Holiday Rentals in Province of Arezzo - Holiday Lettings - Villas

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Province of Arezzo

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143 Holiday homes

(2) Excellent 

21

Holiday 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 km
  • Swimming pool
“Stunning views, lovely house, helpful owner.” Cortona is a very picturesque medieval town and this villa is a longish walk from the town itself up a very windy road. The house is only a few years old but built in the style of the old houses. It has la  …see more

from £145 / night

£1009 - £1639 / week

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from £145 / night

(3) Excellent 

32

Holiday b&b in Ambra

Province of Arezzo / Ambra

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 127 km
  • Suitable for children age 5+
  • Ask about pets
A stay based in Ambra can be as busy or relaxed as wished and caters for all visitor needs, great eating places. Friendly local folk, lots to see and do. There is a outdoor pool complex & hot springs nearby. The countryside is glorious and is wonderful for walking.A  …see more

from £100 / night

£700 / week

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from £100 / night

(33) Excellent 

25

Holiday villa rental

Cortona / Montanare

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 180 km
  • 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 £198 / night

£1387 - £2479 / week

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from £198 / night

35

Cortona / Bagnolo

5 12 Min stay varies

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

 …see more

from £181 / night

£967 - £2143 / week

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from £181 / night

(8) Excellent 

55

Holiday apartment in Centoia

Cortona / Centoia

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
“Great base for discovering Tuscany.” Peter and Nina's apartments are in an ideal situation for exploring Tuscany with the added bonus of a pool to relax by when you return from trips to the surrounding hilltop villages. Il Boccolio is spacious and  …see more

from £68 / night

£471 / week

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from £68 / night

(1) Excellent 

19

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can arrange special days or tours such as;Wine TastingCookingCyclingPaintingWalkingWeddings  …see more

from £59 / night

£409 - £552 / week

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from £59 / night

(53) Excellent 

51

Anghiari holiday villa rental

Province of Arezzo / Anghiari

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 66 km
  • Swimming pool
  • Child friendly
“Fantastic Holiday Villa” What can I say about Casa Leana and Tuscany? Well it was just one of the best holidays ever! Starting with the friendly service from Di and Leigh who both met us in Anghiari and took us to the villa so that we didn't get l  …see more

from £248 / night

£1730 - £2630 / week

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from £248 / night

(9) Excellent 

32

Holiday 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 km
  • Swimming pool
“Fabulous, breathtaking and relaxing - just the right place for a getaway.” The holiday was easy to arrange with good communication on location, directions etc. The villa was lovely and comfortable for our stay. You had the ability to dine inside or  …see more

from £245 / night

£1645 - £2028 / week

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from £245 / night

(1) Excellent 

83

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 18 km
  • Swimming pool
  • Child friendly

 …see more

from £85 / night

£505 - £824 / week

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from £85 / night

(2) Very Good 

23

Holiday farmhouse with swimming pool in Loro Ciuffenna

Province of Arezzo / Loro Ciuffenna

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
On request: special homemade Tuscan dinners, Shiatsu, personal chef service!  …see more

from £145 / night

£589 - £1597 / week

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from £145 / night

35

Cortona holiday villa rental

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
3 bedrooms Tuscan country villa in panoramic location with private swimming pool , private garden and parking . Five minutes away from the beautiful medieval city of Cortona and the famous cooking school I Gustasapori  …see more

from £195 / night

£1135 - £1891 / week

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from £195 / night

(6) Very Good 

44

Holiday apartment rental

Cortona / Centoia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
Delightful spacious self catering apartment in beautifully restored 18th century Tuscan farmhouse with pool. Rural, quiet & relaxing yet close to the charming Etruscan town of Cortona & within easy reach of the major art & cultural centres of Tuscany & U  …see more

from £59 / night

£379 - £664 / week

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from £59 / night

(2) Very Good 

19

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can arrange special days or tours such as;Wine TastingCookingCyclingPaintingWalkingWeddings  …see more

from £63 / night

£438 - £600 / week

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from £63 / night

(4) Very Good 

23

Holiday villa with shared pool in Cortona

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“The perfect base camp to travel around Tuscany” We stayed there for two weeks during the summer with our kids (6 and 2). The property is beautiful and very quiet, the view is amazing. The house was very old (about 400 years) but has just been renova  …see more

from £85 / night

£1093 / week

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from £85 / night

(1) Excellent 

17

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Only 15 minutes from the villa you can easily access the Etruscan town of Cortona.  …see more

from £315 / night

£2200 - £3200 / week

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from £315 / night

(1) Excellent 

20

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can also arrange special days or tours for;Wine TastingCookingCyclingPaintingWalkingWeddings  …see more

