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  • Showing 1-50 of 164
Additional fees apply. Taxes may be added.
    • 3 BR
    • 2 BA
    • Sleeps 4
    House #582440vb
    Viewed 11 times in the last 48 hours
      • 1 BR
      • 1 BA
      • Sleeps 3
      Condo #3813581
      4
      Viewed 15 times in the last 48 hours
        Very Good! 4.2/5
        (6 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 6
        Hotel #708659vb
        6
        Viewed 21 times in the last 48 hours
          Wonderful! 4.8/5
          (5 reviews)
          $98
          avg/night
          • Studio
          • 1 BA
          • Sleeps 6
          Studio #600604vb
          5
          Viewed 13 times in the last 48 hours
            Excellent! 4.4/5
            (11 reviews)
            avg/night
            • 3 BR
            • 2 BA
            • Sleeps 6
            Apartment #3656032
            11
            Viewed 8 times in the last 48 hours
              Wonderful! 4.8/5
              (20 reviews)
              avg/night
              • 3 BR
              • 3 BA
              • 1 HF BA
              • Sleeps 8
              Townhome #87094vb
              20
              Viewed 18 times in the last 48 hours
                Very Good! 4.2/5
                (5 reviews)
                avg/night
                • 3 BR
                • 3 BA
                • Sleeps 8
                Townhome #3924377
                5
                Viewed 7 times in the last 48 hours
                  • 3 BR
                  • 3 BA
                  • 1 HF BA
                  • Sleeps 8
                  Townhome #3770788
                  4
                  Viewed 5 times in the last 48 hours
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    Condo #3761764
                    4
                    Viewed 21 times in the last 48 hours
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      Apartment #3818582
                      3
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                        Condo #123340vb
                        17
                          Excellent! 4.4/5
                          (16 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 8
                          Condo #699864vb
                          16
                          Viewed 11 times in the last 48 hours
                            Excellent! 4.6/5
                            (30 reviews)
                            avg/night
                            • 2 BR
                            • 2 BA
                            • Sleeps 6
                            Condo #699853vb
                            30
                            Viewed 14 times in the last 48 hours
                              • 3 BR
                              • 3 BA
                              • 1 HF BA
                              • Sleeps 10
                              Townhome #699870vb
                              10
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                Condo #699860vb
                                20
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 8
                                  Condo #699872vb
                                  23
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 8
                                    Apartment #3814345
                                    1 Review
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 6
                                      Apartment #3828511
                                      3
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 8
                                        Villa #680971vb
                                        1 Review
                                          Excellent! 4.4/5
                                          (19 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 8
                                          Condo #699848vb
                                          19
                                          Viewed 7 times in the last 48 hours
                                            • Studio
                                            • 1 BA
                                            • Sleeps 4
                                            Hotel #3905320
                                            1 Review
                                            Viewed 6 times in the last 48 hours
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Villa #680965vb
                                              2 Reviews
                                              Viewed 19 times in the last 48 hours
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 8
                                                Condo #3675515
                                                  Wonderful! 4.9/5
                                                  (11 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Boat #3896495
                                                  11
                                                  Viewed 9 times in the last 48 hours
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Hotel #3905334
                                                    Viewed 12 times in the last 48 hours
                                                      Excellent! 4.7/5
                                                      (15 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Hotel #3905187
                                                      15
                                                      Viewed 217 times in the last 48 hours
                                                        • 1 BR
                                                        • 2 BA
                                                        • Sleeps 4
                                                        Hotel #3905329
                                                        Viewed 5 times in the last 48 hours
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Villa #680921vb
                                                          Viewed 5 times in the last 48 hours
                                                            Excellent! 4.6/5
                                                            (9 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Hotel #3905182
                                                            9
                                                            Viewed 61 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (5 reviews)
                                                              avg/night
                                                              • 7 BR
                                                              • 6 BA
                                                              • Sleeps 14
                                                              House #749439vb
                                                              5
                                                              Viewed 15 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (24 reviews)
                                                                avg/night
                                                                • 4 BR
                                                                • 2 BA
                                                                • Sleeps 8
                                                                House #4019138
                                                                24
                                                                Viewed 10 times in the last 48 hours
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Sleeps 8
                                                                  Villa #3817427
                                                                  11
                                                                    Wonderful! 4.9/5
                                                                    (8 reviews)
                                                                    $82
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Villa #1509613
                                                                    8
                                                                    Viewed 7 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (27 reviews)
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • Sleeps 12
                                                                      House #3672406
                                                                      27
                                                                      Viewed 47 times in the last 48 hours
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 8
                                                                        Townhome #3908830
                                                                        5
                                                                          Wonderful! 4.9/5
                                                                          (18 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          House #3534695
                                                                          18
                                                                          Viewed 34 times in the last 48 hours
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 9
                                                                            House #3761633
                                                                              avg/night
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              Villa #3927988
                                                                              3
                                                                              Viewed 8 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (10 reviews)
                                                                                avg/night
                                                                                • 5 BR
                                                                                • 5 BA
                                                                                • Sleeps 11
                                                                                Townhome #736032vb
                                                                                10
                                                                                Viewed 25 times in the last 48 hours
                                                                                  • 4 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 8
                                                                                  Villa #3712986
                                                                                  4
                                                                                    Excellent! 4.5/5
                                                                                    (6 reviews)
                                                                                    $85
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 7
                                                                                    Townhome #999539
                                                                                    6
                                                                                    Viewed 11 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (6 reviews)
                                                                                      $78
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 4
                                                                                      House #3877179
                                                                                      6
                                                                                      Viewed 10 times in the last 48 hours
                                                                                        Excellent! 4.6/5
                                                                                        (20 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Condo #364387vb
                                                                                        20
                                                                                        Viewed 21 times in the last 48 hours
                                                                                          • 5 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 12
                                                                                          House #3675587
                                                                                          2 Reviews
                                                                                          Viewed 16 times in the last 48 hours
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 10
                                                                                            House #3761722
                                                                                            1 Review
                                                                                            Viewed 10 times in the last 48 hours
                                                                                              • 6 BR
                                                                                              • 6 BA
                                                                                              • Sleeps 14
                                                                                              House #3928630
                                                                                              2 Reviews
                                                                                              Viewed 7 times in the last 48 hours
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                Townhome #3761703
                                                                                                1 Review
                                                                                                  Excellent! 4.7/5
                                                                                                  (6 reviews)
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  Villa #8047224
                                                                                                  6
                                                                                                  Viewed 16 times in the last 48 hours
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    House #3930703
                                                                                                    4
                                                                                                    Viewed 10 times in the last 48 hours
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Condo #3617231
                                                                                                      4
                                                                                                      Viewed 9 times in the last 48 hours
                                                                                                      • 1 - 50 of 164

