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Enjoy a Classic Tuscan Hill Town holiday—now with AC!

Photo gallery for Enjoy a Classic Tuscan Hill Town holiday—now with AC!

Welcome to Tuscany, the Crete Sinese region
Balcony view
Balcony second floor
Getting ready for the sunset
Balcony at dawn

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Air conditioning
  • Kitchen
  • Free WiFi

Explore the area

Map
Trequanda, Tuscany
  • The Saints Peter and Andrew Church
    ‪3 min walk‬
  • Valdichiana Outlet Village
    ‪15 min drive‬
  • Pienza Cathedral
    ‪19 min drive‬
  • Siena (SAY-Ampugnano)
    ‪68 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Second floor, Bedroom 1

1 Queen Bed

Second floor, Bedroom 2

1 Queen Bed

Third floor suite

1 Queen Bed

2 bathrooms

3rd floor suite, Bathroom

Soap · Towels provided · Bidet · Toilet · Shower only · Shampoo · Hair dryer

Second floor bathroom

Soap · Towels provided · Bathtub or shower · Bidet · Jetted bathtub · Shampoo · Hair dryer

Spaces

Kitchen
Balcony
Dining Area

About this property

Enjoy a Classic Tuscan Hill Town holiday—now with AC!

Trequanda is a 14th century hilltop town in the heart of Tuscany, surrounded by vineyards, olive groves and lush greenery. Casa Trequanda offers an authentic Tuscan experience in a peaceful and picturesque setting . The town has a regionally renown Zagat and Michelin Bib Gormand rated restaurant, Conte Matto, as well as a charming town square, with a unique vegan Italian pizzeria/restaurant, a pharmacy, local bar, bank with an ATM. In the center of town in the piazza is a 14th century church in the old Romanesque style. Trequanda also has an excellent deli/butcher shop next to the pizzeria that will vacuum pack guanciale and other goodies for your trip home. There is a small but well stocked local market in town as well. On hot days, the community pool below the pizzeria is a great way to spend time with locals under the olive trees for a reasonable per day charge.

Trequanda is one of the famous "Cinque Sorelle" or Five Sister towns, a gateway to many day trips on scenic county roads. Other lovely renaissance hilltop towns, such as Montepulciano, Pienza and Montalcino are just a short distance away and make for an easy outing. Siena is 40 minutes away and Florence is 1-1/2 hours by car. At the end of the day, you can return to the tranquility of Trequanda. All around us are famous restaurants, including several In Monticchielo and Fondo, just outside of town.

Casa Trequanda has the upper two levels of a three-story flat located in the historic center of town. Middle Level: two bedrooms with queen beds, bathroom, full kitchen, living room and balcony. Upper Level: one large bedroom with queen bed, bathroom, sitting room, washer/dryer and microwave. Both units offer spectacular views of a beautiful Tuscan landscape with rolling hills. Enjoy the stunning sunsets from the 2nd floor balcony. Note that there are quite a few stairs leading to the 2nd and 3rd floors and no elevator. We have a cooling system in place for the very hot days using portable AC systems.

Property manager

Indra Obeysekere

Languages

English, Italian

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Mountain view

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House Rules

Check in after 2:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
With adult supervision. Cot
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Including balcony

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

We should mention

All guests, including children, must be present at check-in and show their government-issued photo ID card or passport
Cash transactions at this property cannot exceed USD 5000, due to national regulations; for further details, please contact the property using the information in the booking confirmation
A car is recommended for transport to and from this property

About the area

Trequanda

Trequanda is home to this apartment. The area's natural beauty can be seen at Historic Centre of Pienza and Val di Chiana, while Museo del Tartufo and Museo dell'Antica Grancia e dell'Olio are cultural highlights. Bosco della Ragnaia and RI Crea RE are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Trequanda, Tuscany

What's nearby

  • The Saints Peter and Andrew Church - 3 min walk - 0.3 km
  • Crete Senesi - 15 min drive - 14.3 km
  • Valdichiana Outlet Village - 15 min drive - 16.5 km
  • Pienza Cathedral - 19 min drive - 17.9 km
  • San Giovanni Terme Rapolano - 23 min drive - 21.3 km

Getting around

  • Sinalunga Station - 17 min drive

Restaurants

  • ‪Ristorante Il Conte Matto - ‬1 min walk
  • ‪Forcillo Ristorante Locanda & Camere - ‬8 min drive
  • ‪Hotel Ristorante Apogeo - ‬7 min drive
  • ‪Pizza Delizia - ‬8 min drive
  • ‪Pasticceria Le Fonti - ‬7 min drive

Frequently asked questions

Is Enjoy a Classic Tuscan Hill Town holiday—now with AC! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Enjoy a Classic Tuscan Hill Town holiday—now with AC!?

