Verified Review icon 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 pet-dog svg-multiunit Default Owner Icon heart-filled
Cancel Clear Filters Apply Filters
More Filters

Price Per Night

$ $

Bedrooms

Bathrooms

Booking Options

Booking Options

Location Type

Features

Managed By

Clear Filters
Use filters to narrow your search results!
Favorite
    Viewed 14 times in the last 48 hours
    Wonderful! 4.9/5
    (94 reviews)
    avg/night
    94
    Favorite
      Viewed 26 times in the last 48 hours
      Wonderful! 4.9/5
      (16 reviews)
      avg/night
      16
      Favorite
        Viewed 6 times in the last 48 hours
        Exceptional! 5/5
        (35 reviews)
        avg/night
        35
        Favorite
          Viewed 13 times in the last 48 hours
          Wonderful! 4.9/5
          (87 reviews)
          avg/night
          87
          Favorite
            Viewed 12 times in the last 48 hours
            Excellent! 4.6/5
            (44 reviews)
            avg/night
            44
            Favorite
              Viewed 10 times in the last 48 hours
              Excellent! 4.3/5
              (89 reviews)
              avg/night
              89
              Favorite
                Viewed 7 times in the last 48 hours
                Wonderful! 4.9/5
                (73 reviews)
                avg/night
                73
                Favorite
                  Viewed 18 times in the last 48 hours
                  Wonderful! 4.9/5
                  (43 reviews)
                  avg/night
                  43
                  Favorite
                    Viewed 5 times in the last 48 hours
                    Wonderful! 4.9/5
                    (97 reviews)
                    avg/night
                    97
                    Favorite
                      Viewed 8 times in the last 48 hours
                      Wonderful! 4.8/5
                      (84 reviews)
                      avg/night
                      84
                      Favorite
                        Viewed 6 times in the last 48 hours
                        Wonderful! 4.8/5
                        (84 reviews)
                        avg/night
                        84
                        Favorite
                          Viewed 9 times in the last 48 hours
                          Wonderful! 4.8/5
                          (75 reviews)
                          avg/night
                          75
                          Favorite
                            Viewed 6 times in the last 48 hours
                            Wonderful! 4.9/5
                            (53 reviews)
                            avg/night
                            53
                            Favorite
                              Wonderful! 4.9/5
                              (49 reviews)
                              avg/night
                              49
                              Favorite
                                Viewed 8 times in the last 48 hours
                                Wonderful! 4.9/5
                                (48 reviews)
                                avg/night
                                48
                                Favorite
                                  Viewed 19 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (17 reviews)
                                  avg/night
                                  17
                                  Favorite
                                    Viewed 6 times in the last 48 hours
                                    avg/night
                                    Favorite
                                      Viewed 10 times in the last 48 hours
                                      Excellent! 4.5/5
                                      (70 reviews)
                                      avg/night
                                      70
                                      Favorite
                                        Viewed 6 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (13 reviews)
                                        avg/night
                                        13
                                        Favorite
                                          Viewed 6 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (28 reviews)
                                          avg/night
                                          28
                                          Favorite
                                            Viewed 9 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (46 reviews)
                                            avg/night
                                            46
                                            Favorite
                                              Excellent! 4.7/5
                                              (26 reviews)
                                              avg/night
                                              26
                                              Favorite
                                                avg/night
                                                Favorite
                                                  Viewed 7 times in the last 48 hours
                                                  Excellent! 4.5/5
                                                  (22 reviews)
                                                  avg/night
                                                  22
                                                  Favorite
                                                    Viewed 21 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (26 reviews)
                                                    avg/night
                                                    26
                                                    Favorite
                                                      Viewed 8 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (38 reviews)
                                                      avg/night
                                                      38
                                                      Favorite
                                                        Viewed 8 times in the last 48 hours
                                                        Exceptional! 5/5
                                                        (19 reviews)
                                                        avg/night
                                                        19
                                                        Favorite
                                                          Excellent! 4.5/5
                                                          (83 reviews)
                                                          avg/night
                                                          83
                                                          Favorite
                                                            Viewed 7 times in the last 48 hours
                                                            Excellent! 4.4/5
                                                            (34 reviews)
                                                            avg/night
                                                            34
                                                            Favorite
                                                              avg/night
                                                              Favorite
                                                                Wonderful! 4.9/5
                                                                (37 reviews)
                                                                avg/night
                                                                37
                                                                Favorite
                                                                  Wonderful! 4.9/5
                                                                  (8 reviews)
                                                                  avg/night
                                                                  8
                                                                  Favorite
                                                                    Viewed 6 times in the last 48 hours
                                                                    Very Good! 4.2/5
                                                                    (17 reviews)
                                                                    avg/night
                                                                    17
                                                                    Favorite
                                                                      Viewed 7 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (31 reviews)
                                                                      avg/night
                                                                      31
                                                                      Favorite
                                                                        Viewed 6 times in the last 48 hours
                                                                        Exceptional! 5/5
                                                                        (45 reviews)
                                                                        avg/night
                                                                        45
                                                                        Favorite
                                                                          Viewed 5 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (51 reviews)
                                                                          avg/night
                                                                          51
                                                                          Favorite
                                                                            Excellent! 4.7/5
                                                                            (66 reviews)
                                                                            avg/night
                                                                            66
                                                                            Favorite
                                                                              Excellent! 4.5/5
                                                                              (11 reviews)
                                                                              avg/night
                                                                              11
                                                                              Favorite
                                                                                Excellent! 4.7/5
                                                                                (27 reviews)
                                                                                avg/night
                                                                                27
                                                                                Favorite
                                                                                  Wonderful! 4.9/5
                                                                                  (37 reviews)
                                                                                  avg/night
                                                                                  37
                                                                                  Favorite
                                                                                    Viewed 7 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (21 reviews)
                                                                                    avg/night
                                                                                    21
                                                                                    Favorite
                                                                                      Viewed 5 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (34 reviews)
                                                                                      avg/night
                                                                                      34
                                                                                      Favorite
                                                                                        avg/night
                                                                                        2
                                                                                        Favorite
                                                                                          avg/night
                                                                                          1
                                                                                          Favorite
                                                                                            $73
                                                                                            avg/night
                                                                                            2
                                                                                            Favorite
                                                                                              Wonderful! 4.9/5
                                                                                              (33 reviews)
                                                                                              avg/night
                                                                                              33
                                                                                              Favorite
                                                                                                Wonderful! 4.9/5
                                                                                                (18 reviews)
                                                                                                avg/night
                                                                                                18
                                                                                                Favorite
                                                                                                  Wonderful! 4.9/5
                                                                                                  (68 reviews)
                                                                                                  avg/night
                                                                                                  68
                                                                                                  Favorite
                                                                                                    Viewed 8 times in the last 48 hours
                                                                                                    Excellent! 4.7/5
                                                                                                    (28 reviews)
                                                                                                    avg/night
                                                                                                    28
                                                                                                    Favorite
                                                                                                      Excellent! 4.4/5
                                                                                                      (21 reviews)
                                                                                                      avg/night
                                                                                                      21
                                                                                                       

