Apartments in Simpson Bay and Villas – Holiday Lettings - Holiday Rentals Simpson Bay

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1,701 Holiday homes

    13

    Simpson Bay holiday apartment accommodation

    Sint Maarten / Simpson Bay

    2 4 min stay varies

    • 2 bedrooms
    • sleeps 4
    • min stay varies
    • Swimming pool
    • Child friendly
    • Air conditioning

    from £353 / night

    £2,468 / week

    Book View

    from £353 / night

      21

      Simpson Bay holiday apartment rental

      Sint Maarten / Simpson Bay

      2 4 7 nights min

      • 2 bedrooms
      • sleeps 4
      • 7 nights min
      • Swimming pool
      • Child friendly
      • Air conditioning

      from £213 / night

      £1,738 / week

      Book View

      from £213 / night

        28

        Holiday villa rental

        Sint Maarten / Simpson Bay

        3 6 7 nights min

        • 3 bedrooms
        • sleeps 6
        • 7 nights min
        • Swimming pool
        • Child friendly
        • Air conditioning

        from £889 / night

        £6,218 / week

        Book View

        Responds fast!
        avg. 3 hours 1 minutes

        from £889 / night

        (4) Excellent 

          10

          Holiday condo with shared pool in Simpson Bay

          Simpson Bay / Simpson Bay Beach

          2 6 5 nights min

          • 2 bedrooms
          • sleeps 6
          • 5 nights min
          • Swimming pool
          • Child friendly
          • Air conditioning

          from £311 / night

          £2,212 / week

          Book View

          from £311 / night

          (2) Excellent 

            23

            Simpson Bay holiday condo rental

            Sint Maarten / Simpson Bay

            1 4 3 nights min

            • 1 bedroom
            • sleeps 4
            • 3 nights min
            • Beach / lakeside relaxation
            • Child friendly

            from £164 / night

            £1,148 / week

            Book View

            from £164 / night

            (1) Excellent 

              15

              Holiday apartment in Simpson Bay

              Sint Maarten / Simpson Bay

              2 4 3 nights min

              • 2 bedrooms
              • sleeps 4
              • 3 nights min
              • Beach / lakeside relaxation
              • Child friendly

              from £266 / night

              £1,862 / week

              Book View

              from £266 / night

              (28) Excellent 

              Certificate of Excellence

                22

                Holiday villa with swimming pool in Simpson Bay

                Sint Maarten / Simpson Bay

                2 4 min stay varies

                • 2 bedrooms
                • sleeps 4
                • min stay varies
                • Beach / lakeside relaxation
                • Swimming pool
                • Child friendly

                Certificate of Excellence

                from £178 / night

                £1,397 - £2,607 / week

                Book View

                Responds fast!
                avg. 1 hour 45 minutes

                from £178 / night

                  47

                  Holiday villa in Simpson Bay

                  Sint Maarten / Simpson Bay

                  5 10 min stay varies

                  • 5 bedrooms
                  • sleeps 10
                  • min stay varies
                  • Swimming pool
                  • Child friendly
                  • Air conditioning

                  from £653 / night

                  £4,568 - £6,117 / week

                  Enquire View

                  from £653 / night

                  (2) Excellent 

                    22

                    Simpson Bay holiday condo rental

                    Sint Maarten / Simpson Bay

                    1 4 3 nights min

                    • 1 bedroom
                    • sleeps 4
                    • 3 nights min
                    • Child friendly

                    from £153 / night

                    £1,068 / week

                    Book View

                    from £153 / night

                    (29) Excellent 

                      14

                      Holiday apartment with shared pool in Simpson Bay

                      Sint Maarten / Simpson Bay

                      1 2 min stay varies

                      • 1 bedroom
                      • sleeps 2
                      • min stay varies
                      • Beach / lakeside relaxation
                      • Nearest beach 0 km
                      • Swimming pool

                      from £150 / night

                      £1,173 - £1,235 / week

                      Book View

                      Responds fast!
                      avg. 1 hour 45 minutes

                      from £150 / night

                      (5) Excellent 

                        26

                        Apartment rental in Simpson Bay

                        Simpson Bay / Simpson Bay Beach

                        2 6 min stay varies

                        • 2 bedrooms
                        • sleeps 6
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Nearest beach 0.01 km
                        • Child friendly

