Villas in Kissimmee City and Houses – Holiday Lettings - Holiday Rentals Kissimmee City

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

22,146 Holiday homes

(3) Excellent 

    91

    Villa accommodation in Kissimmee City

    Kissimmee / Kissimmee City

    5 10 6 nights min

    • 5 bedrooms
    • sleeps 10
    • 6 nights min
    • Swimming pool
    • Child friendly
    • Air conditioning

    from £148 / night

    £1,034 / week

    Book View

    from £148 / night

    (34) Very Good 

      22

      Holiday villa in Kissimmee

      Kissimmee / Kissimmee City

      3 6 min stay varies

      • 3 bedrooms
      • sleeps 6
      • min stay varies
      • Nearest beach 60 km
      • Swimming pool
      • Child friendly

      from £59 / night

      £375 - £475 / week

      Enquire View

      from £59 / night

      (18) Excellent 

      Certificate of Excellence

        25

        Holiday villa in Kissimmee City

        Kissimmee / Kissimmee City

        4 10 min stay varies

        • 4 bedrooms
        • sleeps 10
        • min stay varies
        • Nearest beach 120 km
        • Swimming pool
        • Child friendly

        Certificate of Excellence

        from £138 / night

        £745 - £1,386 / week

        Book View

        Responds fast!
        avg. 1 hour 20 minutes

        from £138 / night

        (21) Very Good 

          43

          Villa rental in Kissimmee City with swimming pool

          Kissimmee / Kissimmee City

          4 9 min stay varies

          • 4 bedrooms
          • sleeps 9
          • min stay varies
          • Nearest beach 95 km
          • Swimming pool
          • Child friendly

          from £115 / night

          £705 - £881 / week

          Book View

          Responds fast!
          avg. 1 hour 7 minutes

          from £115 / night

          (1) Very Good 

            20

            Condo rental in Kissimmee City with golf nearby

            Kissimmee / Kissimmee City

            3 6 3 nights min

            • 3 bedrooms
            • sleeps 6
            • 3 nights min
            • Beach / lakeside relaxation
            • Nearest beach 100 km
            • Swimming pool

            from £80 / night

            £559 - £590 / week

            Book View

            from £80 / night

            (2) Excellent 

              41

              Holiday home in Kissimmee City

              Kissimmee / Kissimmee City

              4 8 min stay varies

              • 4 bedrooms
              • sleeps 8
              • min stay varies
              • Nearest beach 100 km
              • Swimming pool
              • Child friendly

              from £107 / night

              £745 / week

              Book View

              Responds fast!
              avg. 2 hours 21 minutes

              from £107 / night

                24

                Holiday townhouse with golf nearby in Kissimmee City

                Kissimmee / Kissimmee City

                3 6 5 nights min

                • 3 bedrooms
                • sleeps 6
                • 5 nights min
                • Child friendly
                • Air conditioning

                from £88 / night

                £559 / week

                Book View

                from £88 / night

                (1) Excellent 

                  26

                  Holiday townhouse with swimming pool in Kissimmee

                  Kissimmee / Kissimmee City

                  4 10 1 night min

                  • 4 bedrooms
                  • sleeps 10
                  • 1 night min
                  • Swimming pool
                  • Child friendly
                  • Air conditioning

                  from £124 / night

                  £863 - £987 / week

                  Book View

                  Responds fast!
                  avg. 2 hours 41 minutes

                  from £124 / night

                  (4) Excellent 

                    49

                    Holiday home with indoor pool in Kissimmee City

                    Kissimmee / Kissimmee City

                    5 10 4 nights min

                    • 5 bedrooms
                    • sleeps 10
                    • 4 nights min
                    • Swimming pool
                    • Child friendly
                    • Air conditioning

