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
“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…”
“Professional service drop off on time pick up on time, But more than that they are great people very nice and respectful , I highly recommend”
“Excellent Customer service, fast response. Flawless delivery. I will definitely will contact Dumpster Drop LLC for my future projects.”
“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…”
“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…”
“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…”
“I like the service the where great and good price I love them I would recommend them anytime”
“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…”
“These guys are AMAZING. I would recommend them to everyone.”
“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…”
“Great service. Don answered all of our questions and was very friendly. They were there when they said they would be. Very happy to have found them. Would recommend to anyone who needs a dumpster.”
“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…”
“Easy drop off to our house and pick up! Nice guys. Huge dumpster!”
“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…”
“Called and they delivered the dumpster same day. Bo was great at dropping the dumpster. Very tentative and answered all my questions. Highly recommend”
“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…”
“Excellent service and communications! Definitely would do business with them again!”
“The folks at Dumpster Drop went above and beyond with their service. I would not hesitate to recommend (and employ again) Dumpster Drop to anyone needing their services.”
“Amazing and convenient service. So easy to book”
“They are one of the best dumpster companies in the business! I would recommend to anyone”
“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…”
“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…”
“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…”
“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…”
“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.”
“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!”
“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!”
“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…”
“Good”
“Bo and the team at Dumpster Drop are great. Their price is fair, and their service is excellent. Will use them again when needed, and highly recommend their services.”
“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…”
“Professional service drop off on time pick up on time, But more than that they are great people very nice and respectful , I highly recommend”
“Excellent Customer service, fast response. Flawless delivery. I will definitely will contact Dumpster Drop LLC for my future projects.”
“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…”
“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…”
“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…”
“I like the service the where great and good price I love them I would recommend them anytime”
“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…”
“These guys are AMAZING. I would recommend them to everyone.”
“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…”
“Great service. Don answered all of our questions and was very friendly. They were there when they said they would be. Very happy to have found them. Would recommend to anyone who needs a dumpster.”
“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…”
“Easy drop off to our house and pick up! Nice guys. Huge dumpster!”
“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…”
“Called and they delivered the dumpster same day. Bo was great at dropping the dumpster. Very tentative and answered all my questions. Highly recommend”
“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…”
“Excellent service and communications! Definitely would do business with them again!”
“The folks at Dumpster Drop went above and beyond with their service. I would not hesitate to recommend (and employ again) Dumpster Drop to anyone needing their services.”
“Amazing and convenient service. So easy to book”
“They are one of the best dumpster companies in the business! I would recommend to anyone”
“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…”
“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…”
“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…”
“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…”
“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.”
“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!”
“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!”
“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…”
“Good”
“Bo and the team at Dumpster Drop are great. Their price is fair, and their service is excellent. Will use them again when needed, and highly recommend their services.”
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 100 reviews • 10 days included • No hidden fees