from £50 / night

£390 - £523 / week

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from £50 / night

(13) Excellent 

21

Holiday cottage in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 27 km
  • Swimming pool
  • Suitable for children age 5+
“Looking forward to next time” We thoroughly enjoyed our holiday at Borgo Tranquillita. It is the perfect place to stay whether you use it as a base for travelling the eastern part of Tuscany or just for a relaxing time at the top of picturesque hill.  …see more

from £106 / night

£606 - £669 / week

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from £106 / night

(2) Excellent 

25

Caprese Michelangelo holiday farmhouse rental

Province of Arezzo / Caprese Michelangelo

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Covivoli is a beatifully restored Tuscan farmhouse with a large pool. It has 4-5 bedrooms and comfortably sleeps 10. Covivoli is in a peaceful location, has amazing views, and is close to historic towns and local amenities. This 100 year old farmhouse has been restor  …see more

from £300 / night

£1400 - £2200 / week

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from £300 / night

19

Holiday apartment with swimming pool in Loro Ciuffenna

Province of Arezzo / Loro Ciuffenna

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
** TRIP ADVISOR 2014 CERTIFICATE OF EXCELLENCE WINNER ** Search for us: PODERE CASAROTTA  …see more

from £70 / night

£303 - £521 / week

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from £70 / night

(1) Very Good 

15

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 25 km
  • Child friendly
  • Car not necessary

 …see more

from £85 / night

£505 - £673 / week

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from £85 / night

(9) Excellent 

38

Holiday 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 km
  • Swimming pool
“Tuscan Dream” I cannot say enough good things about this wonderful Tuscan Dream Villa. The owner Christine was on another continent went out of her way to make us feel at home and cater to our every need through email exchanges and her wonderful hou  …see more

from £245 / night

£1645 - £2023 / week

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from £245 / night

(2) Excellent 

22

Cottage rental in Cortona

Province of Arezzo / Cortona

1 6 7 nights min

  • 1 bedroom
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The most important aspects of Il Glicine are: Location, Size, Silence, Privacy, Cleanliness  …see more

from £68 / night

£471 / week

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from £68 / night

16

Province of Arezzo / Arezzo

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 145 km
  • Swimming pool
  • Child friendly

 …see more

from £83 / night

£577 / week

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from £83 / night

20

Province of Arezzo / Pieve Santo Stefano

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £85 / night

£471 - £706 / week

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from £85 / night

(12) Excellent 

42

Cortona holiday farmhouse rental

Province of Arezzo / Cortona

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
“IDYLLIC VILLA IN AN IDYLLIC SETTING” Our stay commenced with prosecco and snacks served by the lovely pool after our late afternoon swim after arrival, which set the standard for the rest of our visit. The accommodation is of even better quality than  …see more

from £208 / night

£1454 - £3194 / week

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from £208 / night

(22) Excellent 

24

Arezzo holiday apartment rental

Province of Arezzo / Arezzo

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 120 km
  • Child friendly
  • Private garden
“Traditional Tuscan Hospitality” Nestling in the little viaalage of Croce just outside Lucignano, a charming hill-town, Dario’s property is a comfortable and cosy base for exploring Tuscany. It has great views of Lucignano and the surrounding countrysi  …see more

from £43 / night

£269 / week

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from £43 / night

(9) Very Good 

33

Holiday cottage with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 26 km
  • Swimming pool
  • Suitable for children age 5+
“Rustic charm and a five star pool with a breathtaking view” This was indeed a haven of peace high up in the hills with a lovely view across the valley to the hills on the other side. The well appointed cottages make you feel you are part of the local  …see more

from £114 / night

£628 - £711 / week

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from £114 / night

(1) Excellent 

36

Villa rental in Oliveto

Civitella in Val di Chiana / Oliveto

5 14 3 nights min

  • 5 bedrooms
  • Sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Nature, relax, fascination, beauties, pleasant house, all the necessary amenities, as if same house yours  …see more

from £152 / night

£841 - £1597 / week

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from £152 / night

(1) Excellent 

23

Holiday condo with swimming pool in Orzale

Castiglion Fiorentino / Orzale

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Romantic Lovely and Memorable Honeymoon” Thank you Terry for the opportunity to stay at Orzale and the little cottage. It was wonderful. After a few days in Venice and then Modena, the little cottage was a great place for us to enjoy the last 10 days  …see more

from £75 / night

£524 - £638 / week

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from £75 / night

17

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

 …see more

from £64 / night

£429 - £488 / week

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from £64 / night

(8) Excellent 

30

Cortona holiday farmhouse rental

Province of Arezzo / Cortona

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Wonderful house, with beautiful views and flexible set up.” The house can in fact be viewed as three separate apartments each with it's own amenities. This gives great flexibility for people to have some quiet time, whether you're travelling with frie  …see more

