Air Conditioning
AC repair, installation, replacement, and maintenance for Central Florida homes.
All Air Conditioning services Book Air Conditioning service When AC Gets Silly, Call Chilly BillyAC Repair,
AC Repair,
Installation &
Maintenance in
Kissimmee, FL
AC blowing warm, short-cycling, or dead in the August heat? Get upfront pricing from a licensed Central Florida crew — free replacement estimates, free second opinions, and calls answered 24/7.
- Upfront PricingApprove the price before we start
- Licensed & InsuredFL Lic. CAC1821877
- Family Owned& Operated
- 24/7 Call AnsweringBook any hour, day or night
Our Services
AC, Heating & Air Quality Services in Kissimmee & Central Florida
From AC repair to full duct installs, the Chilly Billy herd handles it all across Central Florida.
Heating
Furnace and heat pump repair, installation, and tune-ups for the short — but real — Florida winter.
All Heating services Book Heating serviceIndoor Air Quality
Duct cleaning and duct installation for healthier, more efficient airflow.
All Indoor Air Quality services Book Indoor Air Quality serviceWhat we do
The Silly-o-Meter
What’s Wrong With My AC? Check the Symptoms
Tap everything your system is doing. We’ll point to the likely culprit and the fix — a Chilly Billy tech confirms it on-site.
ChillSilly
Perfectly Chill
Nothing checked yet — nice. Keep it that way with regular maintenance.
Common AC problems we help with
- Blowing warm or weak air → AC Repair
- Weird smell from the vents → Duct Cleaning
- Electric bill keeps climbing → AC Maintenance
- Grinding, banging, or rattling → AC Repair
- Turns on and off constantly → AC Repair
- Water pooling around the unit → AC Maintenance
- No heat on a cold morning → Heating Repair
- Blows cold air in heat mode → Heating Repair
- Won't hold the temperature I set → AC Repair
The Chilly Billy Method
How Our HVAC Service Works, Step by Step
Four steps. No drama. Just fast, friendly comfort — every time.
1
Call or Book Online
Tell us what's going on. We'll confirm a time that works for you — often same-day.
2
We Show Up Ready
A licensed, uniformed Chilly Billy technician arrives on time, fully stocked.
3
Honest, Upfront Pricing
You approve the price before any work begins. No surprises, ever.
4
The AC Stops Being Silly
We fix it right the first time and clean up after ourselves — every visit.
4+Years Keeping
Florida Cool
Florida Cool
Why Choose Us
Why Central Florida Homeowners Choose Chilly Billy
Family-owned and operated, proudly serving Central Florida neighbors year-round with honest, friendly HVAC service.
Licensed & Insured Technicians
Every technician is licensed, insured and trained with the brands we install.
Honest, Upfront Pricing
You'll know the cost before we start — no surprises.
Clean, Respectful Service
We treat your home like our own, every single visit.
Calls Answered 24/7
Calls answered any hour, day or night, with after-hours service visits available across Central Florida.
Fast, Friendly & Reliable
A local crew that shows up on time and treats you like family.
Financing Available
Family Comfort Plan: HVAC Maintenance Membership
Affordable comfort starts here — join for one flat rate and start saving on every visit.
$16.59per month · or $199/year
- Two AC preventative-maintenance visits per year
- 10% off all repairs
- 10% off indoor air quality products
- 5% off new HVAC system installs
- No diagnostic charge for members
*Offers cannot be combined. See the Family Comfort Plan for full terms.
The Comfort Thermometer · Pricing, Explained
What’s in an HVAC Repair or Installation Bill?
Toggle the line items a job can include and watch the mercury rise. No mystery fees — just what the work actually involves.
Your bill, on the scale
3/7
Which lines apply depends on the job — a repair rarely needs a permit; an install in Osceola or Orange County almost always does.
- Itemized quote on request
- No diagnostic charge for Family Comfort Plan members
- Licensed & insured — FL Lic. CAC1821877
Why Homeowners Trust Us
Licensing, Warranties & Plans You Can Verify
Everything on this track is something we actually do — nothing padded.
Built for Here
How Central Florida’s Climate Wears Out Your AC
Kissimmee isn’t Ohio. Flip each card to see the local stressor — and how we handle it.
Humidity
Central Florida stays humid most of the year. A system that cools too fast doesn't run long enough to pull moisture out — rooms feel clammy even at the right temperature.
