Apartments in Simpson Bay Beach and Condos – Holiday Lettings - Holiday Rentals Simpson Bay Beach

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1,710 Holiday homes

(4) Excellent 

    10

    Holiday condo with shared pool in Simpson Bay Beach

    Simpson Bay / Simpson Bay Beach

    2 6 5 nights min

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

    from £305 / night

    £2,173 / week

    Book View

    from £305 / night

    (5) Excellent 

      26

      Apartment rental in Simpson Bay Beach

      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 £261 / night

      £1,825 - £4,655 / week

      Book View

      Responds fast!
      avg. 1 hour 55 minutes

      from £261 / night

      (4) Very Good 

        12

        Holiday apartment in Simpson Bay

        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 £105 / night

        £730 / week

        Book View

        from £105 / night

        (2) Excellent 

          18

          Apartment rental in Simpson Bay Beach

          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 £121 / night

          £848 - £1,216 / week

          Book View

          Responds fast!
          avg. 2 hours 19 minutes

          from £121 / 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 £449 / night

            £3,140 / week

            Book View

            from £449 / 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 £266 / night

              £1,860 / week

              Book View

              from £266 / night

              (1) Excellent 

                26

                Holiday villa in Simpson Bay

                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

                  Holiday condo with shared pool in Simpson Bay Beach

                  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 £449 / night

                  £3,140 / week

                  Book View

                  from £449 / night

                  (1)  

                    5

                    Penthouse accommodation in Simpson Bay Beach with shared pool

                    Simpson Bay / Simpson Bay Beach

                    2 4 1 night min

                    • 2 bedrooms
                    • sleeps 4
                    • 1 night min
                    • Swimming pool
                    • Air conditioning

                    from £262 / night

                    £1,742 / week

                    Book View

                    from £262 / night

                    Great rentals within 20 miles that match your search

                    Distance approx 1.65 miles from Simpson Bay Beach Show on Map

                    (1) Excellent 

                      12

                      Holiday studio with shared pool in Bellevue

                      Saint-Martin / Bellevue

                      Studio 4 5 nights min

                      • Studio
                      • sleeps 4
                      • 5 nights min
                      • Beach / lakeside relaxation
                      • Nearest beach 0 km
                      • Swimming pool

                      from £59 / night

                      £414 - £690 / week

                      Book View

                      from £59 / night

                      Distance approx 9.43 miles from Simpson Bay Beach Show on Map

                        37

                        Holiday villa in Little Harbour

                        Anguilla / Little Harbour

                        4 10 2 nights min

                        • 4 bedrooms
                        • sleeps 10
                        • 2 nights min
                        • Beach / lakeside relaxation
                        • Suitable for children age 5+
                        • Air conditioning

                        from £1,064 / night

                        £7,447 / week

                        Book View

                        from £1,064 / night

                        Distance approx 15.52 miles from Simpson Bay Beach Show on Map

                          65

                          Shoal Bay Village holiday villa rental

                          Anguilla / Shoal Bay Village

                          4 8 min stay varies

                          • 4 bedrooms
                          • sleeps 8
                          • min stay varies
                          • Nearest beach 0.25 km
                          • Child friendly

                          from £712 / night

                          £4,983 / week

                          Book View

                          Responds fast!
                          avg. 1 hour 51 minutes

                          from £712 / night

                          Distance approx 1.63 miles from Simpson Bay Beach Show on Map

                            20

                            Holiday apartment with shared pool in Baie Nettle

                            Saint-Martin / Baie Nettle

                            2 6 min stay varies

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

                            from £136 / night

                            £952 / week

                            Book View

                            Responds fast!
                            avg. 3 hours 19 minutes

                            from £136 / night

                            Distance approx 6.02 miles from Simpson Bay Beach Show on Map

                              28

                              Holiday studio with shared pool in Orient Bay

                              Saint-Martin / Orient Bay

                              Studio 3 4 nights min

                              • Studio
                              • sleeps 3
                              • 4 nights min
                              • Swimming pool
                              • Child friendly
                              • Air conditioning

