Houses in Winter Park and Villas – Holiday Lettings - Holiday Rentals Winter Park

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3,183 Holiday homes

    37

    Holiday home with golf nearby in Winter Park

    Central Florida / Winter Park

    1 2 2 nights min

    • 1 bedroom
    • sleeps 2
    • 2 nights min
    • Nearest beach 60 km
    • Child friendly
    • Air conditioning

    from £67 / night

    £442 / week

    Book View

    Responds fast!
    avg. 2 hours 33 minutes

    from £67 / night

      27

      Holiday home in Winter Park

      Central Florida / Winter Park

      1 2 2 nights min

      • 1 bedroom
      • sleeps 2
      • 2 nights min
      • Nearest beach 100 km
      • Child friendly
      • Air conditioning

      from £67 / night

      £442 / week

      Book View

      Responds fast!
      avg. 2 hours 33 minutes

      from £67 / night

      (2) Excellent 

        27

        Holiday home letting

        Central Florida / Winter Park

        1 2 3 nights min

        • 1 bedroom
        • sleeps 2
        • 3 nights min
        • Nearest beach 100 km
        • Suitable for children age 5+
        • Air conditioning

        from £71 / night

        £452 / week

        Book View

        Responds fast!
        avg. 2 hours 33 minutes

        from £71 / night

        (2) Excellent 

          13

          Holiday home in Winter Park

          Central Florida / Winter Park

          2 5 7 nights min

          • 2 bedrooms
          • sleeps 5
          • 7 nights min
          • Nearest beach 88 km
          • Child friendly
          • Air conditioning

          from £126 / night

          £882 / week

          Book View

          Responds fast!
          avg. 1 hour 25 minutes

          from £126 / night

            35

            Holiday home rental

            Central Florida / Winter Park

            3 6 3 nights min

            • 3 bedrooms
            • sleeps 6
            • 3 nights min
            • Beach / lakeside relaxation
            • Nearest beach 81 km
            • Child friendly

            from £398 / night

            £2,164 / week

            Book View

            from £398 / night

              10

              Townhouse rental in Winter Park

              Central Florida / Winter Park

              2 6 2 nights min

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

              from £116 / night

              £806 / week

              Book View

              from £116 / night

              (3) Very Good 

                22

                Winter Park holiday home rental

                Central Florida / Winter Park

                1 2 2 nights min

                • 1 bedroom
                • sleeps 2
                • 2 nights min
                • Nearest beach 100 km
                • Child friendly
                • Air conditioning

                from £71 / night

                £470 / week

                Book View

                Responds fast!
                avg. 2 hours 33 minutes

                from £71 / night

                  11

                  Holiday home letting

                  Central Florida / Winter Park

                  3 5 1 night min

                  • 3 bedrooms
                  • sleeps 5
                  • 1 night min
                  • Nearest beach 30 km
                  • Child friendly
                  • Air conditioning

                  from £93 / night

                  £532 / week

                  Book View

                  from £93 / night

                  (2) Average 

                    20

                    Winter Park holiday home rental

                    Central Florida / Winter Park

                    1 2 3 nights min

                    • 1 bedroom
                    • sleeps 2
                    • 3 nights min
                    • Nearest beach 100 km
                    • Child friendly
                    • Air conditioning

                    from £71 / night

                    £452 / week

                    Book View

                    Responds fast!
                    avg. 2 hours 33 minutes

                    from £71 / night

                      7

                      Holiday hotel apartment rental

                      Central Florida / Winter Park

                      1 4 7 nights min

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

                      from £54 / night

                      £377 / week

                      Book View

                      from £54 / night

                        29

                        Holiday studio in Winter Park

                        Central Florida / Winter Park

                        Studio 4 2 nights min

                        • Studio
                        • sleeps 4
                        • 2 nights min
                        • Child friendly
                        • Pet friendly

                        from £77 / night

                        £510 / week

                        Book View

                        from £77 / night

                          35

                          Winter Park holiday villa rental

                          Central Florida / Winter Park

                          4 8 min stay varies

                          • 4 bedrooms
                          • sleeps 8
                          • min stay varies
                          • Child friendly
                          • Air conditioning
                          • Private garden

                          from £525 / night

                          £3,522 - £5,211 / week

                          Book View

                          from £525 / night

                            14

                            Winter Park holiday home rental

                            Central Florida / Winter Park

                            1 5 1 night min

                            • 1 bedroom
                            • sleeps 5
                            • 1 night min
                            • Nearest beach 80 km
                            • Child friendly
                            • Air conditioning

                            from £79 / night

                            £514 / week

                            Book View

                            Responds fast!
                            avg. 3 hours 44 minutes

                            from £79 / night

                            Great rentals within 20 miles that match your search

                            Distance approx 18.26 miles from Winter Park Show on Map

                              10

                              Holiday villa in Old Town

                              Florida / Old Town

                              2 8 7 nights min

                              • 2 bedrooms
                              • sleeps 8
                              • 7 nights min
                              • Swimming pool
                              • Child friendly
                              • Air conditioning

