Dumpster Rental in Windermere, FL | Same-Day Delivery | Dumpster Drop
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Dumpster Rental in Windermere

Fast, affordable dumpster rental in Windermere & 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 3,043 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
3,043 residents
1,351 homes
35 yr avg home age
★★★★★

“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
★★★★★

“Good”

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

“Very good communication and reliable”

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

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

Victor
Victor2 years ago • Google
★★★★★

“I use them for my relo company in Orlando. Great service, great prices.”

Mitchell Mays
Mitchell Mays3 months ago • Google
★★★★★

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

Mike G
Mike G9 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
★★★★★

“Bo and the rest of the team at Dumpster Drop have been amazing to work with. When our 1st rental turned into 2, they swapped us out for a new one. Then they swapped us out again when the project…”

Carla Rodden
Carla Rodden7 months 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
★★★★★

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

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

“Amazing and convenient service. So easy to book”

Jeanvilma Family
Jeanvilma Family2 months 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
★★★★★

“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
★★★★★

“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
★★★★★

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

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

“Awesome! Great job!”

Franky
Franky11 months 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
★★★★★

“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
★★★★★

“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…”

Jennifer Tommey
Jennifer Tommey2 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
★★★★★

“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
★★★★★

“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…”

Daniel Soos
Daniel Soos11 months ago • Google
★★★★★

“They where awesome!!! Don was great very informative, patient, and kind. I would definitely rent from them again”

Joel Rodriguez
Joel Rodriguez1 year 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
★★★★★

“Fast, efficiency and very helpful. Recommend. I have use their seẻvice 3 times and no problem”

Dean Nguyen
Dean Nguyen1 month 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
★★★★★

“Dumpster Drop Dumpster Rental aided in making what could have been a stressful process easier. I was coordinating the cleanout of my mother’s home from out of state and needed the dumpster delivered…”

TheKirlewpt
TheKirlewpt2 weeks 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
★★★★★

“Great 👍 👌”

Ken Fudella
Ken Fudella3 weeks 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
★★★★★

“Good”

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

“Very good communication and reliable”

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

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

Victor
Victor2 years ago • Google
★★★★★

“I use them for my relo company in Orlando. Great service, great prices.”

Mitchell Mays
Mitchell Mays3 months ago • Google
★★★★★

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

Mike G
Mike G9 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
★★★★★

“Bo and the rest of the team at Dumpster Drop have been amazing to work with. When our 1st rental turned into 2, they swapped us out for a new one. Then they swapped us out again when the project…”

Carla Rodden
Carla Rodden7 months 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
★★★★★

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

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

“Amazing and convenient service. So easy to book”

Jeanvilma Family
Jeanvilma Family2 months 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
★★★★★

“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
★★★★★

“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
★★★★★

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

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

“Awesome! Great job!”

Franky
Franky11 months 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
★★★★★

“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
★★★★★

“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…”

Jennifer Tommey
Jennifer Tommey2 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
★★★★★

“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
★★★★★

“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…”

Daniel Soos
Daniel Soos11 months ago • Google
★★★★★

“They where awesome!!! Don was great very informative, patient, and kind. I would definitely rent from them again”

Joel Rodriguez
Joel Rodriguez1 year 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
★★★★★

“Fast, efficiency and very helpful. Recommend. I have use their seẻvice 3 times and no problem”

Dean Nguyen
Dean Nguyen1 month 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
★★★★★

“Dumpster Drop Dumpster Rental aided in making what could have been a stressful process easier. I was coordinating the cleanout of my mother’s home from out of state and needed the dumpster delivered…”

TheKirlewpt
TheKirlewpt2 weeks 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
★★★★★

“Great 👍 👌”

Ken Fudella
Ken Fudella3 weeks 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 Windermere

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

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

Windermere is a town in Orange County, Florida, United States. As of the 2020 census, the town population was 3,030. It is situated on an isthmus between Lake Down and Lake Butler, and is part of the Orlando Metropolitan Statistical Area.

With an average home age of 35 years, many Windermere homeowners are investing in renovations that generate debris requiring a properly sized dumpster.

Windermere's 93% owner-occupancy rate means active home improvement across the area.

Dumpster Drop service area - Windermere

We deliver to all neighborhoods and ZIP codes in Windermere

Common Projects in Windermere

  • 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
    LUSCIAN HILLS LANDFILL
    WEST OF HEMPLE AND BETWEEN OLD WINTER GARDEN &408 • 3.40 mi
  • Nearest Transfer Station
    MCLEOD ROAD TRANSFER STATION
    4.30 mi

Why Windermere Chooses Dumpster Drop

Local service, transparent pricing, reliable delivery.

Same-Day Delivery

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

Frequently Asked Questions

Everything you need to know about renting a dumpster in Windermere.

Dumpster Drop offers 10, 15, 20, 30, and 40-yard roll-off dumpsters throughout Windermere and ZIP code 34786. Our 10-yard dumpsters work perfectly for bathroom remodels in Keene's Pointe, while 40-yard containers accommodate major renovations in Isleworth's luxury homes. The 15 and 20-yard sizes handle most kitchen renovations and flooring projects, and 30-yard dumpsters suit whole-house cleanouts common in Windermere's 35-year-old housing stock.

Standard rental periods range from 7-14 days, with extensions available for longer projects. Given Windermere's high property standards and Orange County regulations, we recommend coordinating placement timing with your contractor to minimize neighborhood impact. Many Lake Butler and Lake Tibet residents prefer shorter rental periods for aesthetic reasons, while extensive Isleworth renovations often require extended timelines.

Accepted materials include construction debris, furniture, appliances, yard waste, and general household items common in Windermere renovations. Prohibited items include hazardous chemicals, paint, batteries, and electronics that could contaminate the lake environment. Given the town's location between Lake Down and Lake Butler, we're particularly strict about preventing materials that could impact water quality. Concrete and heavy materials require special arrangements due to weight restrictions.

Dumpsters placed on private property in Windermere typically don't require permits, making placement convenient for most homeowners in neighborhoods like Isleworth and Keene's Pointe. However, if you need street placement due to narrow driveways or landscaping concerns common in lakefront properties, Orange County may require permits. Our team assists with permit applications and coordinates with local authorities to ensure compliant placement throughout ZIP code 34786, protecting both your property and Windermere's scenic streetscapes.

Dumpsters from $300

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

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