                              from £69 / night

                              £483 - £586 / week

                              Book View

                              from £69 / night

                              Distance approx 2.15 miles from Simpson Bay Beach Show on Map

                                24

                                Holiday apartment with shared pool in Marigot, Saint Martin

                                Saint-Martin / Marigot, Saint Martin

                                1 4 5 nights min

                                • 1 bedroom
                                • sleeps 4
                                • 5 nights min
                                • Swimming pool
                                • Ask owner if suitable for children
                                • Air conditioning

                                from £187 / night

                                £1,310 / week

                                Book View

                                from £187 / night

                                Distance approx 5.5 miles from Simpson Bay Beach Show on Map

                                  12

                                  Holiday villa in Orient Bay

                                  Saint-Martin / Orient Bay

                                  4 8 7 nights min

                                  • 4 bedrooms
                                  • sleeps 8
                                  • 7 nights min
                                  • Child friendly

                                  from £504 / night

                                  £3,526 / week

                                  Book View

                                  from £504 / night

                                  Distance approx 17.69 miles from Simpson Bay Beach Show on Map

                                  (1) Excellent 

                                    23

                                    Holiday villa rental

                                    St. Barts / Colombier

                                    4 8 min stay varies

                                    • 4 bedrooms
                                    • sleeps 8
                                    • min stay varies
                                    • Beach / lakeside relaxation
                                    • Swimming pool
                                    • Child friendly

                                    from £1,991 / night

                                    £13,936 - £42,581 / week

                                    Enquire View

                                    from £1,991 / night

                                    Distance approx 3.52 miles from Simpson Bay Beach Show on Map

                                    (1) Very Good 

                                      17

                                      Holiday villa letting

                                      Saint-Martin / Terres Basses

                                      5 10 7 nights min

                                      • 5 bedrooms
                                      • sleeps 10
                                      • 7 nights min
                                      • Beach / lakeside relaxation
                                      • Nearest beach 0.15 km
                                      • Swimming pool

                                      from £985 / night

                                      £6,892 / week

                                      Book View

                                      from £985 / night

                                      Distance approx 6.39 miles from Simpson Bay Beach Show on Map

                                        14

                                        Holiday apartment in Orient Bay

                                        Saint-Martin / Orient Bay

                                        1 4 3 nights min

                                        • 1 bedroom
                                        • sleeps 4
                                        • 3 nights min
                                        • Nearest beach 0 km
                                        • Child friendly
                                        • Air conditioning

                                        from £93 / night

                                        £588 / week

                                        Book View

                                        from £93 / night

                                        Distance approx 4.92 miles from Simpson Bay Beach Show on Map

                                          10

                                          Holiday apartment in Grand Case

                                          Saint-Martin / Grand Case

                                          1 2 3 nights min

                                          • 1 bedroom
                                          • sleeps 2
                                          • 3 nights min
                                          • Child friendly
                                          • Air conditioning

                                          from £89 / night

                                          £621 / week

                                          Book View

                                          Responds fast!
                                          avg. 1 hour 4 minutes

                                          from £89 / night

                                          Distance approx 18.9 miles from Simpson Bay Beach Show on Map

                                            79

                                            Villa rental in Anse des Cayes with swimming pool, golf nearby

                                            St. Barts / Anse des Cayes

                                            2 4 min stay varies

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

                                            from £802 / night

                                            £4,880 - £6,878 / week

                                            Book View

                                            Responds fast!
                                            avg. 1 hour 48 minutes

                                            from £802 / night

                                            Distance approx 1.31 miles from Simpson Bay Beach Show on Map

                                            (1) Excellent 

                                              44

                                              Holiday apartment in Baie Nettle

                                              Saint-Martin / Baie Nettle

                                              1 2 3 nights min

                                              • 1 bedroom
                                              • sleeps 2
                                              • 3 nights min
                                              • Nearest beach 2 km
                                              • Child friendly
                                              • Air conditioning

