Apartments in Westside and Estates - Holiday Lettings - Holiday Rentals Westside

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16,874 Holiday homes

(52) Excellent 

    91

    Holiday villa in Kissimmee

    Kissimmee / Westside

    4 9 2 nights min

    • 4 bedrooms
    • sleeps 9
    • 2 nights min
    • Nearest beach 96 km
    • Swimming pool
    • Child friendly
    “Outstanding home, just perfect for the guys basketball trip” This home was perfect for our group. We had a few middle age guys visiting Orlando for the NCAA March Madness. A long weekend of playing basketball and watching the college kids play basketball. The house worked great for us. Lots of room for us to spread out and keep out of each others way, while still being close enough to grill out or play cards. I can't wait to bring my family back to Disney. They will love the pool and hot tub as much as we did.

    from £121 / night

    £832 - £836 / week

    Book View

    Responds fast!
    avg. 1 hour 28 minutes

    from £121 / night

    (62) Excellent 

    Certificate of Excellence

      45

      Kissimmee holiday villa rental

      Kissimmee / Westside

      4 10 min stay varies

      • 4 bedrooms
      • sleeps 10
      • min stay varies
      • Beach / lakeside relaxation
      • Swimming pool
      • Child friendly
      “Excellent house ! perfect location for the everything.” We had a fantastic holiday in Orlando. The Davella house was everything we hoped it would be and more. It was lovely and clean and had everything we needed. It was in a great location for all the Disney parks, restaurants and shopping outlets. We would recommend this house to anyone. Our 12 year old son loved the pool. The owner of the house was extremely helpful with any information we needed.

      Certificate of Excellence

      from £86 / night

      £682 - £1,088 / week

      Book View

      Responds fast!
      avg. 38 minutes

      from £86 / night

      Great rentals within 20 miles that match your search

      Distance approx 4.99 miles from Westside

        26

        Holiday villa in ChampionsGate

        Central Florida / ChampionsGate

        4 8 1 night min

        • 4 bedrooms
        • sleeps 8
        • 1 night min
        • Swimming pool
        • Child friendly
        • Air conditioning

        from £130 / night

        £906 / week

        Book View

        from £130 / night

        Distance approx 7.02 miles from Westside

          11

          Holiday villa in Loughman

          Central Florida / Loughman

          14 24 min stay varies

          • 14 bedrooms
          • sleeps 24
          • min stay varies
          • Swimming pool
          • Child friendly
          • Air conditioning

          from £418 / night

          £2,923 / week

          Book View

          from £418 / night

          Distance approx 5.33 miles from Westside

            28

            Holiday villa with swimming pool, golf nearby in ChampionsGate

            Central Florida / ChampionsGate

            5 10 min stay varies

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

            from £129 / night

            £902 / week

            Book View

            from £129 / night

            Distance approx 1.69 miles from Westside

              24

              Holiday home in Four Corners

              Central Florida / Four Corners

              6 12 3 nights min

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

              from £138 / night

              £962 / week

              Book View

              from £138 / night

              Distance approx 7.04 miles from Westside

                16

                Holiday villa in Loughman

                Central Florida / Loughman

                6 12 7 nights min

                • 6 bedrooms
                • sleeps 12
                • 7 nights min
                • Swimming pool
                • Air conditioning

                from £308 / night

                £2,156 / week

                Book View

                from £308 / night

                Distance approx 9.48 miles from Westside

                (3) Excellent 

                  43

                  Holiday villa with swimming pool, golf nearby in Davenport

                  Central Florida / Davenport

                  5 12 min stay varies

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

                  from £137 / night

                  £905 - £1,357 / week

                  Book View

                  Responds fast!
                  avg. 2 hours 2 minutes

                  from £137 / night

                  Distance approx 4.99 miles from Westside

                    16

                    Four Corners holiday villa rental

                    Central Florida / Four Corners

                    5 10 7 nights min

                    • 5 bedrooms
                    • sleeps 10
                    • 7 nights min
                    • Swimming pool
                    • Air conditioning

