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Vacation Rentals in Winter Park, Florida (1,310)

  • 1 - 50 of 1,310
Additional fees apply. Taxes may be added.
    • 2 BR
    • 1 BA
    • Sleeps 3
    House #709825vb
      • 2 BR
      • 2 BA
      • Sleeps 4
      Cottage #669117vb
        • 1 BR
        • 1 BA
        • 1 HF BA
        • Sleeps 2
        Bungalow #444585vb
          • 3 BR
          • 2 BA
          • 1 HF BA
          • Sleeps 8
          House #367326vb
            • 2 BR
            • 1 BA
            • Sleeps 5
            Cottage #919138vb
              • 4 BR
              • 3 BA
              • 1 HF BA
              • Sleeps 8
              House #885924vb
                • 4 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 8
                House #3670851
                  • 3 BR
                  • 3 BA
                  • Sleeps 8
                  House #901305vb
                    • 1 BR
                    • 1 BA
                    • Sleeps 2
                    Studio #493118vb
                      • 3 BR
                      • 3 BA
                      • Sleeps 10
                      House #981770
                        • 3 BR
                        • 3 BA
                        • Sleeps 10
                        House #943873
                          • 3 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 6
                          House #823160vb
                            • 2 BR
                            • 2 BA
                            • Sleeps 5
                            Bungalow #322808vb
                              • 1 BR
                              • 1 BA
                              • Sleeps 2
                              Apartment #683231vb
                                • 3 BR
                                • 2 BA
                                • Sleeps 9
                                House #929474
                                  • 3 BR
                                  • 3 BA
                                  • 1 HF BA
                                  • Sleeps 9
                                  House #929471
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Bungalow #780146vb
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 4
                                      House #338205vb
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 6
                                        House #243102
                                          • 4 BR
                                          • 2 BA
                                          • Sleeps 10
                                          House #3023348
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 4
                                            House #450575vb
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 2
                                              Studio #4245895
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 5
                                                House #952054vb
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Condo #724660vb
                                                    • 3 BR
                                                    • 1 BA
                                                    • Sleeps 7
                                                    House #3166620
                                                      • 3 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 6
                                                      House #4303470
                                                        • 4 BR
                                                        • 4 BA
                                                        • Sleeps 8
                                                        Villa #305144vb
                                                          • 3 BR
                                                          • 2 BA
                                                          • 2 HF BA
                                                          • Sleeps 8
                                                          House #3023034
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Apartment #4351693
                                                              • 4 BR
                                                              • 2 BA
                                                              • Sleeps 8
                                                              House #319653vb
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                Townhome #905084vb
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  House #514103vb
                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • Sleeps 10
                                                                    House #787925vb
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 6
                                                                      Townhome #3763171
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 5
                                                                        Bungalow #367651vb
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          House #802507vb
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 3
                                                                            Cottage #490078vb
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 5
                                                                              House #3697726
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                House #4040125
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  Studio #869623vb
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    House #930478vb
                                                                                      • 6 BR
                                                                                      • 5 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 15
                                                                                      Villa #393643vb
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 5
                                                                                        Bungalow #4236191
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                          Cottage #769712vb
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 9
                                                                                            House #762584vb
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              House #907712vb
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                House #157424vb
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Cottage #869318vb
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    House #4292880
                                                                                                    • 1 - 50 of 1,310