                        from £265 / night

                        £1,858 - £4,738 / week

                        Book View

                        Responds fast!
                        avg. 1 hour 55 minutes

                        from £265 / night

                        (1) Excellent 

                          14

                          Condo rental in Simpson Bay

                          Sint Maarten / Simpson Bay

                          1 2 4 nights min

                          • 1 bedroom
                          • sleeps 2
                          • 4 nights min

                          from £133 / night

                          £931 / week

                          Book View

                          from £133 / night

                          (1) Excellent 

                            17

                            Holiday home in Simpson Bay

                            Sint Maarten / Simpson Bay

                            5 10 min stay varies

                            • 5 bedrooms
                            • sleeps 10
                            • min stay varies
                            • Beach / lakeside relaxation
                            • Nearest beach 0.7 km
                            • Swimming pool

                            from £572 / night

                            £3,989 / week

                            Book View

                            from £572 / night

                            (4) Very Good 

                              12

                              Holiday apartment in Simpson Bay Beach

                              Simpson Bay / Simpson Bay Beach

                              1 2 4 nights min

                              • 1 bedroom
                              • sleeps 2
                              • 4 nights min
                              • Beach / lakeside relaxation
                              • Nearest beach 0.8 km
                              • Air conditioning

                              from £106 / night

                              £741 / week

                              Book View

                              from £106 / night

                              (8) Excellent 

                                34

                                Simpson Bay holiday apartment rental

                                Sint Maarten / Simpson Bay

                                3 8 min stay varies

                                • 3 bedrooms
                                • sleeps 8
                                • min stay varies
                                • Beach / lakeside relaxation
                                • Nearest beach 0.01 km
                                • Child friendly

                                from £424 / night

                                £2,970 - £7,668 / week

                                Book View

                                Responds fast!
                                avg. 1 hour 55 minutes

                                from £424 / night

                                  29

                                  Holiday apartment with shared pool in Simpson Bay

                                  Sint Maarten / Simpson Bay

                                  2 4 min stay varies

                                  • 2 bedrooms
                                  • sleeps 4
                                  • min stay varies
                                  • Swimming pool
                                  • Child friendly
                                  • Air conditioning

                                  from £321 / night

                                  £2,246 - £2,710 / week

                                  Enquire View

                                  from £321 / night

                                    39

                                    Villa rental in Simpson Bay with swimming pool

                                    Sint Maarten / Simpson Bay

                                    3 8 min stay varies

                                    • 3 bedrooms
                                    • sleeps 8
                                    • min stay varies
                                    • Swimming pool
                                    • Child friendly
                                    • Air conditioning

                                    from £664 / night

                                    £4,646 - £8,517 / week

                                    Enquire View

                                    from £664 / night

                                    (1) Excellent 

                                      22

                                      Holiday condo in Simpson Bay

                                      Sint Maarten / Simpson Bay

                                      1 4 3 nights min

                                      • 1 bedroom
                                      • sleeps 4
                                      • 3 nights min
                                      • Nearest beach 1 km
                                      • Child friendly
                                      • Air conditioning

                                      from £164 / night

                                      £1,148 / week

                                      Book View

                                      from £164 / night

                                      (3) Very Good 

                                        32

                                        Simpson Bay holiday apartment rental

                                        Sint Maarten / Simpson Bay

                                        1 4 min stay varies

                                        • 1 bedroom
                                        • sleeps 4
                                        • min stay varies
                                        • Beach / lakeside relaxation
                                        • Child friendly
                                        • Air conditioning

                                        from £128 / night

                                        £894 / week

                                        Book View

                                        Responds fast!
                                        avg. 1 hour 4 minutes

                                        from £128 / night

                                          13

                                          Simpson Bay holiday villa rental

                                          Sint Maarten / Simpson Bay

                                          3 6 min stay varies

                                          • 3 bedrooms
                                          • sleeps 6
                                          • min stay varies
                                          • Swimming pool
                                          • Child friendly
                                          • Air conditioning

