Windmere Short-Term Rental Regulation: A Guide For Airbnb Hosts

What are Short-Term Rental (Airbnb, VRBO) Regulations in Windermere, Florida?

Windermere, a picturesque town in Orange County, Florida, has become an increasingly popular destination for short-term rental properties thanks to its proximity to major attractions like Walt Disney World and Universal Studios. However, as the STR market continues to grow, it's crucial for property owners to understand and comply with the local regulations governing vacation rentals. In this article, we'll explore the short-term rental rules in Windermere and provide insights from real estate forums like Bigger Pockets and Reddit.

Starting a Short-Term Rental Business in Windermere

To start a short-term rental business in Windermere, property owners must first obtain a license from the Florida Department of Business and Professional Regulation (DBPR). This requirement applies to any property rented out more than three times a year for stays of less than 30 days. The DBPR offers two types of licenses: one for condominiums and one for dwellings.

In addition to the state-level requirements, Windermere property owners must also adhere to Orange County's zoning regulations. The town itself does not have specific laws regarding short-term rentals, but all rentals are subject to Florida's state laws, which include collecting and remitting the state's 6% sales tax and the county's 6% tourist development tax.

According to discussions on the Bigger Pockets forum, many STR owners in Windermere have found success by offering high-quality amenities and personalized experiences to stand out in the competitive market. One host shared, "I've been running an Airbnb in Windermere for the past two years, and while the regulations can be challenging, focusing on providing exceptional service has helped me maintain a high occupancy rate."

Short-Term Rental Licensing Requirement in Windermere

While the town of Windermere itself does not have specific licensing requirements for short-term rentals, property owners must still comply with state and county regulations. In Florida, any property rented out more than three times a year for stays shorter than 30 days each must obtain a vacation rental license from the Department of Business and Professional Regulation (DBPR).

The DBPR offers two types of licenses for short-term rentals: one for condominiums and one for dwellings. To apply for a license, property owners must submit a completed application along with required documentation, such as a DBPR Form HR-7020 (Balcony Inspection Certificate), proof of registration with the Department of Revenue for tax purposes, and a $50 application fee.

In addition to the state licensing requirement, short-term rentals in Windermere are subject to Orange County's zoning regulations. According to Robert Spivey, manager of Orange County's code enforcement division, short-term rentals are not allowed in single-family residential districts, including communities such as Windermere Trails. This includes both "transient rentals" (single-family dwellings renting for 30 days or fewer) and "short-term rentals" (hotels, motels, and time-shares renting for 179 days or less).

Property owners found to be operating unlicensed or non-compliant short-term rentals in Windermere may face fines of up to $1,000 per day from Orange County. To report a suspected illegal short-term rental, residents can call 311 or use the 311 app and provide code enforcement with a screenshot of the rental listing.

It's important to note that homeowners' association (HOA) regulations in Windermere can be more restrictive than county code. Even if a property is allowed as a vacation rental under county rules, the HOA may still prohibit it. However, the county is not responsible for enforcing private HOA restrictions.

Required Documents for Windermere Short-Term Rentals

To operate a short-term rental in Windermere, Florida, property owners must obtain a vacation rental license from the Florida Department of Business and Professional Regulation (DBPR). This requirement applies to any property rented out more than three times a year for stays shorter than 30 days each.

When applying for a DBPR vacation rental license, the following documents are required:

• Completed DBPR Form HR-7020 (Balcony Inspection Certificate): This form certifies that any balconies, porches, decks, or similar structures higher than 30 inches have been inspected by a person licensed under Chapter 471 (engineer) or Chapter 481 (architect) and are safe for human occupancy.
• Proof of registration with the Florida Department of Revenue for sales tax and tourist development tax purposes: Short-term rental owners must collect and remit the state's 6% sales tax and Orange County's 6% tourist development tax on all bookings.
• A valid Certificate of Occupancy from the Orange County Building Division: This document confirms that the property meets all applicable building codes and safety standards for its intended use as a short-term rental.
• Proof of liability insurance coverage: Property owners should maintain adequate liability insurance to protect themselves and their guests in case of accidents or injuries on the premises.
• A completed Windermere Local Business Tax Receipt application: This local permit is required for all businesses operating within the town limits of Windermere.
• A fire safety inspection report from the Orange County Fire Marshal's office: This report verifies that the property has working smoke detectors, fire extinguishers, and other necessary fire safety equipment.

