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Additional fees apply. Taxes may be added.
    Excellent! 4.6/5
    (13 reviews)
    avg/night
    House #450575vb
    • 2 BR
    • 2 BA
    • Sleeps 4
    13
    Viewed 6 times in the last 48 hours

    Confirmation within 24 hours

    Your booking request will be confirmed or denied within 24 hours.

      avg/night
      Bungalow #780146vb
      • 2 BR
      • 1 BA
      • Sleeps 4
      4
      Viewed 12 times in the last 48 hours

      Confirmation within 24 hours

      Your booking request will be confirmed or denied within 24 hours.

        Bungalow #444585vb
        • 1 BR
        • 1 BA
        • 1 HF BA
        • Sleeps 2
        15

        Confirmation within 24 hours

        Your booking request will be confirmed or denied within 24 hours.

          Wonderful! 4.8/5
          (53 reviews)
          avg/night
          House #981770
          • 3 BR
          • 3 BA
          • Sleeps 10
          53
          Viewed 15 times in the last 48 hours

          Confirmation within 24 hours

          Your booking request will be confirmed or denied within 24 hours.

            Excellent! 4.5/5
            (19 reviews)
            avg/night
            Bungalow #3993910
            • 2 BR
            • 1 BA
            • Sleeps 3
            19
            Viewed 9 times in the last 48 hours

            Confirmation within 24 hours

            Your booking request will be confirmed or denied within 24 hours.

              Bungalow #322808vb
              • 2 BR
              • 2 BA
              • Sleeps 5
              24

              Confirmation within 24 hours

              Your booking request will be confirmed or denied within 24 hours.

                Cottage #919138vb
                • 2 BR
                • 1 BA
                • Sleeps 5
                2

                Confirmation within 24 hours

                Your booking request will be confirmed or denied within 24 hours.

                  Exceptional! 5/5
                  (6 reviews)
                  avg/night
                  House #885924vb
                  • 4 BR
                  • 3 BA
                  • 1 HF BA
                  • Sleeps 8
                  6
                  Viewed 5 times in the last 48 hours

                  Confirmation within 24 hours

                  Your booking request will be confirmed or denied within 24 hours.

                    Apartment #683231vb
                    • 1 BR
                    • 1 BA
                    • Sleeps 2
                    7

                    Confirmation within 24 hours

                    Your booking request will be confirmed or denied within 24 hours.

                      Exceptional! 5/5
                      (10 reviews)
                      avg/night
                      House #823160vb
                      • 3 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 6
                      10
                      Viewed 13 times in the last 48 hours

                      Confirmation within 24 hours

                      Your booking request will be confirmed or denied within 24 hours.

                        Excellent! 4.6/5
                        (31 reviews)
                        avg/night
                        House #929474
                        • 3 BR
                        • 2 BA
                        • Sleeps 9
                        31
                        Viewed 63 times in the last 48 hours

                        Confirmation within 24 hours

                        Your booking request will be confirmed or denied within 24 hours.

                          House #1069947vb
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          Viewed 5 times in the last 48 hours

                          Confirmation within 24 hours

                          Your booking request will be confirmed or denied within 24 hours.

                            Wonderful! 4.8/5
                            (30 reviews)
                            avg/night
                            House #929471
                            • 3 BR
                            • 3 BA
                            • 1 HF BA
                            • Sleeps 9
                            30
                            Viewed 20 times in the last 48 hours

                            Confirmation within 24 hours

                            Your booking request will be confirmed or denied within 24 hours.

                              House #1027239vb
                              • 2 BR
                              • 2 BA
                              • Sleeps 4

                              Confirmation within 24 hours

                              Your booking request will be confirmed or denied within 24 hours.

                                Wonderful! 4.8/5
                                (21 reviews)
                                avg/night
                                House #3023348
                                • 4 BR
                                • 2 BA
                                • Sleeps 10
                                21
                                Viewed 15 times in the last 48 hours

                                Confirmation within 24 hours

                                Your booking request will be confirmed or denied within 24 hours.

                                  Studio #493118vb
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 2
                                  28

                                  Confirmation within 24 hours

                                  Your booking request will be confirmed or denied within 24 hours.

                                    Exceptional! 5/5
                                    (20 reviews)
                                    avg/night
                                    Cottage #669117vb
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 4
                                    20
                                    Viewed 9 times in the last 48 hours

                                    Confirmation within 24 hours

                                    Your booking request will be confirmed or denied within 24 hours.

                                      avg/night
                                      House #990123vb
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 8
                                      4
                                      Viewed 5 times in the last 48 hours

                                      Instant confirmation

                                      Your booking request will be confirmed immediately.

                                        Wonderful! 4.8/5
                                        (4 reviews)
                                        avg/night
                                        House #901305vb
                                        • 3 BR
                                        • 3 BA
                                        • Sleeps 8
                                        4
                                        Viewed 7 times in the last 48 hours

                                        Confirmation within 24 hours

                                        Your booking request will be confirmed or denied within 24 hours.

                                          Wonderful! 4.9/5
                                          (11 reviews)
                                          avg/night
                                          House #243102
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 6
                                          11

                                          Instant confirmation

                                          Your booking request will be confirmed immediately.

