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

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Apartments Cortona
816 properties
Apartments Arezzo
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Monte San Savino
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Loro Ciuffenna
71 properties
Foiano Della Chiana
67 properties
Pergine Valdarno
60 properties
Poppi
59 properties
Castelfranco Piandisco
59 properties
Civitella in Val di Chiana
56 properties
Terranuova Bracciolini
52 properties
Ambra
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Marciano della Chiana
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Monterchi
34 properties
Montevarchi
34 properties

Province of Arezzo

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2,902 Vacation rentals

(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 $235 / night

$1406 - $3280 / week

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from $235 / night

(9) 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

(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 $59 / night

$352 - $563 / week

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Responds fast!
avg. 2 hours 7 minutes

from $59 / night

(36) 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 $352 / night

$2284 - $3455 / week

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Responds fast!
avg. 33 minutes

from $352 / night

(1) Excellent 

21

Vacation apartment with shared pool in Cortona

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The country house "I Nidi di Cortona" is situated in the countryside, in the small rural village of San Marco in Villa (sec. XIV), at the foot of the hill where the Etruscan village of Cortona. Its strategic location allows guests to fully relish the quiet of country li …see more

from $164 / night

$533 - $779 / week

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from $164 / night

9

Ski home to rent in Badia Prataglia

Province of Arezzo / Badia Prataglia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Ski
  • Child friendly
  • Pet friendly
My apartment is in the heart of the Casentino Forest National Park, in the village of Badia Prataglia; at the same time is in a very private area, close only a few meters to the slow-flowing river .... You will like it especially for relaxation and tranquility that you …see more

from $53 / night

$369 / week

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from $53 / night

(4) Very Good 

23

Vacation villa with shared pool in Cortona

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $176 / night

$1523 / week

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Responds fast!
avg. 2 hours 50 minutes

from $176 / night

(4) Excellent 

22

Cottage accommodation in Pieve di Chio

Castiglion Fiorentino / Pieve di Chio

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Charming Restored character stone cottage with beautiful views across the Val Di Chio. Private swimming pool with Stone BBQ. Ideal location for day trips across Tuscany & Umbria, Siena, Montepulciano, Cortona, Perugia & Assisi. 15 minutes to Medieval town with train S …see more

from $161 / night

$1124 / week

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Responds fast!
avg. 3 hours 42 minutes

from $161 / night

(3) Very Good 

10

Apartment rental in Bibbiena

Province of Arezzo / Bibbiena

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets
Casa Vacanze La Contessa is located in a prestigious building of the characteristic village of Bibbiena, in the heart of the Casentino, one of the most beautiful valleys of Tuscany, where you can discover the unique historical treasures, art, nature and traditions of a …see more

from $68 / night

$703 / week

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from $68 / night

(6) Excellent 

40

Lucignano Vacation home accommodation

Province of Arezzo / Lucignano

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Casa Terrazza is located in Lucignano, one of the most outstanding examples of a fortified Tuscan mediaeval village. Casa Terrazza, is just a few steps away from restaurants and cafes.. Featuring a large terrace opening off main living area with views of the Val di Chi …see more

from $175 / night

$1148 - $1320 / week

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from $175 / 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 $208 / night

$1204 - $2015 / week

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Responds fast!
avg. 1 hour 15 minutes

from $208 / 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 $118 / night

$539 - $914 / week

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from $118 / night

(1) Excellent 

53

Cortona Vacation apartment rental

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Beautifully freshly renovated 2 bedroom/2 bathroom apartment with a private terrace overlooking the Valley. Master bedroom with a big mirror closet, fireplace, stunning view of the valley from the window and access to private terrace. The other bedroom has a closet an …see more

from $141 / night

$727 - $1406 / week

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from $141 / night

(2) Very Good 

53

Vacation apartment accommodation

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Ask about pets
Antica casa unico piano, pavimenti in cotto e travi in legno, riscaldamento autonomo (termosifone), a due passi dal centro, silenziosa e circondata dal giardino, facile parcheggio libero nelle vicinanze . Una bella terrazza per mangiare fuori in estate e un camino con l …see more

from $106 / night

$738 / week

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from $106 / night

(54) 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 p …see more

from $469 / night

$3280 - $5856 / week

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from $469 / night

(8) 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 $200 / night

$1523 / week

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from $200 / night

(1) Excellent 

13

Vacation home in Badia Prataglia

Province of Arezzo / Badia Prataglia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • 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 $71 / night

