Dumpster Rental in Windermere
Fast, affordable dumpster rental in Windermere & Orange County. Book online in minutes — delivery as soon as today.
Dumpster rentals as low as $300
*Based on availability
Loved by Homeowners & Contractors
“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…”
“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…”
“If you need a dumpster rental, they are a must hire. They are easy to get a hold of and to work with along with quick and efficient. They all also really flexible Which is rare in this line of work…”
“Hands down the best dumpster drop off/delivery company in central Florida. Both the office employees staff and delivery driver for the dumpster were kind, courteous and extremely helpful. If you live…”
“Very professional, timely, and easy to work with. Not even a scratch on the concrete driveway. Everyone we worked with was very kind and respectful as well.”
“These guys are great. I was in a time crunch and Dumpster Drop was able to schedule a drop off first thing next day. My contractor filled the 15 yard dumpster on first day. Dumpster Drop arranged for…”
“Amazing and convenient service. So easy to book”
“I like the service the where great and good price I love them I would recommend them anytime”
“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…”
“Service and price were great. Would highly recommend!!!!!!”
“After calling around I felt more comfortable with Dumpster Drop than the rest and my instinct was right! They were friendly professional and asked me questions that really helped me plan for the…”
“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 needed a dumpster on short notice, and Don was very quick to reply and get me taken care of with quality service. Highly recommend. Will be using them again!”
“Dumpster Drop was responsive, professional, and went above and beyond with delivery, (clean up, which is not their job), and removal of the dumpster. The next time we need a dumpster, they'll be our…”
“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…”
“Bo and the rest of the team at Dumpster Drop have been amazing to work with. When our 1st rental turned into 2, they swapped us out for a new one. Then they swapped us out again when the project…”
“Literally the best service you could ask for in every possible way!!!”
“Great service, affordable pricing, they make the process effortless.”
“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.”
“Very easy to make a reservation and quick to drop it off. Excellent communication, they're great with answering any questions or concerns you have would definitely use them again if I need it!”
“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…”
“Very professional.. quick service.. responded my queries in time.. and most of all affordable..”
“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 reached out at the last minute for a dumpster for a move and Dumpster Drop Dumpster not only made it easy, the customer service was top tier!! I would recommend them over and over.”
“Very professional to work with. Dumpsters were extremely clean as well. Will use this company again.”
“They where awesome!!! Don was great very informative, patient, and kind. I would definitely rent from them again”
“Super fast service. Mr. Don is the most helpful person I ever seen. I was frustrated trying to find a place to rent a dumpster. Finally, I found Dumpster Drop through a Google search. Drop off at my…”
“We have been trying to find a reliable company who would help us with our Dumpster Rental Needs. We have been having nightmares with awful companies, however that changed as soon as I saw this…”
“Dumpster Drop is a great choice for your dumpster requirements. They brought the right dumpster out when promised, and picked it up when they said. They also made it very simple and easy to extend my…”
“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…”
“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…”
“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…”
“If you need a dumpster rental, they are a must hire. They are easy to get a hold of and to work with along with quick and efficient. They all also really flexible Which is rare in this line of work…”
“Hands down the best dumpster drop off/delivery company in central Florida. Both the office employees staff and delivery driver for the dumpster were kind, courteous and extremely helpful. If you live…”
“Very professional, timely, and easy to work with. Not even a scratch on the concrete driveway. Everyone we worked with was very kind and respectful as well.”
“These guys are great. I was in a time crunch and Dumpster Drop was able to schedule a drop off first thing next day. My contractor filled the 15 yard dumpster on first day. Dumpster Drop arranged for…”
“Amazing and convenient service. So easy to book”
“I like the service the where great and good price I love them I would recommend them anytime”
“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…”
“Service and price were great. Would highly recommend!!!!!!”
“After calling around I felt more comfortable with Dumpster Drop than the rest and my instinct was right! They were friendly professional and asked me questions that really helped me plan for the…”
“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 needed a dumpster on short notice, and Don was very quick to reply and get me taken care of with quality service. Highly recommend. Will be using them again!”
“Dumpster Drop was responsive, professional, and went above and beyond with delivery, (clean up, which is not their job), and removal of the dumpster. The next time we need a dumpster, they'll be our…”
“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…”
“Bo and the rest of the team at Dumpster Drop have been amazing to work with. When our 1st rental turned into 2, they swapped us out for a new one. Then they swapped us out again when the project…”
“Literally the best service you could ask for in every possible way!!!”
“Great service, affordable pricing, they make the process effortless.”
“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.”
“Very easy to make a reservation and quick to drop it off. Excellent communication, they're great with answering any questions or concerns you have would definitely use them again if I need it!”
“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…”
“Very professional.. quick service.. responded my queries in time.. and most of all affordable..”
“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 reached out at the last minute for a dumpster for a move and Dumpster Drop Dumpster not only made it easy, the customer service was top tier!! I would recommend them over and over.”
“Very professional to work with. Dumpsters were extremely clean as well. Will use this company again.”
“They where awesome!!! Don was great very informative, patient, and kind. I would definitely rent from them again”
“Super fast service. Mr. Don is the most helpful person I ever seen. I was frustrated trying to find a place to rent a dumpster. Finally, I found Dumpster Drop through a Google search. Drop off at my…”
“We have been trying to find a reliable company who would help us with our Dumpster Rental Needs. We have been having nightmares with awful companies, however that changed as soon as I saw this…”
“Dumpster Drop is a great choice for your dumpster requirements. They brought the right dumpster out when promised, and picked it up when they said. They also made it very simple and easy to extend my…”
“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…”
Book Your Dumpster
3 steps — takes less than 2 minutes
Dumpster Sizes Available in Windermere
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 Windermere
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 Windermere, Florida
We deliver to all neighborhoods and ZIP codes in Windermere
Common Projects in Windermere
- 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
Why Windermere Chooses Dumpster Drop
Local service, transparent pricing, reliable delivery.
Same-Day Delivery
Order by noon for same-day delivery across Windermere 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 Windermere's neighborhoods and best placement spots.
Frequently Asked Questions
Everything you need to know about renting a dumpster in Windermere.
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 Windermere
Dumpster delivery across every neighborhood and ZIP code.
Nearby Cities
Dumpsters from $300
Enter your address to see sizes, pricing, and same-day availability in Windermere.
Get Your Instant Quote →★★★★★ 5.0 from 94 reviews • 10 days included • No hidden fees