                    from £311 / night

                    £2,172 / week

                    Book View

                    Responds fast!
                    avg. 3 hours 44 minutes

                    from £311 / night

                    (4) Very Good 

                      21

                      Holiday villa in Kissimmee

                      Kissimmee / Kissimmee City

                      8 20 min stay varies

                      • 8 bedrooms
                      • sleeps 20
                      • min stay varies
                      • Swimming pool
                      • Child friendly
                      • Air conditioning

                      from £221 / night

                      £1,329 - £2,482 / week

                      Book View

                      Responds fast!
                      avg. 3 hours 12 minutes

                      from £221 / night

                        8

                        Holiday villa in Kissimmee

                        Kissimmee / Kissimmee City

                        1 4 7 nights min

                        • 1 bedroom
                        • sleeps 4
                        • 7 nights min
                        • Swimming pool
                        • Child friendly
                        • Air conditioning

                        from £89 / night

                        £621 / week

                        Book View

                        from £89 / night

                        Great rentals within 20 miles that match your search

                        Distance approx 17.69 miles from Kissimmee City Show on Map

                        (12) Excellent 

                          20

                          Holiday villa with swimming pool, golf nearby in Haines City

                          Haines City / Calabay Parc at Tower Lake

                          5 10 min stay varies

                          • 5 bedrooms
                          • sleeps 10
                          • min stay varies
                          • Swimming pool
                          • Child friendly
                          • Air conditioning

                          from £135 / night

                          £945 - £1,060 / week

                          Book View

                          from £135 / night

                          Distance approx 13.65 miles from Kissimmee City Show on Map

                            20

                            Kissimmee holiday villa rental

                            Kissimmee / Emerald Isle Kissimmee

                            8 17 min stay varies

                            • 8 bedrooms
                            • sleeps 17
                            • min stay varies
                            • Nearest beach 80 km
                            • Swimming pool
                            • Child friendly

                            from £266 / night

                            £1,197 - £2,118 / week

                            Book View

                            from £266 / night

                            Distance approx 11.99 miles from Kissimmee City Show on Map

                            (4) Excellent 

                              39

                              Holiday villa with golf nearby in Davenport

                              Davenport / Sunridge Woods

                              3 6 7 nights min

                              • 3 bedrooms
                              • sleeps 6
                              • 7 nights min
                              • Beach / lakeside relaxation
                              • Swimming pool
                              • Child friendly

                              from £94 / night

                              £659 / week

                              Book View

                              Responds fast!
                              avg. 3 hours 18 minutes

                              from £94 / night

                              Distance approx 10.4 miles from Kissimmee City Show on Map

                                27

                                Holiday home in Davenport

                                Central Florida / Davenport

                                5 10 6 nights min

                                • 5 bedrooms
                                • sleeps 10
                                • 6 nights min
                                • Child friendly

                                from £218 / night

                                £1,523 / week

                                Book View

                                from £218 / night

                                Distance approx 10.05 miles from Kissimmee City Show on Map

                                (7) Very Good 

                                  21

                                  Holiday villa with golf nearby in Orlando

                                  Central Florida / Orlando

                                  3 12 6 nights min

                                  • 3 bedrooms
                                  • sleeps 12
                                  • 6 nights min
                                  • Beach / lakeside relaxation
                                  • Swimming pool
                                  • Child friendly

                                  from £173 / night

                                  £1,210 / week

                                  Book View

                                  from £173 / night

                                  Distance approx 3.85 miles from Kissimmee City Show on Map

                                  (11) Excellent 

                                    12

                                    Holiday villa with swimming pool in Orlando

                                    Central Florida / Orlando

                                    5 12 7 nights min

                                    • 5 bedrooms
                                    • sleeps 12
                                    • 7 nights min
                                    • Nearest beach 45 km
                                    • Swimming pool
                                    • Air conditioning

                                    from £111 / night

                                    £773 / week

                                    Book View

                                    from £111 / night

                                    Distance approx 12.74 miles from Kissimmee City Show on Map

                                    (51) Excellent 

                                    Certificate of Excellence

                                      21

                                      Holiday villa in Kissimmee

                                      Central Florida / Kissimmee

                                      4 8 7 nights min

                                      • 4 bedrooms
                                      • sleeps 8
                                      • 7 nights min
                                      • Swimming pool
                                      • Child friendly
                                      • Air conditioning