                                            avg/night
                                            House #4303470
                                            • 3 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 6
                                            6
                                            Viewed 8 times in the last 48 hours

                                            Instant confirmation

                                            Your booking request will be confirmed immediately.

                                              Wonderful! 4.8/5
                                              (6 reviews)
                                              avg/night
                                              House #3166620
                                              • 3 BR
                                              • 1 BA
                                              • Sleeps 7
                                              6

                                              Confirmation within 24 hours

                                              Your booking request will be confirmed or denied within 24 hours.

                                                House #3023034
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 8
                                                12

                                                Instant confirmation

                                                Your booking request will be confirmed immediately.

                                                  House #1030436vb
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 7
                                                  1

                                                  Instant confirmation

                                                  Your booking request will be confirmed immediately.

                                                    Excellent! 4.7/5
                                                    (7 reviews)
                                                    $76
                                                    avg/night
                                                    Studio #4245895
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2
                                                    7
                                                    Viewed 8 times in the last 48 hours

                                                    Instant confirmation

                                                    Your booking request will be confirmed immediately.

                                                      avg/night
                                                      Apartment #1069352vb
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      Viewed 6 times in the last 48 hours

                                                      Instant confirmation

                                                      Your booking request will be confirmed immediately.

                                                        avg/night
                                                        House #1097929vb
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Viewed 12 times in the last 48 hours

                                                        Instant confirmation

                                                        Your booking request will be confirmed immediately.

                                                          Apartment #1046545vb
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 6

                                                          Instant confirmation

                                                          Your booking request will be confirmed immediately.

                                                            avg/night
                                                            Guest House #1033184vb
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Viewed 6 times in the last 48 hours

                                                            Confirmation within 24 hours

                                                            Your booking request will be confirmed or denied within 24 hours.

                                                              House #694235vb
                                                              • 4 BR
                                                              • 2 BA
                                                              • Sleeps 10

                                                              Instant confirmation

                                                              Your booking request will be confirmed immediately.

                                                                House #1114835vb
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 2

                                                                Confirmation within 24 hours

                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                  House #1091039vb
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 2

                                                                  Confirmation within 24 hours

                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                    House #4628707
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 2

                                                                    Confirmation within 24 hours

                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                      House #1129469vb
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 6

                                                                      Confirmation within 24 hours

                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                        House #1060352vb
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 4

                                                                        Confirmation within 24 hours

                                                                        Your booking request will be confirmed or denied within 24 hours.

                                                                          Multiple rentals Bed And Breakfast #4621188
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2

                                                                          Instant confirmation

                                                                          Your booking request will be confirmed immediately.

                                                                            Condo #1127343vb
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4

                                                                            Instant confirmation

                                                                            Your booking request will be confirmed immediately.

                                                                              House #1114504vb
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              Viewed 5 times in the last 48 hours

                                                                              Confirmation within 24 hours

                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                avg/night
                                                                                Condo #4626354
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 6
                                                                                Viewed 5 times in the last 48 hours

                                                                                Confirmation within 24 hours

                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                  House #1114391vb
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  Viewed 10 times in the last 48 hours

                                                                                  Confirmation within 24 hours

                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                    Condo #724660vb
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    2

                                                                                    Confirmation within 24 hours

                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                      House #1114809vb
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 2

                                                                                      Confirmation within 24 hours

                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                        House #1056448vb
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Viewed 18 times in the last 48 hours

                                                                                        Instant confirmation

                                                                                        Your booking request will be confirmed immediately.

                                                                                          House #319653vb
                                                                                          • 4 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 8
                                                                                          10

                                                                                          Confirmation within 24 hours

                                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                                            Exceptional! 5/5
                                                                                            (9 reviews)
                                                                                            avg/night
                                                                                            House #338205vb
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            9
                                                                                            Viewed 9 times in the last 48 hours

                                                                                            Confirmation within 24 hours

                                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                                              House #1136926vb
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 2

                                                                                              Confirmation within 24 hours

                                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                                Excellent! 4.7/5
                                                                                                (135 reviews)
                                                                                                avg/night
                                                                                                Hotel #3905183
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                135
                                                                                                Viewed 183 times in the last 48 hours

                                                                                                Instant confirmation

                                                                                                Your booking request will be confirmed immediately.

                                                                                                  Wonderful! 4.8/5
                                                                                                  (9 reviews)
                                                                                                  avg/night
                                                                                                  House #792993vb
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  9
                                                                                                  Viewed 43 times in the last 48 hours

                                                                                                  Confirmation within 24 hours

                                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                                    Excellent! 4.6/5
                                                                                                    (41 reviews)
                                                                                                    avg/night
                                                                                                    Condo #4141115
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 10
                                                                                                    41
                                                                                                    Viewed 146 times in the last 48 hours

                                                                                                    Instant confirmation

                                                                                                    Your booking request will be confirmed immediately.

                                                                                                      Excellent! 4.6/5
                                                                                                      (28 reviews)
                                                                                                      avg/night
                                                                                                      Condo #746426vb
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 8
                                                                                                      28
                                                                                                      Viewed 73 times in the last 48 hours

                                                                                                      Confirmation within 24 hours

                                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                                      • 1 - 50 of 300+

                                                                                                      Winter Park Vacation Rentals (300+)