Villas in Province of Siena: Rent luxury villas in Province of Siena

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Province of Siena

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1,092 Holiday homes

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(5) Excellent 

21

Holiday villa with swimming pool in Casaglia

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
“An awesome villa in the Tuscan hills” A wonderfully restored church with plenty of character. Privacy with trees and hedges. Fab and accessible pool. Well equipped kitchen. An amazing welcome pack. We cycled from here to San Gimignano and to Monterigg  …see more

from £127 / night

£841 - £1933 / week

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from £127 / night

(11) Excellent 

53

Holiday villa in Staggia Senese

Poggibonsi / Staggia Senese

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“Best vacation ever!” Our entire experience at Villa Vianci was beyond expectations. We travelled with 4 generations, ages 3 1/2 to 85! The villa was spectacular, spacious & immaculate. The pictures on line don't do it justice. Tommasso & Chiara we  …see more

from £505 / night

£3530 / week

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from £505 / night

(2) Excellent 

25

Holiday villa with swimming pool in Montisi

Province of Siena / Montisi

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“An undiscovered treasure” A well appointed and comfortable villa facing south overlooking beautiful Tuscan countryside with the abbey S Anna Camprena in the distance. This abbey of the film English Patient fame. Montisi is a wonderful small village w  …see more

from £103 / night

£715 - £1030 / week

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from £103 / night

15

Holiday villa with swimming pool in Montisi

Province of Siena / Montisi

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sun baked stone walls, hand made terracotta floors, chestnut beamed ceilings, pergolas twisted with the perfume of jasmine and wisteria, sitting out on your terrace overlooking your swimming pool,Soaking up the radiant glow of the sun setting over the Val d'Orcia V  …see more

from £145 / night

£1009 - £1219 / week

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from £145 / night

(3) Excellent 

31

Holiday villa in Costalpino

Siena / Costalpino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden
“Belvedere e stupendo” After a beautifully green, bus ride from Rome, I arrived at my designated stop a few kilometer’s before Siena and waited for my transfer to Belvedere, a magical home at the end of a beautiful long winding driveway where views of  …see more

from £152 / night

£925 - £1639 / week

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from £152 / night

(1) Excellent 

24

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
<p><span class="x_style25">Italian village rental - This charming historic residence with private pool is located in the village of San Giovanni d'Asso, and it is just a short stroll from your door to the castle, the truffle museum and a nice  …see more

from £260 / night

£1820 - £2560 / week

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from £260 / night

20

Villa rental in Radicofani with swimming pool

Province of Siena / Radicofani

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Alonestanding villa with private pool in Southern Tuscany. Quiet location and privacy.  …see more

from £253 / night

£1345 - £2942 / week

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from £253 / night

27

Province of Siena / Siena

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £174 / night

£1219 - £1639 / week

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from £174 / night

31

Asciano holiday villa let

Province of Siena / Asciano

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
This is a spectacular villa, immaculately furnished and presented in a wonderful part of Italy. The owners have imported furniture from around the world to create a unique setting for guests to enjoy their stay. Complete with private pool and beautiful gardens, it's a f  …see more

from £295 / night

£1639 - £3530 / week

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from £295 / night

13

Holiday villa with shared pool in Montisi

Province of Siena / Montisi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Beautiful Three bedroom stone house spread over three floors with the master bedroom on the top floorentered by a spiral staricase.Fully fitted kitchen with fridge freezr, dishwasher, oven and hob with all of the cooking equipment supplied.  …see more

from £120 / night

£837 - £1089 / week

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from £120 / night

19

Holiday villa in Pienza

Province of Siena / Pienza

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful independent country house near Pienza. This villa is located few minutes driving from Pienza, in a quiet and beautiful location in the middle of the country side. Private swimming pool.The villa is elegantly furnished, in a perfect combination between comfort  …see more

from £154 / night

£1076 - £2017 / week

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from £154 / night

100

Holiday villa rental

Sinalunga / Guazzino

11 20 Min stay varies

  • 11 bedrooms
  • Sleeps 20
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
This villa offers 4 bedrooms and a suite in the main body and four neighbouring cottages with one or two bedrooms, kitchen or kitchenette.  …see more

from £589 / night

£4118 - £7824 / week

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from £589 / night

(1) Excellent 

32

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect.” The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arri  …see more

from £274 / night

£1916 - £2471 / week

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from £274 / night

(1) Very Good 

13

Montisi holiday villa rental

Province of Siena / Montisi

5 6 Min stay varies

  • 5 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
We offer a relaxed holiday, You can lounge by the pool soaking up the sun or visit the many cities of intrest Siena, Florence and Rome are all very close. And of course the local places of Intrest. The spa, Pienze home of the English Patient and within view of your home  …see more

from £43 / night

£505 - £585 / week

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from £43 / night

(6) Very Good 

20

Holiday villa rental

Province of Siena / Chianciano Terme

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies at 3 kms from the town of Chianciano Terme, one of the most popular thermal Spas in Italy. The villa is located among the hills dividing Val d'Orcia and Valdichiana. The whole property is for your private use and not shared with any other person. The vill  …see more

from £169 / night

£900 - £2269 / week

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from £169 / night

14

Castelnuovo Berardenga / Montaperti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £115 / night