Check-in begins at 2:00 PM.

What time is check-out at Enjoy a Classic Tuscan Hill Town holiday—now with AC!?

Checkout is at 11:00 AM.

Where is Enjoy a Classic Tuscan Hill Town holiday—now with AC! located?

Situated in Trequanda, this apartment building is steps away from Val di Chiana and The Saints Peter and Andrew Church. Monastery of Sant'Anna in Camprena and San Giovanni d'Asso Station are also within 9 miles (15 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 28 out of 29 reviews
Rating 8 - Good. 1 out of 29 reviews
Rating 6 - Okay. 0 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Andrew Q.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great quiet place
Thank you we had a great time
Stayed 2 nights in Jul 2023

10/10 Excellent

Wendy G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Book it!
Perfect! We loved everything about our stay in Trequanda! The quietness and view was a nice change after Florence. Sitting on the deck was a favorite! This is everything I think of when I think of Tuscany.
Stayed 2 nights in Jun 2024

10/10 Excellent

Randy C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
AMAZING -- PERFECT LOCATION
We stayed at this incredible villa for five nights, and it was nothing short of magical. The location is absolutely perfect, offering the most breathtaking views of the Tuscan hillside. Every morning, we were greeted by the serene beauty of the landscape, which made for a truly peaceful and rejuvenating experience. The town of Trequanda itself is amazing, capturing the true essence of Tuscany. It’s the ideal base for exploring Southern Tuscany, with all the major sights and towns just a short drive away. Whether we were visiting local vineyards, exploring historic towns, or just enjoying the local cuisine, everything was easily accessible. The villa was comfortable and well-equipped, providing everything we needed for a perfect vacation. We couldn't have asked for a better place to experience Tuscany. I highly recommend this villa to anyone looking to immerse themselves in the beauty and culture of this incredible region.
Stayed 5 nights in Aug 2024

10/10 Excellent

Bradley T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Last minute wonderful stay
Beautiful view from the second floor of the Tuscan hills. We also had the third story apartment which was perfect for my wife's cousin to stay in. Apartment was large for European standards (we are from California). Trequanda is very small town, but centrally located between Siena, Montelpulciano and Montalcino.
Stayed 2 nights in Oct 2021

10/10 Excellent

Regina K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A hidden gem…Unbeatable view from comfortable apartment!
Oh what a view….Two couples truly enjoyed our time in Trequanda in a lovely, clean, comfortable & well maintained 3 bedroom two bath unit. The small terrace offered unbeatable views of the hillside, vineyards, olive groves and sunset! The kitchen was stocked to allow for easy prep of breakfast, dinners & happy hour! The small Tuscan village this apartment is situated in offered a cafe, small grocery and restaurants within easy walk out your door. We appreciated being away from the crowds of tourist towns! No parking right outside the unit but easy drop off of luggage nearby with a walk to the apartment & parking was right below. There are steps in the apartment up to 2nd & 3rd floor. The beds were comfortable, towels good quality, and washer, dryer & drying racks available. We enjoyed having Alexa for music. There were only dvd movies available for viewing. The property manager was easily reached and very responsive to any requests! We felt like we were living a “locals” life and found it very easy to access many surrounding bigger tourist towns with restaurants, sights, luxury day spa & 360 degrees of breathtaking scenery! An absolute gem for our vacation accommodation!
Stayed 7 nights in Sep 2023

10/10 Excellent

JOANNE R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The best of Tuscany accomodations
We were pleasantly surprised when we arrived in Trequanda and entered these lovely apartments. The furnishing are lovely, the beds comfortable and the kitchen and bathrooms well-equipped, large and meticulously clean. The apartments have a clear view of the magical Tuscan countryside. Walking distance are a cafe, bakery, butcher, small supermarket and restaurants. The people of Trequanda are so warm and welcoming. Indrajit's suggestions for itineraries and the property manager up the street also helped to provide us with the perfect visit!
Stayed 6 nights in Sep 2022

10/10 Excellent

Laura B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Comfortable property - great location
Comfortable apartment located in an excellent location. Clean, well appointed.
Stayed 10 nights in Jun 2022

10/10 Excellent

Debbie N.