                                              from £86 / night

                                              £518 / week

                                              Book View

                                              from £86 / night

                                              Distance approx 3.38 miles from Simpson Bay Beach Show on Map

                                              (19) Excellent 

                                                32

                                                Holiday villa with shared pool in Philipsburg

                                                Sint Maarten / Philipsburg

                                                2 6 min stay varies

                                                • 2 bedrooms
                                                • sleeps 6
                                                • min stay varies
                                                • Beach / lakeside relaxation
                                                • Swimming pool
                                                • Child friendly

                                                from £174 / night

                                                £1,213 - £2,122 / week

                                                Book View

                                                Responds fast!
                                                avg. 2 hours 15 minutes

                                                from £174 / night

                                                Distance approx 10.66 miles from Simpson Bay Beach Show on Map

                                                (4) Excellent 

                                                  21

                                                  Holiday villa in South Hill

                                                  Anguilla / South Hill

                                                  3 6 min stay varies

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • min stay varies
                                                  • Nearest beach 5 km
                                                  • Swimming pool
                                                  • Child friendly

                                                  from £476 / night

                                                  £3,328 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 3 hours 41 minutes

                                                  from £476 / night

                                                  Distance approx 5.89 miles from Simpson Bay Beach Show on Map

                                                    2

                                                    Home rental in St Martin / St Maarten with swimming pool

                                                    St. Maarten - Saint Martin

                                                    3 2 7 nights min

                                                    • 3 bedrooms
                                                    • sleeps 2
                                                    • 7 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 0.8 km
                                                    • Swimming pool

                                                    from £186 / night

                                                    £1,299 / week

                                                    Book View

                                                    from £186 / night

                                                    Distance approx 19.79 miles from Simpson Bay Beach Show on Map

                                                      26

                                                      Holiday villa rental

                                                      St. Barts / Gustavia

                                                      3 6 5 nights min

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • 5 nights min
                                                      • Nearest beach 0.5 km
                                                      • Swimming pool
                                                      • Ask owner if suitable for children

                                                      from £743 / night

                                                      £5,196 / week

                                                      Book View

                                                      from £743 / night

                                                      Distance approx 14.18 miles from Simpson Bay Beach Show on Map

                                                        44

                                                        Holiday villa in East End Village

                                                        Anguilla / East End Village

                                                        1 11 7 nights min

                                                        • 1 bedroom
                                                        • sleeps 11
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Child friendly
                                                        • Air conditioning

                                                        from £607 / night

                                                        £4,244 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 3 hours 43 minutes

                                                        from £607 / night

                                                        Distance approx 10.98 miles from Simpson Bay Beach Show on Map

                                                          16

                                                          Little Harbour holiday villa accommodation

                                                          Anguilla / Little Harbour

                                                          2 4 1 night min

                                                          • 2 bedrooms
                                                          • sleeps 4
                                                          • 1 night min
                                                          • Child friendly

                                                          from £390 / night

                                                          £2,425 / week

                                                          Book View

                                                          from £390 / night

                                                          Distance approx 5.4 miles from Simpson Bay Beach Show on Map

                                                          (1) Very Good 

                                                            12

                                                            Philipsburg holiday apartment rental

                                                            Sint Maarten / Philipsburg

                                                            3 8 7 nights min

                                                            • 3 bedrooms
                                                            • sleeps 8
                                                            • 7 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 0 km
                                                            • Swimming pool

                                                            from £406 / night

                                                            £2,837 / week

                                                            Book View

                                                            from £406 / night

                                                            Distance approx 19.79 miles from Simpson Bay Beach Show on Map

                                                              20

                                                              Holiday villa with swimming pool in Gustavia

                                                              St. Barts / Gustavia

                                                              1 2 5 nights min

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

                                                              from £507 / night

                                                              £3,550 / week

                                                              Book View

                                                              from £507 / night

                                                              Distance approx 6.19 miles from Simpson Bay Beach Show on Map

                                                              (19) Excellent 

                                                                34

                                                                Orient Bay holiday apartment rental

                                                                Saint-Martin / Orient Bay

                                                                1 4 min stay varies

                                                                • 1 bedroom
                                                                • sleeps 4
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Nearest beach 0 km
                                                                • Swimming pool

