Villas in Windsor Hills Resort and Condos - Holiday Lettings - Holiday Rentals Windsor Hills Resort

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22,069 Holiday homes

(13) Very Good 

    24

    Villa rental in Windsor Hills Resort with golf nearby

    Kissimmee / Windsor Hills Resort

    6 14 3 nights min

    • 6 bedrooms
    • sleeps 14
    • 3 nights min
    • Beach / lakeside relaxation
    • Nearest beach 80 km
    • Swimming pool

    from £247 / night

    £1,661 / week

    Book View

    Responds fast!
    avg. 2 hours 50 minutes

    from £247 / night

    (4) Excellent 

      20

      Villa rental in Kissimmee with golf nearby

      Kissimmee / Windsor Hills Resort

      6 12 4 nights min

      • 6 bedrooms
      • sleeps 12
      • 4 nights min
      • Nearest beach 116 km
      • Swimming pool
      • Child friendly

      from £194 / night

      £1,355 / week

      Book View

      from £194 / night

        42

        Condo rental in Kissimmee

        Kissimmee / Windsor Hills Resort

        3 6 3 nights min

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

        from £105 / night

        £733 / week

        Book View

        Responds fast!
        avg. 2 hours 7 minutes

        from £105 / night

        (6) Very Good 

          35

          Holiday townhouse rental

          Kissimmee / Windsor Hills Resort

          3 8 7 nights min

          • 3 bedrooms
          • sleeps 8
          • 7 nights min
          • Nearest beach 60 km
          • Swimming pool
          • Child friendly

          from £84 / night

          £585 - £1,056 / week

          Book View

          from £84 / night

          (15) Excellent 

            21

            Holiday villa with golf nearby in Windsor Hills Resort

            Kissimmee / Windsor Hills Resort

            6 12 min stay varies

            • 6 bedrooms
            • sleeps 12
            • min stay varies
            • Swimming pool
            • Child friendly
            • Air conditioning

            from £207 / night

            £1,443 - £2,164 / week

            Book View

            from £207 / night

            (15) Excellent 

              24

              Holiday bungalow with swimming pool, golf nearby in Windsor Hills Resort

              Kissimmee / Windsor Hills Resort

              4 8 min stay varies

              • 4 bedrooms
              • sleeps 8
              • min stay varies
              • Nearest beach 110 km
              • Swimming pool
              • Child friendly

              from £135 / night

              £942 / week

              Enquire View

              from £135 / night

                18

                Windsor Hills Resort holiday condo let

                Kissimmee / Windsor Hills Resort

                3 8 min stay varies

                • 3 bedrooms
                • sleeps 8
                • min stay varies
                • Beach / lakeside relaxation
                • Nearest beach 89 km
                • Swimming pool

                from £88 / night

                £610 - £733 / week

                Book View

                from £88 / night

                (3) Excellent 

                  36

                  Holiday townhouse in Windsor Hills Resort

                  Kissimmee / Windsor Hills Resort

                  3 6 4 nights min

                  • 3 bedrooms
                  • sleeps 6
                  • 4 nights min
                  • Nearest beach 118 km
                  • Swimming pool
                  • Child friendly

                  from £97 / night

                  £678 / week

                  Book View

                  Responds fast!
                  avg. 1 hour 12 minutes

                  from £97 / night

                  (4) Excellent 

                    12

                    Windsor Hills Resort holiday home rental

                    Kissimmee / Windsor Hills Resort

                    5 10 min stay varies

                    • 5 bedrooms
                    • sleeps 10
                    • min stay varies
                    • Nearest beach 129 km
                    • Swimming pool
                    • Child friendly

                    from £154 / night

                    £1,078 - £1,386 / week

                    Book View

                    from £154 / night

                      23

                      Holiday condo in Windsor Hills Resort

                      Kissimmee / Windsor Hills Resort

                      3 8 min stay varies

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

                      from £79 / night

                      £616 / week

                      Book View

                      Responds fast!
                      avg. 2 hours 43 minutes

                      from £79 / night

                      (2) Excellent 

                        33

                        Holiday villa rental

                        Kissimmee / Windsor Hills Resort

                        5 12 min stay varies

                        • 5 bedrooms
                        • sleeps 12
                        • min stay varies
                        • Swimming pool
                        • Child friendly
                        • Air conditioning

                        from £190 / night

                        £1,231 - £2,112 / week

                        Book View

                        Responds fast!
                        avg. 3 hours 51 minutes

                        from £190 / night

                        (9) Excellent 

                          28

                          Holiday condo with shared pool in Windsor Hills Resort

                          Kissimmee / Windsor Hills Resort

                          3 8 2 nights min

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

                          from £87 / night

                          £640 / week

                          Book View

                          Responds fast!
                          avg. 1 hour 45 minutes

                          from £87 / night

                            38

                            Holiday villa with golf nearby in Windsor Hills Resort

                            Kissimmee / Windsor Hills Resort

                            5 10 1 night min

                            • 5 bedrooms
                            • sleeps 10
                            • 1 night min
                            • Nearest beach 105 km
                            • Swimming pool
                            • Child friendly