The Tuscany of your travel dreams
Out of our six week tour of Northern Italy, we four agreed that our stay in Trequanda at Indra's place was the extra special highlight. A quiet and quaint, hilltop village that has everything you need within a short walking distance, including a great restaurant. From this comfortable apartment, we enjoyed the delicate gray-green olive groves glowing in the changing light, and supplemented our stay with day trips to Pienza, Montepulciano, a local roadside winery, and olive farm to see the harvest in action. Stay here - you will not be disappointed!
Stayed 6 nights in Oct 2018

10/10 Excellent

Verified traveller

Wonderful place to stay in Tuscany!!!
Two couples stayed at Casa Trequanda for five glorious days. The town is small and very quiet but has a cafe, pizzeria and a upscale restaurant. A winery, Fattoria de Colle, with restaurant is nearby (you can see if from the balcony), we went there twice. It is such a great place to stay to explore the small villages of Tuscany. We would set off each day in a different direction after having a capucino and roll at the cozy little cafe on the main square. Casa Trequanda is very modern and has every convenience you might need for a stay in Tuscany including a wonderful view with sunsets every evening. I would highly recommend a stay at Casa Trequanda.
Stayed 5 nights in Sep 2018

10/10 Excellent

sharon g.

A spacious, comfortable home from home, had everything from kitchen sink to details places to visit
It was clean, beds were comfortable and plenty of pillows just what we like. We had 2 nights booked, we had a wedding to go to but encountered a problem with our car and needed a further 3 nights to stay. Sent an email to the owner not knowing what to do, had no car. We had the most loveliest email letting us stay. Being stranded was a scary thing for me and my family but on receiving this email it lifted our spirits, we made it to the wedding with help from other family who had hired cars staying near by. The day after the wedding we realised just how lucky we were being stranded in such a beautiful place. Being from the UK we needed help with calls so we were able to ask for help from Tammy to call the garage as no one could speak English and she was able to get answers to when are car would be ready. We were able to enjoy our extra days, we watched lightning and thunderstorms over the hills and the sunsets from the balcony, bells on a couple of mornings, we felt very spoilt. We have told all our family at the wedding about these 2 perfect apartments we stayed in and will continue to tell the rest of the family and friends on our return. Chatting to people living there, same ones every day made us feel right at home even though we didn’t understand all of what was said. Highly recommend this property, go on book and feel spoilt like us.
Stayed 2 nights in Aug 2018
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Gordon w.

Casa Trequanda
Fantastic! Beautiful pastoral views from the condo; quiet, historic hill town almost tourist free, friendly people, and a 5 star restaurant. Condo has a modern interior with all amenities and is in the middle of the wine country. Only an hours drive from Florence.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Alan E.

Beautiful, quiet, tranquil
Definitely a classic Tuscan hillside town. Few tourists, great scenery, market and restaurants close by. Apartment very comfortable with great view off the balcony.
Stayed 10 nights in Sep 2017
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Karen A., Seattle

Beautiful home in a sweet town!
Casa Trequanda is the perfect place to stay while experiencing Tuscany. The home is luxuriously comfortable and fully-equipped, whether you want a home-away-from-home or just a place to rest between adventures. We ate in town and enjoyed the local community and picked up a few groceries to pack a picnic for our day trips to Pienza, Montisi, Montelpuciano, etc. The pictures don't do it justice - the view is amazing and the town charming. I highly recommend a visit!!
Stayed 4 nights in Aug 2017
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Gay V.

Tranquil Trequanda
Casa Trequanda was lovely spot from which to explore Tuscany. There was so much to do (or not do) in easy day outings. Then to come back to the excellent views, food opportunities and friendly atmosphere of this tucked away village was wonderful. We hope to and plan to return.
Stayed 7 nights in Jun 2017
This review was submitted before 2018 and has not been verified.

10/10 Excellent

SUE H., OAK PARK

Hidden Tuscan Gem
If you are looking for an authentic, off-the-beaten-path experience in Italy, you will find it in Trequanda, a 14th century small town in Tuscany. It has a casual café for breakfast and lunch, a pizzeria and gelateria, and a Zagat rated restaurant, Il Conte Matto, plus a bakery and a small market. The people are friendly and warm, the scenery beautiful. In less than an hour you can drive to Siena, Pienza, Montepulciano and Montalcino. Florence is an hour and a half away. Casa Trequanda is made up of two levels in a three story building. The second level has two bedrooms, one bath, an open kitchen, and eating and sitting area, along with a small balcony with an amazing view. The upper level has one bedroom, one bath, a sitting area, with a sink and microwave, and washer and dryer. Everything was new and clean and comfortable. Four of us stayed there for 10 days, and it was a terrific experience. I would definitely return.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Edith R.