                                      Certificate of Excellence

                                      from £103 / night

                                      £716 - £745 / week

                                      Book View

                                      Responds fast!
                                      avg. 2 hours 2 minutes

                                      from £103 / night

                                      Distance approx 15.26 miles from Kissimmee City Show on Map

                                        59

                                        Villa rental in Davenport with swimming pool, golf nearby

                                        Davenport / Champions Gate

                                        8 20 min stay varies

                                        • 8 bedrooms
                                        • sleeps 20
                                        • min stay varies
                                        • Nearest beach 97 km
                                        • Swimming pool
                                        • Child friendly

                                        from £154 / night

                                        £1,808 / week

                                        Book View

                                        from £154 / night

                                        Distance approx 13.7 miles from Kissimmee City Show on Map

                                        (2) Very Good 

                                          16

                                          Holiday home in Kissimmee

                                          Central Florida / Kissimmee

                                          7 16 6 nights min

                                          • 7 bedrooms
                                          • sleeps 16
                                          • 6 nights min
                                          • Swimming pool
                                          • Child friendly
                                          • Air conditioning

                                          from £444 / night

                                          £2,837 / week

                                          Book View

                                          from £444 / night

                                          Distance approx 11.09 miles from Kissimmee City Show on Map

                                          (4) Excellent 

                                            28

                                            Villa rental in Davenport

                                            Central Florida / Davenport

                                            4 8 3 nights min

                                            • 4 bedrooms
                                            • sleeps 8
                                            • 3 nights min
                                            • Beach / lakeside relaxation
                                            • Swimming pool
                                            • Child friendly

                                            from £98 / night

                                            £683 / week

                                            Book View

                                            from £98 / night

                                            Distance approx 17.55 miles from Kissimmee City Show on Map

                                              10

                                              Holiday home rental

                                              Central Florida / Haines City

                                              4 8 3 nights min

                                              • 4 bedrooms
                                              • sleeps 8
                                              • 3 nights min
                                              • Nearest beach 105 km
                                              • Swimming pool
                                              • Child friendly

                                              from £116 / night

                                              £754 / week

                                              Book View

                                              from £116 / night

                                              Distance approx 14.95 miles from Kissimmee City Show on Map

                                                47

                                                Kissimmee holiday home rental

                                                Central Florida / Kissimmee

                                                4 10 min stay varies

                                                • 4 bedrooms
                                                • sleeps 10
                                                • min stay varies
                                                • Swimming pool
                                                • Child friendly
                                                • Air conditioning

                                                from £107 / night

                                                £745 / week

                                                Book View

                                                from £107 / night

                                                Distance approx 11.31 miles from Kissimmee City Show on Map

                                                  29

                                                  Holiday home rental

                                                  Central Florida / Reunion

                                                  4 10 5 nights min

                                                  • 4 bedrooms
                                                  • sleeps 10
                                                  • 5 nights min
                                                  • Swimming pool
                                                  • Child friendly
                                                  • Air conditioning

                                                  from £151 / night

                                                  £1,055 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 2 hours 51 minutes

                                                  from £151 / night

                                                  Distance approx 4.78 miles from Kissimmee City Show on Map

                                                  (3) Excellent 

                                                    37

                                                    Kissimmee holiday villa rental

                                                    Central Florida / Kissimmee

                                                    3 6 7 nights min

                                                    • 3 bedrooms
                                                    • sleeps 6
                                                    • 7 nights min
                                                    • Swimming pool
                                                    • Child friendly
                                                    • Air conditioning

