Dumpster Rental in Winter Garden, FL | Same-Day Delivery | Dumpster Drop
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Dumpster Rental in Winter Garden

Fast, affordable dumpster rental in Winter Garden & Orange County. Book online in minutes — delivery as soon as today.

★★★★★5.0from 115 Google reviews

Dumpster rentals as low as $300

Same-day delivery*10 days includedNo hidden fees

*Based on availability

Serving 46,518 residents across Orange County

83°F Slight chance of rain — plan ahead but conditions are mostly favorable for outdoor work. Updated 3:00 PM ET

Loved by Homeowners & Contractors

★★★★★5.0from 115 Google reviews
46,518 residents
15,941 homes
20 yr avg home age
★★★★★

“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.”

kimberly ovalles
kimberly ovalles3 months ago • Google
★★★★★

“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…”

Rich Etscorn
Rich Etscorn2 years ago • Google
★★★★★

“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…”

Ryan Webster
Ryan Webster2 years ago • Google
★★★★★

“Good”

Elvira Cleaning Services
Elvira Cleaning Services2 years ago • Google
★★★★★

“Service and price were great. Would highly recommend!!!!!!”

Mike G
Mike G9 months ago • Google
★★★★★

“These guys are always on time and have great communication!! As someone who uses dumpster rental companies weekly for roofing projects. I could not recommend Dumpster Drop enough.”

Tyler Denny
Tyler Denny1 year ago • Google
★★★★★

“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…”

Laura Robbins-Ryan
Laura Robbins-Ryan2 years ago • Google
★★★★★

“Very professional to work with. Dumpsters were extremely clean as well. Will use this company again.”

Bryan Landa
Bryan Landa2 years ago • Google
★★★★★

“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”

Nicholas Terrell
Nicholas Terrell2 years ago • Google
★★★★★

“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…”

keisha allen
keisha allen1 month ago • Google
★★★★★

“Great experience with this company! They respond quickly and through text so I didn’t have to call if I had a question, responded very quickly, and were accommodating to my request! Will definitely…”

Yesselyn Aviles
Yesselyn Aviles8 months ago • Google
★★★★★

“Very reasonable and very professional! Easy to deal with. Makes a contractors job much easier”

Greg Harding
Greg Harding2 years ago • Google
★★★★★

“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…”

yesenia DeJesus
yesenia DeJesus2 years ago • Google
★★★★★

“Always reliable and great service! They attend to your needs on a timely manner. Highly recommended”

Victor
Victor2 years ago • Google
★★★★★

“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…”

Avery Nuckols
Avery Nuckols6 months ago • Google
★★★★★

“This company made my life so much easier! Timely delivery, very reasonable pricing, clear communication — everything was literally perfect. Cannot more highly recommend!”

Cori Kish
Cori Kish3 weeks ago • Google
★★★★★

“Great communication great company let us use dumpster extra days as needed highly recommend this company”

Justin Bateman
Justin Bateman1 week ago • Google
★★★★★

“Clean dumpster quick delivery and pick up!”

RGO
RGO2 months ago • Google
★★★★★

“They are one of the best dumpster companies in the business! I would recommend to anyone”

August Pleveich
August Pleveich2 years ago • Google
★★★★★

“On time dumpster for construction. With quick pick up when we called for pick up.”

Ian Vanier
Ian Vanier1 year ago • Google
★★★★★

“Very good communication and reliable”

Matthew Dix
Matthew Dix2 months ago • Google
★★★★★

“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…”

Justen Moore
Justen Moore2 years ago • Google
★★★★★

“I’ve called several different companies for quotes. Don has gone above and beyond to understand my need and upon doing so, beating any quote per day that I’ve been offered. They were flexible in…”

Carlos
Carlos2 years ago • Google
★★★★★

“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…”

Monica
Monica2 months ago • Google
★★★★★

“I was truly impressed with Dumpster Drop! They were very easy to work with. They were prompt and very professional. I would highly recommend them”

S Long
S Long1 week ago • Google
★★★★★

“Very easy and very responsive company at Dumpster Rental. Very pleased with the service”

Paul Solomon
Paul Solomon2 years ago • Google
★★★★★

“Prompt ,professional, great deal for the money..communication 2nd to none..a go to everytime..”

Jenna White
Jenna White2 years ago • Google
★★★★★

“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…”

Tammi Dooley
Tammi Dooley11 months ago • Google
★★★★★

“"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…”

Joshua McBride
Joshua McBride3 years ago • Google
★★★★★

“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…”

jay rot
jay rot1 year ago • Google
★★★★★

“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.”

kimberly ovalles
kimberly ovalles3 months ago • Google
★★★★★

“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…”

Rich Etscorn
Rich Etscorn2 years ago • Google
★★★★★

“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…”

Ryan Webster
Ryan Webster2 years ago • Google
★★★★★

“Good”

Elvira Cleaning Services
Elvira Cleaning Services2 years ago • Google
★★★★★

“Service and price were great. Would highly recommend!!!!!!”