Lightning & Surges
Florida sees more lightning than any other state. Nearby strikes push surges through the grid that can fry an AC's control board or compressor.
Year-Round Load
In Kissimmee the AC runs most months of the year, so the wear a northern system takes a decade to reach shows up here much sooner.
Family Comfort Plan
Two AC preventative-maintenance visits a year, no diagnostic charge, and 10% off repairs — a plan built for a system that never really gets a season off.
Where the Herd Roams
Find Your HVAC Service Area in Central Florida
Six counties, one home base in Kissimmee. Type your city or ZIP to see if we’re your neighbors.
92 areas across 6 counties
- KissimmeeOsceola
- CelebrationOsceola
- PoincianaOsceola
- St. CloudOsceola
- Meadow WoodsOrange
- Lake NonaOrange
- Hunters CreekOrange
- OrlandoOrange
- Dr. PhillipsOrange
- MetroWestOrange
- College ParkOrange
- ConwayOrange
- Baldwin ParkOrange
- Winter ParkOrange
- WindermereOrange
- Lake MarySeminole
- LongwoodSeminole
- Altamonte SpringsSeminole
Reviews
What Our Customers Are Saying
Rated 5.0 / 5 by 222 Central Florida homeowners.
Very knowledgeable and courteous
Churchill Innovations
Oct 2026
Joshua was the best! His service was great and he got done in a timely manner. I would say the price was pretty reasonable as well. Thanks Joshua!
Phoebe Fuentes
Oct 2026
Called in to Chilly Billy and Trish got me cool again!
Mackenzie Burgess
Oct 2026
I had to call to get some information about a problem I’ve been having. Trish answered the phone and very kindly and patiently answered every question I had! If this lady is any indication of the quality of service they provide, I’ll definitely be using them in the future!
Mary Tracy
Oct 2026
I had a great experience calling Chili Billy Heating and Cooling, thanks to Trisha! She was incredibly professional, courteous, and helpful throughout the entire process. She took the time to answer all of my questions thoroughly and made sure I understood everything. Her excellent communication, patience, and professionalism truly stood out. It's refreshing to receive customer service from someone who genuinely takes the time to help and make customers feel valued. Trisha is a wonderful representation of the company, and I truly appreciate her outstanding customer service. Thank you, Trisha, for making this such a positive experience!
Rebekah Cowart
Oct 2026
I had a great experience with Josh. He diagnosed the problem right away, walked me through the repair, and made sure everything was running perfectly before he left. His customer service is excellent, and the pricing was very reasonable. If you need HVAC repair or maintenance, he’s definitely the one to call.
Shaienne Duckworth
Oct 2026
Learning Center
All Articles HVAC Tips & Guides for Central Florida Homes
Is 24-Hour HVAC Repair Really Necessary for a Leaking AC Drain Line?
Finding a puddle near your indoor air handler late at night is stressful. Discover how to safely shut down your system to stop water damage and wait comfortably for a morning fix.
2026-10-23 14:24:49Read More
AC Installation
What Mistakes Should Homeowners Avoid During AC Installation?
Five AC installation mistakes Kissimmee homeowners regret later: guessed sizing, unchecked ductwork, lowest-bid quotes, and skipped permits.
2026-07-15 09:00:00Read More
HVAC Tips
What Size Air Conditioner Does Your Home Really Need?
Why square footage alone cannot size an AC in Kissimmee, what a Manual J load calculation accounts for, and the signs a unit is the wrong size.
2026-07-03 09:00:00Read More
FAQs
HVAC Service FAQs: Pricing, Scheduling & Repairs
Are your technicians licensed and insured?
Yes. Chilly Billy Heating & Cooling is a licensed and insured Florida HVAC contractor (Lic. CAC1821877), and our technicians train in-house and with the manufacturers whose equipment we install.
Do you offer emergency AC repair?
Calls are answered 24/7, so you can book any hour — our office team during business hours and our automated after-hours agent overnight. After-hours service visits are available; same-day service when scheduling and parts allow.
What areas do you serve?
We serve Kissimmee, Orlando, St. Cloud, and surrounding Central Florida communities across Osceola, Orange, and Seminole counties.
What's included in the Family Comfort Plan?
For $199/year (or $16.59/month), members get two AC tune-ups per year, 10% off repairs, 10% off indoor air quality products, 5% off new system installs, and no diagnostic charge.
