Estagacy Insurance Group

Serving Osceola County families

Affordable Health Insurance in Kissimmee, Florida

Kissimmee households deserve health coverage that fits the budget and the way they work. 8 out of 10 people may qualify for health coverage starting at $10/month or less, and our free eligibility check tells you in about 30 seconds whether you may be one of them.

You do not have to drive anywhere to get started. We meet Kissimmee residents by phone or video, and when you want a face-to-face conversation, our Orlando office is about a 25-minute drive up the road.

Free eligibility check

Takes about 30 seconds · Free · No obligation

(407) 974-5101

How we help Kissimmee residents

Phone and video appointments

Talk with a licensed agent from your kitchen table, your break room, or your car between jobs. We share our screen, walk through each plan together, and answer questions in plain language. Spanish-speaking households are always welcome to ask for help.

A quick trip to our Orlando office

If you would rather sit down in person, our office on S Kirkman Rd is roughly 25 minutes from downtown Kissimmee. Many Osceola County clients combine a visit with other errands in town.

Network checks before you choose

A low premium means little if your pediatrician is out of network. We check whether your doctors and hospitals are in-network, including systems many local families use, such as AdventHealth and Orlando Health, before you commit to a plan.

Income estimates that make sense

Tips, overtime and busy seasons can make yearly income hard to predict. We help you build a realistic estimate so the financial help based on your income is set correctly from the start.

We also help residents across Osceola County and the surrounding communities, including:St. CloudCelebrationPoincianaHunters Creek

Who we help

Families

From toddlers to teenagers, we help Kissimmee parents find one plan for the whole household and check whether the kids may qualify for Florida KidCare through CHIP or Medicaid.

Self-employed and gig workers

Vacation rental cleaners, handymen, delivery drivers and small shop owners can shop the Marketplace directly. You may qualify for financial help based on your income even though no employer offers a plan.

People losing job-based coverage

Tourism and service jobs along US-192 can change quickly. If your employer coverage ends, a Special Enrollment Period usually lets you pick a new plan, and we move fast to keep gaps short.

Early retirees under 65

Retired a few years before Medicare? A Marketplace plan can carry you to 65, and we help you understand how pension or savings withdrawals affect the help you receive.

Key 2027 dates

Busy tourist seasons can make it easy to lose track of deadlines. Here is the calendar Kissimmee families should keep handy:

  • Open Enrollment for 2027 coverage runs November 1 to December 15, 2026.
  • Enroll by December 15, 2026 for coverage starting January 1, 2027.
  • Outside Open Enrollment you need a Special Enrollment Period (moving, losing coverage, marriage, a baby).
  • Medicaid and CHIP can be applied for any time.

If a move, new job, or new baby changed things for your family, ask us whether a Special Enrollment Period applies.

Kissimmee health insurance FAQ

No. Most Kissimmee clients work with us entirely by phone or video. If you would like to meet in person, our Orlando office is about 25 minutes away and open Monday through Friday.

Yes, many people with changing hours may qualify for financial help based on your income. We help you estimate your yearly income and explain how to report changes during the year. That keeps your help accurate and avoids surprises at tax time.

Possibly. Children in many households qualify for Medicaid or CHIP, which you can apply for any time of year. We look at the whole family to see which mix of options may work best.

Networks vary from plan to plan, so we check before you enroll. We confirm whether your doctors and hospitals, such as AdventHealth or Orlando Health, are in-network. Then we show you only the plans that fit.

For many self-employed people it is a strong option, since eligibility for help is based on household income rather than an employer. We compare plans side by side and explain deductibles and copays in plain terms. The review is free.

See all Florida health insurance help. Learn more on our coverage benefits page or read the full health insurance FAQ. We also serve OrlandoSanfordWest Palm Beach.

Get free help in Kissimmee today

Kissimmee families can get answers without leaving home. Book a phone or video appointment, or call now to speak with a licensed agent.

We also speak Haitian Creole - Nou pale Kreyòl.

Need dental or vision too? See dental & vision plans