Dumpster Rental in Winter Park
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
Loved by Homeowners & Contractors
“My Rep Bow was great. He called me back right away. He was knowledgeable about the dumpster and sizes. He communicated on weekends so we were able to confirm delivery. He even messaged me a day…”
“Great experience. Good price, excellent customer service. Flexible when we needed to change pick up date. I will definetely use them again. Highly recommended!!”
“I reached out at the last minute for a dumpster for a move and Dumpster Drop Dumpster not only made it easy, the customer service was top tier!! I would recommend them over and over.”
“I had a very good experience with this company very good communication I knew exactly when everything was being dropped off and picked up so I would highly recommend dealing with Bo and his crew”
“Clean dumpster quick delivery and pick up!”
“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…”
“Easy drop off to our house and pick up! Nice guys. Huge dumpster!”
“Very reasonable and very professional! Easy to deal with. Makes a contractors job much easier”
“Prompt ,professional, great deal for the money..communication 2nd to none..a go to everytime..”
“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.”
“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…”
“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…”
“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…”
“They are one of the best dumpster companies in the business! I would recommend to anyone”
“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!”
“Very professional, it has been great to work with Donnie! We highly recommend them.”
“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 service, affordable pricing, they make the process effortless.”
“Great price, communication and professionalism. Will use again”
“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…”
“Very professional.. quick service.. responded my queries in time.. and most of all affordable..”
“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…”
“Awesome company! Very responsive. On time. Do what they say they’re going to do. Only dumpster company I will ever work with from now on!”
“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.”
“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”
“Very good service. Always on time Fast reply Definitely we’ll call again for another project at home”
“Very easy and very responsive company at Dumpster Rental. Very pleased with the service”
“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…”
“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…”
“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”
“My Rep Bow was great. He called me back right away. He was knowledgeable about the dumpster and sizes. He communicated on weekends so we were able to confirm delivery. He even messaged me a day…”
“Great experience. Good price, excellent customer service. Flexible when we needed to change pick up date. I will definetely use them again. Highly recommended!!”
“I reached out at the last minute for a dumpster for a move and Dumpster Drop Dumpster not only made it easy, the customer service was top tier!! I would recommend them over and over.”
“I had a very good experience with this company very good communication I knew exactly when everything was being dropped off and picked up so I would highly recommend dealing with Bo and his crew”
“Clean dumpster quick delivery and pick up!”
“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…”
“Easy drop off to our house and pick up! Nice guys. Huge dumpster!”
“Very reasonable and very professional! Easy to deal with. Makes a contractors job much easier”
“Prompt ,professional, great deal for the money..communication 2nd to none..a go to everytime..”
“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.”
“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…”
“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…”
“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…”
“They are one of the best dumpster companies in the business! I would recommend to anyone”
“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!”
“Very professional, it has been great to work with Donnie! We highly recommend them.”
“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 service, affordable pricing, they make the process effortless.”
“Great price, communication and professionalism. Will use again”
“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…”
“Very professional.. quick service.. responded my queries in time.. and most of all affordable..”
“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…”
“Awesome company! Very responsive. On time. Do what they say they’re going to do. Only dumpster company I will ever work with from now on!”
“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.”
“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”
“Very good service. Always on time Fast reply Definitely we’ll call again for another project at home”
“Very easy and very responsive company at Dumpster Rental. Very pleased with the service”
“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…”
“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…”
“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”
Book Your Dumpster
3 steps — takes less than 2 minutes
Dumpster Sizes Available in Winter Park
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 Winter Park
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 Winter Park, Florida
Winter 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
Common Projects in Winter Park
- 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
GRINDER LANDFILL
NAVAL TRAINING CENTER MAIN BASE • 1.50 mi - Nearest Transfer Station
MID-TOWN TRANSFER, INC.(AKA: GEMINI WASTE SERVICE)
4.10 mi
Why Winter Park Chooses Dumpster Drop
Local service, transparent pricing, reliable delivery.
Same-Day Delivery
Order by noon for same-day delivery across Winter Park 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 Winter Park's neighborhoods and best placement spots.
Frequently Asked Questions
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.
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 Winter Park
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 Winter Park.
Get Your Instant Quote →★★★★★ 5.0 from 94 reviews • 10 days included • No hidden fees