Windsor at Westside Vacation Rental Management Built Around Your Investment
Edge Property Management provides full-service management for vacation homes and townhomes at Windsor at Westside in Kissimmee, a quieter resort community off Westside Boulevard about 20 minutes from Walt Disney World.
Earn 3x More With 10% Management Fees
Why Windsor at Westside Works So Well for Family Vacation Rentals
Windsor at Westside sits off Westside Boulevard in Kissimmee, in Osceola County, near US-192 and US-27 and about 10 miles from Walt Disney World. It is less commercial than the busiest stretches of US-192, which gives guests a calmer base for a park vacation.
The resort is built around one large clubhouse: a roughly 10,000-square-foot amenity center with a resort pool, waterslide, lazy river, kids' water playground, bar and lounge, arcade, fitness center, and sports courts.
Homes range from townhomes to pool homes of up to nine bedrooms, and its HOA has clear rules on noise and parties. That appeals to families and makes for a smoother guest experience.
Those same rules mean guest screening and house rules matter more here than in most communities, and a home that runs smoothly with the HOA earns better reviews and more repeat bookings.
That is exactly what Edge delivers: local, hands-on management built for Windsor at Westside.
Edge also manages homes in ChampionsGate, Reunion Resort, Solterra Resort and Storey Lake. See our Kissimmee vacation rental management page for market-wide numbers.
Serving Kissimmee's Top Resort Communities
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![Aerial view of a residential community featuring a large lake with a fountain, a swimming pool area with water slides, and a tennis court, surrounded by lush green trees and houses with tan roofs.]()
ChampionsGate
ChampionsGate is one of the most in-demand resort communities in the Disney corridor, located on the Osceola County side despite its Davenport address, known for its championship golf courses, large resort-style pools, and proximity to I-4 and the theme parks. Properties here attract families looking for upscale vacation homes with resort amenities. Edge handles the pricing, listing, guest communication, and on-site operations for ChampionsGate owners — with full knowledge of the community's HOA rental guidelines and registration requirements.
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![Aerial view of a large residential community with a swimming pool, water slides, and recreational areas, surrounded by houses and green landscapes under a clear blue sky.]()
Reunion Resort
Reunion Resort is Kissimmee's premier luxury vacation rental community. Homes here range from five to fifteen bedrooms, featuring private pools, themed game rooms, and access to three championship golf courses. The guest profile is distinctly high-end and the revenue potential is among the highest in the Kissimmee market. Edge's management approach at Reunion is built around premium guest experience, proactive maintenance, and revenue strategies designed for larger luxury properties.
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![Aerial view of a large community park with a lake, playground, swimming pool, sports courts, walking paths, and residential houses in the background.]()
Solterra Resort
Solterra is a gated resort community in Davenport, on the Polk County side of the Disney corridor. It's a strong performer for mid-size vacation homes — typically four to eight bedrooms — with resort amenities including a clubhouse, lazy river, and waterslide. Edge's approach at Solterra focuses on occupancy consistency and competitive nightly rates calibrated against the surrounding Davenport market.
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![Aerial view of a residential community with houses, a water park with pools and slides, a large pond, and green landscaping under a clear blue sky.]()
Storey Lake Resort
Storey Lake is one of Kissimmee's fastest-growing resort communities, situated minutes from Disney World and packed with amenities that guests love — lazy river, mini golf, kayaking, and clubhouse facilities. Properties here perform well for families and large groups. Edge handles full-service management for Storey Lake owners, covering everything from dynamic pricing and platform listing to cleaning coordination, maintenance, and guest support.
What Edge Does Differently in the Windsor at Westside Market
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Windsor at Westside takes its HOA rules seriously. Your local team knows the noise, parking, and occupancy rules and the clubhouse access process, screens guests to match, and handles cleanings, maintenance, and guest issues in person.
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Edge charges a management fee starting at 10% for short term rentals, with no hidden call-out charges, no maintenance markups, and no surprise line items on your monthly statement. You see exactly what your property earned, what was spent, and what you receive — every single month.
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Windsor at Westside pricing moves with Disney park calendars, school holidays, and summer and winter family travel. Edge uses real-time market data and dynamic pricing tools to keep your home competitive all year, with strong occupancy in slower weeks and maximized rates when demand peaks.