                                                    from £92 / night

                                                    £642 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 1 hour 0 minutes

                                                    from £92 / night

                                                    Distance approx 3.96 miles from Kissimmee City Show on Map

                                                      20

                                                      Home rental in Kissimmee

                                                      Central Florida / Kissimmee

                                                      6 12 7 nights min

                                                      • 6 bedrooms
                                                      • sleeps 12
                                                      • 7 nights min
                                                      • Child friendly

                                                      from £142 / night

                                                      £993 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 3 hours 14 minutes

                                                      from £142 / night

                                                      Distance approx 13.16 miles from Kissimmee City Show on Map

                                                        7

                                                        Holiday condo rental

                                                        Central Florida / Kissimmee

                                                        2 8 7 nights min

                                                        • 2 bedrooms
                                                        • sleeps 8
                                                        • 7 nights min
                                                        • Child friendly

                                                        from £142 / night

                                                        £993 / week

                                                        Book View

                                                        from £142 / night

                                                        Distance approx 18.01 miles from Kissimmee City Show on Map

                                                          19

                                                          Haines City holiday home rental

                                                          Central Florida / Haines City

                                                          4 8 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 8
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Ask owner if suitable for children
                                                          • Air conditioning

                                                          from £73 / night

                                                          £509 / week

                                                          Book View

                                                          from £73 / night

                                                          Distance approx 12.37 miles from Kissimmee City Show on Map

                                                            28

                                                            Home rental in Kissimmee with swimming pool

                                                            Central Florida / Kissimmee

                                                            3 8 min stay varies

                                                            • 3 bedrooms
                                                            • sleeps 8
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child friendly
                                                            • Air conditioning

                                                            from £124 / night

                                                            £863 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 36 minutes

                                                            from £124 / night

                                                            Distance approx 17.5 miles from Kissimmee City Show on Map

                                                              12

                                                              Haines City holiday villa rental

                                                              Central Florida / Haines City

                                                              3 6 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Ask owner if suitable for children
                                                              • Air conditioning

                                                              from £83 / night

                                                              £577 / week

                                                              Book View

                                                              from £83 / night

                                                              Distance approx 13.8 miles from Kissimmee City Show on Map

                                                              (1) Excellent 

                                                                16

                                                                Holiday home rental

                                                                Central Florida / Kissimmee

                                                                6 16 min stay varies

                                                                • 6 bedrooms
                                                                • sleeps 16
                                                                • min stay varies
                                                                • Child friendly

                                                                from £177 / night

                                                                £1,506 - £2,393 / week

                                                                Book View

                                                                from £177 / night

                                                                Distance approx 16.11 miles from Kissimmee City Show on Map

                                                                  30

                                                                  Holiday villa with swimming pool in Four Corners

                                                                  Central Florida / Four Corners

                                                                  3 6 7 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 6
                                                                  • 7 nights min
                                                                  • Swimming pool
                                                                  • Ask owner if suitable for children
                                                                  • Air conditioning

                                                                  from £83 / night

                                                                  £580 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 41 minutes

                                                                  from £83 / night

                                                                  Distance approx 4.53 miles from Kissimmee City Show on Map

                                                                    25

                                                                    Apartment rental in Kissimmee

                                                                    Central Florida / Kissimmee

                                                                    2 6 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child friendly
                                                                    • Air conditioning

                                                                    from £79 / night

                                                                    £553 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 19 minutes

                                                                    from £79 / night

                                                                    Distance approx 11.92 miles from Kissimmee City Show on Map

                                                                      26

                                                                      Loughman holiday villa rental

                                                                      Central Florida / Loughman

                                                                      4 8 min stay varies

                                                                      • 4 bedrooms
                                                                      • sleeps 8
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £140 / night

                                                                      £975 / week

                                                                      Book View

                                                                      from £140 / night

                                                                      Distance approx 11.05 miles from Kissimmee City Show on Map

                                                                        41

                                                                        Home rental in Reunion

                                                                        Central Florida / Reunion

                                                                        5 10 4 nights min

                                                                        • 5 bedrooms
                                                                        • sleeps 10
                                                                        • 4 nights min
                                                                        • Nearest beach 65 km
                                                                        • Child friendly