£799 - £1849 / week

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from £115 / night

13

Province of Siena / San Gimignano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £169 / night

£967 - £2774 / week

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from £169 / night

34

Holiday villa in Pienza

Province of Siena / Pienza

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
it is the ideal place if you are looking to relax, private pool and beautiful view  …see more

from £197 / night

£1379 - £2253 / week

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from £197 / night

(7) Excellent 

16

Holiday villa in Casole d'Elsa

Province of Siena / Casole d'Elsa

4 4 3 nights min

  • 4 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Colle Val d'Elsa; 40 from San Gimignano, Volterra and San Galgano and 60 km from Florence.  …see more

from £68 / night

£471 / week

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from £68 / night

32

Holiday villa rental

Province of Siena / Trequanda

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
Villa Leccetino Tuscany Arriving at Leccetino, down a short tree covered road is like arriving at a very secret location. Tucked into the hillside surrounded by olive trees, this is a spectacular masonry villa, made with stones dug up from the ground on this terraced p  …see more

from £271 / night

£1891 - £3353 / week

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from £271 / night

(2) Very Good 

27

San Gusme holiday villa rental

Castelnuovo Berardenga / San Gusme

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Private garden
“wonderful and peaceful place” San Donato is very quiet, a very beautiful place, the garden and all the Villa Arceno aera are amazing, the house is simple but comfortable, and with a soul, as if you ever know this place, I will return one day, for sure  …see more

from £179 / night

£1253 - £1673 / week

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from £179 / night

6

Holiday villa in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The Siena rolling hills, the valley of the Arbia river, the castle of San fabiano and the farm estate with pheasants,and white truffles:a dream!Come to this villa unique for her comforts!Air conditioning, DVD , HI-FI, fully equipped kitchen,balcony with  …see more

from £169 / night

£1093 - £1513 / week

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from £169 / night

(3) Excellent 

22

Holiday villa rental

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Centrum of city only 15 minutes by foot ! The villa was perfectly clean when we arrived. The kitchen is well equipped and fun to cook in.We highly recommend this property for those who are looking for a peaceful setting near all that Siena has to offer.  …see more

from £248 / night

£967 - £1681 / week

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from £248 / night

20

Villa rental in Castiglione D'Orcia with swimming pool

Castiglione D'Orcia / Gallina

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful house with private pool in one of the most interesting area of Tuscany. It also perfect for trekking, jogging and mountain biking among the forests of Monte Amiata.  …see more

from £181 / night

£1261 - £2059 / week

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from £181 / night

20

Chiusi holiday villa rental

Province of Siena / Chiusi

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Villa with lovely swimming pool set in a nature reserve, near the lake, ideal for bird watching and cycling.  …see more

from £142 / night

£992 - £2513 / week

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from £142 / night

24

Villa rental in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
This holiday home has 3 bedrooms and 2 bathrooms and can accomodate 6 people making it ideal for families. Located in Siena, Tuscany this property is a pet friendly space .  …see more

from £72 / night

£504 - £933 / week

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from £72 / night

20

Villa rental in Pienza with swimming pool

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below.  …see more

from £476 / night

£3328 - £3866 / week

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from £476 / night

(1) Excellent 

16

Villa rental in Chiusi with swimming pool

Province of Siena / Chiusi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Casa Baiocco is a typical Tuscan home, newly built in the traditional farmhouse style, perfectly blending with the Italian countryside. Surrounded by a well kept park, for your private use only, it offers all the peace and tranquility that you look for during your holid  …see more

from £61 / night

£421 - £1303 / week

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from £61 / night

(1) Excellent 

23

Holiday villa with shared pool in Montepulciano

Province of Siena / Montepulciano

4 2 Min stay varies

  • 4 bedrooms
  • Sleeps 2
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Ask owner if suitable for children
“Old-world Italian charm in a beautiful Tuscan setting” It's a job to find it it, but once you do, you'll want to stay longer than you've booked for. The house has been in the family since 1812 - they produce their own wine - and Olimpia is a charming  …see more

