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

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Apartments Cortona
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Sansepolcro
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Province of Arezzo

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4,128 Vacation rentals

(1) Excellent 

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 the historic R …see more

from $195 / night

$1,373 - $2,689 / week

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from $195 / night

(13) Excellent 

17

Vacation apartment rental

Province of Arezzo / Ambra

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • 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 $96 / night

$377 - $632 / week

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Responds fast!
avg. 3 hours 33 minutes

from $96 / night

(58) 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 $458 / night

$3,204 - $5,149 / week

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Responds fast!
avg. 3 hours 35 minutes

from $458 / night

(2) Excellent 

33

Home rental in Casentino

Bibbiena / Casentino

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Holiday Apartment Il Molino di Serravalle 2 km from the Monastery of Camaldoli, surrounded by the Casentino Forest Park, where you can feel the charm of nature in every season. The apartment the Squirrel comes with fireplace, central heating and barbecue. Tables for din …see more

from $63 / night

$441 / week

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from $63 / night

(28) 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 $229 / night

$1,145 - $3,204 / week

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from $229 / night

(5) 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
cottage newly renovated in open countryside surrounded by olive groves 2 steps from Arezzo and the Casentino, the house has a large kitchen equipped with appliances and utensils, 5 spacious 4 bathrooms and a typical living room. Excellent overview, large private outdoor …see more

from $149 / night

$1,145 / week

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from $149 / night

15

Vacation villa in Cortona

Province of Arezzo / Cortona

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Villa with garden and barbecue, terrace overlooking the Val di Chiana and Lake Trasimeno in the distance. It is five minutes from the center of Etruscan Cortona and 1 hour from Perugia and Lake Trasimeno. Near Arezzo. The house is made of stone with rustic finishes, cei …see more

from $131 / night

$801 / week

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from $131 / night

(1) Excellent 

27

Vacation villa in Anghiari

Province of Arezzo / Anghiari

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Set in 40 acres of olive groves, oak woods and fields full of wild flowers, Villa Monterosi is a jewel of peace with it's own private swimming pool, rolling gardens and terraces. A place to dream of, this stone built house has been renovated to the highest ecological …see more

from $172 / night

$1,145 - $2,518 / week

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from $172 / night

24

Vacation apartment in Lucignano

Province of Arezzo / Lucignano

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
New apartment with excellent finishes located on the ground floor of a two-story complex. Can accommodate up to 4 people. The apartment consists of a main room with kitchen and living room, a double bedroom, a bedroom with two beds and balcony, and a bathroom with showe …see more

from $86 / night

$572 / week

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from $86 / night

(28) Excellent 

37

Vacation apartment in Sansepolcro

Province of Arezzo / Sansepolcro

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 120 mi
  • Child friendly
  • Car not necessary
Relax in this delightfully spacious 1070 square feet self catering central apartment on the ground floor of the owner's 100 year old house. The apartment, just in front of the town's ancient 15th century walls, features a large private secluded garden ideal for al fresc …see more

from $77 / night

$536 / week

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from $77 / night

(3) Excellent 

27

Vacation home in Anghiari

Province of Arezzo / Anghiari

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Casa Toppole is an old stone farmhouse, full of charm, located in the heart of Tuscany. It is independent, enjoys a panoramic view and is located 6 kilometers from Anghiari, a medieval classified village. The capacity of the house is 6 to 8 people. It was built on the …see more

from $216 / night

$2,380 / week

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from $216 / night

(2) Excellent 

7

Vacation villa in Sansepolcro

Province of Arezzo / Sansepolcro

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Small stone Villa dating back to 1500 with exclusive pool, lounge/kitchen, 3 bedrooms and 3 bathrooms. Outside barbecue, sunshade, table and chairs for dining al fresco. The ee pool lit up at night with Chromotherapy. Altitude: 540 metres above sea level. The Villa is i …see more

from $239 / night

$1,365 / week

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from $239 / night

17

Badia Tedalda Vacation home rental

Province of Arezzo / Badia Tedalda

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Nearest beach 85 mi
  • Child friendly
My little home is ideal for lovers of cultural landscape and beautiful natural environment that are open to art and food culture. - A natural swimming pool with pizzeria (Oasi Cocchiola) is located about 10 minutes from the house eliminator (6.5 km towards Badia). - swi …see more

from $49 / night

$344 / week

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from $49 / night

(5) Excellent 

24

Villa rental in Sansepolcro with swimming pool

Province of Arezzo / Sansepolcro

13 30 1 night min

  • 13 bedrooms
  • sleeps 30
  • 1 night min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Small stone village dating from 1,500 restored with great care, dipped in the green of the hillside 500 metres above sea level with wide views of the Valtiberina. It is composed by living room with fireplace, tv and dvd, kitchen with dishwasher, groups maxi refrigerator …see more

from $1,030 / night

$5,149 / week

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from $1,030 / night

(39) 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
  • Nearest beach 150 mi
  • 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 on the valley beneath! Caratteristica casa …see more