                    from £264 / night

                    £1,849 / week

                    Book View

                    from £264 / night

                    Distance approx 9.99 miles from Westside

                      30

                      Condo rental in Kissimmee

                      Central Florida / Kissimmee

                      2 6 4 nights min

                      • 2 bedrooms
                      • sleeps 6
                      • 4 nights min
                      • Nearest beach 65 km
                      • Swimming pool
                      • Child friendly

                      from £78 / night

                      £512 / week

                      Book View

                      Responds fast!
                      avg. 1 hour 6 minutes

                      from £78 / night

                      Distance approx 3.23 miles from Westside

                        20

                        Holiday villa with shared pool in Four Corners

                        Central Florida / Four Corners

                        1 12 7 nights min

                        • 1 bedroom
                        • sleeps 12
                        • 7 nights min
                        • Swimming pool
                        • Air conditioning

                        from £497 / night

                        £3,473 / week

                        Book View

                        from £497 / night

                        Distance approx 8.22 miles from Westside

                          63

                          Holiday apartment with golf nearby in Celebration

                          Central Florida / Celebration

                          2 6 min stay varies

                          • 2 bedrooms
                          • sleeps 6
                          • min stay varies
                          • Swimming pool
                          • Child friendly
                          • Car not necessary

                          from £137 / night

                          £953 / week

                          Book View

                          from £137 / night

                          Distance approx 1.34 miles from Westside

                            25

                            Holiday villa in Four Corners

                            Central Florida / Four Corners

                            5 12 3 nights min

                            • 5 bedrooms
                            • sleeps 12
                            • 3 nights min
                            • Nearest beach 120 km
                            • Swimming pool
                            • Child friendly

                            from £274 / night

                            £1,916 / week

                            Book View

                            from £274 / night

                            Distance approx 4.41 miles from Westside

                            (17) Excellent 

                            Certificate of Excellence

                              27

                              Villa rental in Davenport

                              Central Florida / Davenport

                              4 8 min stay varies

                              • 4 bedrooms
                              • sleeps 8
                              • min stay varies
                              • Nearest beach 126 km
                              • Swimming pool
                              • Child friendly

                              Certificate of Excellence

                              from £73 / night

                              £767 - £1,022 / week

                              Book View

                              Responds fast!
                              avg. 1 hour 14 minutes

                              from £73 / night

                              Distance approx 11.58 miles from Westside

                              (57) Excellent 

                              Certificate of Excellence

                                90

                                Villa rental in Kissimmee with swimming pool

                                Kissimmee / Eagle Pointe

                                3 6 min stay varies

                                • 3 bedrooms
                                • sleeps 6
                                • min stay varies
                                • Beach / lakeside relaxation
                                • Swimming pool
                                • Child friendly

                                Certificate of Excellence

                                from £92 / night

                                £722 / week

                                Book View

                                Responds fast!
                                avg. 2 hours 49 minutes

                                from £92 / night

                                Distance approx 12.27 miles from Westside

                                (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 £196 / night

                                  £1,369 / week

                                  Book View

                                  from £196 / night

                                  Distance approx 2.78 miles from Westside

                                  (8) Excellent 

                                  Certificate of Excellence

                                    24

                                    Clermont holiday townhouse rental

                                    Lake County / Clermont

                                    3 8 min stay varies

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

                                    Certificate of Excellence

                                    from £114 / night

                                    £799 / week

                                    Book View

                                    from £114 / night

                                    Distance approx 3.79 miles from Westside

                                      15

                                      Kissimmee holiday condo rental

                                      Central Florida / Kissimmee

                                      3 8 1 night min

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

                                      from £96 / night

                                      £593 - £849 / week

                                      Book View

                                      Responds fast!
                                      avg. 2 hours 12 minutes

                                      from £96 / night

                                      Distance approx 7.25 miles from Westside

                                        16

                                        Holiday villa in Loughman

                                        Central Florida / Loughman

                                        5 10 7 nights min

                                        • 5 bedrooms
                                        • sleeps 10
                                        • 7 nights min
                                        • Swimming pool
                                        • Air conditioning

                                        from £242 / night

                                        £1,693 / week

                                        Book View

                                        from £242 / night

                                        Distance approx 10.53 miles from Westside

                                          40

                                          Holiday townhouse with swimming pool in Kissimmee

                                          Central Florida / Kissimmee

                                          4 12 min stay varies

                                          • 4 bedrooms
                                          • sleeps 12
                                          • min stay varies
                                          • Swimming pool
                                          • Ask owner if suitable for children
                                          • Air conditioning

