Vacation Rentals & Villas in Windsor Hills Resort

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

23,851 Houses

(4) Excellent 

    41

    Feb 23-March 2 special-Windsor Hills Luxury pool house/2 miles to Disney

    Kissimmee / Windsor Hills Resort

    Kissimmee house

    6 13 min stay varies

    • 6 bedrooms
    • sleeps 13
    • min stay varies
    • Swimming pool
    • Child Friendly
    • Air conditioning

    Price per night from

    $180

    Responds fast!
    avg. 1 hour 21 minutes

    Price per night from

    $180

      18

      5 Star Windsor Hills condo steps from the pool, renovated 2016

      Kissimmee / Windsor Hills Resort

      Kissimmee condo

      3 8 min stay varies

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

      Price per night from

      $114

      Price per night from

      $114

        23

        Disneys Magical Family Getaway in Windsor Hills

        Kissimmee / Windsor Hills Resort

        Kissimmee condo

        3 8 min stay varies

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

        Price per night from

        $102

        Responds fast!
        avg. 3 hours 55 minutes

        Price per night from

        $102

        (4) Excellent 

          12

          Wow Factor-Interior Designers Own 5 bed/5bath Home

          Kissimmee / Windsor Hills Resort

          Kissimmee house

          5 10 min stay varies

          • 5 bedrooms
          • sleeps 10
          • min stay varies
          • Nearest beach 129 mi
          • Swimming pool
          • Child Friendly

          Price per night from

          $201

          Price per night from

          $201

          (3) Excellent 

            36

            Martha's town house at Disney World

            Kissimmee / Windsor Hills Resort

            Kissimmee townhouse

            3 6 4 nights min

            • 3 bedrooms
            • sleeps 6
            • 4 nights min
            • Nearest beach 118 mi
            • Swimming pool
            • Child Friendly

            Price per night from

            $126

            Responds fast!
            avg. 1 hour 12 minutes

            Price per night from

            $126

            (2) Excellent 

              33

              Windsor Hills 5BR/ 5BA SF Pool Villa,3MI to disney

              Kissimmee / Windsor Hills Resort

              Kissimmee villa

              5 12 min stay varies

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

              Price per night from

              $247

              Responds fast!
              avg. 3 hours 44 minutes

              Price per night from

              $247

              (9) Excellent 

                28

                MINUTES TO WALT DISNEY WORLD'S FRONT GATE

                Kissimmee / Windsor Hills Resort

                Kissimmee condo

                3 8 2 nights min

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

                Price per night from

                $114

                Responds fast!
                avg. 1 hour 45 minutes

                Price per night from

                $114

                  38

                  Pooh's Palace in Windsor Hills

                  Kissimmee / Windsor Hills Resort

                  Kissimmee villa

                  5 10 1 night min

                  • 5 bedrooms
                  • sleeps 10
                  • 1 night min
                  • Nearest beach 105 mi
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $224

                  Responds fast!
                  avg. 36 minutes

                  Price per night from

                  $224

                  (3)  

                    14

                    Renting condo,One mile to Disney's Animal Kingdom

                    Kissimmee / Windsor Hills Resort

                    Kissimmee condo

                    3 6 3 nights min

                    • 3 bedrooms
                    • sleeps 6
                    • 3 nights min
                    • Nearest beach 143 mi
                    • Swimming pool
                    • Child Friendly

                    Price per night from

                    $103

                    Price per night from

                    $103

                    (13) Very Good 

                      24

                      Executive Villa, Pool, Hot tub, WiFi, Games Room

                      Kissimmee / Windsor Hills Resort

                      Kissimmee villa

                      6 14 3 nights min

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

                      Price per night from

                      $318

                      Responds fast!
                      avg. 1 hour 42 minutes

                      Price per night from

                      $318

                      (6) Very Good 

                        35

                        Windsor Hills Townhouse, 3 bedrooms, 3 bathrooms

                        Kissimmee / Windsor Hills Resort

                        Kissimmee townhouse

                        3 8 7 nights min

                        • 3 bedrooms
                        • sleeps 8
                        • 7 nights min
                        • Nearest beach 60 mi
                        • Swimming pool
                        • Child Friendly

