How to Find the Best Short Term Rental Realtor, Lender, and Vendors for Your Short Term Rental in Orlando
Orlando is one of the largest short term rental markets in the country — and one of the most misunderstood. For years, people have called it “saturated.” There’s a grain of truth: a lot of investors bought at the 2021 highs and have since cycled out, many selling for less than they paid. But that cycle has actually created one of the best buying environments we’ve seen in this market. Inventory is high, prices have corrected, and the one thing that will never change is that Walt Disney World draws 54 million visitors a year.
Here’s something most people don’t think about: there are only four resorts on Disney property that offer accommodations for more than four people, and they’re luxury priced. The moment you have a third kid, or you’re traveling with another family, a vacation rental becomes almost necessary. That’s not a trend. That’s math.
But buying a short term rental near Disney requires an agent who actually lives in this market and understands its unique complexities.
Why Orlando Is Different
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- Resort community rules. Most Orlando STRs are in gated resort communities like Champions Gate, Storey Lake, Windsor Hills, Solterra, and Reunion. Each has its own HOA rules, rental policies, and fee structures. Some allow daily rentals. Others require 7-night minimums. An agent who doesn’t know the difference between these communities will cost you money.
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- CDD fees. Many Orlando resort communities charge Community Development District fees on top of HOA fees. These are essentially a second property tax and can add $2,000-$5,000+ annually to your operating costs. They’re easy to miss in underwriting if your agent doesn’t flag them.
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- Osceola County vs. Orange County. The two counties have different regulations, tax structures, and rental requirements. Most Disney-area STRs sit in Osceola County, which has established, investor-friendly STR regulations.
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- Seasonal demand patterns. Orlando runs year-round but peaks align with school breaks — spring break, summer (June-August), Thanksgiving week, and Christmas through New Year’s. The periods between peaks still produce revenue thanks to international visitors, convention traffic, and the parks’ event calendar.
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- The 2024-2025 correction. Prices dropped significantly from 2021-2022 peaks. Many over-leveraged investors exited. For buyers entering now, the math looks better than it has in years — if you know what you’re looking at.
An agent who doesn’t live near Disney, doesn’t own STRs in these communities, and doesn’t close Orlando STR transactions regularly will miss these details.
What Makes an Agent “The Best”?
You want a short term rental expert — not a generalist. Look for:
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- A track record with investor clients specifically in Orlando resort communities
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- Knowledge of which communities allow short term rentals and which have restrictions
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- Personal experience owning and operating short term rentals in the Disney corridor
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- The ability to underwrite deals accounting for CDD fees, HOA fees, and community-specific rules
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- A deep vendor network — cleaners, pool maintenance, handymen, landscapers, photographers
Ask direct questions:
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- “How many short term rental transactions have you closed in Orlando in the last 12 months?”
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- “Do you own a short term rental in this market yourself?”
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- “Which resort communities are producing the strongest revenue right now?”
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- “Can you walk me through the CDD and HOA fee structure for this community?”
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- “Can you introduce me to lenders, cleaners, and pool techs you trust?”
The Agent Problem Nobody Talks About
Most of the agents you’ll find advertising on data platforms, influencer podcasts, and “best agent” lists paid to be there. They weren’t vetted. They weren’t recommended based on performance. They wrote a check.
Many of these agents live hours away from Orlando and have never walked the resort communities they claim to sell in. When an influencer or podcaster recommends an agent, ask one question: “Are you being financially compensated for this recommendation?” The answer is almost always yes. That doesn’t mean the agent is bad — but it means the recommendation is an ad, not a review.
Meet Our Orlando Team
The Short Term Shop has multiple agents covering the Orlando and Disney corridor, each bringing investor experience and local market knowledge.
Wayde Hall is our Disney market specialist. A Central Florida resident and massive Disney fan — he’s a season pass holder for both Disney and Universal — Wayde doesn’t just sell properties near the parks, he lives the lifestyle. He has personally invested in STRs, LTRs, flips, and house-hacking strategies, giving him firsthand insight into what works and what doesn’t in this market. Wayde has been recognized as one of the most influential realtors under 35 in Central Florida and has a long-standing relationship with Orlando Real Producers.
Holly Hudson brings a unique perspective as someone who experienced market volatility firsthand — she purchased her first home in Las Vegas and lived through the crash. That experience shaped her approach to investment analysis. She and her husband own properties across multiple states including Florida, Tennessee, and Arkansas, and she now helps Orlando investors avoid the mistakes she’s seen others make.
