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
“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…”
“Awesome! Great job!”
“Excellent Customer service, fast response. Flawless delivery. I will definitely will contact Dumpster Drop LLC for my future projects.”
“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!”
“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…”
“They are one of the best dumpster companies in the business! I would recommend to anyone”
“This company made my life so much easier! Timely delivery, very reasonable pricing, clear communication — everything was literally perfect. Cannot more highly recommend!”
“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…”
“Very easy to make a reservation and quick to drop it off. Excellent communication, they're great with answering any questions or concerns you have would definitely use them again if I need it!”
“Awesome company to work with, ready to deliver as soon as we call them and 5 star customer service👍🏼”
“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…”
“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…”
“Amazing company, great communication, great fast service. They will definitely be my go to company for whenever I need a dumpster moving forward.”
“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…”
“Easy drop off to our house and pick up! Nice guys. Huge dumpster!”
“Service and price were great. Would highly recommend!!!!!!”
“Reasonable price, great communication. Highly recommended.”
“Excellent company to do businness with. A true star.”
“Very reasonable and very professional! Easy to deal with. Makes a contractors job much easier”
“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!”
“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…”
“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…”
“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.”
“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 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…”
“Great 👍 👌”
“Great price, communication and professionalism. Will use 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.”
“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…”
“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 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…”
“Awesome! Great job!”
“Excellent Customer service, fast response. Flawless delivery. I will definitely will contact Dumpster Drop LLC for my future projects.”
“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!”
“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…”
“They are one of the best dumpster companies in the business! I would recommend to anyone”
“This company made my life so much easier! Timely delivery, very reasonable pricing, clear communication — everything was literally perfect. Cannot more highly recommend!”
“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…”
“Very easy to make a reservation and quick to drop it off. Excellent communication, they're great with answering any questions or concerns you have would definitely use them again if I need it!”
“Awesome company to work with, ready to deliver as soon as we call them and 5 star customer service👍🏼”
“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…”
“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…”
“Amazing company, great communication, great fast service. They will definitely be my go to company for whenever I need a dumpster moving forward.”
“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…”
“Easy drop off to our house and pick up! Nice guys. Huge dumpster!”
“Service and price were great. Would highly recommend!!!!!!”
“Reasonable price, great communication. Highly recommended.”
“Excellent company to do businness with. A true star.”
“Very reasonable and very professional! Easy to deal with. Makes a contractors job much easier”
“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!”
“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…”
“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…”
“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.”
“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 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…”
“Great 👍 👌”
“Great price, communication and professionalism. Will use 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.”
“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…”
“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.”
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