Fast, affordable dumpster rental in Winter Park & Orange County. Book online in minutes — delivery as soon as today.
Dumpster rentals as low as $300
*Based on availability
Serving 29,985 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”
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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 availableWinter Park is a city in Orange County, Florida, United States. The population was 29,795 according to the 2020 census. It is part of the Orlando–Kissimmee–Sanford, Florida Metropolitan Statistical Area.
With an average home age of 52 years, many Winter Park homeowners are investing in renovations that generate debris requiring a properly sized dumpster.
Winter Park's 65% owner-occupancy rate means active home improvement across the area.
We deliver to all neighborhoods and ZIP codes in Winter Park
Local service, transparent pricing, reliable delivery.
Order by noon for same-day delivery across Winter Park 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 Winter Park's neighborhoods and best placement spots.
Everything you need to know about renting a dumpster in Winter Park.
Dumpster Drop offers five container sizes for Winter Park residents: 10-yard dumpsters for small cleanouts and minor renovations, 15-yard containers for landscaping projects and bathroom remodels, 20-yard dumpsters for kitchen renovations and garage cleanouts, 30-yard containers for major home renovations and roofing projects, and 40-yard dumpsters for large construction projects and extensive cleanouts. The 20-yard size is most popular among Winter Park homeowners tackling typical renovation projects in the area's 52-year-old homes.
Standard rental periods range from 7-14 days, with flexible extensions available for longer projects common in Winter Park's extensive home renovations. We coordinate with Orange County regulations and Winter Park city requirements for extended placements. Most residential projects in neighborhoods like Winter Park Shores and Temple Grove complete within our standard timeframe, while larger renovations in historic homes may require extended rental periods.
Acceptable materials include construction debris, household junk, furniture, appliances (without freon), yard waste, and renovation materials typical of Winter Park's home improvement projects. Prohibited items include hazardous materials, paint, chemicals, tires, batteries, and electronics. Orange County regulations require proper disposal of these restricted materials at designated facilities. We provide guidance on acceptable materials when you book your Winter Park dumpster rental.
Winter Park typically requires permits for dumpsters placed on public streets or rights-of-way, particularly in the historic Park Avenue District and established neighborhoods like Hannibal Square. Driveway placement generally doesn't require permits but must comply with setback requirements. We assist Winter Park customers with permit requirements and coordinate with city offices to ensure compliant placement throughout all ZIP codes we serve, including proper positioning that respects Winter Park's mature tree canopy and neighborhood aesthetics.
Dumpster delivery across every neighborhood and ZIP code.
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