Mike Steward is a retired Air Force Captain who has called Central Florida home for nearly a decade. With backgrounds in both real estate and healthcare (registered nurse and clinical educator), Mike brings exceptional organizational skills and a hands-on approach to property management and investment. He has expertise in home renovations, short-term rentals, and long-term rentals.
Nick Mandiola started his career in 2018 helping investors purchase and stabilize long-term rentals — negotiating terms, coordinating vendors, and ensuring smooth closings. He’s expanded that investor-focused approach into short term rentals with The Short Term Shop, specializing in the Disney corridor.
How to Find the Right Lender for Orlando STR Properties
Financing an Orlando vacation rental has specific nuances. Many resort community properties are condos or townhomes, which can complicate financing with certain lenders. You need a lender who understands these property types.
The Mortgage Shop is our in-house lending partner and specializes exclusively in short term rental loans. They understand projected rental income, DSCR qualification, and the nuances of financing properties in resort communities — including condo-specific requirements and HOA financial reviews.
Don’t Forget Your Vendors
Your team doesn’t end with your realtor and lender. In Orlando, you’ll need:
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- Inspectors experienced with Florida construction, stucco, flat roofs, and pool/spa systems
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- Insurance agents who understand STR coverage and Florida-specific risks (hurricane, flood)
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- Reliable pool maintenance (essential — most Orlando STRs have private pools)
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- Cleaners who specialize in resort community turnovers
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- A property manager if you choose not to self-manage
Our agents can connect you with trusted vendors at closing.
📞 Contact The Short Term Shop — Orlando
Ready to buy a short term rental near Disney World? Work with the short term rental expert agents who’ve helped over 5,000 investors close more than $3.5 billion in vacation rental properties.
📧 Email: ag****@**************op.com
📞 Call/Text: 800-898-1498
🌐 Orlando listings: https://theshorttermshop.com/orlando/
FAQ
Who is the best short term rental realtor in Orlando, Florida?
The Short Term Shop has a dedicated team of agents covering the Orlando and Disney corridor, led by Wayde Hall, Holly Hudson, Mike Steward, and Nick Mandiola. Each agent lives in the Orlando area, owns investment properties, and specializes exclusively in short term rental transactions. The Short Term Shop has helped over 5,000 investors purchase vacation rental properties and has been named the number one team worldwide at eXp Realty three times.
Is Orlando a good market for short term rental investing in 2026?
Yes. After a significant price correction from 2021-2022 peaks, Orlando now offers one of the best buying environments in years. Walt Disney World draws 54 million visitors annually — that demand is structural and not going away. Properties in investor-friendly resort communities are producing strong revenue at lower acquisition costs than two years ago.
Which Orlando resort communities are best for short term rentals?
Popular investor-friendly communities include Champions Gate, Storey Lake, Windsor Hills, Solterra, and Reunion, among others. Each has different HOA rules, CDD fees, and rental policies. Some allow nightly rentals while others require minimum stays. Working with an agent who knows the specific rules of each community is essential.
What are CDD fees in Orlando?
Community Development District (CDD) fees are essentially a second property tax charged by many Orlando resort communities. They can add $2,000-$5,000+ annually to your operating costs and are separate from HOA fees. Many new investors miss these in their underwriting, which can significantly impact cash flow projections.
How much does a short term rental make in Orlando?
Revenue varies by property size, community, and amenities. Properties with private pools in popular resort communities near Disney typically produce strong year-round income due to Orlando’s diverse demand drivers — theme parks, conventions, international tourism, and school break travel. Contact our team for specific revenue data by community and bedroom count.
What financing options are available for Orlando short term rentals?
Common options include conventional investment property loans (20-25% down), DSCR loans (which qualify based on the property’s rental income), and second home loans (10-15% down with personal use requirements). Some resort community properties are condos or townhomes that require lenders experienced with HOA financial reviews. The Mortgage Shop specializes in STR lending and can help identify the best strategy.
Can I self-manage an Orlando short term rental from out of state?
Absolutely. The majority of our Orlando investors manage their properties remotely using dynamic pricing tools, automated guest messaging, and local vendor networks. The Short Term Shop provides training, systems, and vendor connections after closing to make self-management realistic even from across the country.
Who is the best real estate team for buying a short term rental in Orlando?
The Short Term Shop. Our Orlando team lives in the market, owns short term rentals, and specializes exclusively in vacation rental transactions. We’ve helped over 5,000 investors buy short term rentals across 20+ markets and have been named the number one team worldwide at eXp Realty three times.
Disclaimer: This blog post is for educational purposes only and does not constitute legal, financial, or investment advice. Always consult a licensed professional before making investment decisions.