$492 / week

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from $71 / night

16

Farmhouse rental in Cortona with golf nearby

Province of Arezzo / Cortona

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
The Hill of the city of Cortona is situated our vacation home, surrounded by nature and immersed in the peace and quiet, offers visitors a unique experience. The 2 apartments, Magnolia and Mimosa are ideal for families and groups of friends. From our hotel you can take …see more

from $77 / night

$504 - $586 / week

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from $77 / night

(13) Excellent 

Certificate of Excellence

38

Vacation cottage with swimming pool in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
ONLY ONE WEEK LEFT FOR SUMMER 2017 - Saturday July 15 to Saturday July 22 July. Book now to secure these fabulous dates! (A late cancellation has released these dates). A dream home just for you. We created our home in Cortona with all the essential mod cons. Musi …see more

Certificate of Excellence

from $319 / night

$2139 - $2630 / week

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from $319 / 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 $201 / night

$1406 - $2694 / week

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from $201 / night

16

Arezzo Vacation farmhouse rental

Province of Arezzo / Arezzo

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 145 mi
  • Swimming pool
  • Child friendly
Splendido casolare del 1600, in pietra situato in collina alle porte di AREZZO, all'inizio della valle del casentino e della valtiberina.Il casolare è contornato da 500 olivi da cui si produce olio extra vergine di oliva doc. Dispone di piscina 6m.per 11m. profonda da …see more

from $115 / night

$879 - $1956 / week

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from $115 / night

49

Vacation villa in Cegliolo

Cortona / Cegliolo

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This stunning villa is located 5 km from Cortona. Recently renovated and nicely furnished, it is an 18th century Tuscan stone house. Surrounded by olive trees and facing south with lovely views across the valley below, Villa San Pietro is very private and quiet with tra …see more

from $402 / night

$2811 - $4802 / week

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from $402 / night

(12) Excellent 

Certificate of Excellence

33

Vacation villa in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
A late cancellation has released the ONLY WEEK LEFT IN SUMMER 2017 - Saturday July 15 to Saturday July 22. Act now to secure this fabulous week. With essential private pool and (Free) Wi-Fi, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive …see more

Certificate of Excellence

from $319 / night

$2139 - $2630 / week

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from $319 / night

10

Vacation townhouse in Poppi

Province of Arezzo / Poppi

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
In the National Park of Casentino in Tuscany panoramic view surrounded by greenery with 700 m bordering the camaldolese forest, near la Verna where stands the Franciscan Sanctuary (13th century) on Mount Penna 1283 metres high: from here you can see the Lake of Ridracol …see more

from $82 / night

$352 / week

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from $82 / night

(14) Excellent 

Certificate of Excellence

32

Vacation home in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
ONLY ONE WEEK LEFT FOR SUMMER 2017 - Saturday July 15 to Saturday July 22. Book now to secure this fabulous week. Your holiday to Tuscany is special. You want a home that will provide you with the essential pool and of course the internet. You want to be close …see more