                            from £172 / night

                            £1,201 / week

                            Book View

                            Responds fast!
                            avg. 36 minutes

                            from £172 / night

                            (3)  

                              14

                              Holiday condo with shared pool, golf nearby in Windsor Hills Resort

                              Kissimmee / Windsor Hills Resort

                              3 6 3 nights min

                              • 3 bedrooms
                              • sleeps 6
                              • 3 nights min
                              • Nearest beach 143 km
                              • Swimming pool
                              • Child friendly

                              from £80 / night

                              £555 / week

                              Book View

                              from £80 / night

                              Great rentals within 20 miles that match your search

                              Distance approx 3.03 miles from Windsor Hills Resort Show on Map

                                4

                                Holiday villa with shared pool in Kissimmee

                                Central Florida / Kissimmee

                                3 12 7 nights min

                                • 3 bedrooms
                                • sleeps 12
                                • 7 nights min
                                • Swimming pool
                                • Child friendly
                                • Air conditioning

                                from £202 / night

                                £1,401 / week

                                Book View

                                from £202 / night

                                Distance approx 9.33 miles from Windsor Hills Resort Show on Map

                                  4

                                  Holiday private room with shared pool in Sand Lake

                                  Florida / Sand Lake

                                  1 4 2 nights min

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

                                  from £176 / night

                                  £1,226 / week

                                  Book View

                                  Responds fast!
                                  avg. 2 hours 20 minutes

                                  from £176 / night

                                  Distance approx 1.78 miles from Windsor Hills Resort Show on Map

                                    20

                                    Home accommodation in Four Corners with swimming pool

                                    Central Florida / Four Corners

                                    7 15 min stay varies

                                    • 7 bedrooms
                                    • sleeps 15
                                    • min stay varies
                                    • Swimming pool
                                    • Child friendly
                                    • Car not necessary

                                    from £219 / night

                                    £1,527 - £3,955 / week

                                    Book View

                                    from £219 / night

                                    Distance approx 8.04 miles from Windsor Hills Resort Show on Map

                                      24

                                      Holiday home with shared pool in Kissimmee

                                      Central Florida / Kissimmee

                                      3 6 2 nights min

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

                                      from £131 / night

                                      £914 / week

                                      Book View

                                      Responds fast!
                                      avg. 12 minutes

                                      from £131 / night

                                      Distance approx 8.07 miles from Windsor Hills Resort Show on Map

                                        4

                                        Orlando holiday condo rental

                                        Central Florida / Orlando

                                        2 6 7 nights min

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

                                        from £238 / night

                                        £1,661 / week

                                        Book View

                                        from £238 / night

                                        Distance approx 0.1 miles from Windsor Hills Resort Show on Map

                                          25

                                          Holiday apartment in Four Corners

                                          Central Florida / Four Corners

                                          2 8 6 nights min

                                          • 2 bedrooms
                                          • sleeps 8
                                          • 6 nights min
                                          • Swimming pool
                                          • Child friendly
                                          • Air conditioning

                                          from £201 / night

                                          £1,403 / week

                                          Book View

                                          from £201 / night

                                          Distance approx 9.56 miles from Windsor Hills Resort Show on Map

                                            16

                                            Holiday villa rental

                                            Central Florida / Kissimmee

                                            8 16 7 nights min

                                            • 8 bedrooms
                                            • sleeps 16
                                            • 7 nights min
                                            • Swimming pool
                                            • Air conditioning

                                            from £397 / night

                                            £2,778 / week

                                            Book View

                                            from £397 / night

                                            Distance approx 1.46 miles from Windsor Hills Resort Show on Map

                                            (1) Excellent 

                                              44

                                              Holiday home in Four Corners

                                              Central Florida / Four Corners

                                              7 16 3 nights min

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

                                              from £250 / night

                                              £1,744 / week

                                              Book View

                                              from £250 / night

                                              Distance approx 8.8 miles from Windsor Hills Resort Show on Map

                                              (2) Excellent 

                                                28

                                                Holiday home in Kissimmee

                                                Central Florida / Kissimmee

                                                4 12 min stay varies

                                                • 4 bedrooms
                                                • sleeps 12
                                                • min stay varies
                                                • Swimming pool
                                                • Child friendly
                                                • Air conditioning

                                                from £87 / night

                                                £606 / week

                                                Book View

                                                Responds fast!
                                                avg. 1 hour 0 minutes