Perfect location
We truly enjoyed the condo in Terquanda. The sunsets are awesome and the location perfect. We liked Conto Mato a lot and explored Tuscany everyday. Beautiful, Edith and Rolf
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Patty H., Walnut Creek

Italy 2016
An absolute jewel location and experience for us. Hospitality in Trequanda superb and the apartment boasts exquisite views and a taste of Tuscan lifestyle. All amenities and accommodations fabulous! Diane & Indra prepared us well with local wineries & restaurants. Tuscan mornings and sunset evenings on the balcony one of our favorite memories. Hope to return again!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Awesome apartment and charming Tuscan town
During our five night stay, my wife and I had an amazing time at the apartment in Trequanda. The apartment is easy to find and access, and has picture-perfect views of the Tuscan countryside. We really loved the town, and were frequent visitors of the bakery, cafe, and the delicious restaurant Il Conte Matto. We made a number of trips via car to various towns and wineries surrounding Trequanda, and found the apartment perfectly situated for our daily adventures. We truly wish we had more time to relax, and enjoy our time in Trequanda. If in the future we find our way back to this part of the world, we will most certainly look to stay at the apartment again.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

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wonderful apartment & beautiful town
We had a wonderful stay in the apartment. Trequanda is a beautiful town, perfectly placed in the Tuscan countryside and within a short distance from Siena and Montepulciano. There are excellent vineyards around and the scenery is breathtaking. The restaurants in Trequanda and surrounding little towns are charming and the food is just wonderful.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

John R.

A wonderful apartment in a beautifully quiet Tuscan town
The property in Trequanda perfectly met the needs of our four member family (mother, father, and two teen boys) during our recent five day stay in Tuscany. I don't recall it being explicitly stated in the property description, but this is actually two apartments, a two bedroom w/kitchen, just below an attic apartment with no kitchen. The format worked just fine for us, with the boys taking the two bedrooms, with us above, but an unaware family with smaller children might be surprised by the locked separation. The apartments were both spotlessly clean, and everything was in proper working order. Beds were all very comfortable, and the kitchen was fully equipped, although we didn't use much more than the fridge for drinks and glassware. Still, the nearby market would make it pretty easy to put together a simple breakfast or lunch. Views from both apartments were stunning at all hours, day and night, and of our five nights in August, there was only one where we were hot and wishing the apartments had A/C; otherwise, the open windows and fans were completely adequate for cool nights. And there are no worries about open windows and excessive noise: Trequanda is INCREDIBLY peaceful with little excess road or neighborhood noise. With the exception of one night when a dog seemed to object to being left outside, silence was the norm. The owner was prompt and thorough with all advance communications and provided excellent directions where to park, how to get to the property, and how to access the key boxes to get in. While there was an identified contact just down the street, we didn't have any reason to visit, since there were no issues with the apartment. Trequanda, itself, is a great jumping off point for the surrounding area, but a peaceful way to start and end the day. I had looked at properties in more touristy towns (like Siena), but was very pleased we chose Trequanda instead. (Better to travel to the crowds, than live in the chaos.) The town has an excellent pizzeria, and another choice for dinner. A third osteria in the center of town is open for breakfast (wonderful and inexpensive), but we were never in the area for lunch. The town also offers a great bakery and butcher's shop, with friendly and helpful staff; well worth the time to find them both. I would have no hesitation in staying at this property again in the future.
Stayed 5 nights in Aug 2016
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Stephen G.

