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
Welcome to the new VacationRentals.com! Use the new filters and search options to find your next vacation rental.

Kissimmee Vacation Rentals (22,422)

  • 1 - 50 of 22,422
Additional fees apply. Taxes may be added.
    House #812230vb
    • 8 BR
    • 5 BA
    • Sleeps 16
    1 Review

    Instant confirmation

    Your booking request will be confirmed immediately.

      House #818383vb
      • 6 BR
      • 5 BA
      • 1 HF BA
      • Sleeps 12
      2 Reviews

      Instant confirmation

      Your booking request will be confirmed immediately.

        House #812115vb
        • 6 BR
        • 4 BA
        • Sleeps 16
        20

        Confirmation within 24 hours

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

          Villa #802215vb
          • 5 BR
          • 4 BA
          • Sleeps 10
          27

          Instant confirmation

          Your booking request will be confirmed immediately.

            House #758691vb
            • 6 BR
            • 6 BA
            • Sleeps 14
            1 Review

            Instant confirmation

            Your booking request will be confirmed immediately.

              Villa #237518vb
              • 4 BR
              • 3 BA
              • Sleeps 8
              50

              Confirmation within 24 hours

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

                House #786284vb
                • 4 BR
                • 2 BA
                • 2 HF BA
                • Sleeps 10
                25

                Confirmation within 24 hours

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

                  Villa #3786282
                  • 6 BR
                  • 4 BA
                  • Sleeps 14
                  36

                  Confirmation within 24 hours

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

                    Villa #1605033
                    • 5 BR
                    • 4 BA
                    • 1 HF BA
                    • Sleeps 12
                    25

                    Confirmation within 24 hours

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

                      Villa #804327vb
                      • 5 BR
                      • 4 BA
                      • Sleeps 10
                      23

                      Instant confirmation

                      Your booking request will be confirmed immediately.

                        House #818381vb
                        • 8 BR
                        • 7 BA
                        • Sleeps 18

                        Instant confirmation

                        Your booking request will be confirmed immediately.

                          House #4153783
                          • 6 BR
                          • 5 BA
                          • Sleeps 14
                          9

                          Instant confirmation

                          Your booking request will be confirmed immediately.

                            Townhome #230461vb
                            • 4 BR
                            • 3 BA
                            • Sleeps 10
                            48

                            Confirmation within 24 hours

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

                              Villa #3952973
                              • 6 BR
                              • 4 BA
                              • Sleeps 14
                              27

                              Confirmation within 24 hours

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

                                House #3851767
                                • 7 BR
                                • 6 BA
                                • Sleeps 16
                                51

                                Instant confirmation

                                Your booking request will be confirmed immediately.

                                  Villa #915319
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 9
                                  56

                                  Instant confirmation

                                  Your booking request will be confirmed immediately.

                                    Villa #770551vb
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 8
                                    26

                                    Instant confirmation

                                    Your booking request will be confirmed immediately.

                                      Villa #4091068
                                      • 8 BR
                                      • 5 BA
                                      • Sleeps 18
                                      17

                                      Confirmation within 24 hours

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

                                        House #4172017
                                        • 9 BR
                                        • 5 BA
                                        • Sleeps 28
                                        12

                                        Confirmation within 24 hours

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

                                          Villa #887138vb
                                          • 6 BR
                                          • 5 BA
                                          • Sleeps 12
                                          6

                                          Confirmation within 24 hours

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

                                            House #3998693
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 8
                                            25

                                            Instant confirmation

                                            Your booking request will be confirmed immediately.

                                              Villa #1052432
                                              • 5 BR
                                              • 4 BA
                                              • Sleeps 10
                                              44

                                              Confirmation within 24 hours

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

                                                Townhome #3471004
                                                • 3 BR
                                                • 2 BA
                                                • 2 HF BA
                                                • Sleeps 6
                                                16

                                                Confirmation within 24 hours

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

                                                  Villa #835586
                                                  • 4 BR
                                                  • 4 BA
                                                  • Sleeps 10
                                                  35

                                                  Confirmation within 24 hours

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

                                                    Villa #585836vb
                                                    • 3 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    34

                                                    Confirmation within 24 hours

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

                                                      Townhome #688037vb
                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 8
                                                      19

                                                      Confirmation within 24 hours

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

                                                        House #779965vb
                                                        • 9 BR
                                                        • 5 BA
                                                        • Sleeps 29
                                                        18

                                                        Instant confirmation

                                                        Your booking request will be confirmed immediately.