                                                from £87 / night

                                                Distance approx 1.47 miles from Windsor Hills Resort Show on Map

                                                  37

                                                  Holiday villa in Kissimmee

                                                  Central Florida / Kissimmee

                                                  8 20 min stay varies

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

                                                  from £218 / night

                                                  £1,136 - £2,989 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 49 minutes

                                                  from £218 / night

                                                  Distance approx 3.3 miles from Windsor Hills Resort Show on Map

                                                  (16) Very Good 

                                                    22

                                                    Kissimmee holiday home rental

                                                    Central Florida / Kissimmee

                                                    5 10 min stay varies

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

                                                    from £132 / night

                                                    £892 - £1,586 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 1 hour 38 minutes

                                                    from £132 / night

                                                    Distance approx 4.31 miles from Windsor Hills Resort Show on Map

                                                    (10) Very Good 

                                                    Certificate of Excellence

                                                      28

                                                      Holiday villa in Davenport

                                                      Central Florida / Davenport

                                                      5 10 4 nights min

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

                                                      Certificate of Excellence

                                                      from £122 / night

                                                      £787 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 3 hours 43 minutes

                                                      from £122 / night

                                                      Distance approx 8.1 miles from Windsor Hills Resort Show on Map

                                                      (1) Very Good 

                                                        65

                                                        Holiday villa in Kissimmee

                                                        Central Florida / Kissimmee

                                                        3 8 3 nights min

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

                                                        from £87 / night

                                                        £606 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 3 hours 21 minutes

                                                        from £87 / night

                                                        Distance approx 3.08 miles from Windsor Hills Resort Show on Map

                                                          35

                                                          Four Corners holiday home rental

                                                          Central Florida / Four Corners

                                                          4 10 7 nights min

                                                          • 4 bedrooms
                                                          • sleeps 10
                                                          • 7 nights min
                                                          • Swimming pool
                                                          • Car not necessary

                                                          from £200 / night

                                                          £1,395 / week

                                                          Book View

                                                          from £200 / night

                                                          Distance approx 5.98 miles from Windsor Hills Resort Show on Map

                                                          (129) Very Good 

                                                          Certificate of Excellence

                                                            29

                                                            Holiday hotel apartment with golf nearby in Orlando

                                                            Central Florida / Orlando

                                                            3 6 3 nights min

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

                                                            Certificate of Excellence

                                                            from £88 / night

                                                            £612 / week

                                                            Book View

                                                            from £88 / night

                                                            Distance approx 10.01 miles from Windsor Hills Resort Show on Map

                                                              20

                                                              Villa rental in Kissimmee

                                                              Central Florida / Kissimmee

                                                              2 8 7 nights min

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

                                                              from £238 / night

                                                              £166,084 / week

                                                              Book View

                                                              from £238 / night

                                                              Distance approx 7.61 miles from Windsor Hills Resort Show on Map

                                                                15

                                                                Holiday home rental

                                                                Central Florida / Davenport

                                                                6 14 3 nights min

                                                                • 6 bedrooms
                                                                • sleeps 14
                                                                • 3 nights min
                                                                • Swimming pool
                                                                • Child friendly
                                                                • Air conditioning

                                                                from £219 / night

                                                                £1,530 / week

                                                                Book View

                                                                from £219 / night

                                                                Distance approx 7.63 miles from Windsor Hills Resort Show on Map

                                                                  14

                                                                  Holiday home with swimming pool in Kissimmee

                                                                  Central Florida / Kissimmee

                                                                  5 11 min stay varies

                                                                  • 5 bedrooms
                                                                  • sleeps 11
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Car not necessary

                                                                  from £185 / night

                                                                  £1,291 - £2,901 / week

                                                                  Book View

                                                                  from £185 / night

                                                                  Distance approx 10.32 miles from Windsor Hills Resort Show on Map

                                                                    13

                                                                    Holiday apartment in Orlando

                                                                    Central Florida / Orlando

                                                                    1 4 7 nights min

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

                                                                    from £132 / night

                                                                    £700 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 2 hours 43 minutes

                                                                    from £132 / night

                                                                    Distance approx 0.1 miles from Windsor Hills Resort Show on Map

                                                                    (2) Very Good 

                                                                      24

                                                                      Home rental in Kissimmee with swimming pool

                                                                      Central Florida / Kissimmee

                                                                      5 10 min stay varies

                                                                      • 5 bedrooms
                                                                      • sleeps 10
                                                                      • min stay varies
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 95 km
                                                                      • Swimming pool

