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
“On time dumpster for construction. With quick pick up when we called for pick up.”
“Don and Bo are fast, honest and timely. I have used them a few times for my home renovation and they were fantastic! I highly recommend Dumpster Drop.”
“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…”
“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 Dumpster Rental is always great to work with. Booking was super easy, and when I called in the morning they were able to deliver the same day. They dropped the dumpster exactly where I…”
“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…”
“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.”
“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…”
“Very professional to work with. Dumpsters were extremely clean as well. Will use this company again.”
“Excellent service and communications! Definitely would do business with them again!”
“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!”
“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!”
“Fast, efficiency and very helpful. Recommend. I have use their seẻvice 3 times and no problem”
“Good”
“Always reliable and great service! They attend to your needs on a timely manner. Highly recommended”
“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…”
“Awesome! Great job!”
“Very easy and very responsive company at Dumpster Rental. Very pleased with the service”
“Awesome company to work with, ready to deliver as soon as we call them and 5 star customer service👍🏼”
“Great service...definitely recommend!”
“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…”
“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…”
“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…”
“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”
“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!”
“I use them for my relo company in Orlando. Great service, great prices.”
“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…”
“They where awesome!!! Don was great very informative, patient, and kind. I would definitely rent from them again”
“Very professional, it has been great to work with Donnie! We highly recommend them.”
“On time dumpster for construction. With quick pick up when we called for pick up.”
“Don and Bo are fast, honest and timely. I have used them a few times for my home renovation and they were fantastic! I highly recommend Dumpster Drop.”
“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…”
“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 Dumpster Rental is always great to work with. Booking was super easy, and when I called in the morning they were able to deliver the same day. They dropped the dumpster exactly where I…”
“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…”
“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.”
“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…”
“Very professional to work with. Dumpsters were extremely clean as well. Will use this company again.”
“Excellent service and communications! Definitely would do business with them again!”
“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!”
“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!”
“Fast, efficiency and very helpful. Recommend. I have use their seẻvice 3 times and no problem”
“Good”
“Always reliable and great service! They attend to your needs on a timely manner. Highly recommended”
“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…”
“Awesome! Great job!”
“Very easy and very responsive company at Dumpster Rental. Very pleased with the service”
“Awesome company to work with, ready to deliver as soon as we call them and 5 star customer service👍🏼”
“Great service...definitely recommend!”
“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…”
“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…”
“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…”
“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”
“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!”
“I use them for my relo company in Orlando. Great service, great prices.”
“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…”
“They where awesome!!! Don was great very informative, patient, and kind. I would definitely rent from them again”
“Very professional, it has been great to work with Donnie! We highly recommend them.”
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 100 reviews • 10 days included • No hidden fees