Holiday Houses in Winter Park

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3,240 Holiday homes

    27

    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 £68 / night

    £451 / week

    Book View

    Responds fast!
    avg. 2 hours 33 minutes

    from £68 / night

      37

      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 £68 / night

      £450 / week

      Book View

      Responds fast!
      avg. 2 hours 33 minutes

      from £68 / night

      (2) Excellent 

        27

        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 £73 / night

        £461 / week

        Book View

        Responds fast!
        avg. 2 hours 33 minutes

        from £73 / night

          35

          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 £405 / night

          £2,203 / week

          Book View

          from £405 / night

          (2) Excellent 

            13

            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 £117 / night

            £820 / week

            Book View

            Responds fast!
            avg. 1 hour 25 minutes

            from £117 / night

            (3) Very Good 

              22

              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 £72 / night

              £478 / week

              Book View

              Responds fast!
              avg. 2 hours 33 minutes

              from £72 / night

                11

                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 £95 / night

                £542 / week

                Book View

                from £95 / night

                  10

                  Central Florida / Winter Park

                  2 6 2 nights min

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

                  from £117 / night

                  £820 / week

                  Book View

                  from £117 / night

                  (2) Average 

                    20

                    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 £72 / night

                    £460 / week

                    Book View

                    Responds fast!
                    avg. 2 hours 33 minutes

                    from £72 / night

                      35

                      Central Florida / Winter Park

                      4 8 min stay varies

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

                      from £536 / night

                      £3,598 - £5,322 / week

                      Book View

                      from £536 / night

                        7

                        Central Florida / Winter Park

                        1 4 7 nights min

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

                        from £55 / night

                        £386 / week

                        Book View

                        from £55 / night

                          29

                          Central Florida / Winter Park

                          Studio 4 2 nights min

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

                          from £79 / night

                          £518 / week

                          Book View

                          from £79 / night

                            14

                            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 £81 / night

                            £524 / week

                            Book View

                            Responds fast!
                            avg. 3 hours 44 minutes

                            from £81 / night

                            Great rentals within 20 miles that match your search

                            Distance approx 29.36 km from Winter Park Show on Map

                              5

                              Central Florida / Orlando

                              2 6 7 nights min

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

                              from £230 / night

                              £1,608 / week

                              Book View

                              from £230 / night

                              Distance approx 31.37 km from Winter Park Show on Map

                                16

                                Central Florida / Kissimmee

                                8 16 7 nights min

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

                                from £406 / night

                                £2,839 / week

                                Book View

                                from £406 / night

                                Distance approx 20.86 km from Winter Park Show on Map

                                  30

                                  Central Florida / Orlando

                                  3 8 min stay varies

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

                                  from £143 / night

                                  £999 - £1,754 / week

                                  Book View

                                  from £143 / night

                                  Distance approx 28.21 km from Winter Park Show on Map

                                    11

                                    Florida / Buena Ventura Lakes

                                    4 10 min stay varies

                                    • 4 bedrooms
                                    • sleeps 10
                                    • min stay varies
                                    • Beach / lakeside relaxation
                                    • Swimming pool
                                    • Child friendly

                                    from £129 / night

                                    £899 / week

                                    Book View

                                    from £129 / night

                                    Distance approx 8.33 km from Winter Park Show on Map

                                      15

                                      Central Florida / Orlando

                                      2 8 7 nights min

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

                                      from £179 / night

                                      £1,251 / week

                                      Book View

                                      Responds fast!
                                      avg. 3 hours 58 minutes

                                      from £179 / night

                                      Distance approx 27.05 km from Winter Park Show on Map

                                        23

                                        Central Florida / Orlando

                                        2 6 7 nights min

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

                                        from £152 / night

                                        £1,058 - £1,418 / week

                                        Book View

                                        Responds fast!
                                        avg. 2 hours 50 minutes

                                        from £152 / night

                                        Distance approx 31.55 km from Winter Park Show on Map

                                          30

                                          Central Florida / Kissimmee

                                          2 6 4 nights min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 4 nights min
                                          • Nearest beach 65 km
                                          • Swimming pool
                                          • Child friendly

                                          from £77 / night

                                          £505 / week

                                          Book View

                                          Responds fast!
                                          avg. 34 minutes

                                          from £77 / night

                                          Distance approx 31.55 km from Winter Park Show on Map

                                            11

                                            Central Florida / Celebration

                                            4 10 min stay varies

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

                                            from £212 / night

                                            £972 - £1,861 / week

                                            Book View

                                            Responds fast!
                                            avg. 2 hours 19 minutes

                                            from £212 / night

                                            Distance approx 31.74 km from Winter Park Show on Map

                                            (1) Excellent 

                                              22

                                              Central Florida / Kissimmee

                                              2 6 1 night min

                                              • 2 bedrooms
                                              • sleeps 6
                                              • 1 night min
                                              • Swimming pool
                                              • Child friendly
                                              • Air conditioning