                        Price per night from

                        $109

                        Price per night from

                        $109

                        (4) Excellent 

                          20

                          Windsor Hills Retreat Villa

                          Kissimmee / Windsor Hills Resort

                          Kissimmee villa

                          6 12 4 nights min

                          • 6 bedrooms
                          • sleeps 12
                          • 4 nights min
                          • Nearest beach 116 mi
                          • Swimming pool
                          • Child Friendly

                          Price per night from

                          $252

                          Price per night from

                          $252

                          (11) Very Good 

                            36

                            Beautiful 6 Bedroom Villa at Windsor Hills

                            Kissimmee / Windsor Hills Resort

                            Kissimmee villa

                            6 13 3 nights min

                            • 6 bedrooms
                            • sleeps 13
                            • 3 nights min
                            • Beach / lakeside relaxation
                            • Child Friendly
                            “Great Disney Villa!” My family loved this Villa. Check-in was easy. The rooms and beds were nicely appointed and comfortable, and my kids loved the pool. Moreover, the location is fantastic for a visit to the Disney parks, and the drive to Universal a
                            …see more

                            Price per night from

                            $264

                            Price per night from

                            $264

                              42

                              Minion Cove

                              Kissimmee / Windsor Hills Resort

                              Kissimmee condo

                              3 6 3 nights min

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

                              Price per night from

                              $137

                              Responds fast!
                              avg. 1 hour 46 minutes

                              Price per night from

                              $137

                              (15) Excellent 

                                21

                                Dunestone Villa

                                Kissimmee / Windsor Hills Resort

                                Kissimmee villa

                                6 12 min stay varies

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

                                Price per night from

                                $281

                                Price per night from

                                $281

                                (13) Excellent 

                                  18

                                  Flagstone Villa

                                  Kissimmee / Windsor Hills Resort

                                  Kissimmee villa

                                  6 12 min stay varies

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

                                  Price per night from

                                  $281

                                  Price per night from

                                  $281

                                  (4) Excellent 

                                    61

                                    Joanna and Sams holiday home from home

                                    Kissimmee / Windsor Hills Resort

                                    Kissimmee villa

                                    5 14 5 nights min

                                    • 5 bedrooms
                                    • sleeps 14
                                    • 5 nights min
                                    • Beach / lakeside relaxation
                                    • Nearest beach 64 mi
                                    • Swimming pool

                                    Price per night from

                                    $221

                                    Price per night from

                                    $221

                                    Great rentals within 20 miles that match your search

                                    Distance approx 11.89 km from Windsor Hills Resort Show on Map

                                    (5) Very Good 

                                      34

                                      Orlando / Vista Cay / 3 Bed/ 2 Bath/ Close To Att

                                      Central Florida / Orlando

                                      Orlando apartment

                                      3 6 7 nights min

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

                                      Price per night from

                                      $144

                                      Responds fast!
                                      avg. 2 hours 59 minutes

                                      Price per night from

                                      $144

                                      Distance approx 1.86 km from Windsor Hills Resort Show on Map

                                      (2) Very Good 

                                        16

                                        Emerald Island 7 bedroom villa 4 miles from Disney

                                        Central Florida / Kissimmee

                                        Kissimmee house

                                        7 16 6 nights min

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

                                        Price per night from

                                        $573

                                        Price per night from

                                        $573

                                        Distance approx 8.72 km from Windsor Hills Resort Show on Map

                                        (1) Excellent 

                                          19

                                          The Fountains- 54 Acre Luxury Family Resort

                                          Central Florida / Orlando

                                          Orlando hotel apartment

                                          2 6 4 nights min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 4 nights min
                                          • Swimming pool
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $229

                                          Price per night from

                                          $229

                                          Distance approx 0.1 km from Windsor Hills Resort Show on Map

                                            23

                                            Tinks Movie Castle

                                            Central Florida / Four Corners

                                            Four Corners villa

                                            5 12 min stay varies

                                            • 5 bedrooms
                                            • sleeps 12
                                            • min stay varies
                                            • Swimming pool
                                            • Ask about children
                                            • Air conditioning

                                            Price per night from

                                            $158

                                            Responds fast!
                                            avg. 41 minutes

                                            Price per night from

                                            $158

                                            Distance approx 5.83 km from Windsor Hills Resort Show on Map

                                            (3) Excellent 

                                              22

                                              6 Br, Amazing Pool and Jacuzzi, Beautiful Resort, Near Disney Paks

                                              Central Florida / Davenport

                                              Davenport house

                                              6 14 min stay varies

                                              • 6 bedrooms
                                              • sleeps 14
                                              • min stay varies
                                              • Swimming pool
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $264

