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🏠 Top 5 · 2026📍 Kissimmee, FL

The 5 best roofing contractors in Kissimmee.

The one thing between your family and the weather.

Chosen by our review committee · Google ratings as of November 9, 2026 · Companies cannot pay to be listed

Roofing Contractors at work
1
Heart Of Florida Roofing
★★★★★ 5.0 · 376 reviews

Hail, wind and sun are hard on a roof. The best roofing contractors in Kissimmee inspect honestly, work with your insurance when a claim is real, and install shingle, metal or tile systems with the underlayment and flashing done right.

  1. 1

    Heart Of Florida Roofing

    🏆 Best roofing contractor in Kissimmee
    ★★★★★ 5.0· 376 Google reviews

    A 5.0 Google rating with 376 reviews behind it puts Heart Of Florida Roofing in rare company. That many reviews is hard to fake and harder to keep that high. Based right in Kissimmee, it takes the top spot among roofing contractors in Kissimmee this year.

    📍 22 W Monument Ave Ste 31, Kissimmee, FL 34741
  2. 2
    ★★★★★ 5.0· 129 Google reviews

    Southeast Roofing & Contracting LLC holds a perfect 5.0 on Google across 129 reviews. A solid body of feedback for a local roofing contractor. Based right in Kissimmee, it lands at #2 on our Kissimmee list.

    📍 4423 S Orange Blossom Trail, Kissimmee, FL 34746
  3. 3
    ★★★★★ 4.9· 356 Google reviews

    With 356 Google reviews averaging 4.9, CFL Roofing | Roofing Contractors in Central Florida has earned its place here. That many reviews is hard to fake and harder to keep that high. Based in Orlando, it rounds out the top three for Kissimmee.

    📍 9500 Satellite Blvd Ste 150, Orlando, FL 32837
  4. 4
    ★★★★★ 4.9· 218 Google reviews

    With 218 Google reviews averaging 4.9, Heart Of Florida Roofing has earned its place here. That many reviews is hard to fake and harder to keep that high. Based in Orlando, it rounds out the top four for Kissimmee.

    📍 2661 Muscatello St, Orlando, FL 32837
  5. 5
    ★★★★★ 5.0· 63 Google reviews

    Every one of Top Rank Builder and Roofing - Florida General Contractor's 63 Google reviews averages out to a flawless 5.0. A solid body of feedback for a local roofing contractor. Based right in Kissimmee, it rounds out the top five for Kissimmee.

    📍 862 Duncan Ave, Kissimmee, FL 34744
How this list was made

Picked by people who read the reviews.

Our review committee researched roofing contractors serving Kissimmee and the surrounding area, read consumer reviews across the web, and settled on these five. We look at how many people have reviewed a company, what they say, and how the company holds up over time. We keep the full recipe to ourselves so it cannot be gamed. Google ratings shown are as of November 9, 2026. No company paid to be here, and none can. More on how we choose →

Before you sign

How to hire a roofing contractor in Kissimmee

1

Ask for proof of insurance and a local, physical address. Storm chasers leave town.

2

Get the manufacturer warranty and the workmanship warranty in writing, separately.

3

Make sure the quote includes tear-off, decking repairs, underlayment, flashing and disposal.

4

Never sign over an insurance check or an assignment of benefits before the work is done.

Good to know

Roofing Contractor questions, answered

How long does a roof replacement take?

Most single-family roofs are replaced in one to three days, depending on size, pitch and material.

Can I put new shingles over old ones?

Some codes allow one overlay, but a full tear-off lets the crew inspect the decking and lasts longer. Most reputable roofers recommend tear-off.

How do I know if hail damaged my roof?

Look for dented gutters, vents and AC fins at ground level. If those show hits, have a roofer inspect the shingles before filing a claim.

For the winners

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#1 Roofing Contractor in Kissimmee, FL 2026
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#2 Roofing Contractor in Kissimmee, FL 2026
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#3 Roofing Contractor in Kissimmee, FL 2026
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#4 Roofing Contractor in Kissimmee, FL 2026
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#5 Roofing Contractor in Kissimmee, FL 2026
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