check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Winter Park: Luxury Vacation Rentals (64)

  • 1 - 50 of 64
Additional fees apply. Taxes may be added.
    Wonderful! 4.9/5
    (67 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 8
    Condo #3165138
    67
    Viewed 11 times in the last 48 hours
      Wonderful! 4.9/5
      (64 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 8
      Condo #200486
      64
      Viewed 15 times in the last 48 hours
        • 2 BR
        • 2 BA
        • Sleeps 8
        Condo #4236149
        1
        Viewed 14 times in the last 48 hours
          • 2 BR
          • 2 BA
          • Sleeps 8
          Condo #4236147
          Viewed 5 times in the last 48 hours
            • 2 BR
            • 2 BA
            • Sleeps 8
            Condo #4236148
            1
            Viewed 6 times in the last 48 hours
              • 2 BR
              • 2 BA
              • Sleeps 8
              Condo #4236150
              2
              Viewed 7 times in the last 48 hours
                Wonderful! 4.9/5
                (24 reviews)
                avg/night
                • 4 BR
                • 3 BA
                • 1 HF BA
                • Sleeps 12
                Cabin #3614429
                24
                Viewed 53 times in the last 48 hours
                  • 2 BR
                  • 2 BA
                  • Sleeps 8
                  Condo #4236151
                  Viewed 7 times in the last 48 hours
                    • 3 BR
                    • 3 BA
                    • Sleeps 11
                    Condo #278429vb
                    2
                    Viewed 25 times in the last 48 hours
                      • 3 BR
                      • 3 BA
                      • 1 HF BA
                      • Sleeps 8
                      Townhome #827618vb
                      1
                      Viewed 21 times in the last 48 hours
                        • 3 BR
                        • 3 BA
                        • 1 HF BA
                        • Sleeps 10
                        Townhome #763021vb
                        2
                          avg/night
                          • 3 BR
                          • 3 BA
                          • 1 HF BA
                          • Sleeps 12
                          House #208343vb
                          2
                          Viewed 9 times in the last 48 hours
                            avg/night
                            • 3 BR
                            • 3 BA
                            • Sleeps 8
                            Townhome #223439vb
                            4
                            Viewed 13 times in the last 48 hours
                              • 1 BR
                              • 1 BA
                              • Sleeps 6
                              Condo #4276372
                              1
                              Viewed 14 times in the last 48 hours
                                avg/night
                                • 3 BR
                                • 2 BA
                                • 1 HF BA
                                • Sleeps 9
                                Townhome #374272vb
                                Viewed 7 times in the last 48 hours
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 12
                                  Condo #855763vb
                                  1
                                  Viewed 10 times in the last 48 hours
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 14
                                    Townhome #771851vb
                                    2
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 6
                                      Condo #4276373
                                      Viewed 8 times in the last 48 hours
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 6
                                        Condo #4276369
                                        Viewed 19 times in the last 48 hours
                                          avg/night
                                          • 5 BR
                                          • 4 BA
                                          • Sleeps 16
                                          House #799824vb
                                          1
                                          Viewed 17 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (15 reviews)
                                            avg/night
                                            • 4 BR
                                            • 3 BA
                                            • 1 HF BA
                                            • Sleeps 12
                                            Condo #265704vb
                                            15
                                            Viewed 9 times in the last 48 hours
                                              • 4 BR
                                              • 4 BA
                                              • 1 HF BA
                                              • Sleeps 15
                                              Townhome #740120vb
                                              1
                                                • 1 BR
                                                • 2 BA
                                                • Sleeps 10
                                                Condo #4276366
                                                1
                                                Viewed 6 times in the last 48 hours
                                                  avg/night
                                                  • 4 BR
                                                  • 5 BA
                                                  • Sleeps 14
                                                  House #130651vb
                                                  4
                                                  Viewed 12 times in the last 48 hours
                                                    • 5 BR
                                                    • 5 BA
                                                    • Sleeps 16
                                                    House #777617vb
                                                    1
                                                    Viewed 13 times in the last 48 hours
                                                      • 4 BR
                                                      • 4 BA
                                                      • 1 HF BA
                                                      • Sleeps 12
                                                      Townhome #180083vb
                                                      4
                                                        avg/night
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 11
                                                        Townhome #777614vb
                                                        1
                                                        Viewed 9 times in the last 48 hours
                                                          avg/night
                                                          • 4 BR
                                                          • 4 BA
                                                          • 1 HF BA
                                                          • Sleeps 16
                                                          House #795423vb
                                                          Viewed 8 times in the last 48 hours
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 6
                                                            Condo #4276365
                                                            Viewed 5 times in the last 48 hours
                                                              • 5 BR
                                                              • 4 BA
                                                              • 1 HF BA
                                                              • Sleeps 19
                                                              House #334872vb
                                                              Viewed 11 times in the last 48 hours
                                                                • 5 BR
                                                                • 5 BA
                                                                • 1 HF BA
                                                                • Sleeps 19
                                                                House #777616vb
                                                                Viewed 18 times in the last 48 hours
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  Condo #4276364
                                                                  1