                                                          Condo #321447vb
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          105

                                                          Confirmation within 24 hours

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

                                                            Villa #3855389
                                                            • 8 BR
                                                            • 5 BA
                                                            • Sleeps 20
                                                            20

                                                            Confirmation within 24 hours

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

                                                              Townhome #332416
                                                              • 3 BR
                                                              • 2 BA
                                                              • 1 HF BA
                                                              • Sleeps 8
                                                              92

                                                              Confirmation within 24 hours

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

                                                                Villa #453935
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                34

                                                                Confirmation within 24 hours

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

                                                                  House #4064497
                                                                  • 5 BR
                                                                  • 4 BA
                                                                  • Sleeps 12
                                                                  24

                                                                  Confirmation within 24 hours

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

                                                                    House #472122vb
                                                                    • 6 BR
                                                                    • 3 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 12
                                                                    20

                                                                    Instant confirmation

                                                                    Your booking request will be confirmed immediately.

                                                                      House #891925vb
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • Sleeps 10
                                                                      10

                                                                      Confirmation within 24 hours

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

                                                                        Villa #53137vb
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 10
                                                                        76

                                                                        Confirmation within 24 hours

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

                                                                          House #4219047
                                                                          • 5 BR
                                                                          • 5 BA
                                                                          • Sleeps 14
                                                                          11

                                                                          Confirmation within 24 hours

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

                                                                            Villa #862382vb
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            9

                                                                            Instant confirmation

                                                                            Your booking request will be confirmed immediately.

                                                                              Villa #379772vb
                                                                              • 6 BR
                                                                              • 3 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 14
                                                                              33

                                                                              Confirmation within 24 hours

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

                                                                                House #562724vb
                                                                                • 5 BR
                                                                                • 4 BA
                                                                                • Sleeps 12
                                                                                35

                                                                                Confirmation within 24 hours

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

                                                                                  Condo #1507058
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  35

                                                                                  Confirmation within 24 hours

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

                                                                                    House #697725vb
                                                                                    • 6 BR
                                                                                    • 5 BA
                                                                                    • Sleeps 14
                                                                                    22

                                                                                    Confirmation within 24 hours

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

                                                                                      House #915075
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 8
                                                                                      43

                                                                                      Confirmation within 24 hours

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

                                                                                        House #87461
                                                                                        • 5 BR
                                                                                        • 3 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 12
                                                                                        16

                                                                                        Confirmation within 24 hours

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

                                                                                          Condo #418363vb
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 8
                                                                                          43

                                                                                          Confirmation within 24 hours

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

                                                                                            Villa #3849793
                                                                                            • 8 BR
                                                                                            • 5 BA
                                                                                            • Sleeps 20
                                                                                            20

                                                                                            Confirmation within 24 hours

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

                                                                                              Villa #887142vb
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              2 Reviews

                                                                                              Confirmation within 24 hours

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

                                                                                                House #448108vb
                                                                                                • 6 BR
                                                                                                • 4 BA
                                                                                                • Sleeps 13
                                                                                                52

                                                                                                Confirmation within 24 hours

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

                                                                                                  Villa #1436290
                                                                                                  • 6 BR
                                                                                                  • 4 BA
                                                                                                  • Sleeps 13
                                                                                                  21

                                                                                                  Confirmation within 24 hours

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

                                                                                                    House #287249
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    67

                                                                                                    Confirmation within 24 hours

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

                                                                                                      House #472885vb
                                                                                                      • 4 BR
                                                                                                      • 4 BA
                                                                                                      • Sleeps 8
                                                                                                      37

                                                                                                      Confirmation within 24 hours

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

                                                                                                      • 1 - 50 of 22,422