Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartment
Bungalow
Cabin
Chalet
Condo
Cottage
Hotel
House
Lodge
Studio
Townhome
Barn
Boat
Castle
Estate
Farmhouse
Villa
Yacht

Location Type

Even More Filters

Features

Managed By

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

Winter Park Area: Condos, Houses & More(900)

900 Results
Book it Now!
2 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
    (22)
    Book it Now!
    2 - 5 night minimum stay
    • 5 BR,
    • 5 BA,
    • 1 HF BA,
    • Sleeps 18
      (29)
      Book it Now!
      3 - 5 night minimum stay
      • 2 BR,
      • 2 BA,
      • Sleeps 6
        (37)
        Book it Now!
        4 - 7 night minimum stay
        • 4 BR,
        • 3 BA,
        • 1 HF BA,
        • Sleeps 12
          (38)
          Book it Now!
          3 - 5 night minimum stay
          • 4 BR,
          • 3 BA,
          • 1 HF BA,
          • Sleeps 11
            (51)
            Book it Now!
            1 - 2 night minimum stay
            • 2 BR,
            • 1 BA,
            • 1 HF BA,
            • Sleeps 6
              (16)
              Book it Now!
              3 - 5 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 8
                (29)
                $1,000 - $1,200
                per night
                Book it Now!
                3 night minimum stay
                • 4 BR,
                • 4 BA,
                • 1 HF BA,
                • Sleeps 14
                  (21)
                  Book it Now!
                  3 - 7 night minimum stay
                  • 4 BR,
                  • 3 BA,
                  • 1 HF BA,
                  • Sleeps 10
                    (27)
                    Book it Now!
                    2 - 6 night minimum stay
                    • 6 BR,
                    • 4 BA,
                    • Sleeps 20
                      (17)
                      Book it Now!
                      3 - 5 night minimum stay
                      • 5 BR,
                      • 3 BA,
                      • Sleeps 19
                        (16)
                        Book it Now!
                        2 - 3 night minimum stay
                        • 1 BR,
                        • 1 BA,
                        • Sleeps 4
                          (16)
                          Book it Now!
                          2 - 7 night minimum stay
                          • 3 BR,
                          • 2 BA,
                          • Sleeps 10
                            (9)
                            $850 - $1,143
                            per night
                            3 - 7 night minimum stay
                            • 6 BR,
                            • 6 BA,
                            • 1 HF BA,
                            • Sleeps 16
                              (25)
                              Book it Now!
                              1 - 5 night minimum stay
                              • 5 BR,
                              • 3 BA,
                              • 1 HF BA,
                              • Sleeps 20
                                (9)
                                Book it Now!
                                2 - 7 night minimum stay
                                • 3 BR,
                                • 4 BA,
                                • Sleeps 12
                                  (9)
                                  Book it Now!
                                  2 - 4 night minimum stay
                                  • 4 BR,
                                  • 3 BA,
                                  • 1 HF BA,
                                  • Sleeps 12
                                    (7)
                                    Book it Now!
                                    2 - 4 night minimum stay
                                    • 2 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                      (10)
                                      Book it Now!
                                      2 - 5 night minimum stay
                                      • 4 BR,
                                      • 4 BA,
                                      • Sleeps 14
                                        (12)
                                        Book it Now!
                                        3 - 4 night minimum stay
                                        • 4 BR,
                                        • 3 BA,
                                        • 1 HF BA,
                                        • Sleeps 12
                                          (35)
                                          Book it Now!
                                          2 - 5 night minimum stay
                                          • 4 BR,
                                          • 3 BA,
                                          • Sleeps 20
                                            (23)
                                            Book it Now!
                                            2 - 6 night minimum stay
                                            • 4 BR,
                                            • 3 BA,
                                            • 1 HF BA,
                                            • Sleeps 20
                                              (4)
                                              Book it Now!
                                              2 - 6 night minimum stay
                                              • 6 BR,
                                              • 3 BA,
                                              • 1 HF BA,
                                              • Sleeps 24
                                                (4)
                                                Book it Now!
                                                2 - 5 night minimum stay
                                                • 4 BR,
                                                • 3 BA,
                                                • 1 HF BA,
                                                • Sleeps 13
                                                  2 - 5 night minimum stay
                                                  • 2 BR,
                                                  • 2 BA,
                                                  • Sleeps 8
                                                    (20)
                                                    3 - 5 night minimum stay
                                                    • 4 BR,
                                                    • 4 BA,
                                                    • Sleeps 12
                                                      (20)
                                                      3 night minimum stay
                                                      • 3 BR,
                                                      • 2 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 8
                                                        (11)
                                                        • 3 BR,
                                                        • 3 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 8