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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    • 6 BR
    • 3 BA
    • Sleeps 14
    Multiple rentals Villa #480039
    Viewed 12 times in the last 48 hours
      • 4 BR
      • 2 BA
      • Sleeps 8
      Multiple rentals Apartment #480039
        • 6 BR
        • 2 BA
        • Sleeps 14
        Apartment #2555340
          • 2 BR
          • 1 BA
          • Sleeps 6
          Villa #6803433
            • 2 BR
            • Sleeps 6
            Villa #4344573
              • 2 BR
              • 1 BA
              • Sleeps 6
              Villa #6559890
                • 2 BR
                • 2 BA
                • Sleeps 5
                Farmhouse #2490019
                  Wonderful! 4.9/5
                  (14 reviews)
                  avg/night
                  • 4 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 8
                  House #1630298
                  14
                  Viewed 172 times in the last 48 hours
                    Exceptional! 5.0/5
                    (5 reviews)
                    avg/night
                    • 2 BR
                    • 2 BA
                    • Sleeps 5
                    Farmhouse #8026002
                    5
                    Viewed 18 times in the last 48 hours
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 6
                      House #582787vb
                      3
                      Viewed 50 times in the last 48 hours
                        Wonderful! 4.9/5
                        (13 reviews)
                        avg/night
                        • 5 BR
                        • 4 BA
                        • Sleeps 12
                        Villa #1029156
                        13
                        Viewed 33 times in the last 48 hours
                          Wonderful! 4.8/5
                          (18 reviews)
                          $70
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          House #17519
                          18
                          Viewed 21 times in the last 48 hours
                            Exceptional! 5.0/5
                            (5 reviews)
                            avg/night
                            • 2 BR
                            • 2 BA
                            • Sleeps 4
                            Apartment #6066838
                            5
                            Viewed 25 times in the last 48 hours
                              Wonderful! 4.8/5
                              (20 reviews)
                              $54
                              avg/night
                              • 2 BR
                              • Sleeps 6
                              House #6046194
                              20
                              Viewed 40 times in the last 48 hours
                                • 4 BR
                                • 3 BA
                                • 1 HF BA
                                • Sleeps 8
                                Villa #6470269
                                3
                                Viewed 28 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (6 reviews)
                                  $53
                                  avg/night
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 4
                                  Apartment #2388890
                                  6
                                  Viewed 26 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (21 reviews)
                                    avg/night
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 9
                                    Villa #504834
                                    21
                                    Viewed 36 times in the last 48 hours
                                      Exceptional! 5.0/5
                                      (32 reviews)
                                      avg/night
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 4
                                      Multiple rentals Chateau / Country House #1067421
                                      32
                                      Viewed 8 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (10 reviews)
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 6
                                        Multiple rentals Farmhouse #6009840
                                        10
                                        Viewed 38 times in the last 48 hours
                                          Exceptional! 5.0/5
                                          (41 reviews)
                                          $72
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 6
                                          Barn #6071185
                                          41
                                          Viewed 6 times in the last 48 hours
                                            Wonderful! 4.8/5
                                            (6 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • 1 HF BA
                                            • Sleeps 4
                                            House #1820331
                                            6
                                            Viewed 6 times in the last 48 hours
                                              $81
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 3
                                              House #1455834
                                              2
                                              Viewed 12 times in the last 48 hours
                                                Exceptional! 5.0/5
                                                (11 reviews)
                                                $99
                                                avg/night
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 5
                                                Apartment #431598
                                                11
                                                Viewed 10 times in the last 48 hours
                                                  $65
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Chateau / Country House #1963556
                                                  3
                                                  Viewed 51 times in the last 48 hours
                                                    • 6 BR
                                                    • 3 BA
                                                    • Sleeps 12
                                                    Villa #1893413
                                                    3
                                                    Viewed 22 times in the last 48 hours
                                                      avg/night
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 6
                                                      Villa #6503714
                                                      3
                                                      Viewed 12 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (6 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Apartment #479613vb
                                                        6
                                                        Viewed 37 times in the last 48 hours
                                                          $46
                                                          avg/night
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 5
                                                          Chateau / Country House #1841578
                                                          3
                                                          Viewed 10 times in the last 48 hours
                                                            avg/night
                                                            • 4 BR
                                                            • 2 BA
                                                            • Sleeps 9
                                                            Chateau / Country House #670725vb
                                                            2
                                                            Viewed 11 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (10 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Multiple rentals Farmhouse #1067421
                                                              10
                                                              Viewed 8 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (20 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • 1 HF BA
                                                                • Sleeps 7
                                                                Multiple rentals Cottage #899555
                                                                20
                                                                Viewed 16 times in the last 48 hours
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 3
                                                                  Apartment #2535098
                                                                  1
                                                                  Viewed 8 times in the last 48 hours
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 3
                                                                    Apartment #2535094
                                                                    Viewed 7 times in the last 48 hours
                                                                      $67
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Apartment #6715725
                                                                      4
                                                                      Viewed 30 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (5 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 8
                                                                        Chateau / Country House #1688510
                                                                        5
                                                                        Viewed 24 times in the last 48 hours
                                                                          Excellent! 4.6/5
                                                                          (5 reviews)
                                                                          $84
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          Apartment #5428740
                                                                          5
                                                                          Viewed 11 times in the last 48 hours
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 2
                                                                            Apartment #6081166
                                                                            29
                                                                              $43
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 5
                                                                              Apartment #1933719
                                                                              1
                                                                              Viewed 13 times in the last 48 hours
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Chateau / Country House #1491791
                                                                                2
                                                                                  Wonderful! 4.9/5
                                                                                  (31 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 11
                                                                                  Multiple rentals Chateau / Country House #899555
                                                                                  31
                                                                                  Viewed 50 times in the last 48 hours
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 7
                                                                                    Chateau / Country House #1766739
                                                                                    1
                                                                                    Viewed 5 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (10 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • Sleeps 6
                                                                                      House #6224261
                                                                                      10
                                                                                      Viewed 15 times in the last 48 hours
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Apartment #772468
                                                                                        4
                                                                                          Exceptional! 5.0/5
                                                                                          (5 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 8
                                                                                          Multiple rentals Chateau / Country House #1000477
                                                                                          5
                                                                                          Viewed 25 times in the last 48 hours
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • Sleeps 6
                                                                                            Chateau / Country House #6401678
                                                                                            2
                                                                                            Viewed 7 times in the last 48 hours
                                                                                              Excellent! 4.6/5
                                                                                              (5 reviews)
                                                                                              $48
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Apartment #6723347
                                                                                              5
                                                                                              Viewed 19 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (29 reviews)
                                                                                                avg/night
                                                                                                • 5 BR
                                                                                                • 4 BA
                                                                                                • Sleeps 12
                                                                                                Villa #833916
                                                                                                29
                                                                                                Viewed 61 times in the last 48 hours
                                                                                                  Excellent! 4.7/5
                                                                                                  (7 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  Multiple rentals Farmhouse #69771
                                                                                                  7
                                                                                                  Viewed 12 times in the last 48 hours
                                                                                                  • 1 - 50 of 300+
                                                                                                   