from £59 / night

£412 / week

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from £59 / night

18

Villa rental in Gaiole in Chianti with swimming pool

Gaiole in Chianti / Montegrossi

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Our close proximi  …see more

from £109 / night

£757 - £1933 / week

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from £109 / night

(11) Excellent 

40

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
3 BDR cosy house with small pool,AC,Wifi,patio; nestled in a village in Siena countryside. Private parking.Please,ALWAYS enquiry about prices.  …see more

from £202 / night

£1412 - £1967 / week

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from £202 / night

(15) Excellent 

23

Casole d'Elsa holiday villa rental

Province of Siena / Casole d'Elsa

7 12 7 nights min

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Villa Podere Scopicciolo is located about 30 miles from Florence. It is 900 ft above sea level in the heart of Tuscany surruonded by cultivated farm land and well preserved forests. It is fully immersed in the countryside enjoying peace and tranquillity, yet convenientl  …see more

from £901 / night

£6303 - £8824 / week

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from £901 / night

(12) Excellent 

78

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Perfect holiday location” Our family group of 8 adults spent 5 nights at Villa LisiDor - a perfect location for both relaxing & a great base for exploring the local region. The roads in Chianti can be narrow & windy but worth the drive to villages lik  …see more

from £398 / night

£2786 - £4286 / week

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from £398 / night

25

Holiday villa with swimming pool in Rigomagno

Sinalunga / Rigomagno

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
On demand services: Tranfer and Taxi serviceWine and Olive Oil TastingsCooking LessonsDinners  …see more

from £211 / night

£1513 - £1975 / week

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from £211 / night

(1) Excellent 

24

Montepulciano holiday villa rental

Province of Siena / Montepulciano

6 12 4 nights min

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
“Fantastic” A great villa in a great location. Because of a minor error in the booking the owner treated us all to a meal by personal chefs Dorians Ottaviana and Claudio from Cooking for You. They came to the villa and prepared a sumptuous 4 course mea  …see more

from £211 / night

£2059 / week

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from £211 / night

(6) Very Good 

19

Holiday villa with swimming pool in Siena

Province of Siena / Siena

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
Villa Le Tolfe is so close to Siena you can almost touch it (only 3 kilometres away). With stunning views and beautiful antique gardens this villa is perfect for relaxed stress free holidays. The house is built on top of a hill covered with olive groves and vineyards.  …see more

from £151 / night

£1051 - £2093 / week

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from £151 / night

100

Holiday villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
At Villa Valpoliziana, which has been described as a ´paradise on earth´ you will rediscover how to relax and get in touch with nature surrounded by wonderful opportunities to discover the amazing Tuscan culture and wonderful towns such as Montepulci  …see more

from £463 / night

£2101 - £3152 / week

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from £463 / night

(4) Excellent 

39

Province of Siena / Vivo d'Orcia

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Ski
  • Child friendly
  • Ask about pets

 …see more

from £84 / night

£517 - £917 / week

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from £84 / night

(2) Excellent 

40

Siena / Val di Merse

6 11 Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £106 / night

£748 - £1664 / week

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from £106 / night

20

Province of Siena / Chiusdino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

 …see more

from £361 / night

£2522 - £3194 / week

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from £361 / night

Top Destination reviews

La Casina Toscana, central with parking and wi-fi
Clean, comfortable and cozy house with privacy and convenience to Montepuciano

We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close enough to walk to the Montepulciano town. The place was very clean and thoughtf … see more
Farm holidays in Chianti
A Christams dream

This year my husband and I decided to spend Christmas on our own, in the Chianti countryside. La Capanna delle Cozzole is just the perfect location: very quiet, romantic and private location. In the village you can find top quality food, wine and d … see more
Pink Holiday-apartment with pool in Chianti
Wanderful stayin

The location of the house is in a very typical Tuscan environment: hills, vineyards, olive trees. Even if you might thing to be in a faraway place, the location is very convenient to Siena, San Giminiano, Firenze, and to other spots, such as Pisa an … see more
Villa Podere Earthly
Perfect, beautifil little place in tuscany

A beautiful place full of happines, were you can stay The time you want for a very very good price ,there's a beautiful view, is very relaxing and you can enjoy The animals and nature … see more
Agriturismo Podere Terrena Appartamento "Papavero"
We found what we were looking for: beauty and relax

I was looking for a beautiful place to relax with my husband and certainly found it in this beautiful borghetto. The apartment is very comfortable and well equipped with everything you need to feel at home itself. Italian typical breakfast was ideal … see more
Very clean and pleasant apartment

The apartment is very clean, the kitchen equipment is brand new. Even the owner changed both the TV's, so we could watch the European Football Championship. Veronica very kindly meet us late in the evening and drove us from the parking lot to the a … see more