Villas in Wailea and Condos - Holiday Lettings - Holiday Rentals Wailea

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1,450 Holiday homes

(2) Excellent 

    23

    Wailea holiday condo rental

    Maui / Wailea

    2 6 3 nights min

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

    from £477 / night

    £3,338 / week

    Book View

    from £477 / night

    (1) Excellent 

      15

      Holiday apartment in Wailea

      Maui / Wailea

      2 8 4 nights min

      • 2 bedrooms
      • sleeps 8
      • 4 nights min
      • Nearest beach 1 km
      • Child friendly

      from £166 / night

      £1,133 - £1,376 / week

      Book View

      Responds fast!
      avg. 3 hours 2 minutes

      from £166 / night

      (4) Excellent 

        16

        Holiday apartment in Wailea

        Maui / Wailea

        2 4 5 nights min

        • 2 bedrooms
        • sleeps 4
        • 5 nights min
        • Swimming pool
        • Child friendly
        • Car not necessary

        from £522 / night

        £3,652 - £6,227 / week

        Enquire View

        from £522 / night

        (17) Excellent 

          17

          Condo rental in Wailea with shared pool, golf nearby

          Maui / Wailea

          1 4 min stay varies

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

          from £191 / night

          £1,335 / week

          Book View

          Responds fast!
          avg. 1 hour 48 minutes

          from £191 / night

            33

            Holiday villa with golf nearby in Wailea

            Maui / Wailea

            3 8 6 nights min

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

            from £605 / night

            £4,232 / week

            Book View

            Responds fast!
            avg. 3 hours 12 minutes

            from £605 / night

              26

              Condo rental in Wailea with shared pool

              Maui / Wailea

              2 4 1 night min

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

              from £130 / night

              £908 / week

              Book View

              Responds fast!
              avg. 3 hours 33 minutes

              from £130 / night

              (7) Excellent 

                40

                Holiday condo rental

                Maui / Wailea

                2 6 min stay varies

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

                from £170 / night

                £1,188 / week

                Book View

                from £170 / night

                (1) Excellent 

                  33

                  Villa rental in Wailea with shared pool

                  Maui / Wailea

                  3 8 6 nights min

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

                  from £648 / night

                  £4,536 / week

                  Book View

                  Responds fast!
                  avg. 3 hours 12 minutes

                  from £648 / night

                    31

                    Wailea holiday condo rental

                    Maui / Wailea

                    2 6 7 nights min

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

                    from £283 / night

                    £1,740 / week

                    Book View

                    from £283 / night

                    (1) Excellent 

                      24

                      Holiday apartment with shared pool in Wailea

                      Maui / Wailea

                      1 4 min stay varies

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

                      from £153 / night

                      £1,013 - £1,273 / week

                      Book View

                      Responds fast!
                      avg. 2 hours 34 minutes

                      from £153 / night

                        23

                        Holiday condo accommodation

                        Maui / Wailea

                        2 6 3 nights min

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

                        from £282 / night

                        £1,972 / week

                        Book View

                        from £282 / night

                        (13) Excellent 

                          0

                          Holiday home in Wailea

                          Maui / Wailea

                          2 4 5 nights min

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

                          from £829 / night

                          £5,803 / week

                          Enquire View

                          from £829 / night

                            36

                            Holiday condo with shared pool in Wailea

                            Maui / Wailea

                            3 9 min stay varies

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

                            from £429 / night

                            £3,004 / week

                            Book View

                            from £429 / night

                            (8) Excellent 

                              31

                              Holiday apartment with shared pool, golf nearby in Wailea

                              Maui / Wailea

                              1 4 1 night min

                              • 1 bedroom
                              • sleeps 4
                              • 1 night min
                              • Beach / lakeside relaxation
                              • Swimming pool
                              • Child friendly

                              from £147 / night

                              £1,026 - £1,208 / week

                              Book View

                              Responds fast!
                              avg. 1 hour 26 minutes

                              from £147 / night

                              (2) Excellent 

                                50

                                Wailea holiday home rental

                                Maui / Wailea

                                3 6 min stay varies

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

                                from £867 / night

                                £6,068 / week

                                Enquire View

                                from £867 / night

                                (5) Excellent 

                                  16

                                  Wailea holiday apartment rental

                                  Maui / Wailea

                                  1 4 5 nights min

                                  • 1 bedroom
                                  • sleeps 4
                                  • 5 nights min
                                  • Swimming pool
                                  • Child friendly
                                  • Car not necessary