                                                                  Viewed 6 times in the last 48 hours
                                                                    • 4 BR
                                                                    • 4 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 12
                                                                    Townhome #308035vb
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 6
                                                                      Condo #4276371
                                                                      Viewed 16 times in the last 48 hours
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        Townhome #201881vb
                                                                        1
                                                                        Viewed 15 times in the last 48 hours
                                                                          • 3 BR
                                                                          • 3 BA
                                                                          • Sleeps 10
                                                                          Condo #331894vb
                                                                          Viewed 6 times in the last 48 hours
                                                                            • 7 BR
                                                                            • 7 BA
                                                                            • Sleeps 30
                                                                            House #326572vb
                                                                            1
                                                                            Viewed 29 times in the last 48 hours
                                                                              • 3 BR
                                                                              • 3 BA
                                                                              • Sleeps 9
                                                                              Townhome #504081vb
                                                                              2
                                                                                • 4 BR
                                                                                • 4 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 11
                                                                                Townhome #763023vb
                                                                                Viewed 7 times in the last 48 hours
                                                                                  • 3 BR
                                                                                  • 3 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 11
                                                                                  Townhome #799831vb
                                                                                  1
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 4 BA
                                                                                    • Sleeps 12
                                                                                    Townhome #763016vb
                                                                                    1
                                                                                    Viewed 11 times in the last 48 hours
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 10
                                                                                      Condo #740122vb
                                                                                      Viewed 21 times in the last 48 hours
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 6
                                                                                        Condo #4276368
                                                                                          • 3 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 11
                                                                                          Condo #763025vb
                                                                                            • 4 BR
                                                                                            • 4 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 12
                                                                                            Townhome #802804vb
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 10
                                                                                              Condo #740121vb
                                                                                              Viewed 16 times in the last 48 hours
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                Condo #4276367
                                                                                                Viewed 7 times in the last 48 hours
                                                                                                  • 5 BR
                                                                                                  • 3 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 12
                                                                                                  Townhome #455707vb
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 10
                                                                                                    Townhome #910745vb
                                                                                                    1
                                                                                                    Viewed 7 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (15 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 4 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 11
                                                                                                      Townhome #175504vb
                                                                                                      15
                                                                                                      Viewed 7 times in the last 48 hours
                                                                                                      • 1 - 50 of 64
                                                                                                       

                                                                                                      Recent Winter Park Reviews

                                                                                                      Great place to stay and well stocked.

                                                                                                      5 of 5
                                                                                                      We went over fall break with our kids and another family. The house is well taken care of and the owners have done a great job having everything you need there at the house. We were lucky enough to have snow one night and they had sleds and a snowman kit in the garage. Great views and great food in Winter Park and the surround area.
                                                                                                      • Submitted: Dec 1, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Amazing property. Great view and hot tub.

                                                                                                      5 of 5
                                                                                                      Luxuary property. Top services all the way to the smallest detail. Will come back
                                                                                                      • Submitted: Nov 27, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Perfect home away from home for a mountain getaway

                                                                                                      5 of 5
                                                                                                      This perfectly kept, modern condo is an absolute gem. Location is awesome, building is new, well designed and super clean. The cleaning fees with vrbo are always tough to stomach ($150) but the actual fee for staying was really low and the unit \ complex was well worth it. Very happy with our stay.
                                                                                                      • Submitted: Nov 2, 2016
                                                                                                      • Stayed: Oct 2016