                                          from £443 / night

                                          £3,097 - £4,646 / week

                                          Enquire View

                                          from £443 / night

                                          (1) Excellent 

                                            11

                                            Holiday apartment letting

                                            Sint Maarten / Simpson Bay

                                            2 3 nights min

                                            • sleeps 2
                                            • 3 nights min
                                            • Beach / lakeside relaxation
                                            • Swimming pool
                                            • Ask owner if suitable for children

                                            from £133 / night

                                            £1,237 / week

                                            Book View

                                            from £133 / night

                                              33

                                              Holiday apartment letting

                                              Sint Maarten / Simpson Bay

                                              1 2 7 nights min

                                              • 1 bedroom
                                              • sleeps 2
                                              • 7 nights min
                                              • Beach / lakeside relaxation
                                              • Swimming pool
                                              • Car not necessary

                                              from £200 / night

                                              £1,552 / week

                                              Book View

                                              from £200 / night

                                              (1) Excellent 

                                                46

                                                Simpson Bay holiday villa rental

                                                Sint Maarten / Simpson Bay

                                                5 10 min stay varies

                                                • 5 bedrooms
                                                • sleeps 10
                                                • min stay varies
                                                • Swimming pool
                                                • Child friendly
                                                • Air conditioning

                                                from £985 / night

                                                £6,891 - £10,839 / week

                                                Enquire View

                                                from £985 / night

                                                  25

                                                  Holiday villa with swimming pool in Simpson Bay

                                                  Sint Maarten / Simpson Bay

                                                  5 12 5 nights min

                                                  • 5 bedrooms
                                                  • sleeps 12
                                                  • 5 nights min
                                                  • Swimming pool
                                                  • Child friendly
                                                  • Air conditioning

                                                  from £843 / night

                                                  £5,895 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 3 hours 19 minutes

                                                  from £843 / night

                                                    11

                                                    Simpson Bay holiday apartment rental

                                                    Sint Maarten / Simpson Bay

                                                    1 4 3 nights min

                                                    • 1 bedroom
                                                    • sleeps 4
                                                    • 3 nights min
                                                    • Child friendly
                                                    • Air conditioning
                                                    • Ask about pets

                                                    from £115 / night

                                                    £801 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 57 minutes

                                                    from £115 / night

                                                    (2) Excellent 

                                                      18

                                                      Apartment rental in Simpson Bay

                                                      Simpson Bay / Simpson Bay Beach

                                                      1 4 4 nights min

                                                      • 1 bedroom
                                                      • sleeps 4
                                                      • 4 nights min
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 2 km
                                                      • Child friendly

                                                      from £124 / night

                                                      £863 - £1,238 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 2 hours 19 minutes

                                                      from £124 / night

                                                        17

                                                        Holiday condo rental

                                                        Simpson Bay / Simpson Bay Beach

                                                        2 4 5 nights min

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • 5 nights min
                                                        • Beach / lakeside relaxation
                                                        • Child friendly

                                                        from £457 / night

                                                        £3,196 / week

                                                        Book View

                                                        from £457 / night

                                                        (1) Excellent 

                                                          32

                                                          Holiday villa rental

                                                          Simpson Bay / Simpson Bay Beach

                                                          2 6 4 nights min

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • 4 nights min
                                                          • Beach / lakeside relaxation
                                                          • Swimming pool
                                                          • Child friendly

                                                          from £271 / night

                                                          £1,893 / week

                                                          Book View

                                                          from £271 / night

                                                            22

                                                            Holiday villa with swimming pool, golf nearby in Simpson Bay

                                                            Sint Maarten / Simpson Bay

                                                            5 16 min stay varies

                                                            • 5 bedrooms
                                                            • sleeps 16
                                                            • min stay varies
                                                            • Beach / lakeside relaxation
                                                            • Swimming pool
                                                            • Child friendly

                                                            from £754 / night

                                                            £23,332 / week

                                                            Book View

                                                            from £754 / night

                                                              25

                                                              Holiday villa rental

                                                              Sint Maarten / Simpson Bay

                                                              3 6 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child friendly
                                                              • Air conditioning