from £337 / night

£2522 - £3362 / week

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from £337 / night

(4) Excellent 

48

Holiday villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
ENCHAINTING VILLA with private POOL on top of TUSCAN HILLS. 10 minutes drive to the town of Castiglion Fiorentino. 25 to CORTONA. One hour to FIRENZE, PERUGIA and SIENA. 30 minutes to the TRASIMENO LAKE.  …see more

from £101 / night

£631 - £1177 / week

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from £101 / night

(2) Excellent 

22

Holiday apartment with shared pool in Monte San Savino

Province of Arezzo / Monte San Savino

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
Villa Ceppeto is an ideal place to stay in Tuscany! To relax and also to start daily drives into the best places of Tuscany and Umbria!  …see more

from £127 / night

£883 / week

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from £127 / night

(1) Excellent 

80

Province of Arezzo / Cortona

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 16 km
  • Swimming pool

 …see more

from £101 / night

£673 - £1000 / week

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from £101 / night

21

Lucignano holiday villa rental

Province of Arezzo / Lucignano

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Other activities available nearby:Horseback Riding, Hot Air Balloon Flights, Thermal Spas, Wine Tours, Bike Rental, Nature Hikes  …see more

from £379 / night

£2648 / week

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from £379 / night

19

Holiday apartment in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can also arrange special days or tours such as;Wine TastingCookingCyclingPaintingWalkWeddings  …see more

from £51 / night

£352 - £466 / week

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from £51 / night

15

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can arrange special days or tours such as;Wine TastingCookingCyclingPaintingWalkingWeddings  …see more

from £54 / night

£371 - £495 / week

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from £54 / night

(7) Very Good 

18

Castiglion Fiorentino holiday 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
“AMAZING!!!” I've had the most wonderful stay in this Tuscan gem! Jacopo is such a great host and was always there to answer my questions. The villa is just beautiful! Each room and corner has something unique about it. The gardner Giancarlo came to ma  …see more

from £169 / night

£1177 - £2269 / week

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from £169 / night

(1) Excellent 

12

Holiday farmhouse rental

Province of Arezzo / Cortona

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
2 bedrooms, full kitchen, living room with sofa bed, bathroom with shower.  …see more

Pricing unknown

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Pricing unknown

14

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
Holiday apartments near Cortona in Tuscany. These self-contained apartments have a large pool, BBQ and Picnic area. There is ample parking space and the surrounding gardens are particularly beautiful, with colour and scent from the many rose bushes, jasmine & lavend  …see more

from £51 / night

£352 - £466 / week

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from £51 / night

Top Destination reviews

Casa dei Sogni, Stefano - An attractive air conditioned stone farmhouse with Private Pool - set within a  small Tuscan borgo
Not to be missed

This Tuscan farmhouse has been tastefully and sympathetically restored. It is situated at the top of the valley with spectacular views of the surrounding countryside. You do need a car to stay here but most of the towns and villages to be explored … see more
Casa Dei Sogni, Tuscan Villa, Private Pool, A/C
Not to be missed

This Tuscan farmhouse has been tastefully and sympathetically restored. It is situated at the top of the valley with spectacular views of the surrounding countryside. You do need a car to stay here but most of the towns and villages to be explored … see more
Sansepolcro Garden apartment
Revisiting the magic of Sansepolcro

Though this was our first stay at Louise and Franco's wonderful house, it was our third visit to Sansepolcro. The garden apartment was spacious,comfortable and quintessentially Italian and though the March weather didn't lend itself to our using the … see more
Tuscany cottage with Private Pool, BBQ, & Parking
The Trip of a Lifetime!!

This was a beautiful experience! The house was out in the country but not too far away from all of the activities and conveniences. It was beautiful at night! A million stars and so very quiet! It was up on a hill so the view was lovely; vineyar … see more
B&B Casa al Moro, romantic flat in a quaint hamlet
Beautiful tuscan countryside and fantastic family

Cannot rate our stay with Norma and her family highly enough, they looked after us so well, even giving us bread they had baked. The flat is perfect, modern (but keeping with tuscan tradition) and very clean and comfortable with a cooker and a fridge … see more
Grace Hayloft-Il Fienile di Grazia
Utterly Idyllic. We will return

I stayed at the Grace Hayloft - Il Fienile di Grazia with my partner in June and it was indescribably wonderful. The hayloft is basically the most adorable rustic cottage imaginable which was perfect for the 2 of us. There is room to sleep 3 more a … see more