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

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Apartments Cortona
802 properties
Apartments Arezzo
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Poppi
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Anghiari
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Monte San Savino
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San Pietro a Cegliolo
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Province of Arezzo

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2,921 Vacation rentals

(34) Excellent 

25

Vacation villa rental

Cortona / Montanare

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 $337 / night

$2186 - $3307 / week

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from $337 / night

(24) 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
15% DISCOUNT FOR JUNE and SEPTEMBER!! 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, overlo …see more

from $225 / night

$1345 - $3138 / week

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from $225 / night

(8) 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 $465 / night

$3250 - $7800 / week

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from $465 / night

(1) Excellent 

29

Vacation farmhouse rental

Province of Arezzo / Sestino

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Pet friendly
The Hamlet of Montondo is located in Sestino (Ar) locations Monterotondo. E 'completely renovated and surrounded by 6 hectares of forest. Montondo is place of beauty and harmony. Montondo is a place isolated and quiet, ideal for those seeking a holiday in nature, with t …see more

from $57 / night

$393 - $471 / week

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from $57 / night

(1) Excellent 

24

Capezzine Vacation apartment rental

Cortona / Capezzine

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Nearest beach 129 mi
  • Swimming pool
  • Child friendly
Villa Capezzine at Palazzuolo Due is the last restoration we started and will be ready to welcome our Guests next May 2013. It has been declared "Historical Monument" Villa Capezzine is situated in the famous community of Cortona (“Under the Tuscan Sun”: have you seen t …see more

from $152 / night

$1065 / week

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from $152 / 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 $449 / night

$3138 - $5604 / week

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from $449 / 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 $68 / night

$421 - $449 / week

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from $68 / night

(1) Excellent 

22

Home rental in Anghiari with swimming pool

Province of Arezzo / Anghiari

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
A Tuscan farmhouse located 5km from the medieval town Anghiari and 10km from the Roman town Sansepolcro. The town of Anghiari is nicely situated in the heart of the Upper Tiber Valley (Alta Valtiberina). Officially listed as “Uno dei Borghi piú belli d'Italia” (one of t …see more

from $193 / night

$1345 - $2578 / week

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from $193 / 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 $40 / night

$269 - $387 / week

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from $40 / night

(54) 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
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 of love on the interior and furnishings to transform our rambling …see more

from $371 / night

$2594 - $3835 / week

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from $371 / night

(27) 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
  • 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 of the valley beneath. Terraced house in t …see more

Certificate of Excellence

from $85 / night

$482 - $908 / week

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from $85 / night

8

Vacation townhouse in Terranuova Bracciolini

Province of Arezzo / Terranuova Bracciolini

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Ask about children
  • Ask about pets
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 $40 / night

$247 - $387 / week

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from $40 / 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 $89 / night

$623 / week

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from $89 / 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 $95 / night

$662 - $1144 / week

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from $95 / night

(3) Very Good 

16

Vacation apartment rental

Province of Arezzo / Anghiari

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Le Stelle is in the smaller house of Tenuta Savorgnano known as La Botteghina.. The name means “little shop” and many years ago it served as a trading-post for a collection of hamlets around Savorgnano. The part of the house that became Le Stelle was originally the sho …see more

from $78 / night

$390 - $507 / week

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from $78 / night

29

Vacation villa accommodation

Province of Arezzo / Loro Ciuffenna

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Pietra e mattoni is a very charming house in the middle of tuscany. We are located close to the main city of tuscany and in the same time we are isolated between vineyard and grass. We are a wine farm and you will have for you a lot of space, silent, and calm where you …see more

from $247 / night

$1569 - $3307 / week

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from $247 / night

(4) Excellent 

26

Home rental in Capolona with swimming pool

Arezzo / Capolona

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
casolare appena ristrutturato in aperta campagna circondato da oliveti a 2 passi da Arezzo e dal Casentino, la casa dispone di ampia cucina attrezzata con elettrodomestici e stoviglie, 5 ampie camere 4 bagni e un caratteristico salotto. Ottima visuale, grandi spazi este …see more

from $124 / night

$863 / week

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from $124 / 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 $90 / night

$359 - $583 / week

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from $90 / 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
  • Pet friendly
  • 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 $113 / night

$617 - $729 / week

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from $113 / 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 main …see more

from $118 / night

$824 / week

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from $118 / night

(4) Excellent 

23

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 $39 / night

$267 / week

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from $39 / night

(1) Very Good 

24

Vacation gite with swimming pool in Loro Ciuffenna

Province of Arezzo / Loro Ciuffenna

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 155 mi
  • Swimming pool
  • Child friendly
Delicious cottage in stone, independent, fully equipped with all the comfort. It expands into a wide panoramic garden of 800sqm with fruit trees, barbecue area and large gazebo for outdoor dining. Surrounded by nature, you can spot wild animals around. The location is a …see more

from $68 / night

$393 / week

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from $68 / night

(1) Excellent 

13

Vacation home in Badia Prataglia

Province of Arezzo / Badia Prataglia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Immerso nel verde del Parco Nazionale delle Foreste Casentinesi, questo grazioso appartamento, di recente ristrutturato, accoglie con il suo arredamento ben curato, la famiglia che si vuole allontanare per un po' dalla vita caotica e cerca il relax. Distribuita su tre …see more