                                              Price per night from

                                              $264

                                              Distance approx 4.2 km from Windsor Hills Resort Show on Map

                                                8

                                                Fabulous 4 bed villa with south facing private pool and spa

                                                Central Florida / Davenport

                                                Davenport house

                                                4 8 min stay varies

                                                • 4 bedrooms
                                                • sleeps 8
                                                • min stay varies
                                                • Ask about children

                                                Price per night from

                                                $138

                                                Price per night from

                                                $138

                                                Distance approx 4.63 km from Windsor Hills Resort Show on Map

                                                (1) Very Good 

                                                  4

                                                  Wyndham Bonnet Creek Resort - Close to Disney 2 BD - 2 BA Deluxe Suite

                                                  Central Florida / Orlando

                                                  Orlando condo

                                                  2 8 7 nights min

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

                                                  Price per night from

                                                  $328

                                                  Responds fast!
                                                  avg. 35 minutes

                                                  Price per night from

                                                  $328

                                                  Distance approx 1.96 km from Windsor Hills Resort Show on Map

                                                  (1) Excellent 

                                                    16

                                                    LUXURY DISNEY VILLA,WATER VIEW,WIFI, 3mi to DISNEY

                                                    Central Florida / Kissimmee

                                                    Kissimmee house

                                                    6 16 min stay varies

                                                    • 6 bedrooms
                                                    • sleeps 16
                                                    • min stay varies
                                                    • Child Friendly
                                                    “Had a blast” Plenty of room for a family of 16. Enjoyed our stay. The pool was great. Quiet neighbor hood and really close to the Disney Parks.
                                                    …see more

                                                    Price per night from

                                                    $228

                                                    Price per night from

                                                    $228

                                                    Distance approx 4.26 km from Windsor Hills Resort Show on Map

                                                      25

                                                      Bloomingdale Villa

                                                      Central Florida / Four Corners

                                                      Four Corners villa

                                                      4 8 min stay varies

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

                                                      Price per night from

                                                      $162

                                                      Price per night from

                                                      $162

                                                      Distance approx 4.12 km from Windsor Hills Resort Show on Map

                                                        26

                                                        My Disney Dream Home

                                                        Central Florida / Four Corners

                                                        Four Corners house

                                                        5 12 3 nights min

                                                        • 5 bedrooms
                                                        • sleeps 12
                                                        • 3 nights min
                                                        • Child Friendly

                                                        Price per night from

                                                        $144

                                                        Price per night from

                                                        $144

                                                        Distance approx 6.89 km from Windsor Hills Resort Show on Map

                                                          31

                                                          Big house, Located Minutes from Disney-World 55

                                                          Central Florida / Kissimmee

                                                          Kissimmee house

                                                          4 8 3 nights min

                                                          • 4 bedrooms
                                                          • sleeps 8
                                                          • 3 nights min
                                                          • Swimming pool
                                                          • Ask about children
                                                          • Air conditioning

                                                          Price per night from

                                                          $149

                                                          Price per night from

                                                          $149

                                                          Distance approx 6.05 km from Windsor Hills Resort Show on Map

                                                            44

                                                            1625 Morning Star Drive Villa #52106

                                                            Central Florida / Four Corners

                                                            Four Corners villa

                                                            5 10 3 nights min

                                                            • 5 bedrooms
                                                            • sleeps 10
                                                            • 3 nights min
                                                            • Swimming pool
                                                            • Car not necessary
                                                            • Air conditioning

                                                            Price per night from

                                                            $174

                                                            Responds fast!
                                                            avg. 3 hours 35 minutes

                                                            Price per night from

                                                            $174

                                                            Distance approx 6.91 km from Windsor Hills Resort Show on Map

                                                              26

                                                              1 BDRM CONDO STAR ISLAND RESORT & CLUB~ HEATED POOLS, LAKE CECILE, OLD TOWN AREA

                                                              Florida / Old Town

                                                              Old Town condo

                                                              1 4 1 night min

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

                                                              Price per night from

                                                              $149

                                                              Responds fast!
                                                              avg. 1 hour 16 minutes

