check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr
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!

Historic Seaport: Houses, Condos & More (150)

  • 1 - 50 of 150
    • 1 BR
    • 1 BA
    • Sleeps 4
    15
      • Studio
      • 1 BA
      • Sleeps 2
      13
        • Studio
        • 1 BA
        • Sleeps 2
        23
          • 3 BR
          • 3 BA
          • Sleeps 10
          25
            • Studio
            • 1 BA
            • Sleeps 2
            25
              • 2 BR
              • 1 BA
              • Sleeps 6
              10
                • Studio
                • 1 BA
                • Sleeps 2
                29
                  • 4 BR
                  • 4 BA
                  • Sleeps 8
                  3
                    • 2 BR
                    • 2 BA
                    • Sleeps 8
                    12
                      • 1 BR
                      • 1 BA
                      • Sleeps 2
                      3
                        • 1 BR
                        • 1 BA
                        • 1 HF BA
                        • Sleeps 2
                        44
                          • Studio
                          • 1 BA
                          • Sleeps 2
                          19
                            • 2 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 6
                            37
                              • Studio
                              • 1 BA
                              • Sleeps 2
                              30
                                • Studio
                                • 1 BA
                                • Sleeps 2
                                25
                                  • Studio
                                  • 1 BA
                                  • Sleeps 2
                                  27
                                    • Studio
                                    • 1 BA
                                    • Sleeps 2
                                    24
                                      • Studio
                                      • 1 BA
                                      • Sleeps 2
                                      25
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 10
                                          • Studio
                                          • 1 BA
                                          • Sleeps 2
                                          33
                                            • Studio
                                            • 1 BA
                                            • Sleeps 2
                                            26
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              1 Review
                                                • 3 BR
                                                • 3 BA
                                                • Sleeps 6
                                                49
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  15
                                                    • 7 BR
                                                    • 7 BA
                                                    • 1 HF BA
                                                    • Sleeps 18
                                                    13
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      4
                                                        • 3 BR
                                                        • 3 BA
                                                        • 1 HF BA
                                                        • Sleeps 6
                                                        13
                                                          • 3 BR
                                                          • 3 BA
                                                          • Sleeps 6
                                                          15
                                                            • 4 BR
                                                            • 3 BA
                                                            • Sleeps 8
                                                            19
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 6
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                  • 3 BR
                                                                  • 3 BA
                                                                  • Sleeps 6
                                                                  3
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 7
                                                                    7
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      7
                                                                        • 1 BR
                                                                        • 2 BA
                                                                        • Sleeps 2
                                                                        2 Reviews
                                                                          • 3 BR
                                                                          • 3 BA
                                                                          • Sleeps 6
                                                                          8
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 4
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              1 Review
                                                                                • 4 BR
                                                                                • 4 BA
                                                                                • Sleeps 8
                                                                                1 Review
                                                                                  • Studio
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  12
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    6
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 9
                                                                                        • 6 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 14
                                                                                        21
                                                                                          • 5 BR
                                                                                          • 2 BA
                                                                                          • 2 HF BA
                                                                                          • Sleeps 10
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 6
                                                                                            1 Review
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              4
                                                                                                • Studio
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                17
                                                                                                  • Studio
                                                                                                  • 1 BA
                                                                                                  • Sleeps 2
                                                                                                  22
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 3
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 6
                                                                                                      8
                                                                                                      • 1 - 50 of 150
                                                                                                       

                                                                                                      Recent Historic Seaport Reviews

                                                                                                      Honeybun Hideaway in Paradise

                                                                                                      5 of 5
                                                                                                      Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The room was nicely appointed and as advertised in its description. The location was excellent--just steps to all the action on Duval Street!
                                                                                                      • Submitted: Aug 26, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      Curry House Key West

                                                                                                      5 of 5
                                                                                                      Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We arrived at the Curry House and it was as nice as the website portrayed. The house and grounds were well maintained. The Concierge team on property, Sandy and Chuck, were very welcoming and accommodating. Sandy gave suggestions to us for activities to do and booked the activities for us. Great service ! We stayed in room # 7 on the 3rd floor and we're pleased with the layout and cleanliness of our room. It has a balcony overlooking the pool. The breakfast on the weekends had hot and cold items. Weekdays had cold items only, yet, enough of what you want. We went to a sunset dinner cruise which was very nice. We rented bikes from WeCycle and their customer service was really good. They drop the bikes off at your place and pick them up there. Hogs Breath Saloon, Schooners Warf, Willie T's and Irish Kevin's were places we really enjoyed. The Curry House is a great place with a perfect location to stay ! The wonderful customer service will bring us back ! Thank you Sandy and Chuck !
                                                                                                      • Submitted: Aug 25, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      Best vacation ever. Loved our Curry House stay

                                                                                                      5 of 5
                                                                                                      Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This was our first visit to Key West and staying in a Bed and Breakfast. We loved our room and Sandy the innkeeper was an amazing hostess. We would recommend the Curry House and will stay there again if we go back to Key West.
                                                                                                      • Submitted: Aug 21, 2016
                                                                                                      • Stayed: Aug 2016