                                          from £155 / night

                                          £1,080 / week

                                          Book View

                                          Responds fast!
                                          avg. 1 hour 25 minutes

                                          from £155 / night

                                          Distance approx 3.57 miles from Westside

                                            18

                                            Townhouse rental in Kissimmee

                                            Central Florida / Kissimmee

                                            3 8 2 nights min

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

                                            from £105 / night

                                            £735 / week

                                            Book View

                                            from £105 / night

                                            Distance approx 2.74 miles from Westside

                                              28

                                              Holiday home in Davenport

                                              Central Florida / Davenport

                                              5 10 7 nights min

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

                                              from £126 / night

                                              £819 / week

                                              Book View

                                              from £126 / night

                                              Distance approx 4.88 miles from Westside

                                              (68) Excellent 

                                                29

                                                Clermont holiday villa rental

                                                Lake County / Clermont

                                                4 8 min stay varies

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

                                                from £96 / night

                                                £639 - £840 / week

                                                Book View

                                                Responds fast!
                                                avg. 2 hours 27 minutes

                                                from £96 / night

                                                Distance approx 12.03 miles from Westside

                                                (20) Excellent 

                                                  18

                                                  Kissimmee holiday villa rental

                                                  Kissimmee / Cumbrian Lakes

                                                  4 8 5 nights min

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

                                                  from £90 / night

                                                  £495 - £1,795 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 3 hours 42 minutes

                                                  from £90 / night

                                                  Distance approx 3.66 miles from Westside

                                                    27

                                                    Kissimmee holiday townhouse rental

                                                    Central Florida / Kissimmee

                                                    3 8 min stay varies

                                                    • 3 bedrooms
                                                    • sleeps 8
                                                    • min stay varies
                                                    • Child friendly
                                                    • Pet friendly

                                                    from £82 / night

                                                    £569 - £749 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 1 hour 22 minutes

                                                    from £82 / night

                                                    Distance approx 10.47 miles from Westside

                                                      85

                                                      Kissimmee holiday home rental

                                                      Central Florida / Kissimmee

                                                      5 12 min stay varies

                                                      • 5 bedrooms
                                                      • sleeps 12
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Ask owner if suitable for children
                                                      • Air conditioning

                                                      from £160 / night

                                                      £1,118 / week

                                                      Book View

                                                      from £160 / night

                                                      Distance approx 3.12 miles from Westside

                                                        20

                                                        Home rental in Davenport

                                                        Central Florida / Davenport

                                                        3 8 4 nights min

                                                        • 3 bedrooms
                                                        • sleeps 8
                                                        • 4 nights min
                                                        • Nearest beach 113 km
                                                        • Swimming pool
                                                        • Child friendly

                                                        from £118 / night

                                                        £820 / week

                                                        Book View

                                                        from £118 / night

                                                        Distance approx 8.56 miles from Westside

                                                          22

                                                          Home rental in Loughman

                                                          Central Florida / Loughman

                                                          5 9 2 nights min

                                                          • 5 bedrooms
                                                          • sleeps 9
                                                          • 2 nights min
                                                          • Nearest beach 85 km
                                                          • Swimming pool
                                                          • Child friendly

                                                          from £160 / night

                                                          £843 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 2 hours 15 minutes

                                                          from £160 / night

                                                          Distance approx 11.05 miles from Westside

                                                            27

                                                            Holiday villa in Intercession City

                                                            Florida / Intercession City

                                                            7 14 min stay varies

                                                            • 7 bedrooms
                                                            • sleeps 14
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child friendly
                                                            • Air conditioning

                                                            from £195 / night

                                                            £1,361 / week

                                                            Book View

                                                            from £195 / night

                                                            Distance approx 11.59 miles from Westside

                                                            (22) Very Good 

                                                              83

                                                              Holiday villa in Orlando

                                                              Central Florida / Orlando

                                                              3 8 3 nights min

                                                              • 3 bedrooms
                                                              • sleeps 8
                                                              • 3 nights min
                                                              • Child friendly
                                                              • Air conditioning
                                                              • Ask about pets

