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Enjoy a Classic Tuscan Hill Town holiday

Trequanda, Siena, Italy
  • Apartment
  • Bedrooms3
  • Sleeps6
  • Bathrooms2
  • Half Baths0
  • Minimum Stay1 - 2 nights

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.


Indra Obeysekere

Member Since 2012
Response rate:
Response time:
within a few hours
english, italian
Calendar last updated:
Apr 19, 2018
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 Trequanda

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.


    • Internet
    • Heater
    • Satellite or Cable
    • Kids Welcome
    • Washer & Dryer
    • TV
    • No Smoking


      • 3 Bedrooms, Sleeps 6
        • Queen size Beds (1) In all 3 bedrooms, plus inflatable mattress in 3rd fl suite


        • 2 Bathrooms
          • Newly renovated modern bathrooms. 2nd floor bath has tub

          Location Type

            • Mountain View
              panoramic view of the Crete Sinese countryside, olive groves, vineyards and farmland


                • Away From It All
                • Historic
                • Romantic
                • Tourist Attractions


                    • Guests provide their own meals


                        • Living Room
                        • Clothes Dryer
                          In upstairs suite only; laundromat available in town 10 mins away in Sinalunga. Drying racks available on request,. Call or email guest services manager.
                        • Heating
                        • Iron & Board
                        • Linens Provided
                        • Hair Dryer
                        • Parking Off Street
                          Ample parking in city owned lot 100 meters away, below Conte Matto. Please do not park on the street except to unload as this will upset the neighbors.
                        • Telephone
                          Local and limited international
                        • Towels Provided
                          We provide 1 towel per guest and a few extras for short stays but will gladly provide more if you let us know.
                        • Washing Machine
                          In upstairs suite only; laundromat available in Sinalunga town 10 mins away
                        • Wireless Internet
                          Available on both floors. See bottom of phone or guestbook


                            • Coffee Maker
                              Both espresso and regular coffee makers on 2nd floor. Regular drip coffee maker on 3rd floor. Bring your own coffee but guests welcome to any coffee left in the units
                            • Cooking Utensils
                              Pots, pans
                            • Dishes & Utensils
                              Adequate silverware and settings for 6-8
                            • Kitchen
                              On 2nd floor; dishes, cups, utensils for 10, pots & pans, full stove and oven 3rd floor has microwave, mini fridge and place settings for 2
                            • Microwave
                              (2) Microwave on each floor
                            • Oven
                              Gas, 2nd floor
                            • Pantry Items
                              Bottled water provided on day 1. Any wine in the fridge is for guest consumption.
                            • Refrigerator
                              (2) Full size on 2nd floor unit. Mini fridge on 3rd Fl. Suite
                            • Stove
                              Gas, 2nd floor


                                • Dining
                                  Dining room table on second floor, bar area on 3rd fl suite
                                • Dining Area
                                • comfy seating for 6 people


                                    • DVD Player
                                    • Satellite / Cable
                                      Limited cable
                                    • Video Library
                                      Limited selection so please bring your favorites.


                                        • Balcony
                                          On 2nd floor unit


                                            • Long-term Renters Welcome
                                            • wheelchair inaccessible
                                              Several levels of stairs and no elevator

                                              Pool / Spa

                                                • Communal Pool
                                                  Beautiful P ublic pool available in town for daily fee. Below the pizzeria Paradiso


                                                    • 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!

                                                                      19 Reviews


                                                                      Latest reviews

                                                                      Casa Trequanda

                                                                      Gordon w.

                                                                      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.

                                                                      Beautiful, quiet, tranquil

                                                                      Alan E.

                                                                      Definitely a classic Tuscan hillside town. Few tourists, great scenery, market and restaurants close by. Apartment very comfortable with great view off the balcony.

                                                                      Beautiful home in a sweet town!

                                                                      Karen A.Seattle

                                                                      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!!

                                                                      Tranquil Trequanda

                                                                      Gay V.

                                                                      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.

                                                                      Hidden Tuscan Gem

                                                                      SUE H.OAK PARK

                                                                      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.

                                                                      Perfect location

                                                                      Edith R.

                                                                      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

                                                                      Owner's Response:

                                                                      Thank you Edith and Rolf! We really enjoyed being able to show you 'la bella toscana'. And yes, Il Conte Matto is one of the great dining experiences in this region. Please come back again and take advantage of our repeat guest discount! Indra


                                                                      Trequanda, Siena, Italy

                                                                      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

                                                                      Additional information about rental rates

                                                                      Cleaning Fee

                                                                      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.

                                                                      19 Reviews
                                                                      Wonderful 4.9/5
                                                                      Enter dates for accurate pricing
                                                                      For booking assistance, call 888-640-7927

                                                                      Property # 440247vb