Osceola County Schools Calendar 2026-27: Winter Break, Spring Break and Rodeo Day

The School District of Osceola County in Florida has no school for students Nov. 23-27, 2026, and winter break runs Monday, Dec. 21, 2026 to Friday, Jan. 1, 2027, by its 2026/2027 School Calendar. Spring break is Mar. 15-19, 2027, and the last student day is Wednesday, May 26, 2027. This is Osceola County, Florida (Kissimmee and St. Cloud).

The calendar PDF is marked “Board Approved: 9/10/2024” and “Revised: 9/8/2026”, and it is linked from the district’s Calendars page. It applies to every school in the district “with the exception of Paths”, which has its own calendar; this story does not give those dates. The next student holiday is Veterans Day, Wednesday, Nov. 11, 2026.

Osceola County school breaks in 2026-27

Students are off Mon., Nov. 23 to Fri., Nov. 27: Nov. 23, 24, 25 and 27 are labeled “Teacher Non-workday/Student Holiday” and Thanksgiving, Nov. 26, is a teacher and student holiday. Weekdays off are our count from the district’s dates.

Break	No school for students	Weekdays off	Classes resume
Thanksgiving week	Mon., Nov. 23 to Fri., Nov. 27, 2026	5	Mon., Nov. 30, 2026 (our inference)
Winter break	Mon., Dec. 21, 2026 to Fri., Jan. 1, 2027	10	Mon., Jan. 4, 2027
Spring break	Mon., Mar. 15 to Fri., Mar. 19, 2027 (Fri., Mar. 12 also off unless used as a make-up day)	5 (6 with Mar. 12)	Mon., Mar. 22, 2027

The calendar prints “Classes Resume” on Jan. 4 and Mar. 22. The Nov. 30 return is inferred because the calendar shows no closure that day.

Osceola County spring break 2027

Spring break is Monday, Mar. 15 to Friday, Mar. 19, 2027, labeled “Spring Break – Teacher/Student Holiday”. Mar. 22 is marked “Classes Resume/First Day of 4th Grading Period”. The Friday before, Mar. 12, is labeled “Teacher Workday/Student Holiday or Emergency Make-up Day”, so students are off from Fri., Mar. 12 through Fri., Mar. 19 unless the district uses Mar. 12 to make up a lost day. Other Florida districts are compared in our Orange County calendar story and the spring break 2027 roundup.

Every Osceola County day off and early release

Date	Weekday	What the district lists
Aug. 3-7, 2026	Monday-Friday	Teachers report, preplanning (5 days)
Aug. 10, 2026	Monday	First day of school for students, first day of the first grading period
Sept. 7, 2026	Monday	Labor Day, teacher and student holiday
Sept. 25, 2026	Friday	Professional learning, student holiday
Oct. 12, 2026	Monday	Teacher workday, student holiday or emergency make-up day
Nov. 11, 2026	Wednesday	Veterans Day, teacher and student holiday
Nov. 20, 2026	Friday	Early release (Wednesday bell schedule)
Nov. 23-27, 2026	Monday-Friday	Thanksgiving week, student holiday
Dec. 18, 2026	Friday	Early release (Wednesday bell schedule)
Dec. 21, 2026 to Jan. 1, 2027	Monday-Friday	Winter break, teacher and student holiday
Jan. 8, 2027	Friday	Teacher workday, student holiday or emergency make-up day
Jan. 18, 2027	Monday	Martin Luther King Jr. Day (“Martin L. King, Jr. Day” on the calendar), teacher and student holiday
Feb. 19, 2027	Friday	Rodeo Day, teacher non-workday and student holiday
Mar. 11, 2027	Thursday	Early release (Wednesday bell schedule)
Mar. 12, 2027	Friday	Teacher workday, student holiday or emergency make-up day
Mar. 15-19, 2027	Monday-Friday	Spring break, teacher and student holiday
May 26, 2027	Wednesday	Last student day, end of the fourth grading period
May 27, 2027	Thursday	Teacher workday, last teacher day or emergency make-up day

The calendar marks no holiday on Feb. 15, 2027, Presidents’ Day. Plan the first break on the November 2026 calendar.

What is Rodeo Day on the Osceola County calendar?

Friday, Feb. 19, 2027 is labeled “Rodeo Day – Teacher Non-workday/Student Holiday”. The calendar does not name the event or say more, so this story does not either.

Osceola County early release days in 2026-27

The calendar sets Early Release Days (Wednesday Bell Schedule) “on the last student days before Thanksgiving, Winter, and Spring Breaks during the 2026-27 school year (e.g., Friday, November 20, 2026; Friday, December 18, 2026; and Thursday, March 11, 2027).” It also lists three dates without early release Wednesdays: March 31, 2027, May 5, 2027 and May 12, 2027.

Can the Osceola County last day of school move?

It can. The last student day is Wednesday, May 26, 2027, marked “End of 4th Grading Period – Last Student Day”, and Thursday, May 27 is a “Teacher Workday/Last Teacher Day or Emergency Make-up Day”. The calendar says: “If two (2) Emergency Make-Up Days for the 2026-27 school year are not used, then the last student day shall adjust up to two (2) workdays earlier within the Academic Calendar (May 26, 2027 to May 24, 2027).” That applies only “If the School District meets the minimum requirements in applicable state law for instructional minutes for students.”

The four emergency make-up days are Oct. 12 (already past), Jan. 8, Mar. 12 and May 27. The calendar adds: “If additional emergency make-up days are required beyond the four noted above, they will be assigned based on the circumstances at time of occurrence.” The calendar counts 180 student days. Memorial Day, May 31, falls after the last student day.

When does the 2027-28 Osceola County school year start?

The district’s 2027/2028 School Calendar is marked “Board Approved: 10/06/2026”. Students start Tuesday, Aug. 10, 2027, and the last student day is Thursday, May 25, 2028.

When does the Osceola County school year start and end in 2026-27?

Students start Monday, Aug. 10, 2026, and finish Wednesday, May 26, 2027. Teachers report Aug. 3-7. The free printable puts the district’s dates on one page, and our printable school-year calendar page has more layouts.