                                                                                                  Recent Roccastrada Reviews

                                                                                                  Angela

                                                                                                  5 of 5
                                                                                                  We loved staying here! The property is absolutely beautiful (and if you're a runner, there are miles of country roads to run on with fantastic views) and Luca and Letizia are fabulous!! We had a HUGE thunderstorm one night that caused a few issues...a quick text to Luca, and he came right out, and had everything fixed and perfect in under an hour! at 9 o'clock at night! The location of this property is also fantastic! It's walking (or super quick driving) distance to San Rocco a Pilli- which has a grocery, a yummy restaurant, coffee, etc.- which is so convenient. It's only a half-hour or so from Siena, and centrally located to so many places! We rented a car and did afternoon/day trips to Siena, Montalcino, Montepulciano, Chianti (for fabulous wine-tasting at Luca's recommendation), and San Gimignano . It was absolutely wonderful, and meeting Luca and Letizia was a highlight of our trip (and their adorable bulldog William : ).
                                                                                                  • Submitted: Oct 26, 2016
                                                                                                  • Stayed: Oct 2016

                                                                                                  Absolutely amazing cottage with great views!

                                                                                                  5 of 5
                                                                                                  This is the farm cottage of you dreams with an amazing view of the countryside! There is such warmth in this home with great decor. Lots of windows for those views. About 1-2K to Montalcino. Cecilia met us on th edge of the city to bring us to the home where she had spent her childhood - which has now been reintrovated into a beautiful farm cottage. Super kitchen - large baths - everything u need! We will be back!
                                                                                                  • Submitted: Oct 4, 2016
                                                                                                  • Stayed: Sep 2016

                                                                                                  Beautiful Tuscan Farmhouse Apartment

                                                                                                  4 of 5
                                                                                                  This was the last leg of our Italian vacation. The property was beautiful and wonderfully maintained. The apartment was big enough for four adults. The pool was delightful and the lounge chairs comfortable. We cooked several dinners and there was enough pots/pans, etc. Our time was relaxing but a car is necessary to get around. The drive north to Siena is about an hour but apparently there is a brand new road making it much easier to get there. We sat out on the porch, drank wine and pretty much relaxed. Wednesday we made our own pizzas (with the help of Gregario's cooks) and dined outside. Bring your bug spray for sure.
                                                                                                  • Submitted: Sep 30, 2016
                                                                                                  • Stayed: Sep 2016