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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Wonderful! 4.9/5
    (49 reviews)
    $57
    avg/night
    • 1 BR
    • 1 HF BA
    • Sleeps 4
    Apartment #6059609
    49
      • 1 BR
      • 1 BA
      • Sleeps 3
      Farmhouse #1752653
        • 2 BR
        • 2 BA
        • Sleeps 5
        Multiple rentals House #1675396
        5
          • 1 BR
          • 1 BA
          • Sleeps 4
          Multiple rentals Apartment #1675396
          10
            • 1 BR
            • 1 BA
            • Sleeps 5
            Chateau / Country House #1052071
            2 Reviews
              Wonderful! 4.8/5
              (19 reviews)
              $89
              avg/night
              • 1 BR
              • 1 BA
              • Sleeps 2
              Castle #825856
              19
              Viewed 21 times in the last 48 hours
                $81
                avg/night
                • Studio
                • 1 BA
                • Sleeps 5
                Apartment #812922
                3
                Viewed 10 times in the last 48 hours
                  Exceptional! 5.0/5
                  (5 reviews)
                  $60
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 4
                  Multiple rentals Apartment #8125211
                  5
                  Viewed 8 times in the last 48 hours
                    Wonderful! 4.9/5
                    (8 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 2
                    Castle #3878711
                    8
                    Viewed 5 times in the last 48 hours
                      • 2 BR
                      • 1 BA
                      • Sleeps 5
                      Apartment #6848209
                        Wonderful! 4.8/5
                        (5 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 4
                        Apartment #1628484
                        5
                        Viewed 8 times in the last 48 hours
                          Wonderful! 4.9/5
                          (66 reviews)
                          $42
                          avg/night
                          • 1 BR
                          • 1 HF BA
                          • Sleeps 5
                          House #6162521
                          66
                          Viewed 5 times in the last 48 hours
                            Excellent! 4.4/5
                            (7 reviews)
                            avg/night
                            • 2 BR
                            • 1 HF BA
                            • Sleeps 6
                            Apartment #6379067
                            7
                            Viewed 6 times in the last 48 hours
                              Exceptional! 5.0/5
                              (11 reviews)
                              $97
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 4
                              Cottage #1207142
                              11
                              Viewed 22 times in the last 48 hours
                                • 3 BR
                                • 2 BA
                                • Sleeps 7
                                House #863601vb
                                Viewed 7 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (7 reviews)
                                  avg/night
                                  • 3 BR
                                  • 1 BA
                                  • 1 HF BA
                                  • Sleeps 7
                                  House #754550
                                  7
                                  Viewed 26 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (6 reviews)
                                    $84
                                    avg/night
                                    • Studio
                                    • 1 BA
                                    • Sleeps 2
                                    Multiple rentals Chateau / Country House #6370016
                                    6
                                    Viewed 19 times in the last 48 hours
                                      avg/night
                                      • 5 BR
                                      • 5 BA
                                      • 1 HF BA
                                      • Sleeps 10
                                      Villa #1097226
                                      4
                                      Viewed 20 times in the last 48 hours
                                        • 3 BR
                                        • 3 BA
                                        • Sleeps 7
                                        Chateau / Country House #1225354
                                        32
                                          Exceptional! 5.0/5
                                          (9 reviews)
                                          $60
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 5
                                          Apartment #1544394
                                          9
                                            avg/night
                                            • 4 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 10
                                            Chateau / Country House #1890995
                                            Viewed 12 times in the last 48 hours
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Apartment #6551145
                                                $63
                                                avg/night
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 4
                                                Apartment #6715725
                                                4
                                                Viewed 13 times in the last 48 hours
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Apartment #6721371
                                                  2 Reviews
                                                    • 2 BR
                                                    • 1 BA
                                                    • 1 HF BA
                                                    • Sleeps 5
                                                    House #6774442
                                                    2 Reviews
                                                      Wonderful! 4.9/5
                                                      (13 reviews)
                                                      $84
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Apartment #13190
                                                      13
                                                      Viewed 53 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (51 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 4
                                                        House #6235319
                                                        51
                                                        Viewed 29 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (8 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 5
                                                          Villa #323419vb
                                                          8
                                                          Viewed 35 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (6 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Apartment #479613vb
                                                            6
                                                            Viewed 6 times in the last 48 hours
                                                              • 2 BR
                                                              • Sleeps 6
                                                              Chateau / Country House #6643924
                                                              2 Reviews
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 7
                                                                Chateau / Country House #1766739
                                                                1 Review
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 4
                                                                  Chateau / Country House #6542271
                                                                  1 Review
                                                                  Viewed 9 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (22 reviews)
                                                                    $75
                                                                    avg/night
                                                                    • 1 BR
                                                                    • Sleeps 5
                                                                    House #6184925
                                                                    22
                                                                    Viewed 15 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (16 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 6
                                                                      House #1614367
                                                                      16
                                                                      Viewed 13 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (5 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 4
                                                                        Apartment #6066838
                                                                        5
                                                                        Viewed 16 times in the last 48 hours
                                                                          Excellent! 4.7/5
                                                                          (10 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Multiple rentals Farmhouse #455240
                                                                          10
                                                                          Viewed 12 times in the last 48 hours
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 6 BA
                                                                            • Sleeps 11
                                                                            Villa #1572064
                                                                            3
                                                                            Viewed 8 times in the last 48 hours
                                                                              • 8 BR
                                                                              • 9 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 26
                                                                              Chateau / Country House #428261
                                                                              3
                                                                                Exceptional! 5.0/5
                                                                                (9 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • Sleeps 4
                                                                                Multiple rentals Chateau / Country House #6370016
                                                                                9
                                                                                Viewed 28 times in the last 48 hours
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Multiple rentals Apartment #8125211
                                                                                  3
                                                                                    Exceptional! 5.0/5
                                                                                    (5 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 4 BA
                                                                                    • Sleeps 6
                                                                                    Villa #1691332
                                                                                    5
                                                                                    Viewed 12 times in the last 48 hours
                                                                                      • 3 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 5
                                                                                      Cottage #8088621
                                                                                      2 Reviews
                                                                                        • 5 BR
                                                                                        • 5 BA
                                                                                        • Sleeps 10
                                                                                        Villa #6895841
                                                                                          Exceptional! 5.0/5
                                                                                          (9 reviews)
                                                                                          avg/night
                                                                                          • 9 BR
                                                                                          • 7 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 18
                                                                                          Villa #620449vb
                                                                                          9
                                                                                          Viewed 9 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (15 reviews)
                                                                                            $76
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            House #2443642
                                                                                            15
                                                                                            Viewed 10 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (13 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 7
                                                                                              Barn #814311vb
                                                                                              13
                                                                                              Viewed 8 times in the last 48 hours
                                                                                                • 2 BR
                                                                                                • Sleeps 7
                                                                                                Apartment #6155033
                                                                                                34
                                                                                                  • 7 BR
                                                                                                  • 5 BA
                                                                                                  • Sleeps 16
                                                                                                  Multiple rentals Villa #6347473
                                                                                                  2 Reviews
                                                                                                  Viewed 12 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (19 reviews)
                                                                                                    $41
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • Sleeps 5
                                                                                                    Apartment #6290526
                                                                                                    19
                                                                                                    Viewed 6 times in the last 48 hours
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 4
                                                                                                      Castle #3878514
                                                                                                      4
                                                                                                      Viewed 13 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Monticiano: Apartments, Villas & More (300+)