                                                              from £69 / night

                                                              £456 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 2 hours 36 minutes

                                                              from £69 / night

                                                              Distance approx 11.57 miles from Westside

                                                                52

                                                                Holiday villa in Kissimmee

                                                                Central Florida / Kissimmee

                                                                6 12 6 nights min

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

                                                                from £149 / night

                                                                £1,042 / week

                                                                Book View

                                                                from £149 / night

                                                                Distance approx 9.81 miles from Westside

                                                                  39

                                                                  Celebration holiday apartment rental

                                                                  Central Florida / Celebration

                                                                  2 6 min stay varies

                                                                  • 2 bedrooms
                                                                  • sleeps 6
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Car not necessary

                                                                  from £117 / night

                                                                  £816 / week

                                                                  Book View

                                                                  from £117 / night

                                                                  Distance approx 1.33 miles from Westside

                                                                    16

                                                                    Holiday villa with swimming pool in Four Corners

                                                                    Central Florida / Four Corners

                                                                    6 14 7 nights min

                                                                    • 6 bedrooms
                                                                    • sleeps 14
                                                                    • 7 nights min
                                                                    • Swimming pool
                                                                    • Air conditioning

                                                                    from £264 / night

                                                                    £1,842 / week

                                                                    Book View

                                                                    from £264 / night

                                                                    Distance approx 12.32 miles from Westside

                                                                    (3) Excellent 

                                                                      24

                                                                      Villa accommodation in Kissimmee

                                                                      Central Florida / Kissimmee

                                                                      3 6 7 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • 7 nights min
                                                                      • Nearest beach 110 km
                                                                      • Swimming pool
                                                                      • Child friendly

                                                                      from £81 / night

                                                                      £561 - £642 / week

                                                                      Book View

                                                                      from £81 / night

                                                                      Distance approx 9.3 miles from Westside

                                                                        38

                                                                        Holiday townhouse with shared pool in Kissimmee

                                                                        Central Florida / Kissimmee

                                                                        3 8 min stay varies

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

                                                                        from £90 / night

                                                                        £625 / week

                                                                        Book View

                                                                        from £90 / night

                                                                        Distance approx 7.05 miles from Westside

                                                                          15

                                                                          Holiday condo accommodation

                                                                          Central Florida / Orlando

                                                                          2 8 3 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 8
                                                                          • 3 nights min
                                                                          • Swimming pool
                                                                          • Child friendly
                                                                          • Car not necessary

                                                                          from £310 / night

                                                                          £2,167 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 44 minutes

                                                                          from £310 / night

                                                                          Distance approx 1.09 miles from Westside

                                                                            23

                                                                            Home rental in Four Corners

                                                                            Central Florida / Four Corners

                                                                            5 10 min stay varies

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

                                                                            from £160 / night

                                                                            £1,093 - £1,229 / week

                                                                            Book View

                                                                            from £160 / night

                                                                            Distance approx 4.9 miles from Westside

                                                                              33

                                                                              Holiday villa rental

                                                                              Central Florida / ChampionsGate

                                                                              5 13 min stay varies

                                                                              • 5 bedrooms
                                                                              • sleeps 13
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child friendly
                                                                              • Air conditioning

                                                                              from £183 / night

                                                                              £1,281 / week

                                                                              Book View

                                                                              from £183 / night

                                                                              Distance approx 9.17 miles from Westside

                                                                                10

                                                                                Villa rental in Orlando with shared pool

                                                                                Central Florida / Orlando

                                                                                2 8 7 nights min

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

                                                                                from £143 / night

                                                                                £1,002 / week

                                                                                Book View

                                                                                from £143 / night

                                                                                Distance approx 0.1 miles from Westside

                                                                                  51

                                                                                  Villa rental in Four Corners with swimming pool

                                                                                  Central Florida / Four Corners

                                                                                  5 12 min stay varies

                                                                                  • 5 bedrooms
                                                                                  • sleeps 12
                                                                                  • min stay varies
                                                                                  • Swimming pool
                                                                                  • Ask owner if suitable for children
                                                                                  • Air conditioning

                                                                                  from £161 / night

                                                                                  £1,122 / week

                                                                                  Book View

                                                                                  from £161 / night

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