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

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Province of Arezzo

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3,181 Vacation rentals

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(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

$1273 - $2969 / week

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from $182 / night

(5) 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

 …see more

from $54 / night

$319 - $509 / week

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from $54 / 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 $250 / night

$1750 - $3129 / week

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from $250 / 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 $182 / night

$1273 - $2068 / week

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from $182 / 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 $304 / night

$2128 - $3235 / week

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from $304 / 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

$340 - $552 / 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 $440 / night

$3075 - $5535 / week

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from $440 / 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

$2651 - $4772 / week

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from $379 / night

32

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 - $531 / week

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from $45 / night

(1) Good 

21

Montebenichi Vacation villa rental

Bucine / Montebenichi

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly
Nice independent house situated on the hillside near the village of Montebenichi in the Chianti area. The place is very quiet and has a beautiful panoramic view of the surroundings, with vineyards, olive groves and woods. Beautiful pool area with a nice panoramic terrac  …see more

from $233 / night

$1625 - $2527 / week

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from $233 / 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 $129 / night

$902 - $2121 / week

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from $129 / night

(1) Excellent 

13

Monte San Savino / Montagnano

3 6 Min stay varies

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

 …see more

from $75 / night

$690 - $1167 / week

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from $75 / night

(6) Excellent 

15

Tower rental in Sansepolcro with shared pool

Province of Arezzo / Sansepolcro

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 110 mi
  • Swimming pool
Torre the Brancialino nestles beautifully in the Tuscan Hills some 10 kilometres from the Renaissance town of Sansepolcro.Being part of a remarkably restored medieval castle (where the owner lives) the tower offers the perfect romantic hideaway with comfortable accommod  …see more

from $62 / night

$431 / week

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from $62 / night

(3) Very Good 

11

Province of Arezzo / Arezzo

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Ask about children
  • Car not necessary
  • Air conditioning

 …see more

from $75 / night

$478 - $671 / week

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from $75 / night

20

Castle rental in Stia

Province of Arezzo / Stia

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 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 $57 / night

$398 - $425 / week

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from $57 / night

(1) Excellent 

16

Vacation cottage in Camaldoli

Province of Arezzo / Camaldoli

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Casa Vacanze Il Molino di Serravalle a 2 km dal Monastero di Camaldoli , immersa nel Parco delle Foreste Casentinesi, dove si respira l'incanto della natura in ogni stagione. L'appartamento lo Scoiattolo è dotato di focolare, riscaldamento autonomo e <  …see more

from $75 / night

$425 / week

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from $75 / 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 $61 / night

$393 - $584 / week

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from $61 / night

(1) Excellent 

30

Arezzo / Antria

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from $89 / night

$621 - $1362 / week

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from $89 / 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

 …see more

from $350 / night

$2450 - $4231 / week

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from $350 / 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

$906 - $1728 / week

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from $170 / 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

$1167 / week

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from $154 / night

10

Province of Arezzo / Anghiari

1 4 Min stay varies

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

 …see more

from $149 / night

$955 - $1167 / week

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from $149 / night

(2) Excellent 

58

Province of Arezzo / Foiano Della Chiana

4 12 Min stay varies

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

 …see more

from $372 / night

$2148 - $3897 / week

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from $372 / night

23

Province of Arezzo / Sansepolcro

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Suitable for children age 5+

 …see more

Pricing unknown

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Pricing unknown

(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 $47 / night

$329 - $573 / week

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from $47 / night

(2) Excellent 

10

Province of Arezzo / Cortona

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Child friendly
  • Private garden

 …see more

from $107 / night

$743 - $1299 / week

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from $107 / night

(1) Excellent 

28

Province of Arezzo / Foiano Della Chiana

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $52 / night

$439 - $662 / week

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from $52 / 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

$758 - $2412 / week

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from $109 / night

(1) Excellent 

21

Vacation villa in Civitella in Val di Chiana

Province of Arezzo / Civitella in Val di Chiana

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Now also featured on Alistair Sawday's 'Special Places to Stay'. If you are looking for a secluded property with beautiful views, yet close to many of the attractions of Tuscany, this could be for you. On a tranquil Tuscan hillside, a comfortable farmhou  …see more

from $176 / night

$1230 - $2706 / week

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from $176 / night

(1) Excellent 

24

Pieve Santo Stefano Vacation villa rental

Province of Arezzo / Pieve Santo Stefano

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
We bought the house back in 2004 as a ruin and spent the next 3 years creating a house that we ourselves would love to stay in and we are very proud of it The house is the last one up the valley with no near neighbours and has wonderful views which you can never tire of  …see more

from $185 / night

$1230 - $1821 / week

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from $185 / 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

$955 / week

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from $137 / night

100

Vacation villa with swimming pool in Talla

Province of Arezzo / Talla

8 23 Min stay varies

  • 8 bedrooms
  • Sleeps 23
  • Min stay varies
  • Swimming pool
  • Child friendly
Beautiful farmhouse situated in the country-side area surrounding the nice town of Arezzo (18 km away). This villa has been completely restored and turned into a welcoming accommodation allowing up to 23 guests. This property offers a main villa and 2 restored former ba  …see more

from $680 / night

$3977 - $5249 / week

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from $680 / night

(4) Excellent 

26

Arezzo / Capolona

5 12 Min stay varies

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

 …see more

from $117 / night

$817 / week

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from $117 / night

(19) Excellent 

24

Cortona / Montecchio, San Lorenzo

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $48 / night

$335 / week

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from $48 / 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 $85 / night

$590 / week

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from $85 / night

(2) Excellent 

11

Province of Arezzo / Arezzo

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

 …see more

from $61 / night

$340 / week

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from $61 / 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

$626 - $1082 / 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 $89 / night

$562 - $794 / week

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from $89 / night

(12) Excellent 

30

Bibbiena Vacation villa rental

Province of Arezzo / Bibbiena

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
The Villa, constructed at the end of the 18th century, offers a relaxing and comfortable stay to whoever wishes to spend their holidays in Tuscany. The Villa has been furnished in a very comfortable way with quality furniture, in part antique and in part in stile, creat  …see more

from $297 / night

$1591 - $4136 / week

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from $297 / night

(1) Excellent 

14

Province of Arezzo / Cortona

2 4 Min stay varies

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

 …see more

from $138 / night

$483 - $706 / week

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from $138 / night