Dumpster Rental in Winter Garden
Fast, affordable dumpster rental in Winter Garden & Orange County. Book online in minutes — delivery as soon as today.
Dumpster rentals as low as $300
*Based on availability
Serving 46,518 residents across Orange County
Loved by Homeowners & Contractors
“Very good service. Always on time Fast reply Definitely we’ll call again for another project at home”
“Great price, communication and professionalism. Will use 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…”
“I had a great experience with Dumpster Drop Dumpster Rentals from start to finish. They were punctual with both delivery and pickup, which made planning my project so much easier. The dumpster itself…”
“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 company, great communication, great fast service. They will definitely be my go to company for whenever I need a dumpster moving forward.”
“These guys are AMAZING. I would recommend them to everyone.”
“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…”
“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…”
“Very easy and very responsive company at Dumpster Rental. Very pleased with the service”
“Excellent service and experience! The online order and payment process was easy and went smoothly. Everyone seemed professional, respectful, and flexible in order to meet our needs. Fast drop-off and…”
“I use them for my relo company in Orlando. Great service, great prices.”
“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.”
“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!”
“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.”
“"I recently used Dumpster Drop for my roll-off dumpster rental needs while redoing my yard and I was extremely impressed with their level of service. The delivery was prompt and efficient, and the…”
“Called and they delivered the dumpster same day. Bo was great at dropping the dumpster. Very tentative and answered all my questions. Highly recommend”
“Great service...definitely recommend!”
“I was desperate and needed a dumpster for what ended up being a major reno ASAP. I called Don on Saturday and he had the dumpster on site Sunday morning! Most places were closed. There will only…”
“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…”
“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…”
“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…”
“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.”
“Dumpster Drop was responsive, professional, and went above and beyond with delivery, (clean up, which is not their job), and removal of the dumpster. The next time we need a dumpster, they'll be our…”
“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…”
“Dumpster Drop is a great choice for your dumpster requirements. They brought the right dumpster out when promised, and picked it up when they said. They also made it very simple and easy to extend my…”
“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…”
“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!”
“Great service, affordable pricing, they make the process effortless.”
“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…”
“Very good service. Always on time Fast reply Definitely we’ll call again for another project at home”
“Great price, communication and professionalism. Will use 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…”
“I had a great experience with Dumpster Drop Dumpster Rentals from start to finish. They were punctual with both delivery and pickup, which made planning my project so much easier. The dumpster itself…”
“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 company, great communication, great fast service. They will definitely be my go to company for whenever I need a dumpster moving forward.”
“These guys are AMAZING. I would recommend them to everyone.”
“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…”
“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…”
“Very easy and very responsive company at Dumpster Rental. Very pleased with the service”
“Excellent service and experience! The online order and payment process was easy and went smoothly. Everyone seemed professional, respectful, and flexible in order to meet our needs. Fast drop-off and…”
“I use them for my relo company in Orlando. Great service, great prices.”
“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.”
“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!”
“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.”
“"I recently used Dumpster Drop for my roll-off dumpster rental needs while redoing my yard and I was extremely impressed with their level of service. The delivery was prompt and efficient, and the…”
“Called and they delivered the dumpster same day. Bo was great at dropping the dumpster. Very tentative and answered all my questions. Highly recommend”
“Great service...definitely recommend!”
“I was desperate and needed a dumpster for what ended up being a major reno ASAP. I called Don on Saturday and he had the dumpster on site Sunday morning! Most places were closed. There will only…”
“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…”
“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…”
“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…”
“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.”
“Dumpster Drop was responsive, professional, and went above and beyond with delivery, (clean up, which is not their job), and removal of the dumpster. The next time we need a dumpster, they'll be our…”
“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…”
“Dumpster Drop is a great choice for your dumpster requirements. They brought the right dumpster out when promised, and picked it up when they said. They also made it very simple and easy to extend my…”
“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…”
“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!”
“Great service, affordable pricing, they make the process effortless.”
“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…”
Book Your Dumpster
3 steps — takes less than 2 minutes
Dumpster Sizes Available in Winter Garden
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 Garden
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 Garden, Florida
Winter Garden is a city in western Orange County, Florida, United States. Located 14 miles (23 km) west of Downtown Orlando, it is part of the Orlando metropolitan area. The population was 46,964 as of the 2020 census.
With an average home age of 20 years, many Winter Garden homeowners are investing in renovations that generate debris requiring a properly sized dumpster.
Winter Garden's 70% owner-occupancy rate means active home improvement across the area.
We deliver to all neighborhoods and ZIP codes in Winter Garden
Common Projects in Winter Garden
- 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
REAVES ROAD LF (AKA: OCOEE LF)
12702 REAVES ROAD • 1.90 mi - Nearest Transfer Station
PORTER TRANSFER STATION
5.80 mi
Why Winter Garden Chooses Dumpster Drop
Local service, transparent pricing, reliable delivery.
Same-Day Delivery
Order by noon for same-day delivery across Winter Garden 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 Garden's neighborhoods and best placement spots.
Frequently Asked Questions
Everything you need to know about renting a dumpster in Winter Garden.
We provide five roll-off dumpster sizes specifically chosen for Winter Garden's project needs: 10-yard containers for small renovations and cleanouts, 15-yard dumpsters for medium projects like kitchen or bathroom remodels, 20-yard containers for larger home improvement projects, 30-yard dumpsters for major renovations or construction debris, and 40-yard containers for extensive commercial or whole-home renovation projects common in Winter Garden's higher-income neighborhoods.
Our standard Winter Garden rental period is 7 days, which accommodates most residential projects in neighborhoods like Stoneybrook West and Independence. We offer flexible extensions for longer projects common among Winter Garden homeowners undertaking extensive renovations. Given the city's proximity to REAVES ROAD LF just 1.90 miles away, we can easily adjust pickup schedules to match your project timeline while maintaining cost-effective service.
You can dispose of construction debris, household junk, furniture, appliances (refrigerant-free), yard waste, and renovation materials common to Winter Garden's 20-year-old housing stock. We cannot accept hazardous materials, paint, chemicals, tires, batteries, or electronics. Given Winter Garden's location in Orange County, we follow all local disposal regulations and can guide you to appropriate facilities for restricted materials not accepted in our containers.
Most Winter Garden residential driveways accommodate our containers without permits, but street placement in neighborhoods like Downtown Winter Garden, Hamlin, or Waterleigh may require Orange County permits. We help coordinate any necessary permits for your 34787 ZIP code location and work with homeowner associations common in Winter Garden's master-planned communities to ensure compliant placement that doesn't interfere with neighborhood aesthetics or traffic flow. Contact Dumpster Drop at dumpsterdrop.co to schedule your Winter Garden dumpster rental and support your next home improvement project with professional waste management services designed for Central Florida's unique needs.
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 Garden
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 Garden.
Get Your Instant Quote →★★★★★ 5.0 from 94 reviews • 10 days included • No hidden fees