In addition to these required documents, short-term rental owners in Windermere should be aware that their properties may be subject to additional zoning regulations and homeowners' association (HOA) rules. Even if a property is allowed as a vacation rental under county code, the HOA may still prohibit it. It's important to carefully review all applicable regulations before investing in or operating a short-term rental in Windermere.

By obtaining the necessary licenses and permits, maintaining proper insurance coverage, and complying with all local rules and regulations, short-term rental owners in Windermere can help ensure a safe and successful experience for themselves and their guests.

Windermere Short-Term Rental Taxes

Short-term rental owners in Windermere are responsible for collecting and remitting several state and local taxes on their rental income. These taxes include:

1. Florida Sales Tax: The state of Florida imposes a 6% sales tax on all transient rental accommodations, which includes short-term rentals. This tax must be collected from guests and remitted to the Florida Department of Revenue.
2. Orange County Tourist Development Tax: Orange County, where Windermere is located, levies a 6% tourist development tax on all short-term rental accommodations. This tax is in addition to the state sales tax and must be collected from guests and remitted to the Orange County Comptroller's Office.
3. Discretionary Sales Surtax: Some Florida counties impose a discretionary sales surtax on transient rentals. As of 2024, Orange County does not have a discretionary sales surtax, but short-term rental owners should stay informed about any potential changes to local tax laws.

It's important to note that short-term rental income is also subject to federal income tax. Owners must report their rental income on their annual tax return and pay the appropriate amount of income tax based on their tax bracket. However, many expenses related to operating a short-term rental, such as cleaning fees, utilities, and property management fees, can be deducted from the rental income to reduce the overall tax liability.

To ensure compliance with all applicable tax laws, short-term rental owners in Windermere should:

1. Register with the Florida Department of Revenue and obtain a sales tax certificate
2. Register with the Orange County Comptroller's Office and obtain a tourist development tax account
3. Collect the appropriate state and local taxes from guests on each rental transaction
4. File regular tax returns with the Florida Department of Revenue and Orange County Comptroller's Office, reporting the amount of taxes collected and remitting payment
5. Keep accurate records of all rental income and expenses for federal income tax purposes

Failure to comply with state and local tax laws can result in penalties, interest charges, and legal consequences. Short-term rental owners in Windermere are encouraged to consult with a qualified tax professional to ensure they are meeting all their tax obligations and taking advantage of any available deductions or credits.

Florida Wide Short-Term Rental Rules

While individual cities and counties in Florida have the authority to regulate short-term rentals to some extent, there are also statewide rules that apply across the Sunshine State. These state-level regulations provide a framework for the operation of vacation rentals while still allowing for local variations.

One of the key statewide requirements is the need for a license from the Florida Department of Business and Professional Regulation (DBPR) for certain types of short-term rentals. Specifically, any property rented out more than three times in a calendar year for periods of less than 30 days or that is advertised as a vacation rental must obtain a DBPR license. This applies to both condominiums and single-family dwellings.

However, there is an exemption for hosts who are only renting out individual rooms within their primary residence. These room rentals do not require a DBPR license, as they are not considered to be "transient public lodging establishments."

Another important aspect of Florida's short-term rental regulations is the requirement to collect and remit various taxes. Vacation rental operators must register with the Florida Department of Revenue to collect and pay the state's 6% sales tax, as well as any applicable county-level tourist development taxes. Failure to comply with these tax obligations can result in significant penalties.

In 2024, the Florida Legislature passed a bill (SB 280) that aimed to create more uniform regulations for short-term rentals across the state. This measure allows local governments to require registration of vacation rentals and charge a "reasonable fee" for doing so. It also sets guidelines for occupancy limits, with a general standard of two guests per bedroom plus two additional guests.

However, the bill still preserves some of the powers that cities and counties have to regulate short-term rentals. For example, local governments can suspend a vacation rental's registration for repeated violations of local ordinances, and they can conduct inspections of properties to ensure compliance with health and safety standards.

On real estate forums like BiggerPockets, Florida investors and hosts have shared their experiences navigating the state's short-term rental landscape. One host noted that "the DBPR license application is a hassle, but it's a necessary step to operate legally." Others have emphasized the importance of carefully researching local regulations, as the rules can vary significantly from one city or county to another.

Overall, while Florida's statewide vacation rental regulations provide a baseline for hosts to follow, it's clear that understanding and complying with local rules remains a critical part of running a successful and compliant short-term rental business in the state. As one BiggerPockets user put it, "You have to do your homework and stay on top of any changes in the laws, both at the state and local level, to avoid any legal issues down the line."

