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
★★★★★

“Great experience and will definitely use them again”

Dean Alfonsi
Dean Alfonsi3 weeks ago • Google
★★★★★

“Great experience. Good price, excellent customer service. Flexible when we needed to change pick up date. I will definetely use them again. Highly recommended!!”

Edward Swanson
Edward Swanson2 years ago • Google
★★★★★

“Excellent Customer service, fast response. Flawless delivery. I will definitely will contact Dumpster Drop LLC for my future projects.”

Carla Hoyos
Carla Hoyos7 months ago • Google
★★★★★

“Amazing and convenient service. So easy to book”

Jeanvilma Family
Jeanvilma Family2 months 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
★★★★★

“On time and great customer service from the office, plus excellent work from the driver. This is the only company I will use while in Kissimmee.”

Dwight Weber
Dwight Weber1 month ago • Google
★★★★★

“Great service! They are pros. 10 out of 10!!”

Pdot Bellows
Pdot Bellows2 weeks ago • Google
★★★★★

“Very professional, it has been great to work with Donnie! We highly recommend them.”

Sergio Rivero
Sergio Rivero2 years ago • Google
★★★★★

“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!”

Jose Fonseca Jr
Jose Fonseca Jr2 years ago • Google
★★★★★

“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!”

Axel Roman
Axel Roman1 year ago • Google
★★★★★

“Very good service. Always on time Fast reply Definitely we’ll call again for another project at home”

javier shiohama
javier shiohama3 years ago • Google
★★★★★

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

Victor
Victor2 years ago • Google
★★★★★

“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.”

S M
S M2 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
★★★★★

“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…”

Edward Wolfrey
Edward Wolfrey2 months ago • Google
★★★★★

“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…”

Jen Patel
Jen Patel1 year ago • Google
★★★★★

“Very good communication and reliable”

Matthew Dix
Matthew Dix2 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
★★★★★

“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…”

Carolyn Shub
Carolyn Shub2 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
★★★★★

“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
★★★★★

“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
★★★★★

“Super friendly and accommodating to my shifting plans. Initial dropoff occurred as scheduled with no surprises. They accommodated my request to extend the rental by 4 days. I highly recommend their…”

Brian Atkinson
Brian Atkinson2 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
★★★★★

“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…”

MOST. Z KHANOAM
MOST. Z KHANOAM3 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
★★★★★

“Friendly customer service fast on time delivery and the only company that would get the dumpster out to me next day(I called multiple companies before this one)”

Cole Schuknecht
Cole Schuknecht1 week ago • Google
★★★★★

“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…”

Bryan Rudd
Bryan Rudd2 years ago • Google
★★★★★

“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…”

Carlos Fonseca
Carlos Fonseca2 months ago • Google
★★★★★

“Awesome company to work with, ready to deliver as soon as we call them and 5 star customer service👍🏼”

Operating Committee
Operating Committee2 months ago • Google
★★★★★

“Great experience and will definitely use them again”

Dean Alfonsi
Dean Alfonsi3 weeks ago • Google
★★★★★

“Great experience. Good price, excellent customer service. Flexible when we needed to change pick up date. I will definetely use them again. Highly recommended!!”

Edward Swanson
Edward Swanson2 years ago • Google
★★★★★

“Excellent Customer service, fast response. Flawless delivery. I will definitely will contact Dumpster Drop LLC for my future projects.”

Carla Hoyos
Carla Hoyos7 months ago • Google
★★★★★

“Amazing and convenient service. So easy to book”

Jeanvilma Family
Jeanvilma Family2 months 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
★★★★★

“On time and great customer service from the office, plus excellent work from the driver. This is the only company I will use while in Kissimmee.”

Dwight Weber
Dwight Weber1 month ago • Google
★★★★★

“Great service! They are pros. 10 out of 10!!”

Pdot Bellows
Pdot Bellows2 weeks ago • Google
★★★★★

“Very professional, it has been great to work with Donnie! We highly recommend them.”

Sergio Rivero
Sergio Rivero2 years ago • Google
★★★★★

“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!”

Jose Fonseca Jr
Jose Fonseca Jr2 years ago • Google
★★★★★

“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!”

Axel Roman
Axel Roman1 year ago • Google
★★★★★

“Very good service. Always on time Fast reply Definitely we’ll call again for another project at home”

javier shiohama
javier shiohama3 years ago • Google
★★★★★

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

Victor
Victor2 years ago • Google
★★★★★

“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.”

S M
S M2 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
★★★★★

“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…”

Edward Wolfrey
Edward Wolfrey2 months ago • Google
★★★★★

“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…”

Jen Patel
Jen Patel1 year ago • Google
★★★★★

“Very good communication and reliable”

Matthew Dix
Matthew Dix2 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
★★★★★

“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…”

Carolyn Shub
Carolyn Shub2 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
★★★★★

“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
★★★★★

“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
★★★★★

“Super friendly and accommodating to my shifting plans. Initial dropoff occurred as scheduled with no surprises. They accommodated my request to extend the rental by 4 days. I highly recommend their…”

Brian Atkinson
Brian Atkinson2 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
★★★★★

“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…”

MOST. Z KHANOAM
MOST. Z KHANOAM3 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
★★★★★

“Friendly customer service fast on time delivery and the only company that would get the dumpster out to me next day(I called multiple companies before this one)”

Cole Schuknecht
Cole Schuknecht1 week ago • Google
★★★★★

“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…”

Bryan Rudd
Bryan Rudd2 years ago • Google
★★★★★

“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…”

Carlos Fonseca
Carlos Fonseca2 months ago • Google
★★★★★

“Awesome company to work with, ready to deliver as soon as we call them and 5 star customer service👍🏼”

Operating Committee
Operating Committee2 months ago • Google

Read all 115 reviews on Google →

Book Your Dumpster

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Where do you need the dumpster?

Enter the delivery address for your dumpster rental

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