The Orlando short-term rental market is evolving fast, but for savvy investors, the opportunity remains massive. With over 80 million annual visitors flocking to Central Florida, the demand for high-quality vacation homes is stronger than ever. But here’s the reality for 2026: not every community is created equal. The days of buying just “anywhere near Disney” are over.
Today, success depends on choosing communities with resort-style amenities, proven occupancy history, and the right zoning to legally own Airbnb near Disney.
From high-end luxury enclaves in Kissimmee to value-driven resorts in Davenport, we’ve curated the top 12 communities poised to perform in 2026.
1. Windsor Hills (Kissimmee)
If there is a “gold standard” for short-term rental investing near Disney, Windsor Hills is often the first name mentioned, and for good reason. Built in 2004 and located just 1.5 miles from Walt Disney World, Windsor Hills has earned its reputation through consistency, not hype.
This gated resort sits at the intersection of US-192 and Old Lake Wilson Road, placing guests minutes from Disney’s Animal Kingdom, Epcot, Magic Kingdom, and within reasonable driving distance to Universal. That proximity directly translates into shorter stays, repeat bookings, and strong year-round occupancy.
2. Storey Lake (Kissimmee)
Storey Lake feels like the kind of place guests remember long after the vacation ends. Tucked into the heart of Kissimmee, this resort community blends convenience, modern design, and true resort energy, one of the reasons it continues to perform well for short-term rental investors in 2026.
Location is one of Storey Lake’s strongest advantages, sitting just 4.5 miles from Walt Disney World. What truly separates Storey Lake is its resort-level amenity package, The Hideaway Club, featuring a lazy river and water slides that actively drive bookings.
3. Windsor at Westside (Kissimmee)
For investors seeking affordable luxury, Windsor at Westside offers a compelling mix of grand home designs and world-class amenities. Located just a few miles from Walt Disney World, this gated community features a 10,000 sq. ft. clubhouse, a lazy river, and a water playground that families adore.
With homes ranging from 5 to 9 bedrooms, you can cater to large multi-generational groups, a highly lucrative segment of the Orlando vacation rental investment market. The close proximity to major attractions ensures your calendar stays full.
4. Solara Resort (Kissimmee)
Solara Resort is designed to take Orlando resort living to new heights. With a focus on high-end amenities, this gated community features a FlowRider surf simulator, a heated grand pool, and a full-service restaurant and bar. The homes here are specifically designed to maximize rentals, offering private pools and spacious layouts perfect for groups.
Solara’s location in Kissimmee places it minutes from theme parks, making it a top choice for guests who want a premium experience without sacrificing convenience.
5. Reunion Resort (Kissimmee)
Reunion Resort is the number one choice for luxury vacation rentals in Orlando. It is a unique master-planned community that offers three signature golf courses, a water park, and diverse dining options. For investors targeting the high-end market, Reunion offers everything from condos to massive custom mansions.
The resort’s reputation for excellence draws affluent travelers willing to pay premium nightly rates for a superior experience. It’s an ideal spot for those looking to build a portfolio of luxury assets.
6. ChampionsGate (Davenport)
ChampionsGate is a massive, globally recognized master-planned community that offers a recreation-rich lifestyle. Located just minutes from Disney, The Retreat at ChampionsGate features lavish amenities, including a lazy river, water slides, and a movie theater.
The sheer scale and brand recognition of ChampionsGate make it a safe bet for investors. With a mix of townhomes and large single-family homes, you can find inventory that fits various budget levels while tapping into a steady stream of demand.
7. Solterra Resort (Davenport)
Solterra Resort offers a fantastic balance of value and amenities. Located in Davenport, just 11 miles from Disney, this community features a beautiful clubhouse with a poolside café, lazy river, and water slide. The homes are designed with the investor in mind, often featuring 5 to 7 bedrooms and private pools.
Solterra’s slightly lower entry price point compared to Kissimmee communities makes it an attractive option for first-time investors looking for solid returns and a family-friendly atmosphere.
8. Windsor Island Resort (Davenport)
Windsor Island Resort is one of the newest and most exciting additions to the Davenport area. With a massive resort pool, splash pad, and mini-golf, the “Aloha Clubhouse” is a major draw for families. The community offers modern 5 to 10-bedroom homes purpose-built for short-term rentals.
Being newer construction, these homes often come with less deferred maintenance, and the fresh, modern aesthetic appeals strongly to guests browsing Airbnb and Vrbo.
9. Regal Palms (Davenport)
Regal Palms offers an entry-level price point with resort-style perks, making it excellent for first-time investors. This community features 3 and 4-bedroom townhomes combined with a lush tropical swimming pavilion, lazy river, and water slide.
It provides a “home away from home” feel that appeals to budget-conscious families who still want a pool and amenities. Located next to Highlands Reserve Golf Club, it offers a quieter retreat while still being close enough to the action, providing steady rental potential.
10. Vista Cay (Orlando)
Vista Cay is a rare gem, a legal short-term rental pocket in the heart of Orlando, next to the Orange County Convention Center and the upcoming Epic Universe. This makes it perfect for targeting both business travelers and vacationers.
The community offers stunning condos and townhomes with resort-style amenities like two pools and a clubhouse. Its location on Universal Boulevard provides incredible access to SeaWorld and Universal Orlando, giving you a unique competitive advantage over properties further south.
11. Encore at Reunion (Orlando/Kissimmee)
Encore at Reunion is all about hospitality and high-end experiences. It functions almost like a boutique hotel with private homes, offering concierge services, complimentary shuttles to theme parks, and a spectacular AquaPark.
The homes here are large, ranging from 4 to 13 bedrooms, catering to reunions, sports teams, and corporate retreats. This focus on large groups allows for high nightly rates. Professional management and consistent resort quality make it a hands-off, high-yield option for serious investors.
12. Magic Village (Kissimmee)
Magic Village offers a sophisticated, boutique feel just minutes from Animal Kingdom. Designed by Pininfarina (known for Ferrari), these upscale townhomes offer a modern, European aesthetic that stands out from typical Florida rental homes. With concierge services and a focus on culinary experiences, it attracts discerning travelers.
Being part of the Wyndham Hotels & Resorts booking channel adds a layer of rental power. It’s perfect for investors looking for a unique, stylish property with strong management support.
Start Your Investment Journey Today
Choosing the right community is the first step in building a successful short-term rental portfolio. The Orlando market is dynamic, and having the right partner to navigate zoning, property management, and revenue projections is crucial.
Don’t leave your investment to chance. Whether you want to explore the ROI of a specific community or are ready to see listings in person, we are here to help you maximize your rental income.
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