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
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 117
Additional fees apply. Taxes may be added.
    • 5 BR
    • 4 BA
    • Sleeps 10
      • 3 BR
      • 2 BA
      • Sleeps 6
        • 1 BR
        • 1 BA
        • Sleeps 2
          • 3 BR
          • 3 BA
          • Sleeps 6
            • 3 BR
            • 3 BA
            • Sleeps 6
              • 1 BR
              • 1 BA
              • Sleeps 2
                • 4 BR
                • 5 BA
                • Sleeps 14
                39
                  • 2 BR
                  • 2 BA
                  • Sleeps 4
                    • 1 BR
                    • 1 BA
                    • Sleeps 2
                      • 5 BR
                      • 5 BA
                      • Sleeps 12
                        • 2 BR
                        • 2 BA
                        • Sleeps 4
                          • 2 BR
                          • 2 BA
                          • Sleeps 4
                            • 2 BR
                            • 2 BA
                            • Sleeps 4
                              • 5 BR
                              • 5 BA
                              • Sleeps 10
                              1 Review
                                • 3 BR
                                • 3 BA
                                • Sleeps 6
                                  • 5 BR
                                  • 5 BA
                                  • Sleeps 16
                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 6
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 4
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 4
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 4
                                            • 5 BR
                                            • 5 BA
                                            • Sleeps 12
                                              • 5 BR
                                              • 5 BA
                                              • Sleeps 10
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 4
                                                  • 2 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 4
                                                    • 5 BR
                                                    • 6 BA
                                                    • Sleeps 10
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                        • 5 BR
                                                        • 5 BA
                                                        • Sleeps 10
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 4
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2
                                                                • 3 BR
                                                                • 3 BA
                                                                • Sleeps 7
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 4
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 4
                                                                        • 6 BR
                                                                        • 6 BA
                                                                        • Sleeps 12
                                                                          • 5 BR
                                                                          • 5 BA
                                                                          • Sleeps 10
                                                                            • 6 BR
                                                                            • 5 BA
                                                                            • Sleeps 12
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 4
                                                                                  • 5 BR
                                                                                  • 5 BA
                                                                                  • Sleeps 10
                                                                                    • 3 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 6
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                        • 3 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 6
                                                                                          • 6 BR
                                                                                          • 6 BA
                                                                                          • Sleeps 12
                                                                                            • 6 BR
                                                                                            • 5 BA
                                                                                            • Sleeps 12
                                                                                            1 Review
                                                                                              • 3 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 6
                                                                                                • 3 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 6
                                                                                                  • 3 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 6
                                                                                                    • 3 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 6
                                                                                                      • 7 BR
                                                                                                      • 7 BA
                                                                                                      • Sleeps 14
                                                                                                      • 1 - 50 of 117
                                                                                                       

                                                                                                      Recent Simpson Bay Reviews

                                                                                                      Sunshine it is!

                                                                                                      5 of 5
                                                                                                      Rikki, the property manager was easy to work with and very helpful. The property was in good condition, clean and ready upon arrival. The villa basically looked like what's represented in the pictures. Unfortunately, some of the windows that we shown open in the pictures in the bedrooms were actually blocked by storm shutters so no visible views to the outside. Although some of the views to the outside were obstructed, the rooms were big so they didn't feel as closed in as they could have. The pool area was very nice, spacious and comfortable. You could see cruise ships and sailboats sailing by. We enjoyed having dinner and hanging out listening to music by the pool. Becky, the housekeeper did a fabulous job keeping the house clean
                                                                                                      • Submitted: Jun 20, 2016
                                                                                                      • Stayed: Jun 2016

                                                                                                      Celebrated an awesome 50th birthday!!

                                                                                                      5 of 5
                                                                                                      We had a party of twelve for a week at this gorgeous house! Celebrating a friends 50th birthday. Beautiful views, amazing pool and several lounging areas. Rooms uniquely decorated with most having a private bath. Whole house flowed to entertain and have everyone feeling very comfortable. Close to nightlife, cool shops, great restaurants and short ride to several beaches . Will definitely go back and recommend to others!
                                                                                                      • Submitted: Jun 11, 2016
                                                                                                      • Stayed: May 2016