                                              from £104 / night

                                              £725 / week

                                              Book View

                                              Responds fast!
                                              avg. 21 minutes

                                              from £104 / night

                                              Distance approx 22.18 km from Winter Park Show on Map

                                                6

                                                Central Florida / Orlando

                                                3 12 7 nights min

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

                                                from £245 / night

                                                £1,711 / week

                                                Book View

                                                from £245 / night

                                                Distance approx 31.93 km from Winter Park Show on Map

                                                  15

                                                  Central Florida / Celebration

                                                  2 8 min stay varies

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

                                                  from £239 / night

                                                  £1,670 / week

                                                  Book View

                                                  from £239 / night

                                                  Distance approx 19.25 km from Winter Park Show on Map

                                                  (3) Excellent 

                                                    16

                                                    Central Florida / Orlando

                                                    2 6 1 night min

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • 1 night min
                                                    • Swimming pool
                                                    • Child friendly
                                                    • Car not necessary

                                                    from £141 / night

                                                    £983 / week

                                                    Book View

                                                    from £141 / night

                                                    Distance approx 29.36 km from Winter Park Show on Map

                                                      5

                                                      Central Florida / Orlando

                                                      2 4 7 nights min

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

                                                      from £110 / night

                                                      £766 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 35 minutes

                                                      from £110 / night

                                                      Distance approx 31.82 km from Winter Park Show on Map

                                                      (3) Very Good 

                                                        24

                                                        Central Florida / Kissimmee

                                                        2 8 7 nights min

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

                                                        from £168 / night

                                                        £1,171 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 2 hours 16 minutes

                                                        from £168 / night

                                                        Distance approx 22.22 km from Winter Park Show on Map

                                                          21

                                                          Central Florida / Orlando

                                                          1 4 7 nights min

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

                                                          from £82 / night

                                                          £574 - £807 / week

                                                          Book View

                                                          from £82 / night

                                                          Distance approx 23.95 km from Winter Park Show on Map

                                                          (1)  

                                                            5

                                                            Central Florida / Orlando

                                                            2 6 7 nights min

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

                                                            from £187 / night

                                                            £1,306 / week

                                                            Book View

                                                            from £187 / night

                                                            Distance approx 31.55 km from Winter Park Show on Map

                                                              11

                                                              Central Florida / Celebration

                                                              4 10 min stay varies

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

                                                              from £212 / night

                                                              £972 - £1,861 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 2 hours 19 minutes

                                                              from £212 / night

                                                              Distance approx 20.68 km from Winter Park Show on Map

                                                                44

                                                                Florida / Pine Castle

                                                                3 6 2 nights min

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

                                                                from £153 / night

                                                                £1,072 - £1,840 / week

                                                                Book View

                                                                from £153 / night

                                                                Distance approx 31.8 km from Winter Park Show on Map

                                                                (29) Very Good 

                                                                  39

                                                                  Kissimmee / Compass Bay

                                                                  3 6 4 nights min

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

                                                                  from £89 / night

                                                                  £629 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 1 hour 41 minutes

                                                                  from £89 / night

                                                                  Distance approx 26.9 km from Winter Park Show on Map

                                                                    15

                                                                    Florida / Buena Ventura Lakes

                                                                    4 8 min stay varies

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

                                                                    from £116 / night

                                                                    £812 / week

                                                                    Book View

                                                                    from £116 / night

                                                                    Distance approx 24.46 km from Winter Park Show on Map

                                                                    (1) Excellent 

                                                                      6

                                                                      Central Florida / Orlando

                                                                      2 8 7 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 8
                                                                      • 7 nights min
                                                                      • Child friendly
                                                                      • Ask about pets

                                                                      from £206 / night

                                                                      £1,439 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 3 hours 20 minutes

                                                                      from £206 / night

                                                                      Distance approx 26.1 km from Winter Park Show on Map

                                                                      (1) Excellent 

                                                                        19

                                                                        Central Florida / Orlando

                                                                        2 6 3 nights min

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

                                                                        from £188 / night

                                                                        £1,316 / week

                                                                        Book View

                                                                        from £188 / night

                                                                        Distance approx 31.84 km from Winter Park Show on Map

                                                                          18

                                                                          Central Florida / Orlando

                                                                          1 4 3 nights min

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

                                                                          from £122 / night

                                                                          £850 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 2 hours 10 minutes

                                                                          from £122 / night

                                                                          Distance approx 7.82 km from Winter Park Show on Map

                                                                            4

                                                                            Central Florida / Orlando

                                                                            1 4 4 nights min

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

                                                                            from £266 / night

                                                                            £1,857 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 1 hour 46 minutes

                                                                            from £266 / night

                                                                            Distance approx 22.53 km from Winter Park Show on Map

                                                                            (1) Excellent 

                                                                              10

                                                                              Central Florida / Orlando

                                                                              3 12 6 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 12
                                                                              • 6 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Swimming pool
                                                                              • Child friendly

                                                                              from £207 / night

                                                                              £1,354 / week

                                                                              Book View

                                                                              from £207 / night

                                                                              Distance approx 31.81 km from Winter Park Show on Map

                                                                              (1) Very Good 

                                                                                4

                                                                                Central Florida / Orlando

                                                                                2 8 7 nights min

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

                                                                                from £257 / night

                                                                                £1,799 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 35 minutes

                                                                                from £257 / night

                                                                                Distance approx 29.96 km from Winter Park Show on Map

                                                                                  11

                                                                                  Central Florida / Orlando

                                                                                  2 6 7 nights min

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

                                                                                  from £155 / night

                                                                                  £1,079 / week

                                                                                  Book View

                                                                                  from £155 / night