                                                                                                       

                                                                                                      Recent Monticiano Reviews

                                                                                                      Quattro Torra - Rocambolesco

                                                                                                      5 of 5
                                                                                                      Our stay in the Castello delle quattro torri, was absolutely amazing; a "rocambolesco" experience! We were met at the door by Nicola on our first day. From the moment we waited for him before entering the castle doors, it felt like we were traveling back in time. The castle is incredibly beautiful. We arrived here later in the afternoon during the magic hour of the sun; the sun was shining on the castle, the colors of the leaves were changing on the vines of the castle walls. It was just stunning. Nicola welcomed us into his family's home as if we were old family and friends. Nicola couldn't have been more helpful and attentive to our every needs. He showed us the best place to park our rental car in Sienna, which was a five minute drive (literally - no more than four or five min) to Sienna. It's a family run business. The adorable woman (I think it was his Aunt) cooking us breakfast in the mornings was so sweet and the breakfast she made us was wonderful and authentic Italian (including cappuccinos!) The rooms were immaculate and beautifully decorated. The tower room we stayed in for one night had a neat spiral staircase leading up into the sleeping area. The view from the castle (bedrooms, living room, dining area) is amazing. You can see the Tuscan hills for miles. The land around the castle is so picturesque and you are encouraged to walk this entire area, walking through the olive groves and walking through the vineyards. It feels like you are in the scene of a movie. Nicola's family owns a farm nearby the castle with a restaurant on the property called Le Pietre Vive restaurant. One of the nights, we had the most "cena deliziosa" delicious dinner. Mauro, our waiter at the restaurant was super helpful with the menu, gave the best recommendations and even shared grappa with us! Nicola also makes his own chianti wine, saffron, honey and oil. We purchased wine and honey from Nicola to take back home with us. Nicola noticed it was my husband's birthday, while we were checking in, and the next morning, on his birthday, he greeted my husband with an Italian happy birthday and so did his Aunt. We absolutely loved our stay here at Castello delle Quattro Torra and would recommend it to everyone. Sienna is an incredible little city and the quick drive from there also makes it so wonderful. Thank you so much, Nicola! Grazie Mille! Love, Nicola & Tanya
                                                                                                      • Submitted: Dec 3, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Wonderful Week

                                                                                                      5 of 5
                                                                                                      We (four of us) stayed for a week in early November. The villa is lovely with a fantastic location and breathtaking scenery. We did need the rental car, but distances to the surrounding towns are not great. The villa is beautifully equipped, especially the kitchen, and the whole house is immaculate. Francesca cooked two delicious and wonderfully Tuscan dinners for us. She was so friendly and we all felt very welcome. We would definitely stay here again!
                                                                                                      • Submitted: Nov 16, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Once in a lifetime experience in Tuscany

                                                                                                      5 of 5
                                                                                                      My wife and I stayed at Castello delle Quattro Torra for two nights while on a trip through Italy. The experience could not have been more perfect. Not only was the setting in the countryside outside of Sienna relaxing and peaceful, but the ability to stay in such a wonderfully preserved landmark was fantastic. Nichola and his mother could not have been more hospitable hosts. We would definitely also recommend dinner at Nichola's restaurant Le Pietre Vive -- the best meal we had while in Italy. My wife and I would definitely wish to stay at Castello again and recommend to friends as well
                                                                                                      • Submitted: Nov 13, 2016
                                                                                                      • Stayed: Oct 2016