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Your Windsor at Westside home is listed and actively managed across Airbnb, VRBO, Booking.com, and our direct booking platform. Every listing is professionally optimized to highlight the clubhouse, the family-friendly setting, and your home's pool and game spaces.
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Edge does not lock owners into long term contracts. We earn your business every month through performance, transparency, and communication.
Windsor at Westside Short Term Rental Rules: What Owners Need to Know
Windsor at Westside is in Osceola County, so Osceola County tax and registration rules apply, along with the community's own HOA rules. Edge handles all of this for every owner we work with. Here is an overview of what applies.
Osceola County Tourist Development Tax
Short term rentals in Osceola County are subject to a Tourist Development Tax (TDT) in addition to Florida state sales tax. Edge, as the operator of record, collects and remits these taxes on your behalf so you remain fully compliant without the administrative burden.
State of Florida DBPR License
The Florida Department of Business and Professional Regulation (DBPR) requires all vacation rental properties to hold a valid state license. Edge assists new owners through the registration process and ensures your license remains current.
HOA Rental Guidelines
Windsor at Westside's HOA sets the rules for short term rentals, including occupancy limits, parking, noise and party restrictions, and guest access to the clubhouse. Edge screens guests, sets clear house rules, and makes sure every stay is compliant.
Business Tax Receipt
Osceola County requires a Business Tax Receipt (BTR) for properties operating as short term rentals. Edge guides owners through this process as part of onboarding.
Meet Your Windsor at Westside Property Manager
Annie Alvarez
Local Property Manager
Annie brings more than 12 years of vacation rental and hospitality experience to Edge, spanning resort operations, maintenance coordination, reservations, and guest services. She leads day-to-day operations for Edge homes across the Orlando area, overseeing inspections, cleanings, vendors, and guest support so homes stay guest-ready and owners always know what is happening with their property.
Known for her organization, quick problem-solving, and clear communication, Annie has years of experience leading teams and keeping properties running smoothly. She is fluent in English and Spanish. When you work with Edge, you deal directly with Annie and our local team: no call center, no ticket queue, just quick answers from people who know your community.
Your Local Support Team
Annie works alongside the management, maintenance, and operations team that supports every Edge home in the Orlando area.
Frequently Asked Questions
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Edge's management fees are 10% for on-site only service and 18% for full service management. There are no hidden fees, no call-out charges, and no maintenance markups. Your monthly statement is fully itemized and transparent.
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Yes. Windsor at Westside is a vacation rental resort community. Its HOA is known for enforcing noise, parking, and occupancy rules, so we review your documents and set house rules and guest screening to match before you list.
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Windsor at Westside is in Osceola County. Florida requires a DBPR vacation rental license, Osceola County requires a business tax receipt, and stays of six months or less are subject to Florida's 6% sales tax, Osceola County's 1.5% sales surtax, and Osceola County's 6% tourist development tax. Edge sets up the licensing and collects and files these taxes for every owner we manage.
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Airbnb, VRBO, Booking.com, and our direct booking platform. Every listing is professionally optimized and monitored, with the clubhouse and family-friendly setting front and center.
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Yes. You can block dates for personal use at any time through your owner portal. There are no restrictions on how often you use your own property.
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No. Edge operates on a month-to-month basis. We do not lock owners into long term contracts.
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Eligible stays are covered by a comprehensive protection plan covering property damage. Edge also conducts a post-stay inspection on every turnover so any damage is identified, documented, and actioned immediately.
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Both compete in the mid-to-premium family market with homes from townhomes up to nine bedrooms. Windsor at Westside offers a quieter setting and one large clubhouse, while Storey Lake has the lake and a location just off Osceola Parkway, close to Disney. We compare your specific property during the revenue analysis.
See What Your Windsor at Westside Property Could Be Earning
Request a free revenue analysis and get a personalized estimate based on your property's location, size, and the current Windsor at Westside market. Our team typically responds within 48 hours. Prefer to talk now? Call (689) 303-9882.
This offer is for current Windsor at Westside property owners looking for hands-off, professional short term rental management.