Mike G
Mike G9 months ago • Google
★★★★★

“These guys are always on time and have great communication!! As someone who uses dumpster rental companies weekly for roofing projects. I could not recommend Dumpster Drop enough.”

Tyler Denny
Tyler Denny1 year ago • Google
★★★★★

“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…”

Laura Robbins-Ryan
Laura Robbins-Ryan2 years ago • Google
★★★★★

“Very professional to work with. Dumpsters were extremely clean as well. Will use this company again.”

Bryan Landa
Bryan Landa2 years ago • Google
★★★★★

“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”

Nicholas Terrell
Nicholas Terrell2 years ago • Google
★★★★★

“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…”

keisha allen
keisha allen1 month ago • Google
★★★★★

“Great experience with this company! They respond quickly and through text so I didn’t have to call if I had a question, responded very quickly, and were accommodating to my request! Will definitely…”

Yesselyn Aviles
Yesselyn Aviles8 months ago • Google
★★★★★

“Very reasonable and very professional! Easy to deal with. Makes a contractors job much easier”

Greg Harding
Greg Harding2 years ago • Google
★★★★★

“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…”

yesenia DeJesus
yesenia DeJesus2 years ago • Google
★★★★★

“Always reliable and great service! They attend to your needs on a timely manner. Highly recommended”

Victor
Victor2 years ago • Google
★★★★★

“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…”

Avery Nuckols
Avery Nuckols6 months ago • Google
★★★★★

“This company made my life so much easier! Timely delivery, very reasonable pricing, clear communication — everything was literally perfect. Cannot more highly recommend!”

Cori Kish
Cori Kish3 weeks ago • Google
★★★★★

“Great communication great company let us use dumpster extra days as needed highly recommend this company”

Justin Bateman
Justin Bateman1 week ago • Google
★★★★★

“Clean dumpster quick delivery and pick up!”

RGO
RGO2 months ago • Google
★★★★★

“They are one of the best dumpster companies in the business! I would recommend to anyone”

August Pleveich
August Pleveich2 years ago • Google
★★★★★

“On time dumpster for construction. With quick pick up when we called for pick up.”

Ian Vanier
Ian Vanier1 year ago • Google
★★★★★

“Very good communication and reliable”

Matthew Dix
Matthew Dix2 months ago • Google
★★★★★

“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…”

Justen Moore
Justen Moore2 years ago • Google
★★★★★

“I’ve called several different companies for quotes. Don has gone above and beyond to understand my need and upon doing so, beating any quote per day that I’ve been offered. They were flexible in…”

Carlos
Carlos2 years ago • Google
★★★★★

“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…”

Monica
Monica2 months ago • Google
★★★★★

“I was truly impressed with Dumpster Drop! They were very easy to work with. They were prompt and very professional. I would highly recommend them”

S Long
S Long1 week ago • Google
★★★★★

“Very easy and very responsive company at Dumpster Rental. Very pleased with the service”

Paul Solomon
Paul Solomon2 years ago • Google
★★★★★

“Prompt ,professional, great deal for the money..communication 2nd to none..a go to everytime..”

Jenna White
Jenna White2 years ago • Google
★★★★★

“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…”

Tammi Dooley
Tammi Dooley11 months ago • Google
★★★★★

“"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…”

Joshua McBride
Joshua McBride3 years ago • Google
★★★★★

“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…”

jay rot
jay rot1 year ago • Google

Read all 115 reviews on Google →

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Where do you need the dumpster?

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Dumpster Sizes Available in Winter Garden

From small cleanouts to major construction — we have the right size.

10 yard dumpster in Winter Garden
10
YARD
From $300
Small Cleanouts
Garage cleanouts, bathroom remodels, yard debris.
10 days included
15 yard dumpster in Winter Garden
15
YARD
From $325
Mid-Size Projects
Kitchen remodels, flooring removal, deck demolition.
10 days included
20 yard dumpster in Winter Garden
20
YARD
From $350
Most Popular
Home Cleanouts & Renovations
Full renovations, roof tear-offs, estate cleanouts.
10 days included
30 yard dumpster in Winter Garden
30
YARD
From $525
Large Construction
New construction, large remodels, commercial cleanouts.
10 days included

Final pricing based on project type. Enter your address for exact pricing →

About 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.

Dumpster Drop service area - Winter Garden

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.

Dumpsters from $300

Enter your address to see sizes, pricing, and same-day availability in Winter Garden.

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★★★★★ 5.0 from 115 reviews • 10 days included • No hidden fees