                              from £176 / night

                              £1,227 / week

                              Book View

                              Responds fast!
                              avg. 42 minutes

                              from £176 / night

                              Distance approx 15.28 miles from Winter Park Show on Map

                                7

                                Home rental in Orlando with shared pool

                                Central Florida / Orlando

                                2 6 7 nights min

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

                                from £252 / night

                                £1,762 / week

                                Book View

                                Responds fast!
                                avg. 45 minutes

                                from £252 / night

                                Distance approx 19.26 miles from Winter Park Show on Map

                                  32

                                  Holiday townhouse in Kissimmee

                                  Central Florida / Kissimmee

                                  4 8 3 nights min

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

                                  from £140 / night

                                  £981 / week

                                  Book View

                                  from £140 / night

                                  Distance approx 19.15 miles from Winter Park Show on Map

                                    45

                                    Holiday townhouse in Kissimmee

                                    Central Florida / Kissimmee

                                    4 12 2 nights min

                                    • 4 bedrooms
                                    • sleeps 12
                                    • 2 nights min
                                    • Child friendly

                                    from £167 / night

                                    £1,102 / week

                                    Book View

                                    from £167 / night

                                    Distance approx 18.24 miles from Winter Park Show on Map

                                      18

                                      Orlando holiday condo rental

                                      Central Florida / Orlando

                                      2 8 7 nights min

                                      • 2 bedrooms
                                      • sleeps 8
                                      • 7 nights min
                                      • Swimming pool
                                      • Child friendly
                                      • Air conditioning

                                      from £172 / night

                                      £1,203 / week

                                      Book View

                                      from £172 / night

                                      Distance approx 19.78 miles from Winter Park Show on Map

                                        18

                                        Holiday condo with shared pool in Orlando

                                        Central Florida / Orlando

                                        1 4 3 nights min

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

                                        from £119 / night

                                        £833 / week

                                        Book View

                                        Responds fast!
                                        avg. 2 hours 10 minutes

                                        from £119 / night

                                        Distance approx 19.34 miles from Winter Park Show on Map

                                        (7) Average 

                                          9

                                          Kissimmee holiday home rental

                                          Central Florida / Kissimmee

                                          3 6 min stay varies

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

                                          from £75 / night

                                          £525 / week

                                          Book View

                                          Responds fast!
                                          avg. 2 hours 8 minutes

                                          from £75 / night

                                          Distance approx 12.66 miles from Winter Park Show on Map

                                          (1) Excellent 

                                            25

                                            Orlando holiday apartment rental

                                            Central Florida / Orlando

                                            2 4 1 night min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 1 night min
                                            • Nearest beach 79 km
                                            • Swimming pool
                                            • Child friendly

                                            from £123 / night

                                            £858 / week

                                            Book View

                                            Responds fast!
                                            avg. 3 hours 1 minutes

                                            from £123 / night

                                            Distance approx 13.87 miles from Winter Park Show on Map

                                              14

                                              Holiday villa rental

                                              Central Florida / Orlando

                                              3 12 7 nights min

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

                                              from £167 / night

                                              £2,578 / week

                                              Book View

                                              Responds fast!
                                              avg. 1 hour 35 minutes

                                              from £167 / night

                                              Distance approx 12.88 miles from Winter Park Show on Map

                                                64

                                                Orlando holiday apartment rental

                                                Central Florida / Orlando

                                                3 8 2 nights min

                                                • 3 bedrooms
                                                • sleeps 8
                                                • 2 nights min
                                                • Swimming pool
                                                • Child friendly
                                                • Car not necessary

                                                from £466 / night

                                                £2,993 / week

                                                Book View

                                                from £466 / night

                                                Distance approx 13.78 miles from Winter Park Show on Map

                                                  5

                                                  Orlando holiday private room rental

                                                  Central Florida / Orlando

                                                  1 12 7 nights min

                                                  • 1 bedroom
                                                  • sleeps 12
                                                  • 7 nights min
                                                  • Swimming pool
                                                  • Child friendly
                                                  • Air conditioning

                                                  from £158 / night

                                                  £1,102 / week

                                                  Book View

                                                  from £158 / night

                                                  Distance approx 19.86 miles from Winter Park Show on Map

                                                  (10) Excellent 

                                                    25

                                                    Holiday home with shared pool in Kissimmee

                                                    Kissimmee / Lucaya Village

                                                    4 10 3 nights min

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

                                                    from £111 / night

                                                    £855 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 1 hour 43 minutes

                                                    from £111 / night

                                                    Distance approx 19.81 miles from Winter Park Show on Map

                                                    (2) Very Good 

                                                      24

                                                      Villa rental in Kissimmee

                                                      Central Florida / Kissimmee

                                                      6 14 4 nights min

                                                      • 6 bedrooms
                                                      • sleeps 14
                                                      • 4 nights min
                                                      • Nearest beach 97 km
                                                      • Swimming pool
                                                      • Child friendly

