The short answer
A child who turns 5 on or before September 1, 2027 can start kindergarten in 2027-28. Families in Kissimmee have three paths: the zoned public school, a district choice or charter school, or a private school, usually with a Step Up For Students scholarship.
The district's School Choice window for 2027-28 opens November 19, 2026 and closes January 25, 2027. Step Up's 2027-28 applications are expected to open around February 1, 2027. Both come before spring kindergarten registration.
Is my child old enough?
Florida lets a child start kindergarten if they turn 5 on or before September 1 of that school year. For 2027-28, that means a birthday on or before September 1, 2022.
If your child turns 5 after September 1, they start kindergarten the following year, and free VPK is the usual step in between.
Path one: your zoned public school
Your zoned elementary school is set by your home address. There is no application, only registration. The School District of Osceola County publishes kindergarten registration dates for the coming year in the spring, so check osceolaschools.net early in 2027.
Path two: district choice, magnet and charter schools
To attend a district school other than your zoned one, including magnet programs, you apply in the School Choice window. For 2027-28 the Osceola dates are:
- November 19, 2026. School Choice and magnet applications open.
- January 8, 2027. Magnet applications close.
- January 25, 2027. School Choice applications close.
- February 5, 2027. School Choice lottery.
- February 12, 2027. Families are notified.
Charter schools run their own windows
Charter schools are tuition-free public schools with their own applications, separate from School Choice. Many hold enrollment lotteries in winter, so apply directly to each one you are considering and ask for its lottery date.
Path three: private school with a Step Up scholarship
Step Up For Students scholarships pay private kindergarten tuition at participating schools, and the average award is around $8,000. Step Up already runs an interest list for 2027-28, and last year its applications opened on February 1, so expect the 2027-28 season to open around February 1, 2027.
Apply early in the season. Funding goes to priority applicants first, and for 2026-27 new-student applications close on November 15, 2026, so the window is not open all year. You can apply to Step Up before you choose a school, and you apply to the school separately.
Coming from a Montessori preschool
Several preschools in Kissimmee use Montessori or Montessori-inspired methods, some of them free. Most stop before kindergarten, and most elementary schools nearby teach from textbook programs instead.
If your child has thrived with hands-on materials and choosing their own work, look for a kindergarten that continues that way of learning, so the change in August is a step forward rather than a reset.
The 2027-28 kindergarten timeline
Dates set by the district and expected from Step Up, as of October 2026.
- Now to November 2026. Visit schools while classes are in session.
- November 19, 2026. Osceola School Choice and magnet windows open.
- January 8, 2027. Magnet window closes.
- January 25, 2027. School Choice window closes.
- Around February 1, 2027. Step Up 2027-28 applications expected to open.
- February 12, 2027. School Choice notifications.
- Spring 2027. District kindergarten registration at zoned schools.
- September 1, 2027. Your child must be 5 by this date.
Where SWREA fits
SWREA's kindergarten is a Christ-centered Montessori classroom on Michigan Avenue, shared with 1st grade. Children start phonics on the first day, work with hands-on materials in English and Spanish, and learn twelve to a teacher.
Tuition is $8,000 with no registration or materials fee, so the average Step Up award covers it. There is no admissions test. If you are planning for 2027-28, visit any time and the office will walk you through the dates.
Common questions
- What is the kindergarten age cutoff in Florida?
- A child must turn 5 on or before September 1 of the school year. For 2027-28, that is a birthday on or before September 1, 2022.
- When is the Osceola County School Choice window for 2027-28?
- November 19, 2026 to January 25, 2027, with the lottery on February 5 and notifications on February 12, 2027. Magnet applications close earlier, on January 8, 2027.
- When can I apply for a Step Up scholarship for 2027-28?
- Step Up has not announced the date yet. Last year applications opened on February 1, so expect around February 1, 2027. Step Up runs an interest list in the meantime.
- Does Step Up pay for private kindergarten?
- Yes, at participating private schools. The average award is around $8,000, which covers SWREA's full kindergarten tuition.