                                                                from £138 / night

                                                                £965 / week

                                                                Book View

                                                                from £138 / night

                                                                Distance approx 1.78 miles from Simpson Bay Beach Show on Map

                                                                  5

                                                                  Holiday apartment in Marigot

                                                                  Saint-Martin / Marigot

                                                                  1 4 4 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • 4 nights min
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Air conditioning

                                                                  from £130 / night

                                                                  £910 / week

                                                                  Book View

                                                                  from £130 / night

                                                                  Distance approx 6.13 miles from Simpson Bay Beach Show on Map

                                                                    12

                                                                    Holiday villa in Orient Bay

                                                                    Saint-Martin / Orient Bay

                                                                    4 8 4 nights min

                                                                    • 4 bedrooms
                                                                    • sleeps 8
                                                                    • 4 nights min
                                                                    • Child friendly
                                                                    • Pet friendly

                                                                    from £665 / night

                                                                    £4,654 / week

                                                                    Book View

                                                                    from £665 / night

                                                                    Distance approx 3.65 miles from Simpson Bay Beach Show on Map

                                                                      6

                                                                      Philipsburg holiday condo rental

                                                                      Sint Maarten / Philipsburg

                                                                      3 8 7 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 8
                                                                      • 7 nights min
                                                                      • Child friendly

                                                                      from £446 / night

                                                                      £3,118 / week

                                                                      Book View

                                                                      from £446 / night

                                                                      Distance approx 5.22 miles from Simpson Bay Beach Show on Map

                                                                        15

                                                                        Oyster Pond holiday condo rental

                                                                        Sint Maarten / Oyster Pond

                                                                        3 8 5 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 8
                                                                        • 5 nights min
                                                                        • Swimming pool
                                                                        • Child friendly
                                                                        • Air conditioning

                                                                        from £433 / night

                                                                        £3,031 / week

                                                                        Book View

                                                                        from £433 / night

                                                                        Distance approx 13.09 miles from Simpson Bay Beach Show on Map

                                                                          49

                                                                          Holiday home with shared pool in Anguilla

                                                                          Anguilla

                                                                          9 10 min stay varies

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

                                                                          from £5,444 / night

                                                                          £38,105 - £49,363 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 3 minutes

                                                                          from £5,444 / night

                                                                          Distance approx 6.32 miles from Simpson Bay Beach Show on Map

                                                                          (1) Excellent 

                                                                            24

                                                                            Holiday studio with shared pool in Orient Bay

                                                                            Saint-Martin / Orient Bay

                                                                            Studio 3 5 nights min

                                                                            • Studio
                                                                            • sleeps 3
                                                                            • 5 nights min
                                                                            • Nearest beach 0.1 km
                                                                            • Swimming pool
                                                                            • Child friendly

                                                                            from £130 / night

                                                                            £858 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 2 hours 25 minutes

                                                                            from £130 / night

                                                                            Distance approx 9.67 miles from Simpson Bay Beach Show on Map

                                                                            (3) Excellent 

                                                                              22

                                                                              West End Village holiday villa rental

                                                                              Anguilla / West End Village

                                                                              3 6 7 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • 7 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Swimming pool
                                                                              • Child friendly

                                                                              from £974 / night

                                                                              £6,813 / week

                                                                              Book View

                                                                              from £974 / night

                                                                              Distance approx 2.67 miles from Simpson Bay Beach Show on Map

                                                                                26

                                                                                Holiday villa in Terres Basses

                                                                                Saint-Martin / Terres Basses

                                                                                5 10 3 nights min

                                                                                • 5 bedrooms
                                                                                • sleeps 10
                                                                                • 3 nights min
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Air conditioning

                                                                                from £1,545 / night

                                                                                £10,811 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 3 hours 1 minutes

                                                                                from £1,545 / night

                                                                                Distance approx 6.92 miles from Simpson Bay Beach Show on Map

                                                                                (6)  

                                                                                  25

                                                                                  Holiday villa with swimming pool in Cul de Sac

                                                                                  Saint-Martin / Cul de Sac

                                                                                  3 6 5 nights min

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

                                                                                  from £509 / night

                                                                                  £3,469 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 3 hours 30 minutes

                                                                                  from £509 / night

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