                                                              from £421 / night

                                                              £2,942 - £3,871 / week

                                                              Enquire View

                                                              from £421 / night

                                                                50

                                                                Holiday villa with swimming pool in Simpson Bay

                                                                Sint Maarten / Simpson Bay

                                                                3 6 min stay varies

                                                                • 3 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Air conditioning

                                                                from £520 / night

                                                                £3,639 - £5,033 / week

                                                                Enquire View

                                                                from £520 / night

                                                                (2) Excellent 

                                                                  20

                                                                  Holiday home rental

                                                                  Sint Maarten / Simpson Bay

                                                                  2 4 7 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • 7 nights min
                                                                  • Beach / lakeside relaxation
                                                                  • Nearest beach 2 km
                                                                  • Swimming pool

                                                                  from £190 / night

                                                                  £1,330 / week

                                                                  Book View

                                                                  from £190 / night

                                                                  (1) Excellent 

                                                                    26

                                                                    Holiday villa in Simpson Bay Beach

                                                                    Simpson Bay / Simpson Bay Beach

                                                                    1 4 7 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 4
                                                                    • 7 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Nearest beach 0.2 km
                                                                    • Swimming pool

                                                                    from £121 / night

                                                                    £843 - £1,326 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 2 hours 6 minutes

                                                                    from £121 / night

                                                                      9

                                                                      Simpson Bay holiday apartment rental

                                                                      Sint Maarten / Simpson Bay

                                                                      1 2 1 night min

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • 1 night min
                                                                      • Beach / lakeside relaxation
                                                                      • Swimming pool
                                                                      • Air conditioning

                                                                      from £80 / night

                                                                      £559 / week

                                                                      Book View

                                                                      from £80 / night

                                                                      (5) Excellent 

                                                                        16

                                                                        Simpson Bay holiday apartment rental

                                                                        Sint Maarten / Simpson Bay

                                                                        2 5 5 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 5
                                                                        • 5 nights min
                                                                        • Beach / lakeside relaxation
                                                                        • Swimming pool
                                                                        • Child friendly

                                                                        from £222 / night

                                                                        £1,552 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 2 hours 4 minutes

                                                                        from £222 / night

                                                                          9

                                                                          Holiday condo with shared pool in Simpson Bay

                                                                          Simpson Bay / Simpson Bay Beach

                                                                          2 4 5 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • 5 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Swimming pool
                                                                          • Child friendly

                                                                          from £457 / night

                                                                          £3,196 / week

                                                                          Book View

                                                                          from £457 / night

                                                                            26

                                                                            Apartment rental in Simpson Bay with swimming pool

                                                                            Sint Maarten / Simpson Bay

                                                                            3 6 3 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • 3 nights min
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £352 / night

                                                                            £2,462 - £5,420 / week

                                                                            Book View

                                                                            from £352 / night

                                                                              25

                                                                              Holiday apartment with shared pool in Simpson Bay

                                                                              Sint Maarten / Simpson Bay

                                                                              2 4 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child friendly
                                                                              • Air conditioning

                                                                              from £255 / night

                                                                              £1,781 - £2,710 / week

                                                                              Enquire View

                                                                              from £255 / night

                                                                                20

                                                                                Holiday villa rental

                                                                                Sint Maarten / Simpson Bay

                                                                                2 4 5 nights min

                                                                                • 2 bedrooms
                                                                                • sleeps 4
                                                                                • 5 nights min
                                                                                • Swimming pool
                                                                                • Air conditioning

                                                                                from £216 / night

                                                                                £1,507 / week

                                                                                Book View

                                                                                from £216 / night

                                                                                  17

                                                                                  Holiday villa in Simpson Bay

                                                                                  Sint Maarten / Simpson Bay

                                                                                  2 4 5 nights min

                                                                                  • 2 bedrooms
                                                                                  • sleeps 4
                                                                                  • 5 nights min
                                                                                  • Swimming pool
                                                                                  • Air conditioning
                                                                                  • Private garden

                                                                                  from £222 / night

                                                                                  £1,552 / week

                                                                                  Book View

                                                                                  from £222 / night

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