                                                                                                      Recent Old Town Reviews

                                                                                                      A PERFECT WEEK IN KEY WEST

                                                                                                      5 of 5
                                                                                                      This was our first visit to Key West and what an amazing trip! Our son had his wedding here. The location of our Truman Annex condo could not have been better.The central location was perfect and we were in walking distance to everything. The two bedrooms provided plenty of room for three adults.We loved the kitchen and the living room provided us room to relax.We will be back again to this unit.Lyle Goodwin,Ottumwa,Iowa
                                                                                                      • Submitted: Sep 20, 2017
                                                                                                      • Stayed: Aug 2017

                                                                                                      The House, Neighbors along with Sheryl and Dan are Spectacular

                                                                                                      5 of 5
                                                                                                      This is our second time staying at the house and it was even better than the first as Sheryl and Dan has the upstairs bathroom completely redone. They give you everything you need and or want for vacation all except for the bathing suits and island attitude. Even though we had to be evacuated due to Irma Sheryl made sure we were well informed and informed ahead of time so that there were no surprises which allowed for us to make extra arrangements in time for our evacuation. I could tell she was as disappointed and we were in leaving, we are glad to see and hear that the place survived with just a few scratches and it will be just as good as before. We are already looking to make our plans for next year for our third visit. Don't hesitate to book this wonderful home if your looking for a great place to more than just sleep and great people to help make you have no surprises on your vacation (all except for mother nature) this is the place to be.
                                                                                                      • Submitted: Sep 20, 2017
                                                                                                      • Stayed: Aug 2017