Does Windermere Strictly Enforce STR Rules?

Based on discussions among Airbnb hosts on forums like Bigger Pockets and Reddit, it appears that while Windermere and Orange County have regulations in place to limit short-term rentals in residential areas, enforcement is inconsistent and many hosts continue to operate despite the rules.

According to Robert Spivey, manager of Orange County's code enforcement division, short-term rentals are not allowed in single-family residential districts, including communities such as Windermere Trails. However, he admitted that it is difficult for the county to stay on top of every listing, and they rely heavily on residents to report suspected violations.

On the Orlando subreddit, one user commented that "short term rentals are not allowed in residential zones" in Orange County, but acknowledged that "it's not very well enforced." Another Redditor observed that a subdivision near their former home in Dr. Phillips "has got to be at least 50% Airbnb."

Compared to other cities and counties in the area, Windermere and Orange County's regulations are relatively strict. For example, the City of Orlando allows owner-occupied home sharing (renting out a portion of one's primary residence) and has a registration process for short-term rentals. Osceola County, which includes popular tourist destinations like Kissimmee, is known for being more permissive of vacation rentals.

Despite the rules, the high demand for short-term rentals in Windermere, driven by its proximity to attractions like Disney World and its upscale neighborhoods, has led many hosts to continue operating. The competitive market and potential for high returns seem to outweigh the risk of fines or legal consequences for some property owners.

In conclusion, while Windermere and Orange County have regulations aimed at restricting short-term rentals in residential areas, the consensus among hosts on real estate forums is that enforcement is spotty and many continue to operate Airbnbs despite the rules. The town's desirability as a vacation destination and the lucrative nature of the short-term rental market appear to be driving factors in this trend. Compared to some neighboring cities and counties, Windermere is less friendly to Airbnb hosts, but the demand and potential profits have led many to navigate the regulations and operate rentals nonetheless.

How to Start a Short-Term Rental Business in Windermere

Despite the challenges posed by local regulations, starting a short-term rental business in Windermere can be a lucrative venture for those willing to navigate the rules and prioritize guest satisfaction. Here is a step-by-step guide to getting started:

1. Research and understand the regulations: Thoroughly review the short-term rental rules set by Orange County and the town of Windermere, as well as any applicable HOA restrictions. Determine if your property is eligible for use as a vacation rental.
2. Obtain necessary licenses and permits: Apply for a vacation rental license from the Florida Department of Business and Professional Regulation (DBPR). Register with the Florida Department of Revenue and Orange County Comptroller's Office for tax purposes. Obtain a Windermere Local Business Tax Receipt.
3. Ensure compliance with safety standards: Schedule a fire safety inspection with the Orange County Fire Marshal's office. Make sure your property meets all building codes and has appropriate safety features, such as smoke detectors and fire extinguishers.
4. Secure insurance coverage: Purchase adequate liability insurance to protect yourself and your guests in case of accidents or injuries on the property.
5. Prepare your property for guests: Make any necessary repairs or upgrades to ensure your rental is attractive, comfortable, and well-maintained. Consider hiring a professional cleaning service to keep the property in top condition between guests.
6. Create a compelling listing:Develop an enticing description of your property, highlighting its unique features, amenities, and proximity to local attractions. Take high-quality photos that showcase your rental in its best light.
7. List your property on popular platforms: Create accounts on vacation rental websites like Airbnb and VRBO. Set competitive rates based on the local market and your property's features.
8. Establish a system for managing bookings and communication: Decide whether you will handle guest inquiries and reservations yourself or use a property management service. Develop a process for promptly responding to guest questions and concerns.
9. Implement a guest screening process: To minimize the risk of disruptive or damaging guests, consider requiring a security deposit and setting clear house rules. Communicate your expectations to guests before their arrival.
10. Provide excellent customer service: Go above and beyond to ensure your guests have a positive experience. Offer local recommendations, promptly address any issues that arise during their stay, and be responsive to feedback.

By following these steps and remaining adaptable to changes in local regulations, aspiring short-term rental hosts in Windermere can build a successful and compliant business. While the path may not be easy, the potential rewards – both financial and in terms of providing memorable experiences for guests – can make the effort worthwhile.

Who to Contact in Windermere about Short-Term Rental Regulations and Zoning?

