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 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…”
“Good”
“Very good communication and reliable”
“Always reliable and great service! They attend to your needs on a timely manner. Highly recommended”
“I use them for my relo company in Orlando. Great service, great prices.”
“Service and price were great. Would highly recommend!!!!!!”
“Awesome company to work with, ready to deliver as soon as we call them and 5 star customer service👍🏼”
“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…”
“I like the service the where great and good price I love them I would recommend them anytime”
“Great price, communication and professionalism. Will use again”
“Amazing and convenient service. So easy to book”
“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”
“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…”
“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, it has been great to work with Donnie! We highly recommend them.”
“Awesome! Great job!”
“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.”
“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 searching for a dumpster in a hurry because we needed to clear out our garage by the next day. I called this company and Beau along with his team was able to drop off the dumpster that…”
“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…”
“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…”
“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…”
“They where awesome!!! Don was great very informative, patient, and kind. I would definitely rent from them again”
“"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…”
“Fast, efficiency and very helpful. Recommend. I have use their seẻvice 3 times and no problem”
“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…”
“Dumpster Drop Dumpster Rental aided in making what could have been a stressful process easier. I was coordinating the cleanout of my mother’s home from out of state and needed the dumpster delivered…”
“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…”
“Great 👍 👌”
“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…”
“Good”
“Very good communication and reliable”
“Always reliable and great service! They attend to your needs on a timely manner. Highly recommended”
“I use them for my relo company in Orlando. Great service, great prices.”
“Service and price were great. Would highly recommend!!!!!!”
“Awesome company to work with, ready to deliver as soon as we call them and 5 star customer service👍🏼”
“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…”
“I like the service the where great and good price I love them I would recommend them anytime”
“Great price, communication and professionalism. Will use again”
“Amazing and convenient service. So easy to book”
“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”
“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…”
“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, it has been great to work with Donnie! We highly recommend them.”
“Awesome! Great job!”
“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.”
“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 searching for a dumpster in a hurry because we needed to clear out our garage by the next day. I called this company and Beau along with his team was able to drop off the dumpster that…”
“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…”
“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…”
“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…”
“They where awesome!!! Don was great very informative, patient, and kind. I would definitely rent from them again”
“"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…”
“Fast, efficiency and very helpful. Recommend. I have use their seẻvice 3 times and no problem”
“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…”
“Dumpster Drop Dumpster Rental aided in making what could have been a stressful process easier. I was coordinating the cleanout of my mother’s home from out of state and needed the dumpster delivered…”
“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…”
“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
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 115 reviews • 10 days included • No hidden fees