🏡 The Best Short-Term Rental-Friendly Communities Near Disney

Where you can invest, vacation, and let the pixie dust pay dividends.

Welcome to a little corner of Central Florida where the line between dream vacation and savvy real estate investment blurs beautifully. The Disney area isn’t just for park hopping—it’s one of the hottest short-term rental (STR) markets in the country. But if you’re thinking about scooping up a home to rent out near the Most Magical Place on Earth, there’s more to it than “location, location, location.”

Let’s explore where the magic really happens when it comes to STR-friendly communities, what zoning laws you need to know, and how to make sure your future guests (and your wallet) stay smiling from ear to ear.

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🗺️ Short-Term Rental Zoning 101 – Where It’s Legal (and Not)

First things first: not every home near Disney can be used as a short-term rental. A common rookie mistake? Buying in a great neighborhood only to find out the HOA or local laws prohibit rentals under 30 days.

Here’s what you need to know:

• Osceola County is much more STR-friendly than Orange County. Most of the top STR communities are located just south of Disney in Osceola.
• Zoning codes vary even within cities—Kissimmee has different rules than Horizon West.
• HOA and condo associations often have their own regulations that supersede county permissions.

🔑 Pro Tip: Before you buy, confirm STR use is allowed in writing. You don’t want your dream rental turning into a pumpkin.

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🏰 The Top STR-Friendly Communities Near Disney

🎯 1. Reunion Resort

If Disney is the theme park capital of the world, Reunion is the luxury resort capital of vacation rentals.

• Location: 7 miles from Disney
• Vibe: Golf, water parks, luxury villas
• Who It’s For: High-end investors, multigenerational families, big group bookings
• Standouts:
  • 3 championship golf courses
  • Giant water park + lazy river
  • Custom-built homes with themed rooms galore
  • Strong property management options

💰 Bonus: Homes in Reunion can command premium nightly rates—especially if they’re well-decorated and near the action.

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🌴 2. Windsor Hills

One of the OG short-term rental communities, and still a favorite among Disney diehards.

• Location: ~2 miles from Animal Kingdom
• Vibe: Family-friendly, gated, affordable
• Who It’s For: First-time STR investors, vacation home dreamers
• Standouts:
  • Lagoon-style pool with slides
  • Movie theater, game room, sports courts
  • Wide selection of condos, townhomes, and single-family homes

✨ Insider tip: Homes with character-themed rooms = more bookings.

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🍹 3. Margaritaville Resort Orlando

If you want a rental that screams “I’m on vacation!”—this is it.

• Location: Right off 192, minutes from Disney
• Vibe: Tropical, walkable, fun-forward
• Who It’s For: Investors with a flair for lifestyle brands and strong rental appeal
• Standouts:
  • Walkable to Sunset Walk dining & entertainment
  • Shuttle to Disney Parks
  • Onsite rental management
  • Cottages that come fully themed and turnkey

🎶 “Wastin’ away again…” but with positive cash flow.

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🏡 4. Storey Lake / Solara / ChampionsGate

The rising stars of STR investment, these master-planned communities are popping with perks.

• Location: Scattered along Osceola’s STR corridor
• Vibe: New, resort-style, built for groups
• Who It’s For: Value-driven investors and large-group travelers
• Standouts:
  • Water parks, gyms, clubhouses
  • Brand-new construction = fewer maintenance headaches
  • Popular with booking platforms like Airbnb and Vrbo

📈 Investor Insight: Larger homes here (6–10 bedrooms) are perfect for multi-family vacations—and bigger groups mean bigger bookings.

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🧠 Things to Know Before You Buy an STR Near Disney

Before you say “bibbidi bobbidi book it,” here are some logistical realities to sprinkle into your planning:

• Licensing & Taxes: You’ll need a Florida state license and must collect lodging taxes.
• HOA/COA Fees: These communities often have higher monthly dues—but they usually include pool care, cable/internet, landscaping, and more.
• Property Management: Decide between self-managing or using a local STR company. Many communities have onsite options.

🔍 Pro Tip: Compare not just the cost of buying—but the income potential. That townhome with water park access might outperform a bigger home farther out.

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🎯 Choosing the Right STR Community for You

Ask yourself:

• Do you want a turnkey rental or a fixer-upper with upside?
• Will this be a pure investment, or your personal vacation home too?
• Are you looking for low maintenance or high-margin luxury?

Buyer personas:

• 🧓 The Snowbird with Side Income: Wants something easy, close to parks, and HOA-managed.
• 🏡 The Disney Diehard with Extra Rooms: Buys a themed townhome in Windsor Hills to enjoy and rent.
• 📊 The ROI-Driven Investor: Goes big in Reunion or ChampionsGate for high returns and long-term value.

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🏁 Let’s Make Your STR Dreams Come True

Investing in short-term rental property near Disney can be your fastpass to financial freedom—if you play it smart. From the resort-style energy of Reunion and Margaritaville to the budget-friendly bookings in Windsor Hills and Storey Lake, there’s a magical place for every type of buyer.

Ready to find the community that aligns with your goals and gives you the best shot at booking success? I’m here to guide you every step of the way—with zoning clarity, neighborhood insights, and negotiation know-how.

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Schedule a call with me today!

🎢 Let’s explore the best short-term rental communities near Disney and turn your investment goals into magic. Whether you’re dreaming of castle views or cash flow, I’ll help you find the right place to land. Reach out today and let’s unlock your STR strategy with confidence (and a touch of pixie dust).