from $68 / night

$471 / week

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from $68 / night

(1) Excellent 

30

Vacation villa rental

Province of Arezzo / Monte San Savino

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa in countryside with private swimming pool , jacuzzi, large garden of 4000mt. Olso there is fenced lake on property. The villa offer a unique privacy and panorama of the Tuscany landscape. Villa Meraviglia is located in Monte San Savino, medieval city of the well k …see more

from $449 / night

$1682 - $3923 / week

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from $449 / night

21

Home accommodation in Castel San Niccolo

Province of Arezzo / Castel San Niccolo

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Private garden
la casa costruita nell' 800 è stata recentemente ristrutturata ma conserva ancora un sapore antico anche nei mobili che l'arredano.E' una casa unifamiliare nel centro del borgo di Prato di Strada.Al primo piano la cucina abitabile, uno studio, un grande soggiorno. Dalla …see more

from $51 / night

$354 / week

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from $51 / night

(6) Excellent 

23

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 80 mi
  • Suitable for children age 5+
  • Ask about pets
The villa sits on the side of the hill overlooking the town & the river valley. Higher up on the hill is the Castel San Niccolo which gives its name to the district. Casa Castello is constructed of local stone & the origins of the house date back to the 13th century whe …see more

Pricing unknown

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Pricing unknown

(7) Excellent 

33

Vacation home with shared pool in Arezzo

Province of Arezzo / Arezzo

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located on top of a small hill, set in beautiful unspoiled Tuscan countryside and within walking distance from the charming medieval town of Arezzo, this beautiful property (and swimming pool) commands amazing views from its terraces and gardens. Composed by Cas …see more

from $191 / night

$1457 / week

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from $191 / night

(1) Excellent 

24

Vacation farmhouse with shared pool in Arezzo

Province of Arezzo / Arezzo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The apartment, recently renovated, is located on the first floor of an old farmhouse in the Tuscan countryside just 5 km from the center of Arezzo. The owners live on the ground floor available for every need of the guests. An external staircase in typical Tuscan style …see more

from $62 / night

$673 - $987 / week

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from $62 / 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 $241 / night

$1682 - $2802 / week

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from $241 / night

12

Arezzo Vacation home rental

Province of Arezzo / Arezzo

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Land House roof in the historic center of Arezzo (Tuscany). A stone's throw from the museum, Vasari Square and the Basilica of St. Francis with frescoes by Piero della Francesca. The house is fully furnished and equipped with all amenities. I am a travel writer and I'm …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

7

Lucignano Vacation b&b rental

Province of Arezzo / Lucignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Private garden
Il B&B Ginevra è situato su un poggio immerso nel verde della campagna Toscana, dal quale si possono ammirare i borghi medioevali di Sinalunga e Scrofiano. Nelle vicinanze potete visitare anche Lucignano, Monte San Savino e tanti altri borghi caratteristici. Con un po' …see more

from $57 / night

$393 / week

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from $57 / night

100

Villa rental in Talla with swimming pool

Province of Arezzo / Talla

6 13 1 night min

  • 6 bedrooms
  • Sleeps 13
  • 1 night min
  • Swimming pool
  • Child friendly
ExteriorThis charming villa is the result of an excellent conversion of the old stone mill which originally stood here and whose many original architectural features still remain well preserved. It is nestled in the Casentino valley at the bottom of the Pratomagno mount …see more

from $337 / night

$2354 - $3755 / week

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from $337 / night

9

Vacation townhouse rental

Province of Arezzo / Arezzo

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Indigo House is in the historic centre of Arezzo, a stone's throw from the most beautiful and famous places of the city: museums, antique galleries, churches, plazas, shops. Just 60 km from Florence and Siena, 25 km from the small Cortona and the beautiful chianti roads …see more

from $135 / night

$953 - $2247 / week

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from $135 / night

(9) Excellent 

55

Vacation apartment in Centoia

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

from $90 / night

$617 - $942 / week

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from $90 / night

20

Castel San Niccolo Vacation farmhouse rental

Province of Arezzo / Castel San Niccolo

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 150 mi
  • Swimming pool
  • Child friendly
La Magnana offers the perfect holidays to relax your body and mind while you'll be strolling in the fantastic National Park of « La Foresta Casentinese » on the Tuscan Apennines. You'll visit the closest cities : Firenze, Arezzo, Siena and Pisa. Or you'll allow yoursel …see more

from $79 / night

$505 - $1121 / week

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from $79 / night

(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 $50 / night

$348 - $606 / week

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from $50 / 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 $113 / night

$516 - $875 / week

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from $113 / night

(1) Excellent 

31

Villa rental in Cortona with swimming pool, golf nearby

Province of Arezzo / Cortona

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • 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 $337 / night

$2242 / week

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from $337 / night

(5) Excellent 

31

Vacation apartment in Anghiari

Province of Arezzo / Anghiari

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
The shower is situated on a hill, about 6 km from the medieval village of Anghiari. It can be reached along a winding road that runs among cypress, oak, holm oak and olive trees and cultivated fields that change colour throughout the year. It is an old stone farmhouse r …see more

from $90 / night

$561 - $707 / week

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from $90 / night

(6) Excellent 

20

Cortona Vacation townhouse accommodation

Province of Arezzo / Cortona

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The apartment is overlooking one of the most beautiful squares of the city, Piazza Signorelli which, with its splendid theatre and the Maec Museum, gives the location a unique and fascinating atmosphere. Thanks to its convenient central location, the apartment is locat …see more

from $57 / night

$337 - $538 / week

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from $57 / night

1