                                  from £227 / night

                                  £1,585 - £2,041 / week

                                  Enquire View

                                  from £227 / night

                                    16

                                    Wailea holiday apartment rental

                                    Maui / Wailea

                                    2 5 5 nights min

                                    • 2 bedrooms
                                    • sleeps 5
                                    • 5 nights min
                                    • Swimming pool
                                    • Child friendly
                                    • Car not necessary

                                    from £333 / night

                                    £2,332 - £5,029 / week

                                    Enquire View

                                    from £333 / night

                                      16

                                      Wailea holiday apartment rental

                                      Maui / Wailea

                                      2 4 min stay varies

                                      • 2 bedrooms
                                      • sleeps 4
                                      • min stay varies
                                      • Swimming pool
                                      • Child friendly
                                      • Car not necessary

                                      from £492 / night

                                      £3,440 - £5,167 / week

                                      Enquire View

                                      from £492 / night

                                      (1) Very Good 

                                        45

                                        Apartment rental in Wailea with shared pool

                                        Maui / Wailea

                                        1 4 min stay varies

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

                                        from £130 / night

                                        £904 - £1,815 / week

                                        Book View

                                        from £130 / night

                                        (7) Very Good 

                                          16

                                          Holiday apartment in Wailea

                                          Maui / Wailea

                                          2 6 min stay varies

                                          • 2 bedrooms
                                          • sleeps 6
                                          • min stay varies
                                          • Swimming pool
                                          • Child friendly
                                          • Car not necessary

                                          from £464 / night

                                          £3,244 - £6,227 / week

                                          Enquire View

                                          from £464 / night

                                          (2) Very Good 

                                            16

                                            Wailea holiday apartment rental

                                            Maui / Wailea

                                            1 4 min stay varies

                                            • 1 bedroom
                                            • sleeps 4
                                            • min stay varies
                                            • Swimming pool
                                            • Child friendly
                                            • Car not necessary

                                            from £178 / night

                                            £1,246 - £1,781 / week

                                            Enquire View

                                            from £178 / night

                                              10

                                              Wailea holiday condo rental

                                              Maui / Wailea

                                              2 6 1 night min

                                              • 2 bedrooms
                                              • sleeps 6
                                              • 1 night min
                                              • Nearest beach 0.01 km
                                              • Swimming pool
                                              • Child friendly

                                              from £153 / night

                                              £1,066 / week

                                              Book View

                                              Responds fast!
                                              avg. 3 hours 33 minutes

                                              from £153 / night

                                              (19) Excellent 

                                                25

                                                Holiday apartment in Wailea

                                                Maui / Wailea

                                                1 4 4 nights min

                                                • 1 bedroom
                                                • sleeps 4
                                                • 4 nights min
                                                • Swimming pool
                                                • Ask owner if suitable for children
                                                • Car not necessary

                                                from £218 / night

                                                £1,927 / week

                                                Book View

                                                Responds fast!
                                                avg. 3 hours 2 minutes

                                                from £218 / night

                                                (13) Average 

                                                  16

                                                  Wailea holiday apartment rental

                                                  Maui / Wailea

                                                  1 4 min stay varies

                                                  • 1 bedroom
                                                  • sleeps 4
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child friendly
                                                  • Car not necessary

                                                  from £125 / night

                                                  £875 - £1,781 / week

                                                  Enquire View

                                                  from £125 / night

                                                    16

                                                    Wailea holiday apartment rental

                                                    Maui / Wailea

                                                    2 6 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • min stay varies
                                                    • Swimming pool
                                                    • Child friendly
                                                    • Car not necessary

                                                    from £310 / night

                                                    £2,168 - £4,499 / week

                                                    Enquire View

                                                    from £310 / night

                                                      22

                                                      Home letting in Wailea with golf nearby

                                                      Maui / Wailea

                                                      3 7 3 nights min

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

                                                      from £1,344 / night

                                                      £9,407 / week

                                                      Book View

                                                      from £1,344 / night

                                                        16

                                                        Apartment rental in Wailea

                                                        Maui / Wailea

                                                        2 6 5 nights min

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • 5 nights min
                                                        • Ask owner if suitable for children
                                                        • Ask about pets

                                                        from £310 / night

                                                        £2,168 - £4,499 / week

                                                        Enquire View

                                                        from £310 / night

                                                        (7) Excellent 

                                                          8

                                                          Holiday apartment in Wailea

                                                          Maui / Wailea

                                                          2 6 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child friendly
                                                          • Car not necessary

