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.
    Exceptional! 5.0/5
    (9 reviews)
    avg/night
    • 4 BR
    • 5 BA
    • Sleeps 10
    Villa #1069180
    9
    Viewed 5 times in the last 48 hours
      • 2 BR
      • 2 BA
      • 1 HF BA
      • Sleeps 4
      Villa #171412
      98
        Excellent! 4.5/5
        (8 reviews)
        avg/night
        • 3 BR
        • 3 BA
        • Sleeps 8
        Villa #1403458
        8
          • 2 BR
          • 2 BA
          • Sleeps 4
          Villa #6790451
          Viewed 5 times in the last 48 hours
            • 3 BR
            • 1 BA
            • Sleeps 7
            Villa #1856415
            3
              Excellent! 4.5/5
              (6 reviews)
              avg/night
              • 5 BR
              • Sleeps 10
              Villa #71084
              6
                • 5 BR
                • 5 BA
                • Sleeps 10
                Villa #6506310
                5
                Viewed 11 times in the last 48 hours
                  • 2 BR
                  • 2 BA
                  • Sleeps 4
                  Villa #1856414
                  5
                    • 3 BR
                    • 2 BA
                    • Sleeps 6
                    Villa #1856420
                    2
                    Viewed 7 times in the last 48 hours
                      • 3 BR
                      • 3 BA
                      • Sleeps 6
                      Villa #6790452
                        • 9 BR
                        • 6 BA
                        • 1 HF BA
                        • Sleeps 17
                        Villa #1845001
                        1
                          • 5 BR
                          • 2 BA
                          • Sleeps 9
                          Villa #1856418
                          2
                          Viewed 7 times in the last 48 hours
                            • 4 BR
                            • 3 BA
                            • Sleeps 8
                            Villa #1664100
                              • 8 BR
                              • 7 BA
                              • 4 HF BA
                              • Sleeps 18
                              Villa #6799358
                                • 4 BR
                                • 3 BA
                                • Sleeps 8
                                Villa #1544721
                                1
                                  • 5 BR
                                  • 8 BA
                                  • Sleeps 12
                                  Villa #3920687
                                  6
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Villa #1644348
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 7
                                      Villa #6790456
                                        • 9 BR
                                        • 1 HF BA
                                        • Sleeps 22
                                        Villa #1150752
                                          • 10 BR
                                          • 10 BA
                                          • 1 HF BA
                                          • Sleeps 20
                                          Villa #3812495
                                          14
                                            • 4 BR
                                            • Sleeps 8
                                            Villa #1150902
                                            1
                                              • 7 BR
                                              • 3 HF BA
                                              • Sleeps 14
                                              Villa #1150847
                                                • 5 BR
                                                • Sleeps 10
                                                Villa #1150869
                                                  • 5 BR
                                                  • 4 BA
                                                  • Sleeps 12
                                                  Villa #1151061
                                                  1
                                                    • 4 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    Villa #6799332
                                                      Wonderful! 4.9/5
                                                      (8 reviews)
                                                      avg/night
                                                      • 7 BR
                                                      • 5 BA
                                                      • Sleeps 15
                                                      Villa #85978
                                                      8
                                                      Viewed 6 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (6 reviews)
                                                        avg/night
                                                        • 10 BR
                                                        • 8 BA
                                                        • 1 HF BA
                                                        • Sleeps 21
                                                        Villa #92790
                                                        6
                                                        Viewed 11 times in the last 48 hours
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Villa #1280315
                                                            • 5 BR
                                                            • 5 BA
                                                            • 1 HF BA
                                                            • Sleeps 12
                                                            Villa #1280273
                                                            1
                                                              • 6 BR
                                                              • 4 BA
                                                              • Sleeps 13
                                                              Villa #1280481
                                                              Viewed 13 times in the last 48 hours
                                                                • 5 BR
                                                                • 5 BA
                                                                • Sleeps 10
                                                                Villa #1280307
                                                                  • 2 BR
                                                                  • 3 BA
                                                                  • Sleeps 4
                                                                  Villa #1654629
                                                                  4
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 5
                                                                    Villa #463746
                                                                    28
                                                                      • 6 BR
                                                                      • 6 BA
                                                                      • 2 HF BA
                                                                      • Sleeps 12
                                                                      Villa #407902
                                                                      15
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 6
                                                                        Villa #8037836
                                                                        4
                                                                          • 7 BR
                                                                          • 5 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 15
                                                                          Villa #1987671
                                                                          3
                                                                            Exceptional! 5.0/5
                                                                            (36 reviews)
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 3 BA
                                                                            • Sleeps 12
                                                                            Villa #60123vb
                                                                            36
                                                                            Viewed 6 times in the last 48 hours
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 6
                                                                              Villa #1619154
                                                                              13
                                                                                • 4 BR
                                                                                • 4 BA
                                                                                • Sleeps 8
                                                                                Villa #8027623
                                                                                8
                                                                                  Wonderful! 4.9/5
                                                                                  (28 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 8
                                                                                  Villa #74671
                                                                                  28
                                                                                  Viewed 9 times in the last 48 hours
                                                                                    • 3 BR
                                                                                    • Sleeps 6
                                                                                    Villa #8003714
                                                                                    4
                                                                                      • 6 BR
                                                                                      • 6 BA
                                                                                      • Sleeps 12
                                                                                      Villa #3828121
                                                                                      4
                                                                                        Exceptional! 5.0/5
                                                                                        (7 reviews)
                                                                                        $95
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 10
                                                                                        Villa #1843539
                                                                                        7
                                                                                        Viewed 5 times in the last 48 hours
                                                                                          Wonderful! 4.8/5
                                                                                          (5 reviews)
                                                                                          avg/night
                                                                                          • 4 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 9
                                                                                          Villa #1638206
                                                                                          5
                                                                                          Viewed 5 times in the last 48 hours
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 4
                                                                                            Villa #6468098
                                                                                              • 5 BR
                                                                                              • 4 BA
                                                                                              • Sleeps 8
                                                                                              Villa #88723
                                                                                              15
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 8
                                                                                                Villa #1750874
                                                                                                1
                                                                                                  • 5 BR
                                                                                                  • 6 BA
                                                                                                  • Sleeps 10
                                                                                                  Villa #669478vb
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 11
                                                                                                    Villa #8081053
                                                                                                    2
                                                                                                    • 1 - 50 of 300+
                                                                                                     

