Dumpster Rental in Winter Park Village, Winter Park FL | Dumpster Drop
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Dumpster Rental in Winter Park Village

Fast, affordable dumpster rental in Winter Park Village & 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

Loved by Homeowners & Contractors

★★★★★5.0from 115 Google reviews
★★★★★

“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
★★★★★

“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
★★★★★

“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
★★★★★

“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
★★★★★

“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
★★★★★

“Reasonable price, great communication. Highly recommended.”

Leon Li
Leon Li3 weeks ago • Google
★★★★★

“We have been trying to find a reliable company who would help us with our Dumpster Rental Needs. We have been having nightmares with awful companies, however that changed as soon as I saw this…”

Karen Ramirez
Karen Ramirez2 years ago • Google
★★★★★

“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!”

Jennifer Soos
Jennifer Soos11 months ago • Google
★★★★★

“Easy drop off to our house and pick up! Nice guys. Huge dumpster!”

Adrienne Davis
Adrienne Davis1 month 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
★★★★★

“"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
★★★★★

“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 professional, timely, and easy to work with. Not even a scratch on the concrete driveway. Everyone we worked with was very kind and respectful as well.”

Trevor H
Trevor H2 years ago • Google
★★★★★

“I had an excellent experience from start to finish. The dumpster was delivered exactly as scheduled and placed perfectly in my driveway without any issues. The unit was clean, well-maintained, and in…”

Yinet Monge
Yinet Monge2 days 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
★★★★★

“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
★★★★★

“I like the service the where great and good price I love them I would recommend them anytime”

keon sukra
keon sukra2 years ago • Google
★★★★★

“Amazing service”

shalom becker
shalom becker3 months 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
★★★★★

“Amazing and convenient service. So easy to book”

Jeanvilma Family
Jeanvilma Family2 months ago • Google
★★★★★

“Very experienced and helpful! And what a great deal! Highly recommend and will continue to use their services.”

Joseph Crownover
Joseph Crownover4 weeks ago • Google
★★★★★

“Very good communication and reliable”

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

“Great price, communication and professionalism. Will use again”

Wesley Happel
Wesley Happel8 months ago • Google
★★★★★

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

Jenna White
Jenna White2 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
★★★★★

“Great experience and will definitely use them again”

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

“Professional service drop off on time pick up on time, But more than that they are great people very nice and respectful , I highly recommend”

Moe Lakeside apartments
Moe Lakeside apartments1 year ago • Google
★★★★★

“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…”

Paul Kozma
Paul Kozma2 years ago • Google
★★★★★

“Awesome company! Very responsive. On time. Do what they say they’re going to do. Only dumpster company I will ever work with from now on!”

Mandy Stewart
Mandy Stewart2 years ago • Google
★★★★★

“Good”

Elvira Cleaning Services
Elvira Cleaning Services2 years 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
★★★★★

“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
★★★★★

“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
★★★★★

“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
★★★★★

“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
★★★★★

“Reasonable price, great communication. Highly recommended.”

Leon Li
Leon Li3 weeks ago • Google
★★★★★

“We have been trying to find a reliable company who would help us with our Dumpster Rental Needs. We have been having nightmares with awful companies, however that changed as soon as I saw this…”

Karen Ramirez
Karen Ramirez2 years ago • Google
★★★★★

“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!”

Jennifer Soos
Jennifer Soos11 months ago • Google
★★★★★

“Easy drop off to our house and pick up! Nice guys. Huge dumpster!”

Adrienne Davis
Adrienne Davis1 month 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
★★★★★

“"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
★★★★★

“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 professional, timely, and easy to work with. Not even a scratch on the concrete driveway. Everyone we worked with was very kind and respectful as well.”

Trevor H
Trevor H2 years ago • Google
★★★★★

“I had an excellent experience from start to finish. The dumpster was delivered exactly as scheduled and placed perfectly in my driveway without any issues. The unit was clean, well-maintained, and in…”

Yinet Monge
Yinet Monge2 days 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
★★★★★

“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
★★★★★

“I like the service the where great and good price I love them I would recommend them anytime”

keon sukra
keon sukra2 years ago • Google
★★★★★

“Amazing service”

shalom becker
shalom becker3 months 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
★★★★★

“Amazing and convenient service. So easy to book”

Jeanvilma Family
Jeanvilma Family2 months ago • Google
★★★★★

“Very experienced and helpful! And what a great deal! Highly recommend and will continue to use their services.”

Joseph Crownover
Joseph Crownover4 weeks ago • Google
★★★★★

“Very good communication and reliable”

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

“Great price, communication and professionalism. Will use again”

Wesley Happel
Wesley Happel8 months ago • Google
★★★★★

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

Jenna White
Jenna White2 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
★★★★★

“Great experience and will definitely use them again”

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

“Professional service drop off on time pick up on time, But more than that they are great people very nice and respectful , I highly recommend”

Moe Lakeside apartments
Moe Lakeside apartments1 year ago • Google
★★★★★

“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…”

Paul Kozma
Paul Kozma2 years ago • Google
★★★★★

“Awesome company! Very responsive. On time. Do what they say they’re going to do. Only dumpster company I will ever work with from now on!”

Mandy Stewart
Mandy Stewart2 years ago • Google
★★★★★

“Good”

Elvira Cleaning Services
Elvira Cleaning Services2 years 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 Park Village

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

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

Dumpster Drop service area - Winter Park Village

We deliver to all neighborhoods and ZIP codes in Winter Park Village

Common Projects in Winter Park Village

  • 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

Why Winter Park Village Chooses Dumpster Drop

Local service, transparent pricing, reliable delivery.

Same-Day Delivery

Order by noon for same-day delivery across Winter Park Village 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 Village's neighborhoods and best placement spots.

Frequently Asked Questions

Everything you need to know about renting a dumpster in Winter Park Village.

Dumpsters from $300

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

Get Your Instant Quote →

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