Certificate of Excellence

from $86 / night

$492 - $927 / week

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Responds fast!
avg. 2 hours 2 minutes

from $86 / night

(4) Excellent 

41

Castiglion Fibocchi Vacation apartment rental

Province of Arezzo / Castiglion Fibocchi

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Close to swallow the Citadel of peace ", at 7 km from Arezzo and close to the towns of Ponte Buriano and Castiglion Fibocchi, surrounded by greenery and away from the noise of city life, in family and private environment. Eliana apartment consists of an independent entr …see more

from $138 / night

$801 / week

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from $138 / night

17

Vacation apartment in Sansepolcro

Province of Arezzo / Sansepolcro

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
the apartment house is on the ground floor between the orchard with the playground and the garden surrounding the pool has a small private garden with table and chairs for outdoor dining, has a bedroom a bathroom and a living room with kitchen is about 38 square meters, …see more

from $72 / night

$481 / week

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from $72 / night

23

Vacation farmhouse with shared pool in Foiano Della Chiana

Province of Arezzo / Foiano Della Chiana

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Property Description Traditional brick farmhouse, situated at the top of a hill, where there is always a cool breeze, and where one can enjoy a magnificent view of the Valdichiana. The original building has been divided into three delightful apartments. The apartments …see more

from $101 / night

$705 - $1,178 / week

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from $101 / night

(14) Excellent 

31

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 $367 / night

$4,806 / week

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Responds fast!
avg. 1 hour 55 minutes

from $367 / night

8

Vacation farmhouse with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

13 5 min stay varies

  • 13 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Der Biohof IL MORO ist ein Familienbetrieb reiner geführt von Roberta und Alberto mit Hilfe ihres Sohnes Sandro und Tochter Guia. Hier werden nach zertifizierten biologischen Richtlinien saisonales Gemüse, Rotwein und Oliven für Olivenöl angebaut. Unsere Hühner laufen t …see more

from $68 / night

$431 - $771 / week

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from $68 / night

(38) Excellent 

31

Poppi Vacation villa rental

Province of Arezzo / Poppi

8 18 7 nights min

  • 8 bedrooms
  • sleeps 18
  • 7 nights min
  • Nearest beach 130 mi
  • Swimming pool
  • Child friendly
The Villa, nestled in a quiet private wood, can accommodate up to 14+6 people in over 400 square meters of space. There are 7 double bedrooms, 1 single room, 8 bathrooms, two lounges with fireplace, panoramic veranda and kitchen furnished with steel furnitures. The …see more

from $360 / night

$2,518 - $5,206 / week

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from $360 / night

(2) Very Good 

24

Poppi Vacation villa rental

Province of Arezzo / Poppi

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Villa Casentino is the perfect accommodation for your holiday in total relax. It consists of 3 bedrooms and 2 bathrooms for a total of 8 sleeping places, very suitable for families with children or small groups. The private pool (6m x 12m) and the surrounding park (3000 …see more

from $277 / night

$1,774 - $1,945 / week

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from $277 / night

(2) Excellent 

22

Vacation home in Anghiari

Province of Arezzo / Anghiari

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 115 mi
  • Child friendly
  • Pet friendly
Recently restored property in the medieval hilltop town of Anghiari. To the side of the property there are steps that lead directly down to the main square where you will find bars, restaurants and shops. As you enter Villa Del Chiassolo on the ground floor you will fi …see more

from $164 / night

$1,145 - $1,385 / week

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from $164 / night

(2) Excellent 

21

Stia Vacation apartment rental

Province of Arezzo / Stia

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Appartamento GIRASOLE La Fagiana Holiday Rental is in an optimal position. You will be able to fully enjoy the peace and the quietness of the region as well as being in a good position for numerous outdoor activities, such as horse riding, golf, tennis, mountain biking …see more

from $92 / night

$641 - $1,122 / week

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from $92 / night

(3) Excellent 

10

Vacation apartment in Cortona

Province of Arezzo / Cortona

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Child friendly
  • Private garden
Wonderfully located only ten minutes walking from the city center of Cortona. From this property you will have one of the most beautiful views of the city, the valley and the lake Trasimeno.It is one apartment on the first floor of a villa, the owner live upstairs. The …see more

from $115 / night

$801 - $1,402 / week

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from $115 / 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 traditional …see more

from $187 / night

$978 - $1,841 / week

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Responds fast!
avg. 2 hours 33 minutes

from $187 / night

21

Vacation apartment with shared pool in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Il Casone lies in the open countryside, a few minutes from Cortona towards Farneta. Immersed in a large garden, among the green olive trees and the delicate scent of the roses that frame the swimming pool area, this ancient farmhouse has been painstakingly restored and …see more

from $123 / night

$859 - $1,087 / week

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from $123 / night

50

Vacation apartment rental

Cortona / Farinaio

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
You will find 4 spacious apartments for your stay in Cortona, bright and comfortable and an outbuilding between the olive trees. Farmhouse La Tesa is the best that a country house can give you for your holiday in the heart of Tuscany. You will experience a rejuvenating …see more