Trequanda - Great Tuscany jumping off place
Trequanda looks like it could be a movie set. Very charming. It's restaurants are great. Really liked getting fresh baked goods each morning from the Trequanda backery. The apartment was very well equipped. The panoramic view from the balcony is terrific. Olive groves, vineyards, and forests all strechted before you. The apartment was large enough for our 6 adults. We took day trips each day to various places in Tuscany and Umbria. All easily reached from Trequanda. The place has great doors and windows that keep the aid circulating nevertheless in the dead of summer air conditioning would-have been great. If you are looking for a place with great amenities friendly locals and away from most of the tourists Casa Trequanda is for you.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Casa Trequanda - A Haven!
“Opening up the double doors that leads into the veranda and being mesmerized by the deep hues of the Tuscan sunset, I sat there staring blankly into the horizon not having a care in the world. I finally understood the phrase, “Dolce far niente” – translation: the sweetness of doing nothing. My translation – taking it all in, immersing myself in the moment and feeling at peace with myself and my universe. It was transformative.” A passage from my travel journal written 5/15/15. Staying in Trequanda, in this beautiful and clean house with amazing views, with its very simple and comfortable furnishings void of clutter, allowed my mind to rest and to be taken on this insightful journey. After exploring and getting lost in the beautiful countryside and hill towns of Tuscana during the day, I always looked forward to each evening, coming back to my sanctuary where I could stare out into the world and feel the transformation taking place inside – my soul was being replenished. I can’t say enough about this haven, yet selfishly, I would much rather keep it a secret. But no, it is only fair that I share my experience of staying in this beautiful home that was generously opened up by its owners for all to enjoy. Even still, trying to express my true sentiments about this place cannot be done justly – you’ll just have to come and experience it for yourself! My only regret was that I did not stay longer. I’ll definitely be back again, but until then, I will cherish my time there and remember the Tuscan sunsets that are etched in my mind. Grazie mille to the owners!
This review was submitted before 2018 and has not been verified.

8/10 Good

Deborah M., SHORT HILLS

Just what we were looking for!
My husband and I and our three children had a wonderful time in Trequanda. The apartment was just what we were looking for to experience living in a small Tuscan village. We loved exploring the little town and finding the bakery, market, cafe and beautiful views of the Tuscan countryside. We had a little trouble finding the apartment and the parking lot but Tammi was very helpful getting us settled in. We were surprised that the 3rd floor bedroom was a separate apartment but it still worked out fine for us. We took day trips to Montepulciano, Pienza, and Sienna and enjoyed all our time in Tuscany even the rainy day we had in Sienna. We had dinner one night in town and the another night in nearby Sinalunga. Staying in Trequanda was the highlight of our trip to Italy which included the Amalfi Coast and Rome!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Laurra , Northridge Ca
We had a wonderful stay at our home away from home in Trequanda. It was as beautiful, comfortable and as well appointed as we imagined. In fact it surpassed all expectations. Not only was Casa Trequanda enchanting and scenic, the owners left a complete notebook with detailed information about any possible questions we may have. We loved being part of this charming village, where everyone was so welcoming and friendly. Starting our mornings off with cappuccino at Cieriera and an afternoon glass of wine in the nearby bar with the locals was a joy. A favorite spot was the yummy pizza and beer at Paradisio with our new friends. Of course Conta Monte is a must with it's incredible view and beautiful menu offerings. This village was the perfect spot to venture off to other hilltop villages such as Pienza, Montalcino and Montepulciano. Everything we needed was easily accessible in Casa Trequanda and we had a fabulous time! We highly recommend this excellent hidden gem to all and can't wait to return!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

A Perfect Tuscan Vacation!
Our stay in Trequanda was the best part of our Italian vacation by far. The apartment itself is beautiful, open, and spacious, and has a balcony with an absolutely gorgeous view of the rolling Tuscan countryside. The giant windows allow for the breeze to cool off the apartment, perfect for a hot Italian summer, and there were also several fans and a refrigerator that made ice, something that had been in very short supply throughout our vacation! The town is adorable, and there are several very good restaurants and a delicious bakery. There is also a very nice grocery store a two minute walk from the apartment where you can buy pretty much anything, and cook yourself an authentic Italian meal. The people are very kind and welcoming, and the town definitely isn't a huge tourist attraction, so it's much more relaxing than other parts of the country. Finally, the location is a perfect jumping off point to get to a variety of places, several of which (Siena, Montepulciano, San Gimignano) make for great day trips. We highly recommend this apartment if you are looking to take a Tuscan vacation.

About the host

Hosted by Indra Obeysekere

Host profile image
Partnership from the United States with management experience from other vacation rental asset in Mexico

Why they chose this property

This location is classic Tuscany, most easily identified with Italy and its rich culture and heritage. It is also centrally located and proximate to many other famous historic towns. You can come back at night make yourself a home cooked meal or walk down the street to one of two great family owned restaurants. For those seeking quiet and calm and more adventurous travelers, the perfect choice

What makes this property unique

Lovely views from all of the rooms, a balcony perfect for a glass of wine and the sunset. Furnished to be tasteful and comfortable in an open, uncluttered way. The bedrooms are great for siestas as the large windows bring the breezes in. The kitchen is modern and well equipped and both bathrooms on both floors are new.

Languages:

English, Italian
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