                                                              Price per night from

                                                              $149

                                                              Distance approx 3.42 km from Windsor Hills Resort Show on Map

                                                              (15) Excellent 

                                                                24

                                                                My Disney Villa

                                                                Kissimmee / Calabria, Orlando

                                                                Kissimmee villa

                                                                5 10 min stay varies

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

                                                                Price per night from

                                                                $275

                                                                Responds fast!
                                                                avg. 3 hours 30 minutes

                                                                Price per night from

                                                                $275

                                                                Distance approx 7.45 km from Windsor Hills Resort Show on Map

                                                                (33) Excellent 

                                                                Certificate of Excellence

                                                                  47

                                                                  4 BEDROOM, 3 BATH VILLA WITH SOUTH FACING POOL ORANGE TREE -15 MINUTES TO DISNEY

                                                                  Lake County / Clermont

                                                                  Clermont villa

                                                                  4 8 7 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • 7 nights min
                                                                  • Nearest beach 129 mi
                                                                  • Swimming pool
                                                                  • Child Friendly

                                                                  Certificate of Excellence

                                                                  Price per night from

                                                                  $126

                                                                  Responds fast!
                                                                  avg. 1 hour 25 minutes

                                                                  Price per night from

                                                                  $126

                                                                  Distance approx 4.1 km from Windsor Hills Resort Show on Map

                                                                  (10) Excellent 

                                                                    29

                                                                    Disney Villa- extra large pool area (south facing)

                                                                    Davenport / Lake Davenport

                                                                    Davenport house

                                                                    4 8 7 nights min

                                                                    • 4 bedrooms
                                                                    • sleeps 8
                                                                    • 7 nights min
                                                                    • Nearest beach 140 mi
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $113

                                                                    Responds fast!
                                                                    avg. 2 hours 18 minutes

                                                                    Price per night from

                                                                    $113

                                                                    Distance approx 4.56 km from Windsor Hills Resort Show on Map

                                                                    (76) Very Good 

                                                                      27

                                                                      Villa Tropico near Disney - FREE cancellation

                                                                      Central Florida / Davenport

                                                                      Davenport villa

                                                                      3 7 4 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 7
                                                                      • 4 nights min
                                                                      • Ask about children
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $137

                                                                      Price per night from

                                                                      $137

                                                                      Distance approx 12.4 km from Windsor Hills Resort Show on Map

                                                                        21

                                                                        Lovely 5BR 3Bth Home with Private Pool, Spa and Pool Table, 15 Minutes to Disney

                                                                        Central Florida / Orlando

                                                                        Orlando house

                                                                        5 10 5 nights min

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

                                                                        Price per night from

                                                                        $176

                                                                        Responds fast!
                                                                        avg. 2 hours 12 minutes

                                                                        Price per night from

                                                                        $176

                                                                        Distance approx 12.39 km from Windsor Hills Resort Show on Map

                                                                          27

                                                                          Chic 6 bedroom 5.5 bath Watersong Resort home from $135nt

                                                                          Central Florida / Orlando

                                                                          Orlando house

                                                                          6 12 min stay varies

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

                                                                          Price per night from

                                                                          $178

                                                                          Responds fast!
                                                                          avg. 2 hours 12 minutes

                                                                          Price per night from

                                                                          $178

                                                                          Distance approx 5.35 km from Windsor Hills Resort Show on Map

                                                                          (8) Excellent 

                                                                            25

                                                                            Beautiful Orlando Villa "Mags Den" Calabay Parc

                                                                            Central Florida / Davenport

                                                                            Davenport villa

                                                                            4 8 5 nights min

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

                                                                            Price per night from

                                                                            $148

                                                                            Price per night from

                                                                            $148

                                                                            Distance approx 6.43 km from Windsor Hills Resort Show on Map

                                                                            (4) Very Good 

                                                                              29

                                                                              Join the Fun & Relax, You Deserve the Best|Premium Resort+Minutes to Disney

                                                                              Central Florida / Kissimmee

                                                                              Kissimmee townhouse

                                                                              3 7 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 7
                                                                              • min stay varies
                                                                              • Nearest beach 90 mi
                                                                              • Swimming pool
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $87

                                                                              Responds fast!
                                                                              avg. 3 hours 4 minutes

                                                                              Price per night from

                                                                              $87