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
Serving 3,043 residents across Orange County
Loved by Homeowners & Contractors
“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…”
“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…”
“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…”
“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 easy and very responsive company at Dumpster Rental. Very pleased with the service”
“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 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.”
“Very professional.. quick service.. responded my queries in time.. and most of all affordable..”
“Great price, communication and professionalism. Will use again”
“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.”
“Service and price were great. Would highly recommend!!!!!!”
“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…”
“Amazing company, great communication, great fast service. They will definitely be my go to company for whenever I need a dumpster moving forward.”
“Amazing service”
“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…”
“Very professional to work with. Dumpsters were extremely clean as well. Will use this company again.”
“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…”
“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…”
“Amazing and convenient service. So easy to book”
“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…”
“Great experience. No problems, easy policy for extensions as well. They drop in Deltona”
“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…”
“On time dumpster for construction. With quick pick up when we called for pick up.”
“Literally the best service you could ask for in every possible way!!!”
“Awesome company to work with, ready to deliver as soon as we call them and 5 star customer service👍🏼”
“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…”
“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!”
“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!”
“They where awesome!!! Don was great very informative, patient, and kind. I would definitely rent from them again”
“Super friendly and accommodating to my shifting plans. Initial dropoff occurred as scheduled with no surprises. They accommodated my request to extend the rental by 4 days. I highly recommend their…”
“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…”
“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…”
“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…”
“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 easy and very responsive company at Dumpster Rental. Very pleased with the service”
“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 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.”
“Very professional.. quick service.. responded my queries in time.. and most of all affordable..”
“Great price, communication and professionalism. Will use again”
“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.”
“Service and price were great. Would highly recommend!!!!!!”
“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…”
“Amazing company, great communication, great fast service. They will definitely be my go to company for whenever I need a dumpster moving forward.”
“Amazing service”
“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…”
“Very professional to work with. Dumpsters were extremely clean as well. Will use this company again.”
“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…”
“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…”
“Amazing and convenient service. So easy to book”
“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…”
“Great experience. No problems, easy policy for extensions as well. They drop in Deltona”
“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…”
“On time dumpster for construction. With quick pick up when we called for pick up.”
“Literally the best service you could ask for in every possible way!!!”
“Awesome company to work with, ready to deliver as soon as we call them and 5 star customer service👍🏼”
“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…”
“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!”
“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!”
“They where awesome!!! Don was great very informative, patient, and kind. I would definitely rent from them again”
“Super friendly and accommodating to my shifting plans. Initial dropoff occurred as scheduled with no surprises. They accommodated my request to extend the rental by 4 days. I highly recommend their…”
Book Your Dumpster
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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
Windermere is a town in Orange County, Florida, United States. As of the 2020 census, the town population was 3,030. It is situated on an isthmus between Lake Down and Lake Butler, and is part of the Orlando Metropolitan Statistical Area.
With an average home age of 35 years, many Windermere homeowners are investing in renovations that generate debris requiring a properly sized dumpster.
Windermere's 93% owner-occupancy rate means active home improvement across the area.
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
Nearby Waste Facilities
- Nearest Landfill
LUSCIAN HILLS LANDFILL
WEST OF HEMPLE AND BETWEEN OLD WINTER GARDEN &408 • 3.40 mi - Nearest Transfer Station
MCLEOD ROAD TRANSFER STATION
4.30 mi
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.
Dumpster Drop offers 10, 15, 20, 30, and 40-yard roll-off dumpsters throughout Windermere and ZIP code 34786. Our 10-yard dumpsters work perfectly for bathroom remodels in Keene's Pointe, while 40-yard containers accommodate major renovations in Isleworth's luxury homes. The 15 and 20-yard sizes handle most kitchen renovations and flooring projects, and 30-yard dumpsters suit whole-house cleanouts common in Windermere's 35-year-old housing stock.
Standard rental periods range from 7-14 days, with extensions available for longer projects. Given Windermere's high property standards and Orange County regulations, we recommend coordinating placement timing with your contractor to minimize neighborhood impact. Many Lake Butler and Lake Tibet residents prefer shorter rental periods for aesthetic reasons, while extensive Isleworth renovations often require extended timelines.
Accepted materials include construction debris, furniture, appliances, yard waste, and general household items common in Windermere renovations. Prohibited items include hazardous chemicals, paint, batteries, and electronics that could contaminate the lake environment. Given the town's location between Lake Down and Lake Butler, we're particularly strict about preventing materials that could impact water quality. Concrete and heavy materials require special arrangements due to weight restrictions.
Dumpsters placed on private property in Windermere typically don't require permits, making placement convenient for most homeowners in neighborhoods like Isleworth and Keene's Pointe. However, if you need street placement due to narrow driveways or landscaping concerns common in lakefront properties, Orange County may require permits. Our team assists with permit applications and coordinates with local authorities to ensure compliant placement throughout ZIP code 34786, protecting both your property and Windermere's scenic streetscapes.
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.
Neighborhoods
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