Apartments in Winter Park and Villas - Holiday Lettings - Holiday Rentals Winter Park

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735 Holiday homes

    24

    Ski townhouse to rent in Winter Park

    Grand County / Winter Park

    3 8 3 nights min

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

    from £429 / night

    £3,004 / week

    Book View

    from £429 / night

      38

      Holiday home in Winter Park

      Grand County / Winter Park

      3 8 min stay varies

      • 3 bedrooms
      • sleeps 8
      • min stay varies
      • Child friendly

      from £241 / night

      £1,687 / week

      Enquire View

      from £241 / night

      (1) Excellent 

        24

        Ski home to rent in Winter Park

        Grand County / Winter Park

        3 7 min stay varies

        • 3 bedrooms
        • sleeps 7
        • min stay varies
        • Ski
        • Child friendly

        from £178 / night

        £1,246 / week

        Book View

        Responds fast!
        avg. 12 minutes

        from £178 / night

          0

          Home rental in Winter Park

          Grand County / Winter Park

          3 15 min stay varies

          • 3 bedrooms
          • sleeps 15
          • min stay varies
          • Child friendly
          • Car not necessary

          from £154 / night

          £1,076 / week

          Book View

          Responds fast!
          avg. 1 hour 18 minutes

          from £154 / night

          (6) Very Good 

            31

            Holiday home rental

            Grand County / Winter Park

            2 8 min stay varies

            • 2 bedrooms
            • sleeps 8
            • min stay varies
            • Child friendly

            from £150 / night

            £1,051 / week

            Enquire View

            from £150 / night

              29

              Ski home to rent in Winter Park

              Grand County / Winter Park

              5 12 min stay varies

              • 5 bedrooms
              • sleeps 12
              • min stay varies
              • Swimming pool
              • Ski
              • Child friendly

              from £347 / night

              £2,427 / week

              Book View

              Responds fast!
              avg. 12 minutes

              from £347 / night

                24

                Ski studio to rent in Winter Park

                Grand County / Winter Park

                Studio 4 min stay varies

                • Studio
                • sleeps 4
                • min stay varies
                • Ski
                • Child friendly

                from £74 / night

                £517 / week

                Book View

                Responds fast!
                avg. 12 minutes

                from £74 / night

                  24

                  Winter Park ski apartment to rent.

                  Grand County / Winter Park

                  1 5 min stay varies

                  • 1 bedroom
                  • sleeps 5
                  • min stay varies
                  • Swimming pool
                  • Ski
                  • Child friendly

                  from £74 / night

                  £516 / week

                  Book View

                  Responds fast!
                  avg. 12 minutes

                  from £74 / night

                  (1) Excellent 

                    18

                    Holiday condo with shared pool in Winter Park

                    Grand County / Winter Park

                    2 6 min stay varies

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

                    from £152 / night

                    £1,063 / week

                    Book View

                    from £152 / night

                    (1) Very Good 

                      25

                      Winter Park ski apartment to rent.

                      Grand County / Winter Park

                      2 7 min stay varies

                      • 2 bedrooms
                      • sleeps 7
                      • min stay varies
                      • Swimming pool
                      • Ski
                      • Child friendly

                      from £109 / night

                      £760 / week

                      Book View

                      Responds fast!
                      avg. 12 minutes

                      from £109 / night

                        24

                        Ski apartment to rent in Winter Park

                        Grand County / Winter Park

                        2 7 min stay varies

                        • 2 bedrooms
                        • sleeps 7
                        • min stay varies
                        • Ski
                        • Child friendly
                        • Pet friendly

                        from £100 / night

                        £698 / week

                        Book View

                        Responds fast!
                        avg. 12 minutes

                        from £100 / night

                        (1) Excellent 

                          38

                          Home rental in Winter Park with shared pool

                          Grand County / Winter Park

                          2 7 min stay varies

                          • 2 bedrooms
                          • sleeps 7
                          • min stay varies
                          • Swimming pool
                          • Child friendly

                          from £132 / night

                          £924 / week

                          Enquire View

                          from £132 / night

                            12

                            Condo accommodation in Winter Park with golf nearby

                            Grand County / Winter Park

                            3 8 min stay varies

                            • 3 bedrooms
                            • sleeps 8
                            • min stay varies
                            • Child friendly
                            • Car not necessary
                            • Pet friendly

                            from £191 / night

                            £1,337 - £3,111 / week

                            Book View

                            from £191 / night

                              24

                              Winter Park ski apartment to rent.