                                                                                                      Winter Park: Vacation Rentals (164)

                                                                                                       

                                                                                                      Recent Winter Park Reviews

                                                                                                      Perfect Getaway!

                                                                                                      5 of 5
                                                                                                      Having lived in cities my whole life, there is nothing better than waking up every morning to horses grazing 20 feet from the backdoor. I stayed here on a work trip with a team of people for a little over two weeks. The place was perfectly clean, quiet, and peaceful. Beth was attentive to every question and flexible with check in and out times. I recommend to anyone!
                                                                                                      • Submitted: Nov 21, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Amazing place to stay

                                                                                                      5 of 5
                                                                                                      This is definitely a five-star home I would recommend to everyone. Lou and Fran are amazing and attentive to our needs. The home is very clean,the beds are extremely comfortable. I have been coming here for years and this is the first time that I have given a five star rating. You have everything you need in this home to cook it's like you're back at home. Thank you Lou, Fran and Mike we really enjoyed our stay. Remember this house is mine next year. See you then Deborah (michigan)
                                                                                                      • Submitted: Nov 17, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Excellent accommodation

                                                                                                      5 of 5
                                                                                                      The complex was extremely quiet both day and night. Our apartment was very spacious and well equipped with a dishwasher, washing machine and tumble dryer. The beds were the best we've ever slept in - a great night's sleep! The staff were very helpful and courteous. Pool and jacuzzi were clean and just the right size for our kids to play in. Thanks for a great stay - we will definitely be back!
                                                                                                      • Submitted: Nov 8, 2016
                                                                                                      • Stayed: Oct 2016