HOLIDAY REALTY LLC
About Us
Central Florida's Most Experienced Windsor Hills Realtors
Holiday Realty LLC is the most experienced short-term rental real estate brokerage specializing in Windsor Hills Resort. With over 25 years of combined experience in the Central Florida vacation home market, we provide unmatched expertise to buyers and sellers looking to invest in one of Orlando's premier resort communities.
Our team understands every aspect of vacation home ownership at Windsor Hills — from property acquisition and rental management to HOA regulations and resale strategy. We've helped hundreds of investors from around the world navigate the process of buying and selling vacation rental properties near Walt Disney World.
Whether you're a first-time investor exploring the Orlando short-term rental market or a seasoned owner looking to sell your Windsor Hills property, we offer personalized guidance every step of the way. Our deep knowledge of the community, combined with our strong relationships with local property managers, lenders, and service providers, ensures a seamless experience.
Why Work With Us
25+ Years Experience
Over two decades of combined expertise in Central Florida's vacation home market.
Local Specialists
Based in Kissimmee, we know Windsor Hills Resort inside and out — every floor plan, every HOA detail.
#1 Community
Windsor Hills was named the #1 vacation home community by Forbes Investors — and we've been here since the beginning.
Global Clients
We assist buyers and sellers from all over the world, guiding international and domestic investors alike.
Meet Our Team
Bryan Rogers
Broker / Owner — Holiday Realty LLC
A licensed Florida Broker with over 25 years of experience in the Central Florida vacation home market. Bryan specializes in Windsor Hills Resort and the greater Kissimmee area, helping buyers and sellers worldwide with honest, knowledgeable service.
Brad Rogers
Realtor — Windsor Hills Market Specialist
A dedicated Realtor at Holiday Realty LLC, Brad brings specialized knowledge of the Windsor Hills market. He works closely with buyers and sellers to ensure every transaction is handled with expertise and care.
Contact Us
Have a question about Windsor Hills? Interested in buying or selling a property? We'd love to hear from you.
Let's Talk
Ready to Find Your Dream Vacation Home?
Contact Holiday Realty LLC today for a free consultation. We'll help you buy or sell your Windsor Hills Resort property.