                              Grand County / Winter Park

                              1 4 min stay varies

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

                              from £83 / night

                              £577 / week

                              Book View

                              Responds fast!
                              avg. 12 minutes

                              from £83 / night

                                26

                                Winter Park ski apartment to rent.

                                Grand County / Winter Park

                                1 4 min stay varies

                                • 1 bedroom
                                • sleeps 4
                                • min stay varies
                                • Ski
                                • Child friendly

                                from £74 / night

                                £517 / week

                                Book View

                                Responds fast!
                                avg. 12 minutes

                                from £74 / night

                                (16) Very Good 

                                  32

                                  Holiday home in Winter Park

                                  Grand County / Winter Park

                                  3 8 min stay varies

                                  • 3 bedrooms
                                  • sleeps 8
                                  • min stay varies
                                  • Child friendly

                                  from £192 / night

                                  £1,343 / week

                                  Enquire View

                                  from £192 / night

                                    34

                                    Holiday home in Winter Park

                                    Grand County / Winter Park

                                    5 18 min stay varies

                                    • 5 bedrooms
                                    • sleeps 18
                                    • min stay varies
                                    • Child friendly

                                    from £531 / night

                                    £3,714 / week

                                    Enquire View

                                    from £531 / night

                                      24

                                      Winter Park ski home to rent.

                                      Grand County / Winter Park

                                      3 10 min stay varies

                                      • 3 bedrooms
                                      • sleeps 10
                                      • min stay varies
                                      • Ski
                                      • Child friendly

                                      from £130 / night

                                      £906 / week

                                      Book View

                                      Responds fast!
                                      avg. 12 minutes

                                      from £130 / night

                                      (27) Very Good 

                                        34

                                        Home letting in Winter Park

                                        Grand County / Winter Park

                                        2 6 min stay varies

                                        • 2 bedrooms
                                        • sleeps 6
                                        • min stay varies
                                        • Child friendly

                                        from £150 / night

                                        £1,051 / week

                                        Enquire View

                                        from £150 / night

                                          24

                                          Winter Park ski apartment to rent.

                                          Grand County / Winter Park

                                          3 8 min stay varies

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

                                          from £143 / night

                                          £1,002 / week

                                          Book View

                                          Responds fast!
                                          avg. 12 minutes

                                          from £143 / night

                                            31

                                            Ski apartment to rent in Winter Park

                                            Grand County / Winter Park

                                            1 4 min stay varies

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

                                            from £86 / night

                                            £601 / week

                                            Book View

                                            Responds fast!
                                            avg. 8 minutes

                                            from £86 / night

                                            (53) Very Good 

                                              32

                                              Winter Park holiday home rental

                                              Grand County / Winter Park

                                              1 4 min stay varies

                                              • 1 bedroom
                                              • sleeps 4
                                              • min stay varies
                                              • Child friendly

                                              from £114 / night

                                              £796 / week

                                              Enquire View

                                              from £114 / night

                                              (1) Excellent 

                                                27

                                                Holiday home in Winter Park

                                                Grand County / Winter Park

                                                4 14 min stay varies

                                                • 4 bedrooms
                                                • sleeps 14
                                                • min stay varies
                                                • Child friendly
                                                • Pet friendly

                                                from £338 / night

                                                £1,942 - £5,928 / week

                                                Book View

                                                Responds fast!
                                                avg. 2 hours 43 minutes

                                                from £338 / night

                                                  24

                                                  Ski apartment to rent in Winter Park

                                                  Grand County / Winter Park

                                                  1 4 min stay varies

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

                                                  from £83 / night

                                                  £577 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 13 minutes

                                                  from £83 / night

                                                  (12) Very Good 

                                                    36

                                                    Holiday home in Winter Park

                                                    Grand County / Winter Park

                                                    2 6 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • min stay varies
                                                    • Child friendly

                                                    from £154 / night

                                                    £1,077 / week

                                                    Enquire View

                                                    from £154 / night

                                                    (1) Excellent 

                                                      26

                                                      Ski home to rent in Winter Park

                                                      Grand County / Winter Park

                                                      4 12 min stay varies

                                                      • 4 bedrooms
                                                      • sleeps 12
                                                      • min stay varies
                                                      • Ski
                                                      • Child friendly

                                                      from £252 / night

                                                      £1,762 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 12 minutes

                                                      from £252 / night

                                                      (1) Excellent 

                                                        23

                                                        Winter Park ski condo to rent.