                                                                        from £311 / night

                                                                        £2,172 / week

                                                                        Book View

                                                                        from £311 / night

                                                                        Distance approx 11.82 miles from Kissimmee City Show on Map

                                                                          20

                                                                          Holiday villa in Four Corners

                                                                          Central Florida / Four Corners

                                                                          4 8 5 nights min

                                                                          • 4 bedrooms
                                                                          • sleeps 8
                                                                          • 5 nights min
                                                                          • Swimming pool
                                                                          • Child friendly
                                                                          • Car not necessary

                                                                          from £312 / night

                                                                          £2,178 / week

                                                                          Book View

                                                                          from £312 / night

                                                                          Distance approx 10.13 miles from Kissimmee City Show on Map

                                                                            6

                                                                            Holiday villa in Orlando

                                                                            Central Florida / Orlando

                                                                            3 8 7 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 8
                                                                            • 7 nights min
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £228 / night

                                                                            £1,596 / week

                                                                            Book View

                                                                            from £228 / night

                                                                            Distance approx 5.52 miles from Kissimmee City Show on Map

                                                                              25

                                                                              Kissimmee holiday condo rental

                                                                              Central Florida / Kissimmee

                                                                              3 6 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • min stay varies
                                                                              • Child friendly
                                                                              • Air conditioning

                                                                              from £115 / night

                                                                              £801 / week

                                                                              Book View

                                                                              from £115 / night

                                                                              Distance approx 12.07 miles from Kissimmee City Show on Map

                                                                                44

                                                                                Holiday condo with golf nearby in Four Corners

                                                                                Central Florida / Four Corners

                                                                                1 4 min stay varies

                                                                                • 1 bedroom
                                                                                • sleeps 4
                                                                                • min stay varies
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Car not necessary

                                                                                from £88 / night

                                                                                £615 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 1 hour 11 minutes

                                                                                from £88 / night

                                                                                Distance approx 5.32 miles from Kissimmee City Show on Map

                                                                                  26

                                                                                  Condo rental in Old Town

                                                                                  Florida / Old Town

                                                                                  1 4 1 night min

                                                                                  • 1 bedroom
                                                                                  • sleeps 4
                                                                                  • 1 night min
                                                                                  • Swimming pool
                                                                                  • Child friendly
                                                                                  • Air conditioning

                                                                                  from £116 / night

                                                                                  £807 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 1 hour 16 minutes

                                                                                  from £116 / night

                                                                                  Top Destination reviews

                                                                                  Funshine Magical Villa with Gameroom and WiFi
                                                                                  One word to sum up this villa...... PERFECT !!!

                                                                                  Choosing a villa was quite a hard task to ensure that the whole family enjoyed their vacation in Florida. It needed to be centrally located to all the main parks, be furnished to a good standard & have enough to keep the children of 10 & 13 years old occupied on our relaxing days between parks. After hours of research, we found Villa Londra which on paper ticked all the boxes. We were all delighted when we arrived at the villa. The description & photos on the website were all spot on. The villa was clean, well kitted out & the pool was lovely (many an hour spent relaxing in it!). Within minutes drive there is everything you could hope for - supermarkets, gas stations & many places to eat. The parks we went to were all within easy access (Universal, Sea World & Busch Gardens). Right from our initial enquiry on the website, Jan was very helpful & very professional - nothing was too much trouble. After having had the best vacation ever, we are now saving to return in 2014. 10 out of 10 Paul, Jo & Familysee more
                                                                                  Very Nr Disney 3 Bedroom Villa With Free WIFI
                                                                                  Home from Home

                                                                                  This place was a home from home. As soon as we entered the villa we felt relaxed. The villa was nice, clean and very spacious. It is literally 5 minutes from Disney. I would definitely say a great find! … see more

                                                                                  Also consider