Dumpster Rental in Winter Garden
Fast, affordable dumpster rental in Winter Garden & Orange County. Book online in minutes — delivery as soon as today.
Dumpster rentals as low as $300
*Based on availability
Serving 46,518 residents across Orange County
Loved by Homeowners & Contractors
“I had an amazing experience dumpster drop they were so sweet.Helped me with figuring out pricing and were extremely helpful would recommend to anyone moving forward.”
“I've always heard that you can't get all of these. Low price, great quality, excellent service. They got all three and are great people. We used to search for the low cost dumpster but we have used…”
“Incredible customer service and up front pricing for nice clean Dumpster rental. Needed a second dumpster mid project. They came out 30 minutes later to swap out a fresh one. Really friendly crew…”
“Good”
“Service and price were great. Would highly recommend!!!!!!”
“These guys are always on time and have great communication!! As someone who uses dumpster rental companies weekly for roofing projects. I could not recommend Dumpster Drop enough.”
“Excellent service and experience! The online order and payment process was easy and went smoothly. Everyone seemed professional, respectful, and flexible in order to meet our needs. Fast drop-off and…”
“Very professional to work with. Dumpsters were extremely clean as well. Will use this company again.”
“These guys are awesome, always on time , very accommodating to the needs needs that you have when it comes to removing trash from your property”
“I had a great experience with Dumpster Drop Dumpster Rentals from start to finish. They were punctual with both delivery and pickup, which made planning my project so much easier. The dumpster itself…”
“Great experience with this company! They respond quickly and through text so I didn’t have to call if I had a question, responded very quickly, and were accommodating to my request! Will definitely…”
“Very reasonable and very professional! Easy to deal with. Makes a contractors job much easier”
“This has by far been one of the best customer services that i have ever received! Not only was Don and Bo very accommodating with availability and response time but their service was absolutely…”
“Always reliable and great service! They attend to your needs on a timely manner. Highly recommended”
“Excellent service. There always on time and professional. Ive used this company three times with no issues only outstanding service. Would recommend to anyone needing a dumpster and they also have…”
“This company made my life so much easier! Timely delivery, very reasonable pricing, clear communication — everything was literally perfect. Cannot more highly recommend!”
“Great communication great company let us use dumpster extra days as needed highly recommend this company”
“Clean dumpster quick delivery and pick up!”
“They are one of the best dumpster companies in the business! I would recommend to anyone”
“On time dumpster for construction. With quick pick up when we called for pick up.”
“Very good communication and reliable”
“I was desperate and needed a dumpster for what ended up being a major reno ASAP. I called Don on Saturday and he had the dumpster on site Sunday morning! Most places were closed. There will only…”
“I’ve called several different companies for quotes. Don has gone above and beyond to understand my need and upon doing so, beating any quote per day that I’ve been offered. They were flexible in…”
“I used Dumpster Drop for my last dumpster service and I was very pleased with them. I called around to a couple different places and they offered the absolute best deal for how many days they let you…”
“I was truly impressed with Dumpster Drop! They were very easy to work with. They were prompt and very professional. I would highly recommend them”
“Very easy and very responsive company at Dumpster Rental. Very pleased with the service”
“Prompt ,professional, great deal for the money..communication 2nd to none..a go to everytime..”
“Amazing customer service! I got their largest dumpster and realized the day I was loading it wasn’t enough. They scrambled and got another one delivered THAT DAY! Highly recommend and great prices…”
“"I recently used Dumpster Drop for my roll-off dumpster rental needs while redoing my yard and I was extremely impressed with their level of service. The delivery was prompt and efficient, and the…”
“First time renting a dumpster, and I will say there are a lot of options out there. I went with Dumpster Drop due to their pricing, size of dumpster and the amount of days. The dumpster was delivered…”
“I had an amazing experience dumpster drop they were so sweet.Helped me with figuring out pricing and were extremely helpful would recommend to anyone moving forward.”
“I've always heard that you can't get all of these. Low price, great quality, excellent service. They got all three and are great people. We used to search for the low cost dumpster but we have used…”
“Incredible customer service and up front pricing for nice clean Dumpster rental. Needed a second dumpster mid project. They came out 30 minutes later to swap out a fresh one. Really friendly crew…”
“Good”
“Service and price were great. Would highly recommend!!!!!!”
“These guys are always on time and have great communication!! As someone who uses dumpster rental companies weekly for roofing projects. I could not recommend Dumpster Drop enough.”
