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
“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!”
“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…”
“I use them for my relo company in Orlando. Great service, great prices.”
“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 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…”
“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…”
“Easy drop off to our house and pick up! Nice guys. Huge dumpster!”
“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…”
“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 experience. Good price, excellent customer service. Flexible when we needed to change pick up date. I will definetely use them again. Highly recommended!!”
“I like the service the where great and good price I love them I would recommend them anytime”
“Good”
“Amazing and convenient service. So easy to book”
“Very good communication and reliable”
“Service and price were great. Would highly recommend!!!!!!”
“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 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!”
“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…”
“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”
“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…”
“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 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…”
“Excellent company to do businness with. A true star.”
“Very professional, it has been great to work with Donnie! We highly recommend them.”
“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…”
“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!”
“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…”
“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…”
“First time renting a dumpster, and I will say there are a lot of options out there. I went with Dumpster Drop due to their pricing, size of dumpster and the amount of days. The dumpster was delivered…”
“Our business used Dumpster Drop in October for a charity job replacing pavers at a church. Don was super helpful - he worked around our schedule and there were no hidden fees or surprises. Everything…”
“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!”
“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…”
“I use them for my relo company in Orlando. Great service, great prices.”
“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 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…”
“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…”
“Easy drop off to our house and pick up! Nice guys. Huge dumpster!”
“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…”
“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 experience. Good price, excellent customer service. Flexible when we needed to change pick up date. I will definetely use them again. Highly recommended!!”
“I like the service the where great and good price I love them I would recommend them anytime”
“Good”
“Amazing and convenient service. So easy to book”
“Very good communication and reliable”
“Service and price were great. Would highly recommend!!!!!!”
“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 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!”
“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…”
“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”
“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…”
“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 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…”
“Excellent company to do businness with. A true star.”
“Very professional, it has been great to work with Donnie! We highly recommend them.”
“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…”
“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!”
“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…”
“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…”
“First time renting a dumpster, and I will say there are a lot of options out there. I went with Dumpster Drop due to their pricing, size of dumpster and the amount of days. The dumpster was delivered…”
“Our business used Dumpster Drop in October for a charity job replacing pavers at a church. Don was super helpful - he worked around our schedule and there were no hidden fees or surprises. Everything…”
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 100 reviews • 10 days included • No hidden fees