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
“Very easy and very responsive company at Dumpster Rental. Very pleased with the service”
“Very good communication and reliable”
“The dumpster was delivered the same day it was ordered, with excellent communication throughout the process. Highly recommended—I would definitely use this service again.”
“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…”
“An easy experience with a very quick response to drop off right where I asked and the price wasn't bad for being able to use the dumbster for ten days.”
“Great experience. Good price, excellent customer service. Flexible when we needed to change pick up date. I will definetely use them again. Highly recommended!!”
“On time and great customer service from the office, plus excellent work from the driver. This is the only company I will use while in Kissimmee.”
“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…”
“Best services in town, driver was great, put Dumpster right where I needed. On time, polite, and professional. They let me keep Dumpster for extra time and even gave me a break on the price. No…”
“This company made my life so much easier! Timely delivery, very reasonable pricing, clear communication — everything was literally perfect. Cannot more highly recommend!”
“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…”
“THE BEST SERVICE IN TOWN! Such a great experience with Dumpster Drop. Excellent customer service, smooth drop-off and pick-up, and great communication. We are customers for life and will absolutely…”
“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…”
“What a great team! Dumpster Drop really knows how to treat their customers. Pricing is a great deal and the drop off and pick up could not be more smooth. Thank you Dumpster Drop!”
“Excellent company to do businness with. A true star.”
“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…”
“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…”
“I use them for my relo company in Orlando. Great service, great prices.”
“I was a bit discouraged after shopping around for a Dumpster for a few days. There is a very strong correlation between cost and quality of service. Thankfully I eventually found Dumpster Drop! I got…”
“We contacted Dumpster Drop during our new home renovation. Bo and Don were very responsive to our needs. Ended up using them for 3 rentals. Reasonable prices with great customer service. Highly…”
“Called and they delivered the dumpster same day. Bo was great at dropping the dumpster. Very tentative and answered all my questions. Highly recommend”
“If you’re reading this, don’t consider any other Dumpster Company! They are super flexible and dropped off my dumpster exactly when they promised. They picked up on my specified date and were so…”
“Our business used Dumpster Drop in October for a charity job replacing pavers at a church. Don was super helpful - he worked around our schedule and there were no hidden fees or surprises. Everything…”
“Very professional, it has been great to work with Donnie! We highly recommend them.”
“Excellent service and communications! Definitely would do business with them again!”
“Amazing company, great communication, great fast service. They will definitely be my go to company for whenever I need a dumpster moving forward.”
“Amazing and convenient service. So easy to book”
“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!”
“Just a great company to do business with. The prices are very reasonable and you get 10 days to fill dumpster, not one or two. The owner Don is great to work with. He delivered and picked up on…”
“Bo was very helpful and very responsive. He was able to get me a dumpster the same day on a last minute call. These guys are great!”
“Very easy and very responsive company at Dumpster Rental. Very pleased with the service”
“Very good communication and reliable”
“The dumpster was delivered the same day it was ordered, with excellent communication throughout the process. Highly recommended—I would definitely use this service again.”
“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…”
“An easy experience with a very quick response to drop off right where I asked and the price wasn't bad for being able to use the dumbster for ten days.”
“Great experience. Good price, excellent customer service. Flexible when we needed to change pick up date. I will definetely use them again. Highly recommended!!”
“On time and great customer service from the office, plus excellent work from the driver. This is the only company I will use while in Kissimmee.”
“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…”
“Best services in town, driver was great, put Dumpster right where I needed. On time, polite, and professional. They let me keep Dumpster for extra time and even gave me a break on the price. No…”
“This company made my life so much easier! Timely delivery, very reasonable pricing, clear communication — everything was literally perfect. Cannot more highly recommend!”
“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…”
“THE BEST SERVICE IN TOWN! Such a great experience with Dumpster Drop. Excellent customer service, smooth drop-off and pick-up, and great communication. We are customers for life and will absolutely…”
“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…”
“What a great team! Dumpster Drop really knows how to treat their customers. Pricing is a great deal and the drop off and pick up could not be more smooth. Thank you Dumpster Drop!”
“Excellent company to do businness with. A true star.”
“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…”
“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…”
“I use them for my relo company in Orlando. Great service, great prices.”
“I was a bit discouraged after shopping around for a Dumpster for a few days. There is a very strong correlation between cost and quality of service. Thankfully I eventually found Dumpster Drop! I got…”
“We contacted Dumpster Drop during our new home renovation. Bo and Don were very responsive to our needs. Ended up using them for 3 rentals. Reasonable prices with great customer service. Highly…”
“Called and they delivered the dumpster same day. Bo was great at dropping the dumpster. Very tentative and answered all my questions. Highly recommend”
“If you’re reading this, don’t consider any other Dumpster Company! They are super flexible and dropped off my dumpster exactly when they promised. They picked up on my specified date and were so…”
“Our business used Dumpster Drop in October for a charity job replacing pavers at a church. Don was super helpful - he worked around our schedule and there were no hidden fees or surprises. Everything…”
“Very professional, it has been great to work with Donnie! We highly recommend them.”
“Excellent service and communications! Definitely would do business with them again!”
“Amazing company, great communication, great fast service. They will definitely be my go to company for whenever I need a dumpster moving forward.”
“Amazing and convenient service. So easy to book”
“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!”
“Just a great company to do business with. The prices are very reasonable and you get 10 days to fill dumpster, not one or two. The owner Don is great to work with. He delivered and picked up on…”
“Bo was very helpful and very responsive. He was able to get me a dumpster the same day on a last minute call. These guys are great!”
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 115 reviews • 10 days included • No hidden fees