                                                        Grand County / Winter Park

                                                        2 6 2 nights min

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • 2 nights min
                                                        • Ski
                                                        • Child friendly

                                                        from £130 / night

                                                        £906 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 2 hours 16 minutes

                                                        from £130 / night

                                                          39

                                                          Winter Park holiday home let

                                                          Grand County / Winter Park

                                                          3 12 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 12
                                                          • min stay varies
                                                          • Child friendly

                                                          from £241 / night

                                                          £1,687 / week

                                                          Enquire View

                                                          from £241 / night

                                                          (3) Very Good 

                                                            29

                                                            Winter Park holiday home rental

                                                            Grand County / Winter Park

                                                            3 10 min stay varies

                                                            • 3 bedrooms
                                                            • sleeps 10
                                                            • min stay varies
                                                            • Child friendly

                                                            from £178 / night

                                                            £1,242 / week

                                                            Enquire View

                                                            from £178 / night

                                                            (1) Excellent 

                                                              37

                                                              Holiday home with shared pool in Winter Park

                                                              Grand County / Winter Park

                                                              3 10 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 10
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child friendly
                                                              • Pet friendly

                                                              from £179 / night

                                                              £1,247 / week

                                                              Enquire View

                                                              from £179 / night

                                                              (1) Very Good 

                                                                33

                                                                Holiday home in Winter Park

                                                                Grand County / Winter Park

                                                                2 6 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Child friendly

                                                                from £150 / night

                                                                £1,051 / week

                                                                Enquire View

                                                                from £150 / night

                                                                (1) Excellent 

                                                                  28

                                                                  Holiday home in Winter Park

                                                                  Grand County / Winter Park

                                                                  2 8 min stay varies

                                                                  • 2 bedrooms
                                                                  • sleeps 8
                                                                  • min stay varies
                                                                  • Child friendly

                                                                  from £154 / night

                                                                  £1,077 / week

                                                                  Enquire View

                                                                  from £154 / night

                                                                    0

                                                                    Holiday home with shared pool in Winter Park

                                                                    Grand County / Winter Park

                                                                    2 7 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 7
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child friendly
                                                                    • Car not necessary

                                                                    from £85 / night

                                                                    £596 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 1 hour 18 minutes

                                                                    from £85 / night

                                                                    (45) Very Good 

                                                                      31

                                                                      Studio rental in Winter Park

                                                                      Grand County / Winter Park

                                                                      Studio 4 min stay varies

                                                                      • Studio
                                                                      • sleeps 4
                                                                      • min stay varies
                                                                      • Child friendly

                                                                      from £94 / night

                                                                      £658 / week

                                                                      Enquire View

                                                                      from £94 / night

                                                                      (2) Excellent 

                                                                        35

                                                                        Winter Park holiday home rental

                                                                        Grand County / Winter Park

                                                                        2 8 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 8
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Child friendly

                                                                        from £160 / night

                                                                        £1,120 / week

                                                                        Enquire View

                                                                        from £160 / night

                                                                          30

                                                                          Holiday home in Winter Park

                                                                          Grand County / Winter Park

                                                                          2 6 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • min stay varies
                                                                          • Child friendly

                                                                          from £150 / night

                                                                          £1,051 / week

                                                                          Enquire View

                                                                          from £150 / night

                                                                            48

                                                                            Holiday home in Winter Park

                                                                            Grand County / Winter Park

                                                                            6 16 min stay varies

                                                                            • 6 bedrooms
                                                                            • sleeps 16
                                                                            • min stay varies
                                                                            • Child friendly
                                                                            • Pet friendly

                                                                            from £561 / night

                                                                            £3,926 / week

                                                                            Enquire View

                                                                            from £561 / night

                                                                              32

                                                                              Holiday home in Winter Park

                                                                              Grand County / Winter Park

                                                                              3 8 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 8
                                                                              • min stay varies
                                                                              • Child friendly

                                                                              from £178 / night

                                                                              £1,242 / week

                                                                              Enquire View

                                                                              from £178 / night

                                                                              (7) Excellent 

                                                                                37

                                                                                Winter Park holiday home rental

                                                                                Grand County / Winter Park

                                                                                3 10 min stay varies

                                                                                • 3 bedrooms
                                                                                • sleeps 10
                                                                                • min stay varies
                                                                                • Child friendly

                                                                                from £183 / night

                                                                                £1,279 / week

                                                                                Enquire View

                                                                                from £183 / night

                                                                                (6) Very Good 

                                                                                  39

                                                                                  Holiday home rental

                                                                                  Grand County / Winter Park

                                                                                  3 8 min stay varies

                                                                                  • 3 bedrooms
                                                                                  • sleeps 8
                                                                                  • min stay varies
                                                                                  • Child friendly

                                                                                  from £178 / night

                                                                                  £1,242 / week

                                                                                  Enquire View

                                                                                  from £178 / night

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