“Excellent service and experience! The online order and payment process was easy and went smoothly. Everyone seemed professional, respectful, and flexible in order to meet our needs. Fast drop-off and…”
“Very professional to work with. Dumpsters were extremely clean as well. Will use this company again.”
“These guys are awesome, always on time , very accommodating to the needs needs that you have when it comes to removing trash from your property”
“I had a great experience with Dumpster Drop Dumpster Rentals from start to finish. They were punctual with both delivery and pickup, which made planning my project so much easier. The dumpster itself…”
“Great experience with this company! They respond quickly and through text so I didn’t have to call if I had a question, responded very quickly, and were accommodating to my request! Will definitely…”
“Very reasonable and very professional! Easy to deal with. Makes a contractors job much easier”
“This has by far been one of the best customer services that i have ever received! Not only was Don and Bo very accommodating with availability and response time but their service was absolutely…”
“Always reliable and great service! They attend to your needs on a timely manner. Highly recommended”
“Excellent service. There always on time and professional. Ive used this company three times with no issues only outstanding service. Would recommend to anyone needing a dumpster and they also have…”
“This company made my life so much easier! Timely delivery, very reasonable pricing, clear communication — everything was literally perfect. Cannot more highly recommend!”
“Great communication great company let us use dumpster extra days as needed highly recommend this company”
“Clean dumpster quick delivery and pick up!”
“They are one of the best dumpster companies in the business! I would recommend to anyone”
“On time dumpster for construction. With quick pick up when we called for pick up.”
“Very good communication and reliable”
“I was desperate and needed a dumpster for what ended up being a major reno ASAP. I called Don on Saturday and he had the dumpster on site Sunday morning! Most places were closed. There will only…”
“I’ve called several different companies for quotes. Don has gone above and beyond to understand my need and upon doing so, beating any quote per day that I’ve been offered. They were flexible in…”
“I used Dumpster Drop for my last dumpster service and I was very pleased with them. I called around to a couple different places and they offered the absolute best deal for how many days they let you…”
“I was truly impressed with Dumpster Drop! They were very easy to work with. They were prompt and very professional. I would highly recommend them”
“Very easy and very responsive company at Dumpster Rental. Very pleased with the service”
“Prompt ,professional, great deal for the money..communication 2nd to none..a go to everytime..”
“Amazing customer service! I got their largest dumpster and realized the day I was loading it wasn’t enough. They scrambled and got another one delivered THAT DAY! Highly recommend and great prices…”
“"I recently used Dumpster Drop for my roll-off dumpster rental needs while redoing my yard and I was extremely impressed with their level of service. The delivery was prompt and efficient, and the…”
“First time renting a dumpster, and I will say there are a lot of options out there. I went with Dumpster Drop due to their pricing, size of dumpster and the amount of days. The dumpster was delivered…”
Book Your Dumpster
3 steps — takes less than 2 minutes
Dumpster Sizes Available in Winter Garden
From small cleanouts to major construction — we have the right size.
Final pricing based on project type. Enter your address for exact pricing →
Projects We Handle in Winter Garden
The right dumpster for every project — we'll help you pick the perfect size.
Home Cleanouts
Moving, estate cleanouts, garage & storage decluttering. A 20 yard fits most whole-home cleanouts — typical load weighs 2-3 tons.
20 yd recommendedRoofing Projects
Asphalt shingle tear-offs — a 20 yard holds ~50 squares (~300 lbs each). Roofing tile loads can be recycled if not contaminated with other materials.
20 yd recommendedRenovation & Remodeling
Kitchen, bath, and whole-house renovations. Tile and mortar are heavy — a 10-15 yard typically handles 1-2 bathroom tear-outs.
10-20 yd depending on scopeConcrete & Heavy Debris
Driveways, sidewalks, patios, foundations. Clean concrete (rebar ok) is recyclable at a lower rate. No wood, PVC, or plant debris mixed in.
10-20 yd • recyclable pricing availableYard & Landscaping
Tree trimming, brush, sod removal, landscape overhauls. Weight varies significantly — wet loads weigh much more than dry.
10-15 yd recommendedStorm Cleanup
Post-hurricane and storm debris removal. Fallen trees, damaged fencing, roofing materials. Weight depends heavily on moisture content.
20-30 yd recommendedNew Construction
New builds, additions, commercial buildouts. Our construction program includes scheduled swap-outs every 2 weeks with 8 extra days free.