                                                                      from £140 / night

                                                                      £979 / week

                                                                      Book View

                                                                      from £140 / night

                                                                      Distance approx 3.31 miles from Windsor Hills Resort Show on Map

                                                                        92

                                                                        Holiday home with golf nearby in Kissimmee

                                                                        Central Florida / Kissimmee

                                                                        9 18 5 nights min

                                                                        • 9 bedrooms
                                                                        • sleeps 18
                                                                        • 5 nights min
                                                                        • Swimming pool
                                                                        • Child friendly
                                                                        • Air conditioning

                                                                        from £306 / night

                                                                        £2,142 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 2 hours 10 minutes

                                                                        from £306 / night

                                                                        Distance approx 4.76 miles from Windsor Hills Resort Show on Map

                                                                        (3) Very Good 

                                                                          24

                                                                          Villa rental in Davenport with golf nearby

                                                                          Davenport / Highlands Reserve Golf Course

                                                                          4 8 5 nights min

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

                                                                          from £103 / night

                                                                          £722 - £1,002 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 3 hours 26 minutes

                                                                          from £103 / night

                                                                          Distance approx 2.68 miles from Windsor Hills Resort Show on Map

                                                                            15

                                                                            Holiday home in Four Corners

                                                                            Central Florida / Four Corners

                                                                            9 22 min stay varies

                                                                            • 9 bedrooms
                                                                            • sleeps 22
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £297 / night

                                                                            £2,010 - £4,367 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 3 hours 46 minutes

                                                                            from £297 / night

                                                                            Distance approx 10.28 miles from Windsor Hills Resort Show on Map

                                                                            (3) Very Good 

                                                                              19

                                                                              Holiday condo with shared pool in Orlando

                                                                              Central Florida / Orlando

                                                                              2 8 7 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 8
                                                                              • 7 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Nearest beach 101 km
                                                                              • Swimming pool

                                                                              from £188 / night

                                                                              £1,312 / week

                                                                              Book View

                                                                              from £188 / night

                                                                              Distance approx 0.1 miles from Windsor Hills Resort Show on Map

                                                                                31

                                                                                Holiday home in Four Corners

                                                                                Central Florida / Four Corners

                                                                                4 8 min stay varies

                                                                                • 4 bedrooms
                                                                                • sleeps 8
                                                                                • min stay varies
                                                                                • Child friendly

                                                                                from £114 / night

                                                                                £796 / week

                                                                                Book View

                                                                                from £114 / night

                                                                                Distance approx 8.56 miles from Windsor Hills Resort Show on Map

                                                                                (23) Very Good 

                                                                                  30

                                                                                  Villa rental in Kissimmee with swimming pool

                                                                                  Central Florida / Kissimmee

                                                                                  3 6 5 nights min

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

                                                                                  from £132 / night

                                                                                  £656 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 2 hours 17 minutes

                                                                                  from £132 / night

                                                                                  Top Destination reviews

                                                                                  Windsor Hills Townhouse, 3 bedrooms, 3 bathrooms
                                                                                  Perfect 'home from home' with great location

                                                                                  This townhouse has a ‘home from home’ feel to it, very clean and well equipped with all the essentials and we were ready to start our holiday right away. Overall, it is spacious and the bedrooms are a good size, with comfortable beds (plenty of pillows and bed linen). Having 3 bathrooms made getting up and out of the house quicker and easier. Especially with having the parks at just a stone’s throw away! (Disney at just a 10 minutes’ drive and Universal just 20 minutes). There are also plenty of restaurants around. The living and kitchen areas are great places to start and end the day with all the necessities needed in the kitchen. The pool area was the perfect touch as well when you want to chill out after a long day at the parks, plenty of space to splash around or enjoy the sunshine. The pool was warm and very clean. If a larger pool is what you want, the complex also has a big shared pool with plenty of loungers and we loved spending the day there. Overall, renting this townhouse was the best way to go. I would definitely recommend and come back here as me and the kids loved it!see more
                                                                                  Windsor Hills 5BR/ 5BA SF Pool Villa,3MI to disney
                                                                                  Great villa

                                                                                  This villa is located within Windsor Hills which is a perfect location as it's very near Disney. The villa was clean and presented well. We had a few little niggles but I do need to complement both Jennifer and her local management company on response rate and resolution. Thanks … see more
                                                                                  Executive Villa, Pool, Hot tub, WiFi, Games Room
                                                                                  Excellent Villa highly recommend it, great location.

                                                                                  Property was excellent, close to Disney and places to eat. The weather was nice and the complex where the villa was situated was well looked after, nice and clean and staff was pleasant. … see more
                                                                                  Dunestone Villa
                                                                                  Fantastic villa, great location!

                                                                                  Dunestone is a very smart, spacious and well-positioned villa in a great gated community. So close to Disney and only mins from the I-4 allowing easy access to all of Orlando's attractions. The owners were a pleasure to deal with and met all of our requests. We have stayed in several properties in Windsor Hills - Dunestone is most definitely our favourite to date!see more

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