                                                      from £172 / night

                                                      £1,603 / week

                                                      Book View

                                                      from £172 / night

                                                      Distance approx 18.24 miles from Winter Park Show on Map

                                                        5

                                                        Holiday villa in Orlando

                                                        Central Florida / Orlando

                                                        2 4 7 nights min

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

                                                        from £107 / night

                                                        £750 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 35 minutes

                                                        from £107 / night

                                                        Distance approx 6.98 miles from Winter Park Show on Map

                                                          21

                                                          Holiday home letting

                                                          Central Florida / Altamonte Springs

                                                          3 5 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 5
                                                          • min stay varies
                                                          • Child friendly
                                                          • Air conditioning
                                                          • Private garden

                                                          from £119 / night

                                                          £705 / week

                                                          Book View

                                                          from £119 / night

                                                          Distance approx 14.97 miles from Winter Park Show on Map

                                                            29

                                                            Holiday home in Orlando

                                                            Central Florida / Orlando

                                                            1 4 7 nights min

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

                                                            from £148 / night

                                                            £1,036 - £1,389 / week

                                                            Book View

                                                            from £148 / night

                                                            Distance approx 13.98 miles from Winter Park Show on Map

                                                              7

                                                              Holiday condo rental

                                                              Central Florida / Orlando

                                                              3 12 7 nights min

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

                                                              from £378 / night

                                                              £2,644 / week

                                                              Book View

                                                              from £378 / night

                                                              Distance approx 12.81 miles from Winter Park Show on Map

                                                              (53) Excellent 

                                                              Certificate of Excellence

                                                                33

                                                                Holiday hotel apartment in Orlando

                                                                Central Florida / Orlando

                                                                3 7 3 nights min

                                                                • 3 bedrooms
                                                                • sleeps 7
                                                                • 3 nights min
                                                                • Ask owner if suitable for children
                                                                • Air conditioning

                                                                Certificate of Excellence

                                                                from £149 / night

                                                                £961 - £1,455 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 3 hours 22 minutes

                                                                from £149 / night

                                                                Distance approx 13.78 miles from Winter Park Show on Map

                                                                  6

                                                                  Holiday villa in Orlando

                                                                  Central Florida / Orlando

                                                                  3 12 7 nights min

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

                                                                  from £240 / night

                                                                  £1,675 / week

                                                                  Book View

                                                                  from £240 / night

                                                                  Distance approx 16.22 miles from Winter Park Show on Map

                                                                    27

                                                                    Holiday villa rental

                                                                    Central Florida / Orlando

                                                                    3 8 7 nights min

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

                                                                    from £243 / night

                                                                    £1,697 / week

                                                                    Book View

                                                                    from £243 / night

                                                                    Distance approx 16.39 miles from Winter Park Show on Map

                                                                      8

                                                                      Villa rental in Orlando with shared pool

                                                                      Central Florida / Orlando

                                                                      2 6 7 nights min

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

                                                                      from £243 / night

                                                                      £1,697 / week

                                                                      Book View

                                                                      from £243 / night

                                                                      Distance approx 16.81 miles from Winter Park Show on Map

                                                                        23

                                                                        Orlando holiday condo rental

                                                                        Central Florida / Orlando

                                                                        2 6 7 nights min

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

                                                                        from £148 / night

                                                                        £1,036 - £1,389 / week

                                                                        Book View

                                                                        from £148 / night

                                                                        Distance approx 13.81 miles from Winter Park Show on Map

                                                                          9

                                                                          Orlando holiday villa rental

                                                                          Orlando / International Drive

                                                                          2 8 7 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 8
                                                                          • 7 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Swimming pool
                                                                          • Child friendly

                                                                          from £137 / night

                                                                          £957 / week

                                                                          Book View

                                                                          from £137 / night

                                                                          Distance approx 6.75 miles from Winter Park Show on Map

                                                                            19

                                                                            Orlando holiday condo rental

                                                                            Central Florida / Orlando

                                                                            2 4 4 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • 4 nights min
                                                                            • Child friendly

                                                                            from £70 / night

                                                                            £488 / week

                                                                            Book View

                                                                            from £70 / night

                                                                            Distance approx 19.49 miles from Winter Park Show on Map

                                                                              16

                                                                              Holiday villa rental

                                                                              Central Florida / Kissimmee

                                                                              8 16 7 nights min

                                                                              • 8 bedrooms
                                                                              • sleeps 16
                                                                              • 7 nights min
                                                                              • Swimming pool
                                                                              • Air conditioning

                                                                              from £401 / night

                                                                              £2,801 / week

                                                                              Book View

                                                                              from £401 / night

                                                                              Distance approx 12.68 miles from Winter Park Show on Map

                                                                                27

                                                                                Apopka holiday home rental

                                                                                Florida / Apopka

                                                                                5 10 2 nights min

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

                                                                                from £264 / night

                                                                                £1,845 / week

                                                                                Book View

                                                                                from £264 / night

                                                                                Distance approx 7.16 miles from Winter Park Show on Map

                                                                                  20

                                                                                  Holiday home in Orlando

                                                                                  Central Florida / Orlando

                                                                                  4 12 30 nights min

                                                                                  • 4 bedrooms
                                                                                  • sleeps 12
                                                                                  • 30 nights min
                                                                                  • Child friendly

                                                                                  from £155 / night

                                                                                  £1,080 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 2 hours 20 minutes

                                                                                  from £155 / night

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