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
“Great service...definitely recommend!”
“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.”
“I use them for my relo company in Orlando. Great service, great prices.”
“Super fast service. Mr. Don is the most helpful person I ever seen. I was frustrated trying to find a place to rent a dumpster. Finally, I found Dumpster Drop through a Google search. Drop off at my driveway same day pick up on time and reasonable price. Best company, good servic”
“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 the best prices.”
“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 turned out bigger than expected. Each interaction has been professional and courteous”
“Excellent Customer service, fast response. Flawless delivery. I will definitely will contact Dumpster Drop LLC for my future projects.”
“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!”
“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 for you! They give you personalized detailed service from the start! They will send”
“Great service...definitely recommend!”
“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.”
“I use them for my relo company in Orlando. Great service, great prices.”
“Super fast service. Mr. Don is the most helpful person I ever seen. I was frustrated trying to find a place to rent a dumpster. Finally, I found Dumpster Drop through a Google search. Drop off at my driveway same day pick up on time and reasonable price. Best company, good servic”
“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 the best prices.”
“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 turned out bigger than expected. Each interaction has been professional and courteous”
“Excellent Customer service, fast response. Flawless delivery. I will definitely will contact Dumpster Drop LLC for my future projects.”
“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!”
“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 for you! They give you personalized detailed service from the start! They will send”
3 steps — takes less than 2 minutes
From small cleanouts to major construction — we have the right size.




Final pricing based on project type. Enter your address for exact pricing →
The right dumpster for every project — we'll help you pick the perfect size.
Moving, estate cleanouts, garage & storage decluttering. A 20 yard fits most whole-home cleanouts — typical load weighs 2-3 tons.
20 yd recommendedAsphalt 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 recommendedKitchen, 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 scopeDriveways, 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 availableTree trimming, brush, sod removal, landscape overhauls. Weight varies significantly — wet loads weigh much more than dry.
10-15 yd recommendedPost-hurricane and storm debris removal. Fallen trees, damaged fencing, roofing materials. Weight depends heavily on moisture content.
20-30 yd recommendedNew builds, additions, commercial buildouts. Our construction program includes scheduled swap-outs every 2 weeks with 8 extra days free.
30 yd • swap program availableWindermere 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
Local service, transparent pricing, reliable delivery.
Order by noon for same-day delivery across Windermere and Orange County.
Standard 10-day rentals with easy extensions.
Flat-rate pricing. No hidden fees.
We live and work in Central Florida. Our drivers know Windermere's neighborhoods and best placement spots.
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.
Dumpster delivery across every neighborhood and ZIP code.
Neighborhoods
ZIP Codes
Nearby Cities
Enter your address to see sizes, pricing, and same-day availability in Windermere.
Get Your Instant Quote →★★★★★ 5.0 from 78 reviews • 10 days included • No hidden fees