                                                          from £302 / night

                                                          £2,115 - £4,234 / week

                                                          Enquire View

                                                          from £302 / night

                                                            16

                                                            Holiday apartment in Wailea

                                                            Maui / Wailea

                                                            2 5 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 5
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child friendly
                                                            • Car not necessary

                                                            from £152 / night

                                                            £1,060 - £2,327 / week

                                                            Enquire View

                                                            from £152 / night

                                                            (1) Excellent 

                                                              16

                                                              Holiday apartment in Wailea

                                                              Maui / Wailea

                                                              2 5 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 5
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child friendly
                                                              • Car not necessary

                                                              from £221 / night

                                                              £1,548 - £2,756 / week

                                                              Enquire View

                                                              from £221 / night

                                                              (3) Excellent 

                                                                14

                                                                Holiday condo in Wailea

                                                                Maui / Wailea

                                                                2 4 min stay varies

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

                                                                from £227 / night

                                                                £1,583 / week

                                                                Book View

                                                                from £227 / night

                                                                  16

                                                                  Holiday apartment rental

                                                                  Maui / Wailea

                                                                  2 6 5 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 6
                                                                  • 5 nights min
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Car not necessary

                                                                  from £492 / night

                                                                  £3,440 - £5,167 / week

                                                                  Enquire View

                                                                  from £492 / night

                                                                    15

                                                                    Wailea holiday apartment rental

                                                                    Maui / Wailea

                                                                    2 4 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child friendly
                                                                    • Car not necessary

                                                                    from £567 / night

                                                                    £3,969 - £7,154 / week

                                                                    Enquire View

                                                                    from £567 / night

                                                                      15

                                                                      Wailea holiday apartment rental

                                                                      Maui / Wailea

                                                                      2 6 5 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 6
                                                                      • 5 nights min
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Car not necessary

                                                                      from £522 / night

                                                                      £3,652 - £6,227 / week

                                                                      Enquire View

                                                                      from £522 / night

                                                                        16

                                                                        Wailea holiday apartment rental

                                                                        Maui / Wailea

                                                                        2 5 5 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 5
                                                                        • 5 nights min
                                                                        • Swimming pool
                                                                        • Child friendly
                                                                        • Car not necessary

                                                                        from £302 / night

                                                                        £2,115 - £5,029 / week

                                                                        Enquire View

                                                                        from £302 / night

                                                                        (11) Excellent 

                                                                          58

                                                                          Holiday apartment in Wailea

                                                                          Maui / Wailea

                                                                          2 6 min stay varies

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

                                                                          from £518 / night

                                                                          £3,623 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 17 minutes

                                                                          from £518 / night

                                                                            34

                                                                            Condo accommodation in Wailea

                                                                            Maui / Wailea

                                                                            2 6 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Child friendly
                                                                            • Air conditioning
                                                                            • Private garden

                                                                            from £225 / night

                                                                            £1,569 / week

                                                                            Enquire View

                                                                            from £225 / night

                                                                            (37) Excellent 

                                                                              18

                                                                              Holiday apartment with shared pool, golf nearby in Wailea

                                                                              Maui / Wailea

                                                                              1 3 7 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 3
                                                                              • 7 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Nearest beach 1 km
                                                                              • Swimming pool

                                                                              from £305 / night

                                                                              £2,073 - £2,561 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 3 hours 1 minutes

                                                                              from £305 / night

                                                                                16

                                                                                Holiday apartment in Wailea

                                                                                Maui / Wailea

                                                                                2 6 min stay varies

                                                                                • 2 bedrooms
                                                                                • sleeps 6
                                                                                • min stay varies
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Car not necessary

                                                                                from £310 / night

                                                                                £2,168 - £4,499 / week

                                                                                Enquire View

                                                                                from £310 / night

                                                                                  16

                                                                                  Holiday apartment in Wailea

                                                                                  Maui / Wailea

                                                                                  2 6 min stay varies

                                                                                  • 2 bedrooms
                                                                                  • sleeps 6
                                                                                  • min stay varies
                                                                                  • Swimming pool
                                                                                  • Child friendly
                                                                                  • Car not necessary

                                                                                  from £310 / night

                                                                                  £2,168 - £4,499 / week

                                                                                  Enquire View

                                                                                  from £310 / night

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