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
  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Wonderful! 4.9/5
    (25 reviews)
    avg/night
    • 5 BR
    • 5 BA
    • Sleeps 12
    Villa #440010vb
    25
      • 5 BR
      • 5 BA
      • Sleeps 16
      Villa #654245vb
      14
        • 2 BR
        • 2 BA
        • Sleeps 6
        Villa #904513vb
        0
          • 3 BR
          • 3 BA
          • Sleeps 6
          Villa #328737vb
          35
            • 5 BR
            • 5 BA
            • Sleeps 10
            Villa #27453vb
            9
              • 6 BR
              • 6 BA
              • Sleeps 12
              Villa #4320638
              3
                • 3 BR
                • 3 BA
                • Sleeps 8
                Villa #4239782
                1
                  • 1 BR
                  • 2 BA
                  • Sleeps 5
                  Villa #831543vb
                  1
                    • 5 BR
                    • 5 BA
                    • Sleeps 10
                    Villa #204449
                    6
                      • 2 BR
                      • 2 BA
                      • Sleeps 5
                      Villa #831545vb
                      1
                        Wonderful! 4.9/5
                        (20 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 5
                        Villa #87855vb
                        20
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          Villa #831547vb
                          0
                            Wonderful! 4.8/5
                            (16 reviews)
                            avg/night
                            • 3 BR
                            • 3 BA
                            • Sleeps 8
                            Villa #89619vb
                            16
                              • Studio
                              • 5 BA
                              • 1 HF BA
                              • Sleeps 10
                              Villa #3950049
                              0
                                • 2 BR
                                • 2 BA
                                • Sleeps 4
                                Villa #233071
                                11
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 5
                                  Villa #947779vb
                                  12
                                    • 4 BR
                                    • 4 BA
                                    • Sleeps 10
                                    Villa #640347vb
                                    16
                                      • 4 BR
                                      • 4 BA
                                      • Sleeps 10
                                      Villa #859201vb
                                      0
                                        • 2 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 4
                                        Villa #329528vb
                                        1
                                          • 5 BR
                                          • 5 BA
                                          • 1 HF BA
                                          • Sleeps 10
                                          Villa #4320612
                                          0
                                            • 5 BR
                                            • 4 BA
                                            • Sleeps 10
                                            Villa #4046116
                                            0
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Villa #1274922a
                                              0
                                                • 5 BR
                                                • 4 BA
                                                • Sleeps 12
                                                Villa #904370vb
                                                0
                                                  • 3 BR
                                                  • 3 BA
                                                  • Sleeps 6
                                                  Villa #3236570
                                                  1
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Villa #904634vb
                                                    0
                                                      • 2 BR
                                                      • 3 BA
                                                      • Sleeps 4
                                                      Villa #3603937
                                                      0
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                        Villa #904404vb
                                                        0
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Villa #884654vb
                                                          0
                                                            • 5 BR
                                                            • 5 BA
                                                            • 1 HF BA
                                                            • Sleeps 12
                                                            Villa #975279vb
                                                            0
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Villa #882431vb
                                                              0
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Villa #904506vb
                                                                0
                                                                  • 3 BR
                                                                  • 3 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 6
                                                                  Villa #995197vb
                                                                  0
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Villa #859189vb
                                                                    0
                                                                      • 5 BR
                                                                      • 5 BA
                                                                      • Sleeps 10
                                                                      Villa #4164935
                                                                      0
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Villa #858943vb
                                                                        0
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 6
                                                                          Villa #4321257
                                                                          0
                                                                            • 4 BR
                                                                            • 4 BA
                                                                            • Sleeps 10
                                                                            Villa #858955vb
                                                                            0
                                                                              • 5 BR
                                                                              • 5 BA
                                                                              • Sleeps 12
                                                                              Villa #858957vb
                                                                              0
                                                                                • 3 BR
                                                                                • 3 BA
                                                                                • Sleeps 6
                                                                                Villa #574685vb
                                                                                1
                                                                                  • 3 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 8
                                                                                  Villa #858949vb
                                                                                  0
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    Villa #904496vb
                                                                                    0
                                                                                      • 3 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 8
                                                                                      Villa #859195vb
                                                                                      0
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Villa #896643vb
                                                                                        0
                                                                                          • 5 BR
                                                                                          • 6 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 10
                                                                                          Villa #4321530
                                                                                          0
                                                                                            • 6 BR
                                                                                            • 6 BA
                                                                                            • Sleeps 14
                                                                                            Villa #858963vb
                                                                                            0
                                                                                              • 5 BR
                                                                                              • 5 BA
                                                                                              • Sleeps 12
                                                                                              Villa #4283376
                                                                                              0
                                                                                                • 5 BR
                                                                                                • 5 BA
                                                                                                • Sleeps 12
                                                                                                Villa #859203vb
                                                                                                0
                                                                                                  • 3 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 6
                                                                                                  Villa #4287998
                                                                                                  0
                                                                                                    • 3 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 6
                                                                                                    Villa #4313601
                                                                                                    0
                                                                                                    • 1 - 50 of 300+
                                                                                                     