                                                                                                    Recent Cortona Reviews

                                                                                                    Family Vacation in Tuscany

                                                                                                    5 of 5
                                                                                                    We purchased a week at Villa Santa Margherita at The Chisholm Trail Museum Gala in Cuero, Texas in April 2016. What a pleasant surprise when we arrived October 8 - such beauty and peacefulness awaited us. Mariella was there to greet us and had arranged for a private chef for a couple of nights - we were so impressed with Carlo and Grazia that we had them cook for us 5 nights. We had 13 family members at the Villa for the week and found it very comfortable for such a large group. The Villa's location is wonderful for side day trips to Florence and other small villages. We all fell in love with Tuscany and will most certainly return.
                                                                                                    • Submitted: Oct 28, 2016
                                                                                                    • Stayed: Oct 2016

                                                                                                    Beautiful villa, beautiful setting

                                                                                                    4 of 5
                                                                                                    This beautiful villa is only about 10 minutes from Cortona. You must drive through an olive orchard up a windy gravel road where you will reach the remote control wrought iron gates. Once you enter through the gates, you will see the meticulous landscaping and the three-story stone villa. We enjoyed the entire property, but there were some issues with things not working correctly. There were problems with the dishwasher, microwave, kitchen sink, washing machine, television and even trash can. Some of the features we are used to are not available such as hairdryers or even oven mitts. At first we were told we could not use the basement or the top floor for some reason. We needed at least one extra bedroom so the property manager finally said it was okay to use the top floor. Even though the basement level had no bedding, nobody would have wanted to stay down there anyway because it has a terrible musty smell, it was dark and was sparsely furnished. We were also told that we could not use the fireplace, but with further prying the manager said it was okay. (Like you, we were expecting to be able to use all of the amenities and rooms listed on the website) It was also clear that the house had not been cleaned in a long time. All of that aside, this is a gorgeous property with gorgeous grounds and views. If the property manager would take care of these comfort issues and not limit the rooms and amenities , this would actually be one of the nicer properties you may ever rent.
                                                                                                    • Submitted: Oct 27, 2016
                                                                                                    • Stayed: Oct 2016

                                                                                                    A lovely Italian Villa with private garden

                                                                                                    5 of 5
                                                                                                    A lovely spacious villa in its own private garden. All mod cons are there including dishwasher and washing machine. Federico and his son received us on arrival and showed us how everything works. He was extremely helpful throughout our stay with any questions or information we required. We were able to visit many beautiful towns and villages in the area, all within an easy drive. Assisi was our favourite but Gubbio, Montepulciano, Pienza, Castiglione and many others were all amazing. The villa felt like home from home. We highly recommend this villa for families or couples
                                                                                                    • Submitted: Oct 13, 2016
                                                                                                    • Stayed: Sep 2016