Certificate of Excellence

from $319 / night

$2139 - $2637 / week

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from $319 / night

22

Vacation villa in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Name: PICCOLA BRAMASOLE Accommodation: Ville Location: CORTONA Sleep: 4 Bedrooms: 2 Bathrooms: 2 Description: This charming Tuscan, rustic stone Villa has maintained many of its authentic original features without compromising modern comfort. It is surrounded by ol …see more

from $392 / night

$2741 - $4264 / week

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from $392 / night

25

Vacation villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely stone villa is located on the hills between Arezzo (18km) and Cortona (12km), only few minutes from Castiglion Fiorentino (3km), a lovely medieval village dominating the green valleys of the Val di Chio and the Val di Chiana. This strategic position offers …see more

from $352 / night

$1874 - $3514 / week

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from $352 / night

(9) Excellent 

57

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 $94 / night

$645 - $984 / week

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Responds fast!
avg. 2 hours 43 minutes

from $94 / night

(5) 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 $40 / night

$279 / week

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from $40 / night

8

Vacation studio in Castiglion Fibocchi

Province of Arezzo / Castiglion Fibocchi

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Lovely Studio in stone in the garden at guests ' disposal, a classic Tuscan home. Completely renovated, very bright and welcoming. The House has a sofa bed with linen and towels changed weekly and a fully equipped kitchen. …see more

from $47 / night

$328 / week

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Responds fast!
avg. 17 minutes

from $47 / night

(2) Good 

37

Cortona Vacation apartment rental

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Garibaldi is a finely furnished and welcoming apartment, located on the first floor of a historic building having the same name of the Piazza that leads into the promenade in the centre of Cortona. The architecture of each area is enhanced by the choice of tones and fur …see more

from $118 / night

$879 - $1172 / week

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from $118 / 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 $335 / night

$2343 - $2811 / week

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from $335 / night

21

Lucignano Vacation b&b rental

Province of Arezzo / Lucignano

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
...a charming, delightful and peaceful staying for every season... La Casalta is a wonderful place where our guests can find a warm and friendly welcome. Our guests will find themselves in the middle of a magic circle, from where are reachable, in twenty/sixty …see more

Pricing unknown

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Pricing unknown

(5) Excellent 

39

Vacation farmhouse in Brolio

Castiglion Fiorentino / Brolio

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
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 comf …see more

from $176 / night

$1464 - $1874 / week

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from $176 / night

(1) Very Good 

24

Vacation apartment in Loro Ciuffenna

Loro Ciuffenna / Malva

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 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 $41 / night

$282 - $510 / week

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from $41 / night

(7) Excellent 

Certificate of Excellence

30

Vacation home with swimming pool in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
ONLY ONE WEEK LEFT FOR SUMMER 2017 - Saturday July 15 to Saturday July 22. Act now to secure this fabulous week. A two bedroom, two bathrooms, fully furnished beautiful private house for your Tuscan holiday. Complete with the essential private sparkling pool an …see more

Certificate of Excellence

from $319 / night

$2139 - $2630 / week

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from $319 / night

41

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 $170 / night

$1172 - $2109 / week

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Responds fast!
avg. 57 minutes

from $170 / night

14

Vacation villa with swimming pool in Teverina

Cortona / Teverina

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This magnificent country house is perfect for a family reunion or a group trip as it has 14 bedrooms. The complex has a large garden with a private swimming pool (12x6 m. Deep from 1.20 to 2.00 m), garden furniture, sunbeds and umbrellas. The main villa is divided in …see more

from $469 / night

$3280 - $3747 / week

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from $469 / night

(7) Very Good 

18

Castiglion Fiorentino Vacation villa rental

Province of Arezzo / Castiglion Fiorentino

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The ideal destination for combining relax with culture. The unique location of the villa, the accuracy of design and all the comforts inside allow guests to fully enjoy the tuscan countryside by a unique view on it. Furthermore, the villa is situated in a strategic poin …see more

from $334 / night

$2343 - $3163 / week

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from $334 / night

46

Vacation farmhouse with swimming pool in Pergine Valdarno

Province of Arezzo / Pergine Valdarno

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
It's a countryhouse built in 19th century called "Podere La Vignaccia". The house, on two floors, has been recently restored and has all the comforts. At the groundfloor there's a double sitting room with a fireplace, a big kitchenroom with kitchenette, one bedro …see more

from $130 / night

$910 / week

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from $130 / night