                                                                                                    Recent Simpson Bay Reviews

                                                                                                    Everything you would want in a vacation

                                                                                                    4 of 5
                                                                                                    Identical to the pics on the internet. Ice maker was broken since 2013 read it in the guest book has not been repaired need to purchase ice. the ac for the living room and kitchen was not functioning however bedrooms ac worked beautifully. It was a great location and the condo was great for our needs.
                                                                                                    • Submitted: Nov 19, 2016
                                                                                                    • Stayed: Nov 2016

                                                                                                    Vacation Get Away

                                                                                                    5 of 5
                                                                                                    This beautiful 6 bedroom villa with private pool and kitchens was a wonderful and delightful experience for everyone. The villa was clean and the staff was kind and helpful and was able to answer all our questions. We loved the island food, lobster, crab and all seafood food but especially loved the shopping in Philipsburg, in particular Alpha Jewels on Front Street. I would definitely recommend this vacation home to anyone interested in a private home with pool and in close proximity to restaurants, shopping and of course the beach. Loved the place!!!
                                                                                                    • Submitted: Nov 2, 2016
                                                                                                    • Stayed: Oct 2016

                                                                                                    Perfect Location- Amazing Penthouse Right on the Beach!

                                                                                                    5 of 5
                                                                                                    We have never been to Sint Maarten, and my husband and I were very excited to visit, but also nervous since we didn't know much about the island and the different areas. I can't imagine a better place to stay than this private penthouse on Simpson Bay. We fell in love immediately. From the rooftop pool to the prime location, we were in heaven. Simpson Bay is well-situated... just about a 10 minute drive from the airport. We rented a car (you'd be fine without one, but we always like to explore with ease), and did not have any trouble locating the place. We were also able to easily park every time we came and went, as the unit has a little lot nearby. We were met at the property and given the keys and a quick tour of the home, then left to relax and unpack. Management was always supportive and available to give us tips, etc as needed, but not ever-present and pushy- it was a perfect balance and they did an amazing job to ensure our visit to St. Maarten was everything we hoped. I loved the decor and style of the home. Each of the rooms was well-appointed and had an attached bathroom. The home has a comfy living room with a big TV and wireless internet. The dining room table is huge, which is great for a group! It was just the 2 of us, but this would be an amazing place to accommodate a whole family. The penthouse has an open floor plan between the kitchen, dining, and living areas, with a wrap around balcony overhanging the beach directly below! The rooftop pool area was deluxe- we listened to music, BBQed, and watched the sunsets. It is like you are on the beach, but also have a private area to relax and enjoy. Simpson Bay is a fun area and we enjoyed meals and drinks at the restaurants and bars directly below the Penthouse. These areas can be pretty busy in the evening, but they are not too loud into the night. We adventured all over the island and loved every minute of it. The beaches range from the popular, expansive family areas at Orient Beach to bird watching at Oyster Bay to the snorkel haven of Grand Case to the elite, exclusive escape at Anse Marcel and we enjoyed them all! Shopping in Marigot, golfing at Mullet Bay, watching the airplanes fly right overhead at Maho Beach... we did it all. We also booked a deep sea fishing expedition and caught a bunch of barracuda and a massive King Fish- definitely a highlight for my husband. Sint Maarten is a great destination for families, with activities for all ages!
                                                                                                    • Submitted: Oct 10, 2016
                                                                                                    • Stayed: Jan 2016