check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    • 6 BR
    • 3 BA
    • Sleeps 14
    Multiple rentals Villa #480039
    Viewed 11 times in the last 48 hours
      • 4 BR
      • 2 BA
      • Sleeps 8
      Multiple rentals Apartment #480039
        • 3 BR
        • 1 BA
        • Sleeps 8
        House #774675
        2
          • 2 BR
          • Sleeps 6
          Villa #4344573
            • 2 BR
            • 1 BA
            • Sleeps 6
            Villa #6559890
              • 2 BR
              • 3 BA
              • Sleeps 7
              House #2388210
              1
              Viewed 5 times in the last 48 hours
                $62
                avg/night
                • 2 BR
                • 1 BA
                • Sleeps 4
                Apartment #6715725
                4
                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
                    • 3 BR
                    • 2 BA
                    • Sleeps 7
                    Chateau / Country House #1766739
                    1
                      Exceptional! 5.0/5
                      (5 reviews)
                      avg/night
                      • 2 BR
                      • 2 BA
                      • Sleeps 4
                      Apartment #6066838
                      5
                      Viewed 11 times in the last 48 hours
                        • 2 BR
                        • 1 BA
                        • Sleeps 5
                        Chateau / Country House #1841578
                        3
                          Wonderful! 4.9/5
                          (36 reviews)
                          $96
                          avg/night
                          • 2 BR
                          • 2 BA
                          • Sleeps 5
                          Villa #261912vb
                          36
                          Viewed 7 times in the last 48 hours
                            Wonderful! 4.8/5
                            (6 reviews)
                            $53
                            avg/night
                            • 2 BR
                            • 1 BA
                            • Sleeps 4
                            Apartment #2388890
                            6
                              avg/night
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                              House #582787vb
                              3
                              Viewed 36 times in the last 48 hours
                                • 2 BR
                                • 2 BA
                                • 1 HF BA
                                • Sleeps 6
                                House #6467953
                                1
                                  • 3 BR
                                  • 1 BA
                                  • 1 HF BA
                                  • Sleeps 8
                                  House #754551
                                    • 1 BR
                                    • Sleeps 4
                                    Multiple rentals Farmhouse #6054053
                                    1
                                      • 8 BR
                                      • 4 BA
                                      • Sleeps 15
                                      Farmhouse #686504vb
                                        $79
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 3
                                        House #1455834
                                        2
                                        Viewed 7 times in the last 48 hours
                                          Excellent! 4.6/5
                                          (5 reviews)
                                          $45
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Apartment #6723347
                                          5
                                            $43
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 5
                                            Apartment #1933719
                                            1
                                            Viewed 5 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (49 reviews)
                                              $56
                                              avg/night
                                              • 1 BR
                                              • 1 HF BA
                                              • Sleeps 4
                                              Apartment #6059609
                                              49
                                                Exceptional! 5.0/5
                                                (41 reviews)
                                                $71
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                Barn #6071185
                                                41
                                                Viewed 9 times in the last 48 hours
                                                  • 2 BR
                                                  • Sleeps 5
                                                  Multiple rentals Farmhouse #6054053
                                                  20
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 5
                                                    Multiple rentals Chateau / Country House #1304946
                                                    1
                                                      • 4 BR
                                                      • 3 BA
                                                      • 1 HF BA
                                                      • Sleeps 8
                                                      Villa #6470269
                                                      3
                                                      Viewed 20 times in the last 48 hours
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 3
                                                        Apartment #2535098
                                                        1
                                                          • 9 BR
                                                          • 10 BA
                                                          • Sleeps 16
                                                          Villa #1945067
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Apartment #835349vb
                                                            3
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 3
                                                              Farmhouse #1752653
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 2
                                                                Apartment #6559524
                                                                Viewed 8 times in the last 48 hours
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • Sleeps 9
                                                                  Chateau / Country House #670725vb
                                                                  2
                                                                  Viewed 8 times in the last 48 hours
                                                                    Excellent! 4.7/5
                                                                    (6 reviews)
                                                                    $86
                                                                    avg/night
                                                                    • 3 BR
                                                                    • Sleeps 6
                                                                    Farmhouse #6044756
                                                                    6
                                                                      Excellent! 4.7/5
                                                                      (7 reviews)
                                                                      $50
                                                                      avg/night
                                                                      • 1 BR
                                                                      • Sleeps 4
                                                                      Apartment #6690748
                                                                      7
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Multiple rentals Apartment #2093207
                                                                        3
                                                                        Viewed 6 times in the last 48 hours
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 5
                                                                          Multiple rentals House #1675396
                                                                          5
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 3
                                                                            Apartment #2535108
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              Apartment #772468
                                                                              4
                                                                                Wonderful! 4.8/5
                                                                                (20 reviews)
                                                                                $53
                                                                                avg/night
                                                                                • 2 BR
                                                                                • Sleeps 6
                                                                                House #6046194
                                                                                20
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 3
                                                                                  Multiple rentals Cottage #41310
                                                                                  11
                                                                                    Exceptional! 5.0/5
                                                                                    (5 reviews)
                                                                                    $87
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    House #1707805
                                                                                    5
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      Apartment #6558620
                                                                                      • 1 - 50 of 300+
                                                                                       

                                                                                      Recent Roccastrada Reviews

                                                                                      Get away from it all

                                                                                      4 of 5
                                                                                      After a long curved drive we arrived at this little gem. Just out of town with a view to take your breath away. The hosts are so nice, can only speak Italian though, giving us one day a plate of tomatoes and the next one with figs. An exceptional stay for us if you like quiet and natural scenery.
                                                                                      • Submitted: Sep 1, 2016
                                                                                      • Stayed: Aug 2016

                                                                                      Best place for family holidays

                                                                                      5 of 5
                                                                                      We spent brilliant time in this place. House is very stylish, clean and fully equipped. It looks much better, than on photos. If you travel with kids - there are many toys, books and even 2 playgrounds. Location is also very good: 15min to the beach, 20min to Punta Ala, 25min to Castiglione della Pescaia. I hope we will come back next year.
                                                                                      • Submitted: Aug 6, 2016
                                                                                      • Stayed: Jun 2016

                                                                                      We were immersed in the charm of Montalcino the moment we walked into this apartment.

                                                                                      5 of 5
                                                                                      The apartment was absolutely wonderful. While it had the old world charm with its exposed beams in the ceiling it was very spacious and comfortable. The location within the city walls with private parking is a must for this city making access to the city and surrounding area so much easier. Lisa was so pleasant and helpful with directions, restaurant recommendations as well as private tour recommendations. We will not only recommend this property to others I am sure we will be back.
                                                                                      • Submitted: May 22, 2016
                                                                                      • Stayed: May 2016