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Enjoy a Classic Tuscan Hill Town holiday

Bedrooms 3
Space sq. ft.
Property type apartment
Minimum Stay 1 - 4 nights
Popular Features
  • Washing Machine
  • non smoking only
  • Wireless Internet
  • children welcome


About the property

2 bedroom appt and 1 bedroom suite, 2 bathrooms, panoramic views

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 rated restaurant, Conte Matto, as well as a charming town square with casual dining, a pharmacy, bank and a church in the old Romanesque style. Trequanda also has a museum of antiquities, a lovely bakery, pizzeria and gelateria, and the convenience of a small market. During the summer months, there is a large and inviting public pool surrounded by olive groves and vineyards.

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.

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 and stunning sunsets.

More Details

Indra Obeysekere
Member since: 2012
Speaks: italian
Response time:
Within a few hours
Response rate:
Calendar last updated:
March 8, 2017

About Indra Obeysekere

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

Indra Obeysekere purchased this apartment in 2012

Why Indra Obeysekere chose Val di Chiana

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 apartment 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.


Trequanda Apartment Accommodation and Amenities

Property Type:
  • apartment
  • floor 2
  • Guests provide their own meals
  • Housekeeper Optional
House Rules:
  • Max. occupancy 6
  • non smoking only ...
  • pets not allowed
  • Minimum Age Limit for Renters ...
  • children welcome ...
Location Type:
  • Mountain View ...
  • Away From It All
  • Historic
  • Romantic
  • Tourist Attractions
  • Clothes Dryer ...
  • Hair Dryer
  • Heating
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking Off Street ...
  • Telephone ...
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • Newly renovated modern bathrooms. 2nd floor bath has tub
  • 3 Bedrooms, Sleeps 6
  • Queen size Beds (1) In all 3 bedrooms, plus inflatable mattress in 3rd fl suite
  • DVD Player
  • Satellite / Cable ...
  • Video Library ...
  • Balcony ...
  • Long-term Renters Welcome
  • wheelchair inaccessible ...
Pool / Spa:
  • Communal Pool ...
  • arboretum
  • botanical garden
  • churches
  • museums
  • playground
  • restaurants
  • ruins
  • winery tours
Leisure Activities:
  • antiquing
  • bird watching
  • eco tourism
  • horseback riding
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • laundromat
  • medical services
Sports & Adventure Activities:
  • cycling
  • hiking
  • hot air ballooning
  • mountain biking
Casa Trequanda has magnificent views from both floors of the Tuscan countryside. From Trequanda you can do day trips to most of the famous Tuscan hill towns of Pienza, Montepulciano, Siena, Assisi, Perugia, Montalcino and San Gimignano. Trequanda has many outstanding restaurants and wineries within a 10 minute drive. This area of Tuscany is a foodie paradise!


Wonderful! 4.9/5 -
(13 traveler reviews)

Enjoy a Classic Tuscan Hill Town holiday
average rating of 4.923077 based on 13 reviews
Walnut Creek

Italy 2016

  • 5 of 5

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!

  • Submitted: Oct 4, 2016
  • Stayed: Sep 2016
  • Source: VRBO, from HomeAway
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Awesome apartment and charming Tuscan town

  • 5 of 5

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.

  • Submitted: Sep 11, 2016
  • Stayed: Aug 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thanks, and please come back! There's a ton more to see!
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wonderful apartment & beautiful town

  • 5 of 5

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.

  • Submitted: Sep 11, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
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A wonderful apartment in a beautifully quiet Tuscan town

  • 5 of 5

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.

  • Submitted: Aug 19, 2016
  • Stayed: Aug 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you very much for you thoughtful response John. We do hope you visit again and take advantage of our repeat customer discount! Ci vediamo pronto! Indra
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Trequanda - Great Tuscany jumping off place

  • 5 of 5

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.

  • Submitted: Aug 24, 2015
  • Stayed: Jul 2015
  • Source: VRBO, from HomeAway
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Benicia, CA

Casa Trequanda - A Haven!

  • 5 of 5

“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!

  • Submitted: Jun 14, 2015
  • Stayed: May 2015
  • Source: VRBO, from HomeAway
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Nearest Airport
100 Miles
Florence (Rome Fumiciano is 2 hours south)
Nearest Barpub
50 Metres
In town
Nearest Motorway
10 Miles
A-1 at Sinalunga
Nearest Restaurant
50 Metres
In town
Car: recommended

Casa Trequanda is located in the heart of Tuscany, but just a short drive from the A-1 highway. The town of Trequanda has several outstanding restaurants, a pharmacy, bank, butcher, grocery, bar, public pool, pizzaria, bakery within a short walk of Casa Trequanda. The nearby town of Sinalunga offers other amenities. This area of Tuscany is serene and cool, with wonderful walks and vistas, outstanding wineries, famous restaurants and lovely churches. Trequanda is a short drive to Pienza and is close to many of the most famous Tuscan cities and towns, including Pienza, Montepulciano, Siena and Montalcino. It is an hour and 20 minutes to Florence as well and 2 hours from Rome.


Rates & Availability

Trequanda Apartment Rental Rates

Rental Basis:
per property
Owner accepts payment in:
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Rate Period Nightly Weekend Night Weekly Monthly Event
Spring Season 2017
Mar 1 2017 - Apr 30 2017
3 night minimum stay
High Season 2017
May 1 2017 - Sep 29 2017
4 night minimum stay
Fall Season 2017
Sep 30 2017 - Nov 30 2017
3 night minimum stay
My Standard Rate
1 night minimum stay

Additional information about rental rates

Cleaning Fee $100

Rates above are for renting the 2nd floor & upstairs suite together for high season. Low season combo rates are $165.00 for both. Please contact the owner for rates for just the 2 bedroom second floor or the third floor suite only.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
Enter dates for accurate pricing
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