For those seeking information or guidance on short-term rental regulations and zoning in Windermere, there are several key local government offices and departments to contact:

Orange County Zoning Division
Phone: (407) 836-5525
Email: Zoning@ocfl.net
Address: 201 S Rosalind Ave, Orlando, FL 32801

The Orange County Zoning Division is responsible for enforcing zoning regulations related to short-term rentals in unincorporated areas of the county, including Windermere. They can provide information on whether a specific property is zoned for vacation rental use and assist with any necessary zoning approvals or variances.

Orange County Code Enforcement Division
Phone: (407) 836-3111
Email: CodeEnforcement@ocfl.net
Address: 2450 W 33rd St, Orlando, FL 32839

The Code Enforcement Division investigates complaints about potential violations of county ordinances, including those related to short-term rentals. They can provide guidance on compliance with local regulations and help resolve any issues that may arise.

Town of Windermere Building Department
Phone: (407) 876-2563 ext. 5323
Email: building@town.windermere.fl.us
Address: 614 Main St, Windermere, FL 34786

While the town of Windermere does not have its own specific short-term rental ordinance, the Building Department can assist with questions about local permitting requirements, such as obtaining a Local Business Tax Receipt or scheduling necessary inspections.

Florida Department of Business and Professional Regulation (DBPR)
Phone: (850) 487-1395
Email: info@myfloridalicense.com
Address: 2601 Blair Stone Rd, Tallahassee, FL 32399

The DBPR is the state agency responsible for licensing and regulating vacation rentals in Florida. They can provide information on the process for obtaining a vacation rental license and answer questions about state-level requirements for short-term rentals.

By reaching out to these local and state offices, short-term rental operators and property owners in Windermere can get the most up-to-date and accurate information about the regulations and zoning rules that apply to their specific situation. Building positive relationships with these departments can also help ensure a smoother process for navigating the complex landscape of vacation rental compliance.

What Do Airbnb Hosts in Windermere on Reddit and Bigger Pockets Think about Local Regulations?

Based on discussions among Airbnb hosts on Reddit and Bigger Pockets forums, there is a general consensus that Windermere and Orange County have strict regulations in place that make it challenging to operate short-term rentals legally. Many hosts express frustration with the inconsistent enforcement of these rules and the impact on their ability to run profitable Airbnb businesses.

On the Orlando subreddit, several users have shared their experiences navigating the local regulatory landscape:

One user noted that "short term rentals are not allowed in residential zones" in Orange County, with some exceptions for owner-occupied home sharing. They added that while these rules are "not very well enforced," HOAs can be effective in cracking down on violations. (Source: )

Another Redditor observed that a subdivision near their former home in Dr. Phillips "has got to be at least 50% Airbnb," suggesting that many hosts continue to operate despite the regulations. (Source: )

In a discussion about rising housing costs, one commenter pointed out that Orlando is number 10 on the list of most Airbnb listings per 50,000 residents, with neighboring Kissimmee coming in at number 2. They argued that banning Airbnbs could help slow the increase in real estate prices. (Source: )

On Bigger Pockets, while there are fewer discussions specific to Windermere, hosts share similar sentiments about the challenges of operating in markets with strict regulations:

In a thread about starting an Airbnb business, one user cautioned that "strict new regulations put the kibosh on both Miami and Manhattan," making it illegal to rent by the week in those cities. (Source: )

Another host advised a prospective Airbnb operator to carefully research city laws and HOA rules before pursuing short-term rentals, noting that restrictive regulations are becoming more common in many areas. (Source: )

Overall, the prevailing sentiment among Airbnb hosts on these forums is that Windermere and the surrounding Orange County area have a challenging regulatory environment for short-term rentals. While some hosts continue to operate under the radar, the risk of fines and legal consequences is a significant concern. Many emphasize the importance of thoroughly understanding local rules and weighing the potential benefits against the compliance costs before starting an Airbnb business in Windermere.

Disclaimer: While we here at BNBCalc strive to keep all of our city regulation guides updated and accurate with all the latest local laws, we still do not suggest using them as your sole or primary source for local regulations. We also do not recommend you rely on the third-party sources we link to or reference, and we are not responsible for any of the information on these third-party sites. These guides are for entertainment purposes only and only provide basic information and should not be considered as legal advice.

We highly recommend directly contacting the responsible parties for each city and hearing what their officials have to say. Ultimately, it's your responsibility as an investor to ensure you fully comply with the local laws, and it's best to speak with professionals before making an investment decision.