30 yd • swap program availableAbout Winter Garden, Florida
Winter Garden is a city in western Orange County, Florida, United States. Located 14 miles (23 km) west of Downtown Orlando, it is part of the Orlando metropolitan area. The population was 46,964 as of the 2020 census.
With an average home age of 20 years, many Winter Garden homeowners are investing in renovations that generate debris requiring a properly sized dumpster.
Winter Garden's 70% owner-occupancy rate means active home improvement across the area.
We deliver to all neighborhoods and ZIP codes in Winter Garden
Common Projects in Winter Garden
- Kitchen & bathroom remodels
- Roof tear-offs & replacement
- Garage & estate cleanouts
- Storm debris cleanup
- Landscaping & yard waste
- New construction & additions
What Can Go in a Dumpster?
- ✓ Furniture, appliances, junk
- ✓ Construction debris (drywall, lumber, tile)
- ✓ Roofing shingles
- ✓ Yard waste, branches, sod
- ✗ No hazardous materials, paint, tires
- ✗ No batteries, chemicals, electronics
Nearby Waste Facilities
- Nearest Landfill
REAVES ROAD LF (AKA: OCOEE LF)
12702 REAVES ROAD • 1.90 mi - Nearest Transfer Station
PORTER TRANSFER STATION
5.80 mi
Why Winter Garden Chooses Dumpster Drop
Local service, transparent pricing, reliable delivery.
Same-Day Delivery
Order by noon for same-day delivery across Winter Garden and Orange County.
Flexible Rental Periods
Standard 10-day rentals with easy extensions.
Transparent Pricing
Flat-rate pricing. No hidden fees.
Locally Operated
We live and work in Central Florida. Our drivers know Winter Garden's neighborhoods and best placement spots.
Frequently Asked Questions
Everything you need to know about renting a dumpster in Winter Garden.
We provide five roll-off dumpster sizes specifically chosen for Winter Garden's project needs: 10-yard containers for small renovations and cleanouts, 15-yard dumpsters for medium projects like kitchen or bathroom remodels, 20-yard containers for larger home improvement projects, 30-yard dumpsters for major renovations or construction debris, and 40-yard containers for extensive commercial or whole-home renovation projects common in Winter Garden's higher-income neighborhoods.
Our standard Winter Garden rental period is 7 days, which accommodates most residential projects in neighborhoods like Stoneybrook West and Independence. We offer flexible extensions for longer projects common among Winter Garden homeowners undertaking extensive renovations. Given the city's proximity to REAVES ROAD LF just 1.90 miles away, we can easily adjust pickup schedules to match your project timeline while maintaining cost-effective service.
You can dispose of construction debris, household junk, furniture, appliances (refrigerant-free), yard waste, and renovation materials common to Winter Garden's 20-year-old housing stock. We cannot accept hazardous materials, paint, chemicals, tires, batteries, or electronics. Given Winter Garden's location in Orange County, we follow all local disposal regulations and can guide you to appropriate facilities for restricted materials not accepted in our containers.
Most Winter Garden residential driveways accommodate our containers without permits, but street placement in neighborhoods like Downtown Winter Garden, Hamlin, or Waterleigh may require Orange County permits. We help coordinate any necessary permits for your 34787 ZIP code location and work with homeowner associations common in Winter Garden's master-planned communities to ensure compliant placement that doesn't interfere with neighborhood aesthetics or traffic flow. Contact Dumpster Drop at dumpsterdrop.co to schedule your Winter Garden dumpster rental and support your next home improvement project with professional waste management services designed for Central Florida's unique needs.
Helpful Guides
Everything you need to know before renting a dumpster.
What Size Dumpster Do I Need?
Compare 10, 15, 20, and 30 yard dumpsters by project type.
What Can Go in a Dumpster?
Accepted materials, prohibited items, and disposal tips.
Permits & HOA Rules
Do you need a permit? City and HOA requirements explained.
How Much Does It Cost?
Pricing breakdown by size, weight, and project type.
How Long Can I Keep It?
Rental periods, extensions, and our construction program.
Compare Orlando Companies
How DumpsterDrop compares to other dumpster rental providers.
Areas We Serve in Winter Garden
Dumpster delivery across every neighborhood and ZIP code.
Neighborhoods
Nearby Cities
Dumpsters from $300
Enter your address to see sizes, pricing, and same-day availability in Winter Garden.
Get Your Instant Quote →★★★★★ 5.0 from 115 reviews • 10 days included • No hidden fees