from $119 / night

$836 / week

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from $119 / night

(2) Excellent 

56

Vacation apartment rental

Province of Arezzo / Poppi

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Cozy apartment in an old farm of 1800, in the green hills of Tuscany. In quiet and panoramic, it is ideal for those who wish to savor the slow pace of nature and indulge in complete relaxation. It overlooks a beautiful garden with swimming pool and is the perfect soluti …see more

from $46 / night

$321 / week

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Responds fast!
avg. 2 hours 15 minutes

from $46 / night

19

Townhouse rental in Anghiari

Province of Arezzo / Anghiari

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Just A few kilometres from the medieval village of Anghiari, in a panoramic position, apartment of 100 sqm, elegantly restored. The apartment, situated on the first floor of a typical Tuscan style farmhouse, consists of two bedrooms and two bathrooms, one en suite. The …see more

from $80 / night

$558 / week

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from $80 / night

14

Vacation home with shared pool in Monte San Savino

Province of Arezzo / Monte San Savino

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Swimming pool
80 m², 75 m² floors in good condition energy class: (ipe not shown) Central hot water heating-wood/coal Southeast orientation 2 floor, 2-storey building with no elevator built between 1950 and 1970, 1 apartment for 150 euro plan charges amenities: furnished …see more

from $126 / night

$859 / week

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from $126 / night

10

Vacation apartment in Lucignano

Province of Arezzo / Lucignano

2 3 1 night min

  • 2 bedrooms
  • sleeps 3
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Traditional yet modern, the apartment is a perfect accommodation for those looking to enjoy a stay in the tranquility of the Tuscan countryside but having a few steps the city center and the services offered by the country. With private garden and parking space, the apa …see more

from $56 / night

$373 / week

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from $56 / night

11

Sansepolcro Vacation apartment rental

Province of Arezzo / Sansepolcro

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The beauty and the Green Tuscan countryside backdrop to Antico Borgo de ' Romolini Sansepolcro in the province of Arezzo, a village of 3 ancient farmhouses have been completely renovated, where, with antique furnishings and finishes, you can relive the fascination of th …see more

from $90 / night

$626 / week

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from $90 / night

(1) Excellent 

13

Home rental in Monte San Savino with swimming pool

Monte San Savino / Montagnano

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Renovated farmhouse with 3 bedrooms (6 beds, 1 bathroom, large garden In the heart of the Tuscan countryside, completely restored stone and brick farmhouse with large garden and private pool (6 X 12 m, depth 1.30 to 2 meters). Built in a panoramic position, 3 bedrooms ( …see more

from $80 / night

$1,316 / week

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from $80 / night

33

Arezzo Vacation villa rental

Province of Arezzo / Arezzo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Comfort and relaxation, country life or strategic point to visit important sites (Siena, Florence, Cortona, Montepulciano ect). Swim in the pool surrounded by cypress trees, a good glass of wine and cozy apartments will be a reminder of an unforgettable stay. Just 3 km …see more

from $69 / night

$961 - $1,602 / week

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Responds fast!
avg. 2 hours 33 minutes

from $69 / night

(1) Excellent 

18

Vacation apartment rental

Province of Arezzo / Anghiari

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
~300 year old stone farmhouse ~Countryside location, a short drive from Anghiari ~Easy reach of major attractions in Tuscany & Umbria ~Large garden with swimming pool ~Flexible change-over day and length of stay A traditional 18th Century stone farmhouse situated in wo …see more

from $242 / night

$1,691 / week

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from $242 / night

(3) Excellent 

24

Bucine Vacation home rental

Province of Arezzo / Bucine

10 7 3 nights min

  • 10 bedrooms
  • sleeps 7
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
On the hills of Chianti right in the centre of beautiful Tuscany, you can find our farm holidays villa apartments. The Villa, which has been completely restructurated, is equipped with all comforts. The villa consists of 6 independent apartments, air conditioning an int …see more

from $126 / night

$1,252 / week

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from $126 / night

(10) Excellent 

31

Vacation b&b in Pieve A Presciano

Pergine Valdarno / Pieve A Presciano

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 110 mi
  • Child friendly
  • Pet friendly
The b & b is located in the historic center of Pieve a Presciano small Tuscan village, and 'a Tower belonging to the medieval castle of the country, restored according to the Tuscan tradition, and' fresh and bright atmosphere. The village of Pieve a Presciano and 'a sma …see more

from $40 / night

$286 - $607 / week

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from $40 / 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 $143 / night

$996 / week

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from $143 / night

(2) Excellent 

27

Vacation lodge in Cortona

Province of Arezzo / Cortona

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
The "Fattoria Borgonuovo" is located in an agricultural and hilly area of the Val di Chiana, very close to the beautiful and old town of Cortona, and a short distance from the most important historical and wine centers of the southern part of Tuscany, as, Montepulciano, …see more

from $75 / night

$515 - $744 / week

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Responds fast!
avg. 1 hour 19 minutes

from $75 / night