night

(5) Excellent 

19

Home rental in Anghiari

Province of Arezzo / Anghiari

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 mi
  • Child friendly
Casa La Portaccia is one of the the towns original houses built on the edge of the wall which give this house its unique and wonderful views over olive groves and the valley below. It also has a rare advantage of free parking outside but is within a 2' walk to the …see more

from $114 / night

$793 / week

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from $114 / 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 $90 / night

$582 - $807 / week

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from $90 / 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 $157 / night

$1078 - $1940 / week

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from $157 / 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 $91 / night

$636 - $1100 / week

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from $91 / 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 $108 / night

$496 - $841 / week

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from $108 / night

30

Vacation villa with swimming pool in Lucignano

Lucignano / Pozzo della Chiana

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 135 mi
  • Swimming pool
  • Child friendly
Situated on a hillside and surrounded by the vineyards of a famous local wine producing farm, Villa Al Pozzo is the ideal place to spend a holiday in complete relaxation and tranquility. Recently renovated, the villa will allow its guests to enjoy the experience of livi …see more

from $289 / night

$2021 - $3179 / week

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from $289 / night

(3) Very Good 

24

Vacation apartment with shared pool in Chiusi della Verna

Province of Arezzo / Chiusi della Verna

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
The idyllic hamlet of “Doccione di Sotto” which consists of three former farm houses, is located in a quite remote area of the Tuscan mountains. We carefully restored our old stone cottages. To the houses belong two large lawns with a pool (9x6m) for swimm …see more

from $62 / night

$399 - $593 / week

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from $62 / night

(3) Excellent 

23

Vacation villa in Cortona

Province of Arezzo / Cortona

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded …see more

from $130 / night

$970 / week

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from $130 / night

(4) Excellent 

10

Bibbiena / Casentino

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

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1