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
“Dumpster drop was amazing, they drop the can when they said they would. They even worked us in the schedule. The driver took extra care to place wood runners on our pavers so nothing got damaged…”
“Amazing service! Dumpster's were delivered and picked with great friendly service. Great communication from Don in the admin office to Lee the delivery guy! A true company that goes the extra mile…”
“Excellent customer service! Highly communicative, flexible options for length of rental, size of bin, etc. at the BEST PRICE in town. Would DEFINITELY use again!”
“These guys are AMAZING. I would recommend them to everyone.”
“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…”
“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…”
“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…”
“Great service...definitely recommend!”
“Had to move pretty much last minute. Bo was extremely helpful and went out of his way to accommodate what we needed. They alerted me on the exact arrival of my dumpster and the price was extremely…”
“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.”
“Great service, affordable pricing, they make the process effortless.”
“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…”
“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…”
“Excellent service and communications! Definitely would do business with them again!”
“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!”
“Excellent Customer service, fast response. Flawless delivery. I will definitely will contact Dumpster Drop LLC for my future projects.”
“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!”
“Great service and good communication. Price is competitive with other services in town if not a little better then some. Dumpster looked brand new and not a dented or abused. Would use again.”
“On time dumpster for construction. With quick pick up when we called for pick up.”
“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.”
“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…”
“Very good service. Always on time Fast reply Definitely we’ll call again for another project at home”
“Great price, communication and professionalism. Will use 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…”
“They are one of the best dumpster companies in the business! I would recommend to anyone”
“They where awesome!!! Don was great very informative, patient, and kind. I would definitely rent from them again”
“Great job! Dumpster was delivered on time and picked up without any issues. Communication was great. They informed us when the dumpster was delivered and even sent a picture to make sure it was…”
“Awesome company! Very responsive. On time. Do what they say they’re going to do. Only dumpster company I will ever work with from now on!”
“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…”
“Awesome! Great job!”
“Dumpster drop was amazing, they drop the can when they said they would. They even worked us in the schedule. The driver took extra care to place wood runners on our pavers so nothing got damaged…”
“Amazing service! Dumpster's were delivered and picked with great friendly service. Great communication from Don in the admin office to Lee the delivery guy! A true company that goes the extra mile…”
“Excellent customer service! Highly communicative, flexible options for length of rental, size of bin, etc. at the BEST PRICE in town. Would DEFINITELY use again!”
“These guys are AMAZING. I would recommend them to everyone.”
“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…”
“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…”
“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…”
“Great service...definitely recommend!”
“Had to move pretty much last minute. Bo was extremely helpful and went out of his way to accommodate what we needed. They alerted me on the exact arrival of my dumpster and the price was extremely…”
“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.”
“Great service, affordable pricing, they make the process effortless.”
“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…”
“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…”
“Excellent service and communications! Definitely would do business with them again!”
“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!”
“Excellent Customer service, fast response. Flawless delivery. I will definitely will contact Dumpster Drop LLC for my future projects.”
“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!”
“Great service and good communication. Price is competitive with other services in town if not a little better then some. Dumpster looked brand new and not a dented or abused. Would use again.”
“On time dumpster for construction. With quick pick up when we called for pick up.”
“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.”
“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…”
“Very good service. Always on time Fast reply Definitely we’ll call again for another project at home”
“Great price, communication and professionalism. Will use 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…”
“They are one of the best dumpster companies in the business! I would recommend to anyone”
“They where awesome!!! Don was great very informative, patient, and kind. I would definitely rent from them again”
“Great job! Dumpster was delivered on time and picked up without any issues. Communication was great. They informed us when the dumpster was delivered and even sent a picture to make sure it was…”
“Awesome company! Very responsive. On time. Do what they say they’re going to do. Only dumpster company I will ever work with from now on!”
“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…”
“Awesome! Great job!”
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 99 reviews • 10 days included • No hidden fees