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Winter Park Area Vacation Rentals (899)

  • 1 - 50 of 899
Additional fees apply. Taxes may be added.
    Condo #512724vb
    • 1 BR
    • 1 BA
    • Sleeps 4
    75

    Instant confirmation

    Your booking request will be confirmed immediately.

      Condo #475530vb
      • 3 BR
      • 2 BA
      • Sleeps 8
      35

      Confirmation within 24 hours

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

        House #514160vb
        • 5 BR
        • 3 BA
        • 1 HF BA
        • Sleeps 20
        44

        Confirmation within 24 hours

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

          House #364546
          • 4 BR
          • 3 BA
          • 1 HF BA
          • Sleeps 12
          45

          Confirmation within 24 hours

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

            House #726292vb
            • 2 BR
            • 2 BA
            • Sleeps 8
            32

            Instant confirmation

            Your booking request will be confirmed immediately.

              House #450578vb
              • 5 BR
              • 3 BA
              • Sleeps 19
              34

              Confirmation within 24 hours

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

                Condo #797205vb
                • 2 BR
                • 2 BA
                • Sleeps 10
                8

                Confirmation within 24 hours

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

                  House #765124vb
                  • 4 BR
                  • 4 BA
                  • Sleeps 8
                  18

                  Instant confirmation

                  Your booking request will be confirmed immediately.

                    Condo #40955vb
                    • 2 BR
                    • 2 BA
                    • Sleeps 6
                    12

                    Confirmation within 24 hours

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

                      Condo #3707913
                      • 3 BR
                      • 4 BA
                      • Sleeps 12
                      40

                      Confirmation within 24 hours

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

                        House #714254vb
                        • 6 BR
                        • 4 BA
                        • Sleeps 24
                        7

                        Confirmation within 24 hours

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

                          House #3634714
                          • 4 BR
                          • 3 BA
                          • 2 HF BA
                          • Sleeps 20
                          16

                          Confirmation within 24 hours

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

                            Condo #252429vb
                            • 2 BR
                            • 2 BA
                            • Sleeps 8
                            34

                            Confirmation within 24 hours

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

                              House #973869
                              • 6 BR
                              • 4 BA
                              • Sleeps 30
                              27

                              Confirmation within 24 hours

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

                                Condo #3947427
                                • 5 BR
                                • 4 BA
                                • 1 HF BA
                                • Sleeps 18
                                17

                                Confirmation within 24 hours

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

                                  House #860363vb
                                  • 7 BR
                                  • 5 BA
                                  • 1 HF BA
                                  • Sleeps 24
                                  4

                                  Confirmation within 24 hours

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

                                    House #561533vb
                                    • 6 BR
                                    • 3 BA
                                    • 1 HF BA
                                    • Sleeps 24
                                    16

                                    Confirmation within 24 hours

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

                                      Townhome #884461vb
                                      • 4 BR
                                      • 4 BA
                                      • 1 HF BA
                                      • Sleeps 14
                                      6

                                      Instant confirmation

                                      Your booking request will be confirmed immediately.

                                        House #233055
                                        • 6 BR
                                        • 6 BA
                                        • 1 HF BA
                                        • Sleeps 16
                                        35

                                        Confirmation within 24 hours

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

                                          Townhome #776816vb
                                          • 3 BR
                                          • 3 BA
                                          • Sleeps 8
                                          7

                                          Confirmation within 24 hours

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

                                            Townhome #657875vb
                                            • 4 BR
                                            • 3 BA
                                            • 1 HF BA
                                            • Sleeps 13
                                            15

                                            Confirmation within 24 hours

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

                                              Townhome #384604vb
                                              • 3 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 8
                                              22

                                              Confirmation within 24 hours

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

                                                House #152394
                                                • 4 BR
                                                • 3 BA
                                                • Sleeps 20
                                                24

                                                Confirmation within 24 hours

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

                                                  House #710667vb
                                                  • 3 BR
                                                  • 3 BA
                                                  • 1 HF BA
                                                  • Sleeps 10
                                                  12

                                                  Instant confirmation

                                                  Your booking request will be confirmed immediately.

                                                    Townhome #107714vb
                                                    • 4 BR
                                                    • 3 BA
                                                    • 1 HF BA
                                                    • Sleeps 12
                                                    44

                                                    Confirmation within 24 hours

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

                                                      House #714264vb
                                                      • 6 BR
                                                      • 3 BA
                                                      • 1 HF BA
                                                      • Sleeps 24
                                                      7

                                                      Confirmation within 24 hours

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

                                                        House #822974vb
                                                        • 3 BR
                                                        • 3 BA
                                                        • 1 HF BA
                                                        • Sleeps 8
                                                        4

                                                        Instant confirmation

                                                        Your booking request will be confirmed immediately.

                                                          House #3015261
                                                          • 4 BR
                                                          • 4 BA
                                                          • Sleeps 12
                                                          26

                                                          Confirmation within 24 hours

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

                                                            Townhome #47475vb
                                                            • 3 BR
                                                            • 3 BA
                                                            • 1 HF BA
                                                            • Sleeps 8
                                                            37

                                                            Confirmation within 24 hours

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

                                                              House #876626vb
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              4

                                                              Instant confirmation

                                                              Your booking request will be confirmed immediately.

                                                                House #570328vb
                                                                • 9 BR
                                                                • 8 BA
                                                                • Sleeps 25
                                                                3

                                                                Confirmation within 24 hours

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

                                                                  House #961890
                                                                  • 4 BR
                                                                  • 4 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 14
                                                                  29

                                                                  Confirmation within 24 hours

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

                                                                    Condo #308388vb
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    32

                                                                    Confirmation within 24 hours

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

                                                                      House #222565vb
                                                                      • 4 BR
                                                                      • 4 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 22
                                                                      31

                                                                      Confirmation within 24 hours

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

                                                                        House #820400vb
                                                                        • 5 BR
                                                                        • 3 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 14
                                                                        2 Reviews

                                                                        Instant confirmation

                                                                        Your booking request will be confirmed immediately.

                                                                          Condo #3886685
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                            Condo #234948
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            17
                                                                              Condo #287440vb
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                                Townhome #3887069
                                                                                • 3 BR
                                                                                • 3 BA
                                                                                • Sleeps 10
                                                                                  Cabin #58373vb
                                                                                  • 5 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 18
                                                                                  4

                                                                                  Confirmation within 24 hours

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

                                                                                    Townhome #735501vb
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    7

                                                                                    Confirmation within 24 hours

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

                                                                                      Cabin #3948037
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 10
                                                                                      14

                                                                                      Confirmation within 24 hours

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

                                                                                        Condo #390156vb
                                                                                        • Studio
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        7

                                                                                        Confirmation within 24 hours

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

                                                                                          Condo #781992vb
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          23

                                                                                          Instant confirmation

                                                                                          Your booking request will be confirmed immediately.

                                                                                            Studio #649556vb
                                                                                            • Studio
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            33

                                                                                            Confirmation within 24 hours

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

                                                                                              Condo #481720vb
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              59

                                                                                              Confirmation within 24 hours

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

                                                                                                Condo #3672497
                                                                                                • Studio
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                28

                                                                                                Confirmation within 24 hours

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

                                                                                                  Townhome #100296vb
                                                                                                  • 3 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 8
                                                                                                  41

                                                                                                  Confirmation within 24 hours

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

                                                                                                    Condo #321055vb
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    39

                                                                                                    Confirmation within 24 hours

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

                                                                                                    • 1 - 50 of 899